<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd" xmlns:googleplay="http://www.google.com/schemas/play-podcasts/1.0"><channel><title><![CDATA[Memos by Sooraj]]></title><description><![CDATA[Musings on tech, startups and life]]></description><link>https://www.memos.soorajchandran.com</link><image><url>https://substackcdn.com/image/fetch/$s_!YE6b!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F07fd6693-bb4d-4862-ae34-0456412fd759_608x608.png</url><title>Memos by Sooraj</title><link>https://www.memos.soorajchandran.com</link></image><generator>Substack</generator><lastBuildDate>Tue, 21 Apr 2026 03:15:37 GMT</lastBuildDate><atom:link href="https://www.memos.soorajchandran.com/feed" rel="self" type="application/rss+xml"/><copyright><![CDATA[Sooraj Chandran]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[9to5exe@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[9to5exe@substack.com]]></itunes:email><itunes:name><![CDATA[Sooraj Chandran]]></itunes:name></itunes:owner><itunes:author><![CDATA[Sooraj Chandran]]></itunes:author><googleplay:owner><![CDATA[9to5exe@substack.com]]></googleplay:owner><googleplay:email><![CDATA[9to5exe@substack.com]]></googleplay:email><googleplay:author><![CDATA[Sooraj Chandran]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[46. Chill Mode]]></title><description><![CDATA[Reflections on slowing down in life]]></description><link>https://www.memos.soorajchandran.com/p/46-chill-mode</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/46-chill-mode</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 26 Feb 2026 06:17:52 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/e883e35d-0b75-4297-9c45-8ff1c0264691_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I&#8217;ve been living life in chill mode for a few years now.</p><p>As someone who was raised in India, I constantly felt the pressure to succeed in my career and win. I started running the rat race right after college. But I&#8217;m glad I met some good people very early in my career who proved pivotal, and that I found some stubborn motivation to make a few very hard career switches that laid the foundation for my journey.</p><p>I built a couple of startups at what now seems like a young age, and while I had more energy than competence, it was formative. The first one was an experience in itself. We made a lot of mistakes. The second was a decent success, as it laid a strong financial and career foundation for my onward journey, with a small exit.</p><p>While I was building my second startup, at least in the early stage, I was working a full-time job. It was a hustle, working on weeknights and weekends. My cofounder was my wife. We hustled together. We had fun. We still have fun.</p><p>Ever since I sold my second startup, I&#8217;ve been deliberately trying to live in chill mode. I&#8217;ve travelled a lot in the last few years, to almost 35 of my favourite countries. I&#8217;ve leaned strongly into photography, which I&#8217;m passionate about. I&#8217;ve bought a house, made friends, and recently got a motorbike.</p><p>Chill mode is not floating without intention. During this period, I&#8217;ve invested in my health and relationships. I started writing. I&#8217;ve travelled. I feel physically stronger than ever. I&#8217;ve worked on my mental health. I&#8217;ve built perspective and optionality.</p><p>I sometimes find myself swinging back to my hustling self, especially with the AI revolution. When I get back to hustle mode, I want to be deliberate and go all in.</p><p>Mentally, I&#8217;m getting ready. I feel like there is a lot of opportunity cost in what&#8217;s happening in AI right now. Exciting times. But the mood swings are strong. The swings between wanting to go all-in on AI or completely leave tech and live somewhere far away from all of it.</p><p>Living in chill mode was a deliberate choice. One of the things I discussed with my wife when I said I wanted to live a chill life was regret minimisation. I didn&#8217;t want to feel like I spent my entire life hustling. I&#8217;m really glad I made that decision. While I enjoy working and hustling on meaningful things, I definitely know there is more to life. I want to experience life fully.</p><p>The early hustle in life gave me that optionality. What&#8217;s the point of it if I don&#8217;t choose to exercise that a bit? I didn&#8217;t want to be the person who hustles forever, especially while I&#8217;m healthy.</p><p>It has also helped me disconnect from my identity a bit. I used to think of myself as the tech or founder guy, and I thought that&#8217;s what I was supposed to do all the time, or else I&#8217;d be a failure. I feel less attached to that identity now. </p><p>I&#8217;m trying to enjoy the things I do, whatever that is. Photography, travel, building stuff. I don&#8217;t know how long this phase lasts. But I know I&#8217;ll look back and be grateful I didn&#8217;t skip it.</p>]]></content:encoded></item><item><title><![CDATA[45. If AI takes all jobs what will we do?]]></title><description><![CDATA[I see a lot of questions on my feeds around &#8220;If AI takes all jobs, what will we do?&#8221;]]></description><link>https://www.memos.soorajchandran.com/p/45-if-ai-takes-all-jobs-what-will</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/45-if-ai-takes-all-jobs-what-will</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 12 Feb 2026 07:25:47 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/57f50f10-ea51-4f29-bfcf-60915f14f063_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I see a lot of questions on my feeds around &#8220;If AI takes all jobs, what will we do?&#8221;</p><p>I don&#8217;t know if people are seriously asking that question, or if it&#8217;s clickbait. It&#8217;s hard to tell these days.</p><p>AI won&#8217;t replace all jobs. It will replace some jobs. It will change many jobs. And new jobs will be created. Also, a large part of the AI discourse only applies to knowledge work.</p><p>YouTuber wasn&#8217;t a thing 25 years ago. Software engineering wasn&#8217;t a thing 100 years ago.</p><p>At work, I spend a lot of time looking at agentic use cases and how roles are going to evolve in an operations-intensive world. If the job you do now doesn&#8217;t require a lot of judgment, there is a big chance that it will be fully replaced.</p><p>Think about the main tasks you do at work. If those tasks can be written down step by step somewhere, an AI agent can probably do that.</p><p>If your entire job is full of such tasks, there is a chance that the job will be replaced. If only part of your job can be written down, then it will change your job. You&#8217;ll get to do less of the boring parts. If it&#8217;s not easy to describe what you do, for example, you make a lot of decisions driven by gut feeling and your wisdom, it&#8217;s much harder to replace that. At least for a while.</p><p>I don&#8217;t think all jobs fall strictly into those categories, so a more likely outcome is large parts of certain jobs getting automated and small parts of some others. One person will be able to do the job of 3 to 5 people. </p><p>This is what has always happened in the past - with electricity, machines, computers, internet. It will keep happening. But it will also lead to the creation of new jobs. I don&#8217;t know what jobs will exist 10 years from now, but think of all the jobs that didn&#8217;t exist 100 years ago, but were created due to advances in technology. Air traffic controllers, video editors, programmers, YouTubers, and influencers. </p><p>The world will always have needs. Businesses will come up catering those needs, and businesses will need some sort of workers. We just don&#8217;t know it yet. </p><p><strong>What can you do about it?</strong></p><p>The best way to react to this is to lean into it. You can either disrupt yourself or be disrupted by others. In the 90s, if you refused to use computers, you probably would have a hard time finding jobs a decade later. Learn to work with AI.</p><p>Think about your unfair advantages, maybe you can start that business you always wanted to start. AI replaces things, but it is also a force multiplier for many other things - are you good at one of those?</p><p>Cars replaced horses, but created an entire industry. Life will go on.</p><p><strong>Also, don&#8217;t forget to touch grass.</strong></p>]]></content:encoded></item><item><title><![CDATA[44. Our parents were kids once]]></title><description><![CDATA[Do you ever really think about that?]]></description><link>https://www.memos.soorajchandran.com/p/44-our-parents-were-kids-once</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/44-our-parents-were-kids-once</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Fri, 30 Jan 2026 11:15:52 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/34aa678d-bf9a-4900-a9ba-69068a2cfced_2816x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Do you ever really think about that? Like, in a deeply understanding and empathetic way. Imagining they had a childhood that was fun (maybe not), and innocent like ours. Had a teenage phase probably as complicated as ours (again, maybe not), with dreams as colourful as ours. And that they were young adults once, figuring things out for the first time and becoming parents for the first time.</p><p>Like, do you really, really think about that? And fully visualise that they were just like us. But they definitely had a life that was much harder than ours.</p><p>My parents definitely had to deal with more shit than I ever had to in my thirties. In her 30s, at my age now, or my sister&#8217;s current age, my mother was dealing with banks, notices threatening attachment of property, and the uncertainty that came with it. Along with that came creditors, sending two kids to school, preparing all their meals, and managing her 9 to 5 job, all on her own. My dad was away, trying to get the family out of debt.</p><p>Man, I cannot even fathom how hard that must have been. My biggest problems are not having enough vacation days to go to Antarctica, choosing between comfort and legroom on a flight, or being irritated by an annoying co-worker.</p><p>Now, as we notice them getting older, and as we are getting wiser, I am starting to see it. In the first three decades of my life, it never really occurred to me that way. Duh, it is obvious. Everybody was a kid once. But knowing something and truly understanding it are very different.</p><p>Now I understand it. I look at my parents differently. I have always been a decent kid. I did not create a lot of problems as a teenager, did not talk back much, maybe very rarely. I&#8217;ll never know if I&#8217;m a good son, but I try to be. </p><p>But understanding what I just said above has given me a very different perspective on how I talk to my parents. They are just people. They have their fears, anxiety, and dreams, which they probably sacrificed so that I could have mine.</p><p>I think it is a phase. You notice your parents getting older, and you slowly accept that time is not on your side. Someday, we will exist in this world without them, and that honestly scares the shit out of me. All you can really do is cherish the time. It is finite.</p>]]></content:encoded></item><item><title><![CDATA[43. Slop Didn't Start with AI]]></title><description><![CDATA[It has always existed]]></description><link>https://www.memos.soorajchandran.com/p/43-slop-didnt-start-with-ai</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/43-slop-didnt-start-with-ai</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Wed, 28 Jan 2026 12:30:50 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/4ba31b62-df4c-472b-89a7-de02bb1b67fe_2816x1536.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>We talk a lot about AI shipping slop. Take a look at any enterprise software, and you&#8217;ll see the slop humans have shipped over the  years, slowly and inefficiently.</p><p>Most of it comes from people with no skin in the game. People who don&#8217;t care about outcomes because they&#8217;re not measured on outcomes. AI will get better. Mindset is harder to change.</p><p>AI just makes the slop more visible. It accelerates whatever incentives already exist. In the hands of teams that care, it removes busywork and sharpens focus. In the hands of teams that don&#8217;t, it produces faster, shinier slop.</p><p>Good software has always come from ownership, taste, and accountability. That doesn&#8217;t change. If anything, the bar gets higher. When building becomes cheaper, judgment becomes the constraint.</p><h3>This Isn&#8217;t New</h3><p>Shipping mediocre software isn&#8217;t new. Slop didn&#8217;t arrive with AI. It&#8217;s been around forever. Not just in software either. </p><p>Look at most Netflix movies. Endless content, forgettable plots, safe characters, zero risk. A large chunk of those scripts could already be replaced by an LLM and no one would notice. That&#8217;s not a statement about how good AI is. It&#8217;s a statement about how low the bar already was.</p><h3>Slop Is an Incentive Problem</h3><p>If a team ships slop with AI, they would have shipped slop anyway. AI just removes the &#8220;it was hard&#8221; excuse.</p><p>I&#8217;ve watched big teams spend months building features that got discarded. Useless work dressed up with meetings, status updates and slide decks. This is what happens when you incentivise optics over outcomes. When &#8220;looking busy&#8221; matters more than &#8220;being useful.&#8221;</p><p>The things that provide optics, like meetings, processes and alignment sessions, don&#8217;t necessarily lead to good outcomes. They just look like work. AI helps you get to bad outcomes faster. It exposes the lack of skill that the process used to hide.</p><h3>The case for small teams</h3><p>Yes, AI floods the world with average output. </p><p>But it also lets small teams with taste compete against large teams without it. When shipping becomes cheap, taste becomes rare. And taste and care don&#8217;t scale through headcount.</p><p>A two-person team that knows what they&#8217;re building can now outship a fifty-person team that doesn&#8217;t. The bottleneck isn&#8217;t execution anymore. It&#8217;s knowing what&#8217;s worth executing and caring about the outcomes and customers.</p><h3>Slop is not the same as shipping fast</h3><p>There&#8217;s a difference between shipping something imperfect because you don&#8217;t care, and shipping something imperfect because you want to learn. The first is slop. The second is craft.</p><p>Slop is careless speed. They look similar on the surface, but the intent is completely different. One ships to get it over with. The other ships to start a conversation.</p><p>AI makes this gap more obvious. It lets you run the learning loop faster. Ship, listen, adjust, ship again. But if you&#8217;re not listening, you&#8217;re just making noise.</p><h3>The one-day test</h3><p>Here&#8217;s a simple filter: What&#8217;s the most valuable, most imperfect version of this we could ship in one day?</p><p>Slop-shippers can&#8217;t answer that question. They don&#8217;t know what&#8217;s valuable. They just know what looks like work. They&#8217;ll spend weeks on something that didn&#8217;t need to exist.</p><p>Teams that care can answer it immediately. They know what matters. They know what to cut. The one-day constraint forces clarity. It separates the people who understand the problem from the people who are just filling time.</p><h3>Fewer excuses</h3><p>For years, you could hide behind &#8220;it takes time&#8221; or &#8220;we need more resources&#8221; or &#8220;the technology isn&#8217;t there yet.&#8221; AI takes those excuses away.</p><p>What&#8217;s left is just the work. And whether you actually cared about making it good.</p><p>Start shipping and care about what you ship.</p><p></p>]]></content:encoded></item><item><title><![CDATA[42. Building a personal data assistant using Claude Code]]></title><description><![CDATA[My first (kinda) useful non-coding Claude sub-agent]]></description><link>https://www.memos.soorajchandran.com/p/42-building-a-personal-data-assistant</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/42-building-a-personal-data-assistant</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Mon, 12 Jan 2026 09:24:28 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/9c3e02f9-5883-467c-9a51-e51fe674213b_1000x420.webp" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I made a simple Claude sub-agent to access my personal data. If you are not very familiar with agents, hearing the word &#8220;sub-agents&#8221; might seem like a technically challenging thing to do. But trust me, it is probably the simplest thing you will do today. Creating a sub-agent in Claude is as simple as writing a text file.</p><h4>Prerequesites</h4><ul><li><p>You need a Claude Code subscription</p></li><li><p>You can use a terminal (iTerm or whatever terminal your PC comes with)</p></li></ul><p>That&#8217;s it.</p><p>Here&#8217;s how I did it.</p><p>All my important files are stored as PDFs or JPEGs in an <a href="https://obsidian.md/">Obsidian</a> vault. It&#8217;s local, sitting on my machine. </p><p>You don&#8217;t need an Obsidian vault for this. In essence, an Obsidian vault is just another folder. I use it to organise all my personal notes and writing, so I use it. You can keep all your files in a folder in your system. </p><p>This includes items such as my passport, local IDs, energy contracts, house documents, and so on. But I highly recommend starting to use a local-first note taker to organise your knowledge in the AI-first era.</p><p>I created a sub-agent specifically to look up these files. Creating a sub-agent is super simple. Go to your terminal and start Claude. Then type in &#8220;/agents&#8221; and just follow the instructions. All you need to do is type in a fancy system prompt describing how this agent will act.</p><p>You can actually ask Claude itself to generate the system prompt for this. Just share the path to your Obsidian vault or the folder, so it knows where to look. Naming your files properly helps Claude find things easily.</p><p>Here is my prompt:</p><pre><code># Document Data Extraction Agent

## Role
You are a specialised data extraction assistant. Your job is to help users quickly retrieve important information from their personal documents (passports, IDs, visas, contracts, etc.) so they can easily copy-paste values into online forms.

## Document Location
Always look for files in: &lt;your local file path here&gt;

Supported formats: PDF, JPEG, JPG, PNG

## Core Behaviour

### When the user asks for information:
1. Search the document folder for relevant files
2. Extract the requested data points
3. Present the information in a clean, copy-friendly format

### Data points you commonly extract:
- **Identity documents**: Passport number, national ID number, BSN, document expiry dates, issue dates, place of issue, nationality, full legal name (as written on document)
- **Travel documents**: Visa numbers, validity periods, entry/exit stamps
- **Financial documents**: Account numbers, IBAN, BIC/SWIFT codes
- **Property/Legal**: Contract dates, registration numbers, addresses as officially recorded
- **Personal details**: Date of birth, place of birth, gender marker
- If the documents are in Dutch, or a different language, always present the final output in English. Only give Dutch answers if the user specifically ask for it.

## Output Format

Always present extracted data like this:

**[Document Type] - [Document Name]**

Field Name: `value`
Field Name: `value`
Field Name: `value`

Expiry: `DD-MM-YYYY` (X days/months remaining)


Use backticks around values so they're easy to select and copy.

### Date formatting
Provide dates in multiple formats when relevant for form-filling:
- `DD-MM-YYYY`
- `YYYY-MM-DD`
- `DD/MM/YYYY`
- Written: `11 January 2026`


## Privacy &amp; Safety
- Never share this information outside the conversation
- Treat all extracted data as sensitive personal information
- If you cannot read a document clearly, say so rather than guessing

## Example Interactions

**User**: "What's my passport number?"
**Response**: 

**Passport - IN**

Passport Number: `ABC123456`
Expiry: `15-08-2028` (2 years, 7 months remaining)


**User**: "I need my details for a visa application"
**Response**:

**Passport - NL**

Full Name: `LASTNAME, FIRSTNAME`
Passport Number: `ABC123456`
Nationality: `INDIAN`
Date of Birth: `22-02-2022`
Place of Birth: `CITY NAME`
Issue Date: `15-08-2018` | `2018-08-15`
Expiry Date: `15-08-2028` | `2028-08-15`
Issuing Authority: `Passport office`


**User**: "What documents do I have?"
**Response**: List all documents found in the folder with document type and key identifier (e.g., "Indian Passport - expires Aug 2028")</code></pre><p>Now I can ask &#8220;when is my energy contract expiring?&#8221; and it gives me a date.</p><p>Is this a life-changing agentic use case? No. But it&#8217;s good enough to satisfy the geek in me, and it actually solves a real problem. It was a Sunday well spent. Also, writing about what I learn helps me understand things a bit better.</p><p>I no longer have to dig through multiple documents, in Dutch (as an expat living in the Netherlands) and otherwise, to find some important piece of information.</p><p>For example, it also makes filling out visa forms easier. The agent improves with more data you give it, and the better you organise your files.</p><p>This also proves something I&#8217;ve been thinking about for a while. In a world where data will power workflows, there are many more reasons to organise your data well.</p><p>Have fun!</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Memos by Sooraj! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[41. Do It Anxious]]></title><description><![CDATA[A note to my anxious self]]></description><link>https://www.memos.soorajchandran.com/p/41-do-it-anxious</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/41-do-it-anxious</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Sun, 11 Jan 2026 08:33:20 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/02fa7486-8d99-4770-a04f-0d692c718912_2048x1379.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I get anxious a lot. For a long time, I thought I had to fix that before I could do anything important. I kept waiting to feel confident before I started. But I was looking at it all wrong. That anxiety isn&#8217;t really a problem. It&#8217;s more like a signal.</p><p>You don&#8217;t get nervous about things you don&#8217;t care about. That feeling in your stomach just tells you that you&#8217;re working on something that matters to you. It means you&#8217;re thinking about the future and you want it to turn out well.</p><p>People talk a lot about chasing happiness and avoiding stress. But a life with zero stress is a life where you&#8217;re not really growing. If it were all about being comfortable, we&#8217;d just stay home. Yet people still choose to do hard things, like start a company, run marathons or raise a family.</p><p>Those things are a struggle, but it&#8217;s a struggle you choose. And that makes all the difference. It&#8217;s a privilege to get to choose your own hard things. To pick the challenges that give you a reason to get up in the morning. The goal isn&#8217;t to have an easy life, but to have a life with meaning.</p><p>When you think of it that way, you don&#8217;t have to wait for the fear to disappear. You just do it anxious. You make the call, write the code, or publish the post, even with your heart pounding. That feeling is just proof that you&#8217;re doing something that matters.</p><p>I see this with travel all the time. I love seeing new places, experiencing nature, and soaking in other cultures. But before every long trip, I get anxious. For years, I thought I had to fix this feeling before I could travel freely. Now, I&#8217;ve changed my mind. I look at the anxiety, acknowledge it&#8217;s there, and get on the plane anyway. The experience on the other side is always worth it.</p><p>And when you do brave things, you&#8217;re going to mess up sometimes. That&#8217;s just how it works. But failure isn&#8217;t the opposite of success. It&#8217;s just part of the learning process. Every time you fall, you learn something. </p><p>So next time you feel that anxiety, don&#8217;t let it stop you. It&#8217;s probably a sign that you&#8217;re about to do something important. The thing that makes you nervous is usually the thing worth doing. Do it anyway. Do it anxious.</p>]]></content:encoded></item><item><title><![CDATA[40. Custom software + AI agents as an alternative for B2B SaaS]]></title><description><![CDATA[Musings on future of B2B SaaS]]></description><link>https://www.memos.soorajchandran.com/p/custom-software-ai-agents-as-an-alternative</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/custom-software-ai-agents-as-an-alternative</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 08 Jan 2026 09:58:49 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!hAi7!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I&#8217;m increasingly convinced that custom software, combined with specialised AI agents, will be the path to replacing B2B SaaS, at least to some extent.</p><p>Traditionally, buying software is a compromise. You pick the option that&#8217;s the closest fit, not necessarily one that solves all your problems. You then fit your workflows and processes around the software. Over time, this software grows and becomes bloated, while you might only need 30% of the feature set. It can even get to a point where the software slows down progress.</p><p>But building software is, or at least was, costly. When you compare the two, the compromise of buying software makes more sense in most cases.</p><p>Most companies today are already in a place where they pay for one or more LLM providers, and also pay an additional usage fee for third-party software that makes API calls to the same LLMs. The first step of this transition will be &#8220;bring your own AI,&#8221; where customers will be able to plug in their own AI or LLMs into pre-built software.</p><p>Eventually, as LLMs improve and become increasingly proficient at coding, a combination of custom, pre-built software and a specialised AI agent that thoroughly understands the codebase can ship all the necessary features.</p><p>Think of Claude Code or Cursor as a generic software developer you hire from Upwork. They&#8217;re good, but they&#8217;re not your developer. You have to explain the problems you&#8217;re trying to solve, and even then, they don&#8217;t have the company context, business goals, or your best practices.</p><p>We&#8217;ll get to a place where we have a specialised developer who is an expert in your codebase, business requirements, and company context. The role of builders will mostly shift towards maintaining these agents and deeply understanding customer problems to solve. This shift will show up first in internal-facing, workflow-heavy systems where context matters more than polish, such as HR software and internal tools.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!hAi7!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!hAi7!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 424w, https://substackcdn.com/image/fetch/$s_!hAi7!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 848w, https://substackcdn.com/image/fetch/$s_!hAi7!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 1272w, https://substackcdn.com/image/fetch/$s_!hAi7!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!hAi7!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png" width="1024" height="608" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:608,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:871482,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://www.memos.soorajchandran.com/i/183890838?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9a56d857-01e8-4813-8357-31160c36a44a_1024x1024.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!hAi7!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 424w, https://substackcdn.com/image/fetch/$s_!hAi7!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 848w, https://substackcdn.com/image/fetch/$s_!hAi7!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 1272w, https://substackcdn.com/image/fetch/$s_!hAi7!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F84d40e81-b91a-4b3e-a385-691ad6848a71_1024x608.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p><p>I also feel there will be a comeback of open-source B2B software: generic software with basic feature sets that companies can build on top of. Agents specialised in understanding that codebase will maintain it with the help of humans.</p><p>There are several second-order impacts in play here. Organisational memory becomes the moat: the accumulated understanding of why systems exist the way they do, encoded in codebases and the agents that maintain them. Maybe &#8220;<a href="https://foundationcapital.com/context-graphs-ais-trillion-dollar-opportunity/">Context Graphs</a>&#8221; (from the recent essay) are part of the solution here, but it might also be something every company builds and maintains, rather than a standalone product.</p>]]></content:encoded></item><item><title><![CDATA[39. Career Advice To Younger Self]]></title><description><![CDATA[If I could talk to my 20-something self, here&#8217;s what I&#8217;d say.]]></description><link>https://www.memos.soorajchandran.com/p/39-career-advice-to-younger-self</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/39-career-advice-to-younger-self</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Fri, 05 Dec 2025 07:55:52 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/fc850d69-81c3-4504-a32d-6859c6f45ed7_2048x1115.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><strong>Take risks early.</strong><br>Your 20s are the only time when your downside is small, and your upside is massive. You have fewer responsibilities, more energy, and more time to recover if things go wrong. If something works, it can set you up for the rest of your life. Don&#8217;t waste those years playing it safe.</p><p><strong>Increase the surface area of luck.</strong><br>Hard work alone isn&#8217;t enough. You need to put yourself in situations where luck can find you. Meet people, share your work, talk to strangers, try new ideas, and be active online. Luck usually comes from small actions that compound over time.</p><p><strong>Lift weights.</strong><br>Building muscle is simply easier in your 20s. But it&#8217;s not just about health. Lifting makes you look better, feel more confident, and builds discipline. It&#8217;s an apex habit. Once you get consistent with it, it spills into other parts of your life. You eat better, sleep better, and generally show up better.</p><p><strong>Fuck around and find out.</strong><br>Try a lot of things. Experiment without overthinking. You can&#8217;t just copy someone else&#8217;s success &#8212; most paths are unique. But you can avoid a lot of mistakes by learning from others.<br>And fail often. Failure is not a bad thing. It&#8217;s feedback. Every failure is a learning opportunity that nudges you closer to what actually works for you.</p><p><strong>Save money, but know that saving alone won&#8217;t make you wealthy.</strong><br>Build financial discipline early: automate your SIPs, invest consistently, avoid lifestyle creep, and keep your fixed costs low. Saving creates stability, but wealth comes from compounding. Your skills, your experiences, and your investments grow over time.</p><p><strong>Travel.</strong><br>Travel will shape you in ways nothing else can. New places and cultures give you perspective, humility, and a better understanding of the world. It makes you more curious, open, grounded, and even kinder. It genuinely makes you a better person.</p><p><strong>Choose momentum over perfection.</strong><br>Most people get stuck thinking instead of doing. Action gives you clarity. Like Rumi said, <em>&#8220;As you start to walk on the way, the way appears.&#8221;</em> Start moving. Push things forward. Momentum is one of the biggest advantages you can build in life.</p><p></p><p>Don&#8217;t forget to have fun, whatever you are up to. You can&#8217;t compete with people having fun.</p>]]></content:encoded></item><item><title><![CDATA[38. AI agents are having their "React" moment]]></title><description><![CDATA[A quick note on the mindset shift needed for agentic AI]]></description><link>https://www.memos.soorajchandran.com/p/38-ai-agents-are-having-their-react</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/38-ai-agents-are-having-their-react</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 27 Nov 2025 14:20:42 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/48e0b0c6-6d04-47fe-915d-6e3e60b95cb6_1280x720.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p></p><p>Over the past few months, I&#8217;ve been leading a bunch of projects at work where we&#8217;ve built real AI agents. Actual agents that think, decide, and execute.</p><p>And there&#8217;s one big learning that keeps coming back to me.</p><p>When you start building agentic tools, you realise there&#8217;s a shift in thinking required. If you&#8217;ve been a developer long enough, you probably remember the jQuery to React transition. Back then, we all knew how to manipulate the DOM directly. You <em>could</em> build anything that way. But React forced us to rethink the whole thing: components, state, data flow. It felt weird at first, then it became obvious.</p><p>That&#8217;s exactly where AI agents are today.</p><p>Yes, a lot of things can be done with traditional engineering. APIs, workflows, cron jobs, pipelines - all of that still works, and will always be required. But for a certain category of problems, agents do it better. And that category is only going to grow as LLMs get better. </p><p>The tricky part is, you won&#8217;t see the &#8220;better way&#8221; unless you spend time actually building agents. Once you immerse yourself in it, patterns start showing up. Suddenly, you start thinking, <em>&#8220;Wait, why am I manually stitching all this logic together? An agent could handle this entire flow.&#8221;</em></p><p>Processes have to be reimagined with a new question in mind - <br><strong>&#8220;How would an agent do this?&#8221;</strong></p><p>Once you put on that lens, your brain rewires itself a bit. You start spotting opportunities everywhere, places where agents can reduce complexity, automate decisions, or create new experiences that weren&#8217;t possible before.</p><p>That&#8217;s why I keep saying: <strong>AI is having its React moment</strong>. It&#8217;s the same mental leap. Same initial discomfort. Same &#8220;oh wow, this is a different way of building software&#8221; realisation.</p><p>If you haven&#8217;t tried building an agent yet, just start.<br>It&#8217;s not as hard as it looks. And once it clicks, it opens up a whole new way of thinking.</p><p>Go build one today.</p>]]></content:encoded></item><item><title><![CDATA[37. Taking Care, While Being Ambitious]]></title><description><![CDATA[A personal reflection on being ambitious and learning to take care of myself.]]></description><link>https://www.memos.soorajchandran.com/p/37-taking-care-while-being-ambitious</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/37-taking-care-while-being-ambitious</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Tue, 18 Nov 2025 03:08:35 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/8332da55-4a30-4606-9184-6246cd41fff3_2048x1363.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Being ambitious takes its toll. One part of being ambitious is thinking long-term. When I am a long-term thinker, I am always living in the future. My head is two years ahead, while my body is still here today. And when my mind constantly runs ahead, it creates anxiety and restlessness.</p><p>Over time, this becomes heavy. I sometimes forget to live in the present. I need to take extra care of myself if I want to remain ambitious in a healthy way. My mental health can take a hit if I do not consciously protect it.</p><p>I am learning to accept and deal with who I am. Self-awareness has solved more than I expected. Knowing what I want, understanding that life is not meant to be all comfort and fun, and creating my own narratives to find meaning helps me stay grounded. Meaning works like that. It is not found. It is made. I can make meaning out of nothing. It may look pointless to someone else and still be the most important thing to me.</p><p>Ambition forces my brain to live ahead of my timeline. I think in arcs. The next startup, the next career chapter, the next country, the next big trip. It is a fun place to live mentally, but it is not always kind. At some point, I realise that I cannot experience the future with a tired mind and a stressed body. So I have to learn to pull myself back to the present, even for a few hours.</p><h2><strong>Worst-Case Scenario Thinking</strong></h2><p>Ambitious people naturally imagine futures, and I am no different. But sometimes that becomes imagining dangerous futures. Things going wrong, loved ones getting hurt, health declining, opportunities slipping away. This does not come from weakness. It comes from a sense of responsibility. But it creates a heavy mental load.</p><p>I need grounding rituals to bring myself back. Breathing. Slow walks. Conversations. Moments of stillness. Travel that resets me. It is not about eliminating these thoughts. It is about not letting them control my entire day.</p><h2><strong>When I Move Fast in a Slow World</strong></h2><p>One of the biggest unseen costs of ambition is friction. I move fast in environments that move slowly. I have felt this in corporate setups, in teams, and in systems that prefer processes over momentum. The frustration is not because I am impatient. It is because my inner engine runs on velocity.</p><p>Learning to navigate this without burning out is a skill. Sometimes I slow down. Sometimes I bypass. Sometimes I find my own lane. But I do not dim my pace. I simply learn where to use it.</p><h2><strong>The Burden of Wanting All Experiences</strong></h2><p>Ambition does not just make me dream big. It makes me want everything. Not in a greedy way, but in a human way. I want to see every country, build multiple companies, learn new languages, write, create, travel, make films, grow, and evolve. I do not want a narrow life. I want a wide one. It&#8217;s like having multiple browser tabs open in my head. Someday I want to be a content creator, other days I want to be a founder. And on some other days, I want to quit everything and start a farm in the countryside.</p><p>But wanting to experience everything becomes a quiet burden. It creates an urgency that never fully turns off. I am always aware of time. I am always aware of what I have not done yet. I feel responsible for making the most of this one short life, and that responsibility can feel heavy.</p><p>Taking care of myself means accepting that I can live a wide, full life, but I do not have to live all of it at once. Some chapters can wait. Some dreams can rest. I am not running out of time as fast as I think.</p><h2><strong>Finding Stillness When My Mind Is Loud</strong></h2><p>Everyone has a place that resets them. For some, it is meditation. For some, time with friends. For me, it is travel, especially nature and cold places, where the world is quiet enough for my mind to slow down. I also enjoy intense gaming because it forces my brain to stop thinking for a while.</p><p>Stillness is not the opposite of ambition. It is the fuel that keeps it going. I need pockets of silence to function well.</p><p>Presence is not a mystical state. I find it in a slow coffee, a walk around a new neighbourhood, a quiet afternoon, a supermarket aisle in another country, or a small moment of stillness. These tiny moments keep me sane when my brain is living in 2027.</p><h2><strong>The Guilt of Rest</strong></h2><p>Rest should not be complicated, but if I am ambitious, it often is. Even when my body stops, my mind keeps running, reminding me of what I could be building, learning, or improving. I feel guilty for slowing down, as if rest is a form of falling behind. The truth is that ambition without rest becomes self-sabotage. When I force myself to keep going, I eventually lose clarity, creativity, and joy, which are the very things my ambition depends on.</p><p>Taking care of myself means treating rest as part of the work, not the opposite of it. I am not wasting time resting. I am making sure I have enough life in me to keep going.</p><h2><strong>The Importance of Having an Anchor</strong></h2><p>Ambition makes me drift. I am always thinking ahead, planning the next chapter, imagining the next version of my life. It is exciting, but it also pulls me away from the present. This is why having an anchor matters, someone or something that brings me back to who I am right now. For me, that anchor is my wife. She slows down the noise, adds warmth to the chaos, and makes every experience feel grounded and real. Ambition can make me feel like I am floating between futures, but an anchor reminds me that life is happening here, in the small moments, with the people I love. Without an anchor, I can achieve a lot and still feel oddly untethered.</p><h2><strong>Never Choose Settling as a Coping Strategy</strong></h2><p>I would never recommend settling down in the sense of giving up ambition. Life is too short for that. People settle because they think their dreams have slipped away. And while I am happy for anyone who finds peace there, it is not the life I want. Unfulfilled potential is the biggest regret. I have one life. I want to experience everything. I want ambition to stretch me, but I also want to take care of the version of me who is doing the stretching.</p><div><hr></div><p>I know I am not the first or the last to feel this way. If you think and feel like this, too, this is for you. Keep going.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/37-taking-care-while-being-ambitious?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.memos.soorajchandran.com/p/37-taking-care-while-being-ambitious?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p>]]></content:encoded></item><item><title><![CDATA[36. Enjoy your falls]]></title><description><![CDATA[and fail often]]></description><link>https://www.memos.soorajchandran.com/p/36-enjoy-your-falls</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/36-enjoy-your-falls</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 30 Oct 2025 12:08:36 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/070ed6f9-0ec7-411a-a86c-e6db28c4938c_1477x2048.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>If you are going to be brave, you are going to fall. That is how it works. There is no getting around it. Courage means trying things that are uncertain. It means taking steps where the outcome is not guaranteed. And when you do that, you will fail sometimes, often many times.</p><p>Most of us grow up thinking failure is bad. From school to work, we are taught that success is good and failure is something to avoid. Because of that, we start to fear failure and feel embarrassed when it happens. Failure is often seen as the opposite of success. It is definitely not. In most cases, failure is part of the same path that leads to success. You fail, you learn, you adjust, and then you succeed.</p><p>When you think about it, every skill we learned, came through failures. We learned to ride bicycle after falling. We learned to drive a car after stalling it. That&#8217;s true in life too - when I look back at my &#8220;failures&#8221; they were the foundation of the life I have today. The startups I shut down, the rejections I&#8217;ve received etc.</p><p>As long as you are healthy and alive, every failure teaches you something. It helps you understand what went wrong and how to do better next time. In that way, failing is as valuable as winning. You can lose the outcome but still gain the lesson.</p><p>Be curious when you fail. Ask what you learned. Enjoy the process of learning, even when it comes through mistakes. Every time you fail, you move a little closer to doing things better. Once you free yourself from the societal definition of failures, you can freely explore and fail often.</p><p>Try to fail often. That does not mean being careless. Just try new things and step out of your comfort zone. Each time you try, you learn something new about yourself and your work. The thing is, when you aim high and get out of your comfort zone, even your &#8220;falls&#8221; are going to put you in a better place than you started. When you fail, you still make progress because you are no longer standing still.</p><p>Let each failure teach you something. The goal is not to avoid failure but to use it to get better. Failing often means you are trying often, and that is how you grow.</p><div><hr></div><div class="captioned-button-wrap" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/36-enjoy-your-falls?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="CaptionedButtonToDOM"><div class="preamble"><p class="cta-caption">Thanks for reading Memos by Sooraj! If you found this useful, share it with a friend.</p></div><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/36-enjoy-your-falls?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.memos.soorajchandran.com/p/36-enjoy-your-falls?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p></div><p></p>]]></content:encoded></item><item><title><![CDATA[35. Not waiting for tomorrow.]]></title><description><![CDATA[...and why I got a Motorcycle]]></description><link>https://www.memos.soorajchandran.com/p/35-not-waiting-for-tomorrow</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/35-not-waiting-for-tomorrow</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Fri, 17 Oct 2025 07:42:00 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!j-4o!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I got a motorbike last week.  </p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!j-4o!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!j-4o!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 424w, https://substackcdn.com/image/fetch/$s_!j-4o!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 848w, https://substackcdn.com/image/fetch/$s_!j-4o!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!j-4o!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!j-4o!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg" width="1456" height="970" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/e5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:970,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:759460,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://www.memos.soorajchandran.com/i/176211786?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!j-4o!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 424w, https://substackcdn.com/image/fetch/$s_!j-4o!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 848w, https://substackcdn.com/image/fetch/$s_!j-4o!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!j-4o!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe5672c23-7da6-4b3c-a924-636030d6758b_2048x1365.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>It wasn&#8217;t an impulse buy. I&#8217;ve always been a bike enthusiast. I&#8217;d been thinking about it for over a year.</p><p>The only thing that stopped me from buying one, even when I could afford it, was practicality. The summer months are short where I live, insurance is high, and so on. I tend to look at everything through a financial lens. Once I got over that, I told myself I&#8217;d get one next year.</p><p>But then I reminded myself of something I decided earlier this year. To live with a bit of urgency.  </p><p>It&#8217;s what Kabir Das said long ago,  <em>&#8220;Do tomorrow&#8217;s work today, today&#8217;s work now.&#8221;</em> (&#2325;&#2366;&#2354; &#2325;&#2352;&#2375; &#2360;&#2379; &#2310;&#2332; &#2325;&#2352;, &#2310;&#2332; &#2325;&#2352;&#2375; &#2360;&#2379; &#2309;&#2348;).</p><p>That applies to life, too. If there&#8217;s something I&#8217;ve always wanted to do, and I can do it today, I&#8217;d rather not wait for later. So when I saw the bike I loved, I just bought it.</p><p>This is the principle I&#8217;m trying to live by these days. I&#8217;ve started to really embrace the finite nature of life. Not in a fearful way, not because I think I might die tomorrow, but because I don&#8217;t want to keep postponing things to some imaginary &#8220;later.&#8221;</p><p>We&#8217;re all surrounded by people who live with regrets. The &#8220;should have done it earlier&#8221; kind. Perhaps we&#8217;ll all have some regrets, regardless of how we live. And that&#8217;s fine. But I&#8217;d rather not let hesitation be one of them.</p><p>So these days, I try to do it now. Not because I&#8217;m scared of running out of time, but because I might not be able to do it next year. Or enjoy it in the same way. The &#8220;someday&#8221; bucket is getting smaller. And it should.</p><p>Urgency doesn&#8217;t mean rushing. It means choosing now over later by default. It gives you a sense of clarity and focus on the important things in life. Things that mean something to you, which can lead to an intentional life.</p><p>This mindset isn&#8217;t about bucket lists. It&#8217;s about small, everyday choices. Saying yes to a trip instead of waiting for the &#8220;right time.&#8221; Starting the project, writing the post, recording the memory. Because really, what are we waiting for?</p><p>I still plan for the future, a lot. But I try not to postpone life for it.</p><p>There&#8217;s a Japanese idea I love called <em>mono no aware</em> - an awareness of impermanence. It makes you present. Urgency feels similar. It reminds you that things end, and that&#8217;s exactly what makes them meaningful.</p><div><hr></div><div class="captioned-button-wrap" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/35-not-waiting-for-tomorrow?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="CaptionedButtonToDOM"><div class="preamble"><p class="cta-caption">If you enjoyed reading this post, share it with a friend. I appreciate your support.</p></div><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/35-not-waiting-for-tomorrow?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.memos.soorajchandran.com/p/35-not-waiting-for-tomorrow?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p></div><p></p>]]></content:encoded></item><item><title><![CDATA[34. A Longing for Things That Don’t Exist]]></title><description><![CDATA[Ramblings of a confused expat]]></description><link>https://www.memos.soorajchandran.com/p/a-longing-for-things-that-dont-exist</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/a-longing-for-things-that-dont-exist</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Mon, 08 Sep 2025 06:27:39 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/90c88e9b-7293-4d29-9ffe-9ff564824c17_1363x2048.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Sometimes I wonder if what I long for ever truly existed.</p><p>It&#8217;s nostalgia, or something close to it. A memory of a past that is more dream than truth, a version of home that feels real in my head but dissolves the moment I try to grasp it. I see a reel on Instagram of familiar old streets or festivals, and I feel a pull, a desire to go back. But when I actually arrive home, I&#8217;m met with another truth: life there isn&#8217;t quite like the picture in my mind. The longing is for an idea, not a reality. That feeling sharpens in places where civic order stands out.</p><p>I&#8217;ve built a higher-quality life elsewhere, one that in many ways exceeds what I once dreamed of. Logically, I know this. My routines, my work, my travels, my friend circle, and even my comforts are all signs of a life that has moved forward. And yet, in the quiet, I still feel a tug towards something that no longer exists. Or perhaps never did.</p><p>Maybe it&#8217;s just overthinking, my mind replaying loops of what-ifs and half-memories. Maybe it&#8217;s the absence of daily gratitude, the failure to pause and truly see the life I already have. Or maybe it&#8217;s something deeper: the ache of not fully belonging anywhere.</p><p>At home, the feeling is stronger. The rooms and voices carry memories of who I once was, and yet I stand both inside them and outside them at once. I belong there by blood and memory, but also not quite, because life has carried me elsewhere. Currently, I am home, celebrating Onam with family and friends, and that has only made the feeling stronger.</p><p>This is probably a dilemma every male NRI faces at some point in life: the confusion between belonging and nostalgia. We move forward and build lives elsewhere, yet the pull of home is never fully gone. This is simply my journey, and my version of it.</p><p>Longing, I realise, is rarely about place. It is about belonging. It is about the way we want to be claimed by a moment, a community, a memory, even if the version we yearn for is imagined.</p><p>And so I hold both truths: the life I have built, which is richer than my dreams, and the longing for something half-real, half-invented. Perhaps the work is not to resolve it, but to live with it, to let nostalgia visit without letting it claim ownership over the present.</p><p>Because maybe that longing is simply a reminder of who I was, and how far I have travelled. </p><div><hr></div><div class="captioned-button-wrap" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/a-longing-for-things-that-dont-exist?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="CaptionedButtonToDOM"><div class="preamble"><p class="cta-caption">Thanks for reading Memos by Sooraj! This post is public, so feel free to share it.</p></div><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/a-longing-for-things-that-dont-exist?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.memos.soorajchandran.com/p/a-longing-for-things-that-dont-exist?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p></div><p></p>]]></content:encoded></item><item><title><![CDATA[33. Don't Meet In The Middle]]></title><description><![CDATA[and stop shipping mediocre products]]></description><link>https://www.memos.soorajchandran.com/p/33-dont-meet-in-the-middle</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/33-dont-meet-in-the-middle</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 21 Aug 2025 11:26:46 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/d480f5e7-9e4d-47b1-960d-c6b016004cde_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>When a team ships something meaningful, it&#8217;s obvious that somebody cared. Startups often manage to do this because they have no choice. Conviction is the only fuel they&#8217;ve got. In large companies, it&#8217;s different. It&#8217;s easy not to care. People go through the motions, make safe calls, and prioritise optics over outcomes. Ownership becomes blurred, accountability is lost, and decisions are diluted until they mean nothing.</p><p>That&#8217;s how mediocrity gets shipped. And the root cause, more often than not, is this: <strong>meeting in the middle.</strong></p><h3>Why &#8220;middle ground&#8221; is overrated</h3><p>&#8220;Meeting in the middle&#8221; feels safe. It looks diplomatic, fair, and balanced. But in practice, it&#8217;s usually the worst outcome. Instead of the best of both worlds, you get the worst of both: mediocrity.</p><p>If you want to build meaningful products, you can&#8217;t afford watered-down decisions. Middle ground kills conviction, blurs vision, and leaves you with outcomes nobody truly believes in.</p><h3>The psychology of compromise</h3><p>Compromise is attractive because it avoids conflict. It keeps the peace. It makes everyone feel heard. But easy decisions rarely lead to great outcomes.</p><p>Conviction is what matters. When teams compromise, both sides lose it. No one feels full ownership, and energy drains away. That&#8217;s how you end up shipping safe, forgettable products.</p><p>The fix is to allow <strong>rigorous debates upfront</strong>. Stress-test ideas, challenge assumptions, push each other hard. But once the decision is made, commit. At that point, it&#8217;s no longer &#8220;their idea&#8221; or &#8220;your idea.&#8221; It&#8217;s <em>the team&#8217;s decision</em>. And you go all in. Importantly, make sure the path you choose is closer to an extreme than to the middle. That&#8217;s where clarity and conviction live.</p><h3>The cost of compromise</h3><p>Compromise strips away conviction. Products lose their edge, strategies lose direction, and teams lose their sense of purpose.</p><p>In startups, meaningful products emerge because someone takes a stand. In bigger organisations, it&#8217;s easy to fall into process theatre &#8212; endless meetings, consensus-seeking, and decisions optimised for appearances rather than outcomes. Teams waste weeks debating reversible, low-stakes choices instead of simply trying one path. The result: safe decisions and work nobody truly believes in.</p><p>The antidote is clarity. Assign a decision maker, give space for input, then let them call it. Record the trade-offs so everyone understands why the path was chosen, and move forward with conviction.</p><h3>Disagree and commit</h3><p>The better approach is to <strong>disagree and commit</strong>. This doesn&#8217;t mean blind obedience. It means recognising conviction.</p><p>If someone is pushing hard for a direction, assume they know or believe something you don&#8217;t. Borrow some of that conviction. Let their clarity pull you forward. And when it&#8217;s your turn to lead, communicate your conviction so strongly that others can align with you.</p><p>This is how great teams work: conviction gets transferred, not diluted. The result is a clear direction, backed by shared commitment, even if not everyone started on the same page.</p><h3>Practical guidance</h3><ul><li><p><strong>Debate hard, then commit</strong>: Don&#8217;t avoid conflict. Push until you surface a real conviction.</p></li><li><p><strong>Define ownership</strong>: Democracy in decisions often dilutes outcomes. Someone must make the call.</p></li><li><p><strong>Don&#8217;t force consensus</strong>: Harmony isn&#8217;t the goal. </p></li><li><p><strong>Move fast on Type 2 decisions</strong>: Don&#8217;t burn weeks on reversible choices. Pick a path and try. Action leads to clarity.</p></li><li><p><strong>Document decisions</strong>: Record why you chose one path over another, so the team rallies around it.</p></li></ul><h3>Courage beats compromise</h3><p>Compromise feels safe, but safety rarely builds anything meaningful. Strong products, bold strategies, and high-performing teams are born from conviction, not middle ground. If you want to stop shipping mediocre products, stop meeting in the middle.</p><div><hr></div><p>If you found this post useful, share it with a friend or a co-worker. Thanks for reading. Your support means a lot.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/33-dont-meet-in-the-middle?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.memos.soorajchandran.com/p/33-dont-meet-in-the-middle?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p><p></p>]]></content:encoded></item><item><title><![CDATA[32. Better Meetings]]></title><description><![CDATA[Run meetings that matter, chuck the rest]]></description><link>https://www.memos.soorajchandran.com/p/32-better-meetings</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/32-better-meetings</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 14 Aug 2025 11:42:43 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/a5088710-44d5-48e9-b4fd-61016b4e7fae_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>While I&#8217;m a big fan of fully async work, that&#8217;s not often the reality. We still need meetings. But most of them are bloated, unfocused, and a poor use of time.</p><p>The good news&nbsp;is that in almost every meeting,&nbsp;a significant portion of the work can be done asynchronously. Doing that not only saves time but also gives people space to think more clearly, run tighter meetings, and sometimes eliminates the need for a meeting.</p><p>Of course, there is an exception to every meeting here. These are guidelines, not rules. The point is - be more intentional about meetings. You need a lot less than you think. The best thing about fewer meetings is that it leaves more time for higher-quality spontaneous meetings. Like setting up a coffee chat with a cross-functional counterpart, or a person who works on an interesting problem in a different area in your company. </p><p>Meetings are also a great tool to talk about sensitive problems, get people excited about new projects, etc. It&#8217;s more effective if they are used sparingly. </p><p>Here&#8217;s a breakdown of common meeting types, their purpose, and which parts should be async vs in-meeting.</p><h3>1) Status Update</h3><p><strong>Purpose:</strong> Share progress, next steps, and blockers.</p><p>This should be fully async. There is no reason to spend time every day trying to ask people for status updates that can simply be written down. It also forced accountability - to make sure folks do actual outcome-focused work.</p><ul><li><p><strong>What did we accomplish since the last update?</strong> &#8594; <strong>Async.</strong> Use a template. One line per workstream, with links to proof.</p></li><li><p><strong>What&#8217;s next?</strong> &#8594; <strong>Async.</strong> </p></li><li><p><strong>What&#8217;s blocking progress?</strong> &#8594; <strong>In-meeting only if a decision or escalation is needed.</strong> Otherwise, log it and tag the resolver.</p></li></ul><h3>2) Brainstorm / Ideation</h3><p><strong>Purpose:</strong> Generate creative ideas or solutions.</p><p>One of the useful meetings. But a lot of work can be done upfront. I&#8217;ve been in brainstorming meetings with no pre-work, and half of the meeting is lost in setting the context. It&#8217;s pointless to do brainstorming meetings without giving people time to think beforehand.</p><ul><li><p><strong>What&#8217;s the challenge or opportunity?</strong> &#8594; <strong>Async.</strong> Share a clear brief and guardrails.</p></li><li><p><strong>What ideas can we explore?</strong> &#8594; <strong>Async first.</strong> Collect ideas in a board or doc to avoid groupthink.</p></li><li><p><strong>Which ideas are worth refining?</strong> &#8594; <strong>In-meeting.</strong> Time-box selection using clear criteria. End with owners for the top ideas.</p></li></ul><h3>3) Planning</h3><p><strong>Purpose:</strong> Set goals, timelines, and responsibilities.</p><p>Writing things down brings clarity. Sometimes the need for a planning meeting completely goes away. </p><ul><li><p><strong>What&#8217;s our objective?</strong> &#8594; <strong>Async.</strong> Pre-read with the goal, scope, and non-goals.</p></li><li><p><strong>What&#8217;s the timeline?</strong> &#8594; <strong>Async draft, in-meeting confirm.</strong> Bring a v1 plan and adjust live only where needed.</p></li><li><p><strong>Who owns each part?</strong> &#8594; <strong>In-meeting/async</strong> Confirm RACI and deadlines.</p></li></ul><h3>4) Problem-Solving</h3><p><strong>Purpose:</strong> Address a specific issue and decide on a path forward.</p><ul><li><p><strong>What&#8217;s the problem?</strong> &#8594; <strong>Async.</strong> Provide data, constraints, and success criteria in advance.</p></li><li><p><strong>What options do we have?</strong> &#8594; <strong>Async first.</strong> Share 2&#8211;4 viable options with pros/cons.</p></li><li><p><strong>What&#8217;s our agreed next step?</strong> &#8594; <strong>In-meeting. </strong> Decide, assign an owner, and set a time frame. (sometimes it&#8217;ll turn out this can be done async too)</p></li></ul><h3>5) Retrospective / Post-Mortem</h3><p><strong>Purpose:</strong> Learn from what worked and what didn&#8217;t.</p><ul><li><p><strong>What went well?</strong> &#8594; <strong>Async.</strong> Collect notes in advance to maximise voices.</p></li><li><p><strong>What could be improved?</strong> &#8594; <strong>Async collection, in-meeting discussion</strong> for sensitive or complex topics.</p></li><li><p><strong>What will we do differently next time?</strong> &#8594; <strong>In-meeting.</strong> Turn insights into a small set of action items with owners. This mostly becomes a readout. Can be done async too. But probably a good idea to be intentional, depending on the magnitude of what went wrong.</p></li></ul><h3>6) One-on-One</h3><p><strong>Purpose:</strong> Build alignment, coach, and unblock.</p><p>Obviously, in person. </p><ul><li><p><strong>How are things going for you?</strong> &#8594; <strong>In-meeting.</strong> Human conversations don&#8217;t work well async.</p></li><li><p><strong>Where can I help or unblock you?</strong> &#8594; <strong>In-meeting.</strong> Agree clearly on support.</p></li><li><p><strong>What&#8217;s next for your growth or priorities?</strong> &#8594; <strong>In-meeting, then async</strong> to document goals.</p></li></ul><h3>7) Kick-Off</h3><p><strong>Purpose:</strong> Launch a new project or initiative.</p><p>Kick-off is a good ritual to bring excitement to the project, and that&#8217;s exactly what it should be used for. Instead of discussing project details, sell the vision, tell the story and get people excited about the opportunity and problem. </p><ul><li><p><strong>What&#8217;s the project goal?</strong> &#8594; <strong>Async.</strong> Share the brief so everyone starts aligned.</p></li><li><p><strong>Who is responsible for what?</strong> &#8594; <strong>In-meeting/async.</strong> Confirm roles and responsibilities live.</p></li><li><p><strong>How will we track progress?</strong> &#8594; <strong>In-meeting.</strong> Pick the cadence, dashboard, and decision forum.</p></li></ul><h2>The takeaway</h2><p>Information gathering, status updates, and option listing are almost always better async. Use meetings for <strong>decisions, alignment on trade-offs, and confirming ownership</strong>.</p><p>If a meeting ends without an owner, a deadline, and updated notes, it wasn&#8217;t a good meeting. Always a good idea to ask &#8220;What would make this meeting successful&#8221; before the meeting starts, and see if you have achieved that. </p><p>Also, good meetings are about better writing. Writing will only be effective if the teams also have a reading culture. That&#8217;s a bigger problem to solve.</p><p>Most meetings should be fully async. If something can&#8217;t be resolved in the docs, run a short decision-making meeting.</p><div><hr></div><p></p>]]></content:encoded></item><item><title><![CDATA[31. Slow Travel]]></title><description><![CDATA[and why I stopped counting countries]]></description><link>https://www.memos.soorajchandran.com/p/31-slow-travel</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/31-slow-travel</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Fri, 08 Aug 2025 07:39:34 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/5b2e9097-3da7-4c9e-b3fb-d77d0833921e_2048x1430.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I&#8217;m writing this from an old polar rig, now a hotel, in the northernmost city in the world - Longyearbyen, Svalbard. Sounds cool, right? (By the time this goes out, I&#8217;ll be back home).</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!jSRI!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!jSRI!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 424w, https://substackcdn.com/image/fetch/$s_!jSRI!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 848w, https://substackcdn.com/image/fetch/$s_!jSRI!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 1272w, https://substackcdn.com/image/fetch/$s_!jSRI!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!jSRI!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic" width="1456" height="1941" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/a4399b62-dcdf-4e9b-a076-be28091d9388.heic&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1941,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:2101018,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/heic&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://www.memos.soorajchandran.com/i/170427063?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!jSRI!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 424w, https://substackcdn.com/image/fetch/$s_!jSRI!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 848w, https://substackcdn.com/image/fetch/$s_!jSRI!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 1272w, https://substackcdn.com/image/fetch/$s_!jSRI!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa4399b62-dcdf-4e9b-a076-be28091d9388.heic 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a><figcaption class="image-caption">(More pictures on my instagram: @sooraj_chandran)</figcaption></figure></div><p>I&#8217;ve fallen in love with slow travel, and I want to share what it means to me.</p><p>If you&#8217;ve played open-world games, you&#8217;ve probably used &#8220;fast travel&#8221; to jump quickly from point A to point B. Slow travel is the opposite. You&#8217;re not rushing to your next destination. If you truly enjoy the game, you take the long road. Driving across the map, or riding a horse through valleys, just to soak it all in.</p><p>That&#8217;s slow travel. You enjoy the journey. You&#8217;re not racing through a checklist or chasing the next photo spot. You&#8217;re simply living in a different place, in a different rhythm.</p><p>It wasn&#8217;t always like this for me. When I first started travelling, I was obsessed with counting countries. I wanted to keep adding more, ticking off names on a list. Now, I&#8217;ve stopped counting altogether. I chase experiences instead. I ask myself: <em>Where can I find this feeling, this moment, this view?</em> Sometimes that means going to a new place. Other times, it means returning to a country I&#8217;ve already visited. Because the experience I&#8217;m seeking lives there. Travel isn&#8217;t a competition, though social media can make it seem like one.</p><p>For me, travelling better is about noticing more, and photography helps with it to an extent. When I look at things through a viewfinder, I&#8217;m in that moment for a bit longer, and I notice a bit harder.</p><p>I love going to supermarkets in new places, just to see what people buy, what&#8217;s on the shelves, and how different (or similar) everyday life feels. I love walking without any destination, just letting the streets decide where I end up. Taking public transport is fun. Sitting somewhere and noticing people tells you a lot about the place. Observing how houses are built is exciting. These moments aren&#8217;t on anyone&#8217;s &#8220;must-see&#8221; list, but they&#8217;re often the ones I remember most. And I guess, what makes all of this a lot more fun is travelling with the right person.</p><p>I live with a voice in my head that rarely stops talking. It questions, plans, reminds, and worries. But when I travel in the wild, quiet places like Svalbard, that voice softens. Sometimes it goes silent. Sounds of nature can be very calming. The only sounds left are birds calling, wind moving through valleys, and the hush of falling snow or rain.</p><p>I no longer keep a rigid itinerary. Sure, I have a rough plan and book a few things in advance, but I leave plenty of space for nothing in particular. That&#8217;s when the best moments happen. I stumble upon something I didn&#8217;t plan for, or simply sit somewhere and notice the world.</p><p>Slow travel is about how a place makes me feel. The stillness it brings, the small details it reveals, the way it changes me without me even realising.</p><p><strong>In the end, slow travel is a choice to live fully in the present. To collect moments that stay with you long after the trip is over.</strong></p><p></p>]]></content:encoded></item><item><title><![CDATA[30. Claude Pro and Code - First Impressions]]></title><description><![CDATA[And how it compares to Cursor and ChatGPT]]></description><link>https://www.memos.soorajchandran.com/p/30-claude-pro-and-code-first-impressions</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/30-claude-pro-and-code-first-impressions</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Wed, 23 Jul 2025 04:34:20 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/6ecfb4be-cc74-494a-a936-374334845a02_909x527.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I've been using ChatGPT Pro and  Cursor for a while, and Claude Pro (with Claude Code) for a few days. Here are my first impressions and thoughts.</p><h4>Claude Code &gt; Cursor</h4><p>I thought I needed an AI-powered IDE like Cursor to build meaningful projects. I was wrong. VSCode + Claude Code in the terminal works just as well, with better code quality and more control. Both my wife and I cancelled our Cursor subscriptions.</p><p>There are areas where an integrated IDE might make some sense. But for most, I&#8217;d take the better code Claude writes. It feels safer.</p><h4>Claude is a Better Designer</h4><p>This was the biggest surprise. Claude consistently produces superior design outputs compared to Cursor. It feels like Claude examines what you're building rather than just following generic patterns.</p><p>The attention to detail is noticeable &#8211; Claude considers context, user experience, and visual hierarchy in ways that feel more thoughtful. Every redesign project I've tackled with Claude has significantly outperformed Cursor's results. It's not just about writing better CSS; it's about understanding design intent.</p><p>I asked it to redesign a SaaS app front-end in Next + Tailwind Typescript and a simple website in HTML and CSS. Both times, the results were significantly better.</p><h4>Frontend Development is Changing Fast</h4><p>All AI tools write decent CSS, but Claude has a slight edge. Basic frontend development feels increasingly automated &#8211; this trend will likely accelerate.</p><h4><strong>Artifacts Are Game-Changing</strong></h4><p>Claude's artifacts feature is my favourite part of Claude Pro. Unlike other AI tools that just give you code to copy-paste, artifacts create interactive, working applications directly in the chat interface.</p><p>I built a Dutch flashcard learning app in 10 minutes that perfectly fits my specific learning needs &#8211; complete with progress tracking and spaced repetition. No deployment hassles, no setup required. Just describe what you want and get a working prototype instantly.</p><p>This opens up entirely new workflows. Need a quick calculator for a specific use case? A data visualisation tool? A simple game for testing an idea? Artifacts make it trivial to create custom tools that would traditionally require setting up projects, dependencies, and hosting. The possibilities for rapid prototyping and personal productivity tools are endless.</p><h4>Value Proposition</h4><p>Claude Pro effectively replaces both Cursor and ChatGPT for technical work, making it excellent value for money. If you're already paying for Cursor, Claude Pro is worth considering.</p><h3>ChatGPT vs Claude</h3><p>The two tools excel in different areas, and I've found specific use cases where each shines:</p><p><strong>Claude excels at:</strong></p><ul><li><p>Technical tasks: Coding, debugging, technical specs, architecture discussions</p></li><li><p>Development brainstorming: Breaking down complex technical problems, suggesting implementation approaches</p></li><li><p>Code review and optimisation: Analysing existing code and suggesting improvements</p></li><li><p>Technical writing: API documentation, technical blog posts, engineering specs</p></li></ul><p><strong>ChatGPT is better for:</strong></p><ul><li><p>Creative writing: Blog posts, marketing copy, storytelling</p></li><li><p>General conversation: More natural dialogue, better at understanding context and nuance</p></li><li><p>Business strategy: Market analysis, business planning, competitive research</p></li><li><p>Content ideation: Brainstorming topics, angles, and creative approaches</p></li></ul><p>In practice, I find myself reaching for Claude when I'm in "building mode" and ChatGPT when I'm in "thinking mode." Claude feels more like a technical partner, while ChatGPT feels more like a creative collaborator.</p><p>I'll keep using both for now since they complement each other well, though Claude's technical superiority makes it my primary tool for development work.</p><h4>What About Gemini?</h4><p>Gemini works well for local file manipulation, but it's not close to replacing ChatGPT or Claude for my workflows. One of my favourite use cases with Gemini is to talk to my Obsidian notes. It&#8217;s like talking to my brain at different points in time. The free Gemini plan is pretty good to cover most cases.</p><h3>Conclusion</h3><p>The AI development landscape is moving fast, and tool consolidation is happening quicker than I expected. Claude Pro has become my primary development tool, effectively replacing Cursor while offering capabilities that complement ChatGPT.</p><p>If you're currently paying for multiple AI subscriptions, it's worth reassessing your stack. Claude Pro's combination of superior code quality, design capabilities, and the artifacts feature makes it an exceptional value &#8211; especially if you're doing any kind of technical work.</p><p>The future feels like it's heading toward specialised AI tools for different use cases, but for now, Claude + ChatGPT covers most of my needs. The question isn't whether AI will change how we build software, but how quickly we can adapt to these rapidly evolving capabilities.</p><div><hr></div><p>If you found this useful, share it with an AI enthusiast.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/30-claude-pro-and-code-first-impressions?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.memos.soorajchandran.com/p/30-claude-pro-and-code-first-impressions?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p><p></p>]]></content:encoded></item><item><title><![CDATA[29. Advice for Founder Turned PMs]]></title><description><![CDATA[and to myself on how to navigate life after acquisitions and avoid burnouts]]></description><link>https://www.memos.soorajchandran.com/p/advice-for-founder-turned-pms</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/advice-for-founder-turned-pms</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Thu, 17 Jul 2025 08:59:34 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/eac5040c-754c-4d4c-a06d-cdfd56bbe5a3_1522x1014.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I&#8217;ve been through startup acquisitions with my startup and as head of function in larger startups.</p><p>Both transitions taught me something critical:<br>Going from <em>founder</em> (or head-of-function in a startup) to product leader in a scaling company is a huge identity shift.</p><p>And that shift isn&#8217;t always easy.</p><p><strong>On burnout, detachment, and identity</strong></p><p>Like many former founders, I&#8217;ve often felt frustrated, out of control, and over-invested. </p><p>You care deeply. Too deeply. You attach yourself to the outcomes of a project. That emotional weight can lead to burnout, or worse, a slow resentment that chips away at your joy and energy.</p><p>You can't keep operating with founder-level intensity inside a larger system.</p><p>A few things I&#8217;ve learned and am trying to change along the way. Emphasis on <strong>trying.</strong></p><p><strong>1. Let Go of Total Ownership</strong></p><p>As a founder, you own everything - vision, execution, outcomes, and morale. As a PM, you own some things and influence the rest. Learn to be okay with partial control. It&#8217;s not your company anymore, and that&#8217;s not a failure. It&#8217;s reality.</p><p><strong>2. Your Speed Will Feel Threatening. Use It Wisely</strong></p><p>You&#8217;ll naturally want to move fast. But corporate systems often optimise for alignment and stability, not velocity. Use your bias for speed to prototype thinking, not bulldoze people. Lead by showing what&#8217;s possible. Leave room for others to catch up.</p><p><strong>3. Don&#8217;t Try to "Fix Everything"</strong></p><p>Founders see broken systems and instinctively want to fix them. But not every inefficiency is yours to solve. Ask: Is this problem worth solving in this context, or do I just hate inefficiency? Sometimes, the fix is not worth the political or emotional capital.</p><p><strong>4. You&#8217;re Not the Final Decider </strong></p><p>You&#8217;re used to making the final call. But as a PM, you&#8217;re often the glue, not the decider. The real skill: influencing outcomes without authority, and finding satisfaction in wins you didn&#8217;t directly control.</p><p><strong>5. Resist the Founder Ego Trap</strong></p><p>It&#8217;s tempting to believe you &#8220;could do it better.&#8221; Maybe you could. But unless you&#8217;re the one running the company, that belief becomes toxic (and takes a toll on your mental health) over time. Trade ego for empathy. The system isn&#8217;t dumb. It&#8217;s just optimised for constraints you don&#8217;t always see.</p><p><strong>6. Balance Vision with Reality</strong></p><p>You&#8217;re probably future-obsessed. But inside a bigger org, you also need to play the game of incremental wins, stakeholder buy-in, and timing. Your challenge: make bold bets without becoming &#8220;the unrealistic one.&#8221;</p><p><strong>7. Redefine Success for Yourself</strong></p><p>As a founder, success was company success. As a PM, success can be:</p><p>Elevating your team. Driving clarity in chaos. Shipping something that gets used.</p><p>Don&#8217;t measure yourself by founder metrics in a non-founder role.</p><p><strong>8. Protect Your Energy (The most important one)</strong></p><p>You&#8217;re used to running hot, running deep, running all the time. But in corporate life, that can lead to burnout, and no one will stop you. Protect your energy for the things that matter: the right problems, the right people, the right stakes.</p><p><strong>9. Pick Your Battles</strong></p><p>You&#8217;ll see 100 things wrong. Pick 3. Win those. Let the rest go. Victory in corporate life often comes from selective intensity, not full-spectrum domination.</p><p><strong>10. Keep Building Something on the Side</strong></p><p>Your founder brain still needs an outlet. Build outside work. A newsletter, a tool, a product - best time to play around with AI, or start 3D printing projects - a different kind of mid-life crisis. It&#8217;ll keep your skills sharp, your identity anchored, and your sanity intact.</p><p><strong>Parting thoughts</strong></p><p>You don&#8217;t need to kill your founder instincts. Just retrain them for the context you're in. Keep the bias to action. Keep the clarity. Keep the hunger.</p><p>But learn to detach. Learn to rest. Learn to reframe success.</p><div><hr></div><p>If you are in a similar boat, don&#8217;t hesitate to reach out, and if you found this post useful, share it with a founder turned PM.</p>]]></content:encoded></item><item><title><![CDATA[28. Wabi-Sabi Mindset for 0 to 1 Builders]]></title><description><![CDATA[How to embrace flaws, move fast, and build winning product.]]></description><link>https://www.memos.soorajchandran.com/p/28-wabi-sabi-mindset-for-0-to-1-builders</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/28-wabi-sabi-mindset-for-0-to-1-builders</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Sun, 13 Jul 2025 10:47:41 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/4630cb7c-444e-4e8f-b2f4-2de25f26109c_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<h4>The Cult of the Flawless Product</h4><p>I remember the early days of my first startup, building a marketing automation tool. We envisioned a comprehensive suite: email marketing, website builders, landing pages, push notifications, even blog features. We poured weeks and months into perfecting every design pixel, crafting fancy UIs for complex automations. The pressure to deliver something flawless was immense.</p><p>I always remind myself of this quote:</p><blockquote><p>As you start to walk on the way, the way appears - Rumi</p></blockquote><p>As builders, we're often trapped in a relentless pursuit of perfection. We dream of launching products that are polished, bug-free, and universally adored from day one. </p><p>No one cared about our perfectly polished features. That experience was a harsh, but invaluable, lesson - our desire to build beautiful, complete things was at odds with the market's brutal reality, which rewards speed and learning above all else. The need for speed is amplified tenfold in the age of AI.</p><p>What do I do differently today? </p><p>Embrace the philosophy of <strong>Wabi-Sabi</strong>. It's the art of finding power in the imperfect, the incomplete, and the impermanent. It's about embracing the "good enough" to get to "great" faster. My second startup's MVP was a simple Google Form.</p><h4>Wabi (&#20376;): Simplicity and Scrappiness</h4><p>The first pillar of Wabi-Sabi for builders is Wabi, which we can translate as "simplicity and scrappiness." It's about an almost brutal clarity of purpose. It's finding beauty in the purely functional aspect of something.</p><p>This means:</p><ul><li><p>Focusing on the single, core function that solves a real, urgent problem.</p></li><li><p>Ruthlessly cutting everything else. If it doesn't directly serve that core function, it's a distraction, a delay, a potential source of bloat.</p></li></ul><p>Think of the elegance of a simple script that does one thing perfectly, or a single-purpose tool that solves a specific pain point. This is the essence of Wabi. It's the mindset that led to my second startup's MVP being a Google Form &#8211; because it was the simplest, fastest path to validate a core idea.</p><h4>Sabi (&#23490;): The Beauty of Impermanence and Evolution</h4><p>The second pillar is Sabi, which speaks to the beauty of impermanence and evolution. It's the acknowledgement that all things are in flux. </p><p>For a builder, Sabi means:</p><ul><li><p>Your V1 is not the final state. It&#8217;s a single moment in time. It's a snapshot of your understanding and capabilities at that precise point.</p></li><li><p>The "flaws" and "bugs" are not failures. They are the record of your product&#8217;s interaction with the real world, the scars that tell a story of learning and adaptation.</p></li></ul><p>I've had the privilege of building from 0 to 1 multiple times &#8211; with my startup(s), as an early employee, as a head of function, and even as a "startup within a startup." Across all those roles, the hardest thing has often been getting people to believe that speed matters more than almost anything else. You can recover from mistakes. What you can&#8217;t recover is time wasted standing still. As Rumi put it, &#8220;When you start walking on the path, the path appears.&#8221; That&#8217;s true for products too. The journey, with all its missteps and course corrections, is what ultimately makes it strong.</p><h4>The Wabi-Sabi Mindset in the Age of AI</h4><p>The Wabi-Sabi philosophy is becoming a survival imperative, especially in the age of Artificial Intelligence. </p><p>The principle here is clear: Don't try to sculpt a perfect masterpiece from a single block of marble. Start with a rough clay model. Get it into the hands of your audience, gather their reactions, and refine the form with every touch. You might even learn that people never really cared about the marble; all they wanted was a functional model that could stand on its own. The cost of building and deploying has plummeted, making learning and iterating in the wild more accessible and critical than ever before.</p><p><strong>Perfection is a Trap</strong></p><p>In the realm of AI, "perfect" is not always possible. The models are probabilistic, the outputs can be unpredictable, and the edge cases are infinite. Waiting for perfection means waiting forever.</p><p>The Wabi-Sabi Principle acknowledges this inherent imperfection: Your goal is not a flawless output. An 80% correct AI summary that saves a user an hour of work is infinitely better than a 99% correct one that never ships because you're stuck chasing that last percentage point. Embrace the "good enough" as your launchpad to real-world learning.</p><p><strong>Your Product is a Conversation</strong></p><p>A "perfect" product, meticulously crafted in isolation, often ends up being a monologue. The builder is telling the user what they need. </p><p>A Wabi-Sabi product is a conversation. You ship something incomplete, something that might have rough edges, and you ask, "Is this useful? What do you think?" The user&#8217;s response, the feedback, the "bugs" they encounter etc, is their side of the conversation. It's their input that guides your next iteration.</p><p>This continuous dialogue with your users, fueled by rapid iteration, is how truly great products are born. Of course, there are always exceptions to these rules, but for most builders in the AI age, speed and learning trump all.</p><h4>Practical Framework: How to Build with Wabi-Sabi</h4><p>So, how do you actually put the Wabi-Sabi mindset into practice? It requires concrete changes to your building process and mindset. </p><p>Here are five practical approaches:</p><p><strong>1. The "One-Day" Test:</strong></p><p>Before you start building any new feature or product, ask yourself: "What is the most valuable, most imperfect version of this we could build and ship in a single day?" It's a thought experiment designed to force you to identify the absolute core value. It strips away all the nice-to-haves and focuses on the essential, functional element that delivers immediate utility. If you can't define a "one-day" version, you're likely over-engineering.</p><p><strong>2. The "Honest" Beta:</strong></p><p>Launch with explicit imperfection. Instead of trying to hide flaws, embrace them as part of the journey. Use language that sets expectations and invites collaboration: "This is our first attempt. It might be slow. It might get things wrong. But we wanted you to have it now. Tell us how to make it better." This approach turns your early users into allies and co-creators, rather than critics. They become invested in the product's evolution, providing invaluable feedback that you wouldn't get from a perfectly polished, delayed launch. The key is to solve a problem that&#8217;s painful enough, so that people can give their time to be your partners.</p><p><strong>3. The "Asymmetrical" Roadmap</strong></p><p>A traditional, "perfect" roadmap aims for balance across all features and areas. A Wabi-Sabi roadmap is intentionally asymmetrical. It focuses all its energy on the one or two things that truly matter right now, and accepts that other areas will remain "imperfect" or underdeveloped for a period. This requires discipline and a willingness to say "not yet" to many good ideas. It ensures you're always delivering maximum impact where it counts most.</p><p><strong>4. The "Kintsugi" Approach to Bugs</strong></p><p>Kintsugi is the Japanese art of repairing broken pottery with gold lacquer, highlighting the cracks as part of its history and beauty. Apply this to your product's "breaks." When a bug appears, don't just fix it and move on. Ask: "What does this 'crack' teach us about our users? About our assumptions? About our system?" </p><p>Each bug fixed with this mindset becomes a lesson learned, a system strengthened, and a testament to your product&#8217;s resilience.</p><p>When building teams to embrace this Wabi-Sabi approach, it's crucial to hire the right people. I've seen it multiple times: big shots from big brand-name companies fail miserably at a startup because they spend an awful lot of time talking about strategy and no execution.</p><p><strong>5. Jump in</strong></p><p>Did I tell you this is my favourite quote about building products? &#8220;As you start to walk on the way, the way appears&#8221;</p><p>Yes, now act that. When you are not clear about where you are going, just look at the immediate next step. Forget about bringing clarity to every single step you have to take. You should have a general understanding of your direction (vision) and the first step to take (first milestone). The future milestones will reveal themselves. Trust your gut, and the dots will connect. </p><p><strong>Conclusion: The Unfinished Builder</strong></p><p>In the age of AI, where change is the only constant, the most successful builders will not be the ones who avoid mistakes, but the ones who learn from them the fastest. The Wabi-Sabi builder understands that true mastery comes not from flawless execution but from embracing the unpredictable reality of creation.</p><p>So this week, embrace one Wabi-Sabi principle. Ship something unfinished. Launch an honest beta, setting clear expectations for its imperfections. Celebrate a "flaw" not as a failure, but as a learning moment that strengthens your product and your understanding.</p><p>Wabi-Sabi is not an excuse for sloppiness. It&#8217;s an approach for speed. It&#8217;s a mindset that frees you from the paralysis of perfection and allows you to do what you do best: build, learn, and build again.</p><div><hr></div><p>If you found this useful, share it with a founder or a builder who might find this useful.</p><p>Thank you for reading. </p>]]></content:encoded></item><item><title><![CDATA[27. How to get lucky in your career]]></title><description><![CDATA[Practical tips to increase your chances of career breakthroughs by maximising your 'luck surface area']]></description><link>https://www.memos.soorajchandran.com/p/27-how-to-get-lucky-in-your-career</link><guid isPermaLink="false">https://www.memos.soorajchandran.com/p/27-how-to-get-lucky-in-your-career</guid><dc:creator><![CDATA[Sooraj Chandran]]></dc:creator><pubDate>Fri, 04 Jul 2025 06:30:42 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/15a616a0-e359-4f38-a97c-8f664ddcea6a_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>We often celebrate hard work, talent, and perseverance as the cornerstones of success. And they are. But for truly extreme success, there's almost always a hidden variable at play. That unseen hand, that perfect timing, that unexpected connection &#8211; we call it luck.</p><p>No matter how much you plan, how hard you work, or how smart you are, there's always an element of chance that contributes to breakthrough achievements. You can't control luck, but you can influence how often it finds you.</p><p>Think of it like this: if you're searching for a job, your chances of getting "lucky" with an unexpected lead or a perfect connection are far higher at a startup event than they are sitting at home watching Netflix. You're increasing your "luck surface area."</p><p>In this post, we will go through a few things you can try to improve your luck surface area.</p><h3>Prepare the Soil by Becoming Radically T-Shaped</h3><p>For years, we&#8217;ve been fed a false dichotomy: should you be a generalist or a specialist? The debate is a trap. It encourages you to choose between being a jack-of-all-trades with no real depth, or a niche expert with crippling blind spots.</p><p>The most effective and "lucky" people I know have rejected this choice. They aren't an "I" (a specialist) or a "&#8212;" (a generalist). They are a "T".</p><p>The T-shaped individual has two key components:</p><p>1.  <strong>The Horizontal Bar:</strong> A broad base of knowledge across many disciplines. They can talk to marketers, understand the basics of finance, and grasp the core concepts of different programming languages.</p><p>2.  <strong>The Vertical Bar:</strong> A deep, spiky area of true expertise. This is the one thing they are exceptionally good at, the skill they have honed through deliberate practice and real-world experience.</p><p>This model isn't new, but the arrival of AI has supercharged its importance and changed the rules of the game.</p><p><strong>AI Owns the Horizontal Bar</strong></p><p>Acquiring general knowledge used to take years of reading and study. Today, AI makes it nearly instantaneous. With a few prompts, you can get a working summary of quantum computing, a boilerplate Python script for web scraping, or the key principles of behavioural economics.</p><p>This means that being just a generalist is no longer a defensible career strategy. The barrier to entry for broad knowledge has collapsed.</p><p> <strong>Expertise is Your New Moat</strong></p><p>What AI cannot do is replicate true, earned expertise. It can't replicate the intuition you gain from shipping a product and watching it fail, the nuance you learn from debugging a system under pressure for hours, or the wisdom that comes from making a thousand tiny decisions within your domain.</p><p>This is the vertical bar of your "T," and it is more valuable than ever.</p><p>Your goal, then, is not to choose between being a generalist or a specialist. It is to use AI to aggressively expand your horizontal bar while you relentlessly deepen your vertical one. Your deep expertise gives you the context to ask AI the right questions, and AI gives you the leverage to apply your expertise in ways you never could before.</p><p><strong>Actionable Steps:</strong></p><p><strong>Define Your Vertical Bar:</strong> What is the vertical bar of your T? If you're not sure, find the intersection of three things: </p><p>1) What are you genuinely excited about? </p><p>2) What do you have a natural talent for? </p><p>3) What does the market value? </p><p>This is where you should be investing your time in deliberate, focused practice.</p><p><strong>Appoint AI as Your "Generalist Intern":</strong> For everything outside your vertical bar, treat AI as an infinitely knowledgeable intern. Need to understand a new marketing trend for a meeting? Ask your AI. Need to write a SQL query to pull some basic data? Ask your AI. This frees up your cognitive bandwidth to focus on deepening your core expertise. But also know how to use AI well to get the best out of it. </p><p>Here are some tips for that: </p><div class="digest-post-embed" data-attrs="{&quot;nodeId&quot;:&quot;04b8d944-94b9-469d-b703-e200b2307979&quot;,&quot;caption&quot;:&quot;In this post, I&#8217;m going through a few common techniques I&#8217;ve picked up over the last few weeks, that you can use to improve your prompts and get better results from LLMs. Some of them yield better results, some not so much. But based on your use cases, that can change. Play around with it and try to have fun.&quot;,&quot;cta&quot;:&quot;Read full story&quot;,&quot;showBylines&quot;:true,&quot;size&quot;:&quot;sm&quot;,&quot;isEditorNode&quot;:true,&quot;title&quot;:&quot;23. Prompt hacking&quot;,&quot;publishedBylines&quot;:[{&quot;id&quot;:11679997,&quot;name&quot;:&quot;Sooraj Chandran&quot;,&quot;bio&quot;:&quot;Musing on tech, career and life.&quot;,&quot;photo_url&quot;:&quot;https://bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com/public/images/2629d6a3-dbb0-44bf-a766-8b8d38ea98b9_400x400.jpeg&quot;,&quot;is_guest&quot;:false,&quot;bestseller_tier&quot;:null}],&quot;post_date&quot;:&quot;2025-06-03T08:56:32.774Z&quot;,&quot;cover_image&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/2ac5bdc4-ef6e-42c0-b71c-4137c280d95f_1024x1024.png&quot;,&quot;cover_image_alt&quot;:null,&quot;canonical_url&quot;:&quot;https://www.memos.soorajchandran.com/p/23-prompt-hacking&quot;,&quot;section_name&quot;:null,&quot;video_upload_id&quot;:null,&quot;id&quot;:164937760,&quot;type&quot;:&quot;newsletter&quot;,&quot;reaction_count&quot;:3,&quot;comment_count&quot;:0,&quot;publication_id&quot;:null,&quot;publication_name&quot;:&quot;9to5.exe&quot;,&quot;publication_logo_url&quot;:&quot;https://substackcdn.com/image/fetch/$s_!YE6b!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F07fd6693-bb4d-4862-ae34-0456412fd759_608x608.png&quot;,&quot;belowTheFold&quot;:true,&quot;youtube_url&quot;:null,&quot;show_links&quot;:null,&quot;feed_url&quot;:null}"></div><h3>Plant the Seeds</h3><p>An expert with deep, T-shaped skills who stays silent is invisible. Opportunities can't find you if they don't know you exist. The antidote to invisibility is simple, not easy: you must make your thoughts and your work visible.</p><p>The gold standard for this is "Building in Public." We see indie hackers and open-source developers sharing their revenue dashboards, their code, and their user feedback. It's incredibly effective, but it's also intimidating. Many of us think, "I don't have a product to build," or "I don't have the time for a side project," or simply, "I'm not an expert yet."</p><p>This is where a more powerful and accessible strategy comes in: "Learning in Public."</p><p>If you don't have something to build in public, you can learn in public. The principle is the same: you are creating a public trail of your curiosity, your process, and your growth. This simple shift from "expert" to "curious learner" lowers the stakes and removes the pressure of perfection.</p><p>I wrote about it here in detail:<br></p><div class="digest-post-embed" data-attrs="{&quot;nodeId&quot;:&quot;a5f500aa-6ad5-4955-9e1f-193dbc12e740&quot;,&quot;caption&quot;:&quot;Why Writing Online Is the Best Career Investment in Uncertain Times&quot;,&quot;cta&quot;:&quot;Read full story&quot;,&quot;showBylines&quot;:true,&quot;size&quot;:&quot;sm&quot;,&quot;isEditorNode&quot;:true,&quot;title&quot;:&quot;18. Writing online as a career bet&quot;,&quot;publishedBylines&quot;:[{&quot;id&quot;:11679997,&quot;name&quot;:&quot;Sooraj Chandran&quot;,&quot;bio&quot;:&quot;Musing on tech, career and life.&quot;,&quot;photo_url&quot;:&quot;https://bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com/public/images/2629d6a3-dbb0-44bf-a766-8b8d38ea98b9_400x400.jpeg&quot;,&quot;is_guest&quot;:false,&quot;bestseller_tier&quot;:null}],&quot;post_date&quot;:&quot;2025-04-04T11:10:09.940Z&quot;,&quot;cover_image&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/1fa09146-39bf-4a4c-b3a3-7040865b3f8d_1536x1024.png&quot;,&quot;cover_image_alt&quot;:null,&quot;canonical_url&quot;:&quot;https://www.memos.soorajchandran.com/p/18-writing-online-as-a-career-bet&quot;,&quot;section_name&quot;:null,&quot;video_upload_id&quot;:null,&quot;id&quot;:160570237,&quot;type&quot;:&quot;newsletter&quot;,&quot;reaction_count&quot;:16,&quot;comment_count&quot;:2,&quot;publication_id&quot;:null,&quot;publication_name&quot;:&quot;9to5.exe&quot;,&quot;publication_logo_url&quot;:&quot;https://substackcdn.com/image/fetch/$s_!YE6b!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F07fd6693-bb4d-4862-ae34-0456412fd759_608x608.png&quot;,&quot;belowTheFold&quot;:true,&quot;youtube_url&quot;:null,&quot;show_links&quot;:null,&quot;feed_url&quot;:null}"></div><p>More importantly, it dramatically increases your luck surface area. By sharing what you're learning, you attract a specific set of people:</p><ul><li><p>Fellow learners on the same path who become your peers.</p></li><li><p>Experts who see your curiosity and want to help you go further.</p></li><li><p>Hiring Managers and Leaders who value initiative and a growth mindset far more than quiet, stagnant expertise.</p></li></ul><p>The best part is that you can start this in the safest environment you have: your current workplace.</p><p>You don't need to launch a blog or a newsletter tomorrow. You can start by sharing your learnings asynchronously. The next time you go down a rabbit hole to solve a problem, post a quick summary in your team's Slack channel:</p><blockquote><p>"Hey team, I was figuring out why our build times were so slow. Discovered it was an issue with X. Here's the 2-minute article that explained it all, in case anyone else runs into it."</p></blockquote><p>Or you can be more structured. Offer to host a 30-minute "lunch and learn" session on a new technology you've been exploring.</p><p>Not everyone will engage. Most will scroll past. But some will. And that's enough. The people who do, the ones who ask questions, add their insights, or thank you for sharing, are the most engaged and curious people in your organisation. They are the collaborators, mentors, and sponsors you want on your side. You are making yourself known to the people who matter.</p><h3>Water the Garden</h3><p>The word "networking" makes most of us cringe. It brings images of crowded rooms, forced small talk, and transactional exchanges. If you're a selective introvert like me, this is actively draining.</p><p>The good news is that this model of networking is ineffective. The goal is to make connections. For introverts, this is a superpower. We don't thrive on shallow, wide-ranging interactions. We thrive on deep, meaningful connections built around shared interests and values.</p><p>So, how do you find these people without exhausting yourself? </p><p>Your efforts to "learn in public" act as a powerful filter. The content you share is a beacon. It doesn't attract everyone. It attracts your tribe. The ones who are interested in the same things, who appreciate your way of thinking, and who are on a similar journey.</p><p>This turns networking on its head. Instead of a draining outbound activity, it becomes a manageable inbound one. You're not hunting for needles in a haystack. You're tending to the high-quality leads that your public learning has already generated.</p><p><strong>Actionable Steps:</strong></p><p><strong>Tend to Your Inbound:</strong> When someone responds to your post, asks a follow-up question, or shares your work, they are raising their hand. This is your signal. Your only job is to have a genuine conversation with them. Send a DM. Ask them what they're working on. You'll find that vibing with these self-selected people is often effortless.</p><p><strong>Master Low-Lift "Give":</strong> The easiest way to build a connection is to be helpful. When you're talking to one of these like-minded people, look for an opportunity to help them in a small, low-energy way.</p><ul><li><p>"I just read a great article on that, here's the link."</p></li><li><p>"I know someone who is an expert in that area. I'd be happy to introduce you.&#8221;</p></li><li><p> "That's a cool project. If you ever want a second pair of eyes on it for 15 minutes, let me know."</p></li></ul><p></p><p><strong>Schedule One "Comfort Zone" Coffee a Month:</strong> While inbound is powerful, there is still immense value in occasionally pushing your boundaries. But do it on your terms. Once a month, intentionally reach out to one person you find interesting but don't know. It could be the author of a blog post you admired or someone in a different department at your company. Send them a specific, appreciative message and ask for 20 minutes of their time. Also, ask specific questions - or even ask for help on a problem you are having - to get better responses.</p><p></p><h3>Creating Your Catalysts</h3><p>You've done the hard work. You've built your skills, shared your knowledge, and connected with good people. You've set the stage for luck to find you. But sometimes, even with the best setup, you still need a little push.</p><p>This final step is about actively creating small sparks that can ignite bigger opportunities. Think of them as "catalysts". Tiny actions that can lead to big reactions. You're not waiting for luck to strike; you're giving it a clear target.</p><p>Here's how to do it:</p><p><strong>Build a tiny thing:</strong> Don't wait for a big project. If you learn a new skill, use it to build something small and useful, even if it's just for yourself. A simple script, a quick tool, a small website. It doesn't have to be perfect. The act of building it and then sharing it (even just with a few people) shows initiative and capability. It gives people something concrete to react to.</p><p><strong>Ask a Smart Question:</strong> In a meeting, an online forum, or a public discussion, don't just listen. If you have a genuine, thoughtful question that shows you've been paying attention and thinking deeply, ask it. A well-placed question can make you stand out and start a valuable conversation with someone important.</p><p><strong>Offer a Small Help:</strong> See someone struggling with a problem you know how to solve? Offer a quick tip, a useful link, or a five-minute explanation. Don't expect anything in return. These small acts of generosity are memorable. They build goodwill and can lead to unexpected opportunities down the line.</p><p>The point is to stop waiting for the perfect moment or the big break. Instead, create many small moments. Most of these little sparks might fizzle out, and that's okay. But every now and then, one will catch fire and lead to something you never expected. </p><div><hr></div><p>Found this useful? A quick share helps me continue bringing you new insights each week. Thank you!</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://www.memos.soorajchandran.com/p/27-how-to-get-lucky-in-your-career?utm_source=substack&utm_medium=email&utm_content=share&action=share&quot;,&quot;text&quot;:&quot;Share&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://www.memos.soorajchandran.com/p/27-how-to-get-lucky-in-your-career?utm_source=substack&utm_medium=email&utm_content=share&action=share"><span>Share</span></a></p><p></p>]]></content:encoded></item></channel></rss>