Back to the Ol' Grind
a year-long sabbatical, and my lessons + experiences along the way
Almost exactly a year ago, I made the decision to leave my cushy software job at WhatsApp to figure out what I actually wanted to do with my career. At the time, it felt indulgent and kind of reckless, but looking back, it was totally the right move. Burnt out and bored with big tech, the only thing I knew for sure was that cranking out widgets as a hired gun wasn't for me.
Reflecting on my sabbatical a few months in I wrote:
“I’ll be the first to admit it. I have no idea what I’m doing. I have no idea if I made a mistake by stepping off of the career path I was previously on. I have no idea if my current entrepreneurial endeavors will pan out. I have no idea if I’ll find myself at another job in 6-8 months.
One of my core ideals is to never make a decision (or not make one) out of fear. I’m certain that I have no regrets about leaving my job. No matter what comes of this chapter, I know that 90-year-old Nikhil will look back at 25-year-old Nikhil with pride. He’ll be proud that I had the courage to leap into the abyss without knowing the outcome, and proud that I didn’t let fear or comfort stop me from becoming who I have the potential to become.”
Now I can say with certainty that I truly do have no regrets about the decision to take a sabbatical. In fact, I think it was one of the best decisions I’ve ever made, and am all-in on incorporating extended breaks between future career chapters.
Over the past year, I've plunged headfirst into a wild array of experiences that have stretched my beliefs and helped reveal my true passions. In this post, I'll take you through the highlights of my journey, which include attempting to start a startup, freelancing in a DAO, venturing into software consulting, making small bets on promising startups, and navigating the ever-evolving landscape of trends and industries — all of which have led me to an exciting new chapter.
After bidding adieu to WhatsApp, I set my sights on starting a startup. I began by "co-founder dating" other free birds in my network and through YC’s platform. This process taught me a ton about myself and the founder marketplace (and, weirdly enough, mirrored actual dating — more for a future post).
Key takeaways: do a trial project ASAP, understand that uncertainty is the name of the game, and never underestimate the make-or-break nature of co-founder chemistry. My explorations led me through identity & community in Web3, cozier social networks, crypto-native CRMs, and personal search engines.
I soon found myself spinning my wheels, stymied by roadblocks and lacking conviction in my own ideas, and in the industries I was exploring. Despite my long-term entrepreneurial ambitions (which haven’t changed), I realized that San Francisco’s intoxicating and mimetic energy was leading me astray (I started dreaming about B2B SaaS). So, I hit pause on the startup journey and turned my focus towards joining a startup in an intriguing space that I could develop conviction for over time.
To reset and sustain myself during this period, I did contract work for a few interesting startups (Premise, Cheez, and Cent). These freelance gigs gave me the flexibility to pursue my interests while earning enough to sustain myself (while also living in a 30 bedroom co-living house).
Then, seizing an opportunity, I shot my shot via Twitter DMs and found myself in a position to be one of the first hires at Texts.com, a seed-stage startup unifying all messaging apps. My Facebook Messenger and WhatsApp experience, coupled with Texts’ cyberpunk vision of reverse engineering private APIs to deliver superior user experience, seemed perfect. However, I soon realized I hadn't put enough thought into what to do this next chapter. I’d fallen into this “messaging infrastructure” niche and was driven by momentum — I needed to reassess my direction yet again.
Enter AI. After some meandering, I discovered the space, ignited by my fascination with Stable Diffusion and vector embeddings (while implementing semantic search over my personal data). Immediately after a transformative 10-day meditation retreat (post on this coming soon™️), ChatGPT launched and it was game over. From that moment on, I couldn't imagine working on anything else.
This timely alignment pushed me to go all-in on the AI space, and I spent the next three months learning as much as I could, hacking on interesting ideas, and eventually interviewing at cutting-edge startups. After a wild ride, I found a team and product that truly resonated with me, setting the stage for the next chapter of my career. More on that below 👀
This was the longest time that I’ve been “unstructured” and able to focus on areas my life outside of the standard ones (school & work) more fully. When I wasn’t thrashing at the lack of clear objectives, I was able to connect more deeply with myself and the world around me.
A profound experience I had during this time was attending a Vipassana meditation retreat. This 10-day
retreat bootcamp gave me an immeasurable amount of insight into my thoughts, emotions, and inner workings. It’s hard to understate the timing of this experience, and its powerful impact on my conviction still astounds me.
In San Francisco, I found a deeper connection with my city through its unique duality, nurtured by the spiritual sanctuary of The Center and the cerebral pulse of Genesis, my home. The Center, a haven of introspection soothed my soul, while Genesis, a hive of brilliant scientists & entrepreneurs sparked my mind.
I also rediscovered the true essence of quality time, devoting my attention to the people who matter most. Reconnecting with my family in Florida on multiple occasions, I played the role of their personal chauffeur, driving them through the windy streets of San Francisco. Between the comfortable energy of ski trips with old friends and the invigorating curiosity of coffee chats with new ones, I spent time rekindling and deepening friendships. Additionally, I was fortunate to share this transformative period with Mack, who had just moved to SF and recently embarked on her own thrilling journey into the unknown.
When I decided to commit to joining a startup in the AI space, the interview process itself became an odyssey of self-discovery and growth. Rejection, my old friend, tested my resilience and nearly pushed me to the brink (I often fantasized about applying to FAANG). Eventually, the journey of honing my interviewing and engineering skills and discovering my true aspirations evolved into its own reward. A fire was kindled within, and I found confidence in my own abilities.
Now, if you’ll excuse me I’m going to be a bit pithy and share some concrete lessons that I’ve learned during this time and have (hopefully) internalized.
Embrace intentionality: Don't hesitate or linger in indecision—test theories, iterate, and dive headfirst into exploration. Fortune favors the bold.
Liminality is a double-edged sword: While it's comfortable (and advantageous for a certain while) to dwell in the realm of possibilities, you must eventually break free from this state and take action.
Beware of mimetic traps: It's easy to get swept up in the contagious ambitions of your surroundings, like the desire to be a founder in San Francisco. Always question if a path aligns with your current stage and aspirations.
Timing is unpredictable: I found myself interviewing in the worst possible market conditions in which, ironically, staying at WhatsApp and underperforming could have yielded a generous severance package. On the contrary, the timing and coinciding events around my pivot into AI couldn’t have been better. Life's twists and turns defy our best-laid plans.
Balance flexibility with purpose: While I value flexibility (being able to take an afternoon off to play tennis), I've discovered that my true satisfaction stems from a sense of purpose and growth in whatever I do.
Life oscillates between extremes: My ideal way to live life is as an ever-changing dance between work and leisure, where I’m at either 2 or 10 in terms of effort output, with nothing in between. Hell Yeah or No.
So, What's Next?
I’m thrilled to announce that I’ve joined the team at Perplexity as a Member of the Technical Staff!
As I look back on this winding journey, I’m confident that AI is the right direction for me. The field offers a unique opportunity to explore the fundamental questions of intelligence and consciousness that captivate my curiosity, while also creating and delivering immense value to people. Perplexity's focus on search and user experience dovetails nicely with my passion for personal data and knowledge representation, making this a great match.
So there we go! Perhaps jobs aren’t a scam after all. I highly recommend taking a sabbatical, professional break, or whatever you’d like to call it, if circumstances permit. It
likely definitely won’t be easy, but the personal and professional growth you'll experience is well worth it. If you’re considering a similar adventure and need a gentle nudge, don’t hesitate to reach out to me. ✌🏽
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Nothing wrong with cranking out widgets though! ⚙️
One thing I found pleasantly surprising was that by working intensely for just a few months, I was able to earn enough to sustain myself — even in an expensive city like San Francisco. This challenged my preconceived notions about traditional work structures and narratives around “security”. Though, I have no kids or debt so this might be a
zero interest rate “20s-only” phenomena.
Congratulations on your success and learning! 25-year-old Nikhil is doing pretty well for himself.
(I also picked up Hell Yeah or No, thanks for the rec!)