Notes on Sabbatical

Long list of reasons and hopes.

As some of you may already know, I’m on a sabbatical right now.

After four incredible years of building and partying, I quit Headout and am taking a long break. Many friends (both irl and internet) reached out to me asking what drove me to this decision and what I expect to achieve out of this break. So, I figured I'll pen down my thoughts so that the next time this question comes up, I can send them this post.

But first,

Headout is Home..

Headout is a fantastic workplace and I love it with all my heart. I thoroughly enjoyed my 4 years there - made so many friends, learned so many things. 10/10, strongly recommend. My deep attachment to Headout and its people made this decision all the more difficult.

Reasons

Low Intrinsic Motivation

Starting in December 2022, my intrinsic drive to work began to drastically decrease. Most days, I just didn’t feel like working. I struggled to find a flow state. This was the first sign that I needed a break.

In early 2023, I lived in Bangalore for a few months (living out of a hotel 😬). Going to the office boosted my motivation levels initially, but after a few months, the feelings resurfaced.

Role Dissatisfaction

I was an Engineering Lead at Headout. Engg Lead is a notorious role as it often means you are part individual contributor (IC) & part managerial. A typical workday would involve project syncups, calls with fellow devs to help unblock them, code reviews etc. I was good at this role (or at least my performance reviews says so 💰) but I wasn’t happy.

I considered going back to being a pure IC, but I wasn't certain about that path. I also contemplated exploring the PM track, but I lacked confidence.

Headout offered me all these options, but I remained unsure of my next step.

I'm still confused. I hope the coming months will bring more clarity.

Savings Safety Net 💸

I have no dependents. My family, while not filthy rich, can thankfully manage without my income. I’m unmarried. I have no debt. I live a simple lifestyle and am a man of few desires.

This meant that the last few years of ZIPR-era high tech-salary allowed me to build a decent savings corpus that I can comfortably rely upon for a while, even if there’s no new income.

I’ve done the math. I have 5-6 years of runway with my current lifestyle, accounting for 8% inflation & assuming no major medical emergencies or an expensive wedding 😂.

If I still end up going bankrupt, I'll at least get to use this favourite meme:

If not now then when

Macro

I was talking to a friend who was considering a sabbatical, and he expressed his concerns about the current job market. "What if I can’t find a job when I want to re-enter the market?". It’s a valid concern. But honestly I am not really afraid of this. I’ll figure something out.

But I do have another perspective to add here. Okay, so the tech-industry is in bad shape. Very few companies hiring, low hikes, massive layoffs everywhere.

The flip side to this is: If you're thinking about taking a sabbatical, wouldn't it make sense to do so when the market is down?

Imagine taking a break during a bull market. You’d would miss out on high salaries, mad perks, double digit % hikes. So isn't it better to take a sabbatical during a down market than a bull market?

Personal

I’m 28 now. Responsibilities & pressures of adult life are only going to get bigger and scarier going forward. I may not have the luxury of taking a break few years down the line - who knows what life has in store for me. Best to take the plunge while I can.

ChatGPT ?!

Okay, so this one is a doozy, but let me explain. We know that the world is at an inflection point. If you like building or learning things, there has never been a better time.

You wanna learn about SEO? Ask ChatGPT for a lesson plan, explain topics like you’re a 5yo, questions & clarifications - you name it.

You wanna build a telegram bot? Describe the requirements clearly, specify your language of choice and ChatGPT will walk you through building one.

The more I use ChatGPT to learn or build new things I started wishing for more time to capitalize on this new god-in-a-box. I need time to leverage this gift to level up myself.

Rise of IndieHacking

With the advent of ChatGPT, the barriers to building products have considerably dropped. You now have an assistant coder, copywriter, marketing stretegist etc which drastically improves your velocity when building products as an individual.

As a result, we’ll see a huge rise in IndieHackers and 1-person companies.

Those of you who spend time in the IndieHacker corner of Twitter (to get started follow folks like levelsio, dannypostma, damengchen, pbteja1998) will know that the recent AI boom has lead to an explosion of Indiehackers - mostly people building ChatGPT wrappers for niche use-cases, but still..

So did I.

I too dabbled in Indiehacking. I built SopCreator.com, a product to help students write their Statement of Purpose for applying to universities.

I wish to spend more time in life exploring opportunities to build indie products. I’m hoping that this sabbatical will help explore such opportunities. If not, atleast I’ll learn skills that’ll help me do this when the opportunity strikes.

Travel

I’m a nomad. Last 2.5 years I spent travelling and working from different parts of the country - sometimes outside India too.

While I’ve gotten used to managing work and travel together, it sure is a hell lot more fun to travel unbothered with meetings and responsibilities and deliverables.

Working while travelling in India also severely limits the places you can stay at. For examples, when in Himachal I have to restrict myself to keep my base in Old Manali, Bir, Dharamshala etc - places with good internet. I never explored North-East India because of fears of poor/unstable internet. Now I’m free to go wherever I want 😊 .

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Yup that’s pretty much it. This got a lot longer that I expected. I’ll probably start writing weekly updates of how my break is going - I’ll include excerpts from interesting blogs/books I read, niche youtube videos I watched, new microskills I learned etc.

Stay tuned!