My first sabbatical happened on a whim.

I was twenty-four, twenty-five maybe, and I thought I’d take all the time to get fit and all that. I was also experimenting with a bunch of ideas in my head, and was very excited about building something great.

Close to three months later, I realised I hadn't shipped anything. It wasn’t a nice feeling, especially if you spent half your life on Twitter. 

So I randomly started consulting with companies, and that led to me meeting a bunch of people who are very good friends of mine now. Then in December, very accidentally, I was hanging out with someone who was with Superteam Solana. The conversation went like this.
Me, to him: "You know, you guys should perhaps do this thing."
Him, to me: "Why don't you build it out? We can perhaps offer an Instagrant for that."
Me, to myself: "Yeah, this is good."

It was one of those December days, the first time in like six months where I worked properly, properly. Where I woke up at 10:00 a.m., sat in front of my laptop and worked till 1:00 a.m. And I think that project went viral (We saw 25k people come onto their site and check their Solana Wrapped). We took over Crypto Twitter for a day. That felt pretty nice, and also when I realised this is something I wanted to work on. I want to build random fun projects.
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Call it post-rut clarity.

I took my second sabbatical a few months ago. What was an extended sabbatical has now become my life. The last 8-10 months have been transformative in the best possible way, where I’ve learned more about myself and how I view my career.

In pure Buzzfeed fashion, here are 15 things I learned over the last 8 months during my sabbatical:

  1. Sabbaticals are taken during a time when you are seeking a different version of yourself.
  2. If you decide to take a sabbatical today without a plan, the best thing to do is to take a month-long vacation. The next best thing for them would be to do cool things in public. Broadcasting curiosity is a beautiful way to meet your new friends. As Henrik Karlsson says, a blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox.
  3. This period has helped me realize where I derive validation from. If I wake up and don't put on a T-shirt, put on jeans and go to a coffee shop, I would lose my mind. I get my dopamine hits when I learn something new. When you think something is cool, and it just takes over your life for the next twenty-four hours. So that happens to me a lot. So I think I'm just always seeking out new forms of curiosity, new ways to live life. It can be an issue sometimes but my 30 year old friends say “you should be having way more fun”
  4. A sabbatical gives you the freedom to choose your projects, your support system, your schedules. It can be a builder's dream if you play it right. Over the last eight months I've focused a lot on my fitness. I now have stronger friendships than I ever did in my life. A lot of my friends come from the idea that this guy makes something, he's always working on something very cool all the time. So I also end up helping them here and there with their things.
  5. I think being mentally stable during a sabbatical is a function of having a really cool set of people around you who are like, "Yeah, you know what? You'll figure it out eventually." But you can't call someone to give you a pep talk at 3:00.
  6. Embrace the professional insecurity. One moment you’re exhilarated about what you’ve built and the next moment you’re dealing with the crashout of someone you know raising a 70mil series A. That said, the best way to avoid crashouts is taking the long term view. It's like a lunch break in a test match on day one. You know what you want to be at the end of day five of this test. But for now, what is your strategy for the second session? So it's basically looking at your own career from a third-person view.   
  7. What all the sabbaticals have done for me is that it has just told me how my life is malleable, and how much of it is actually just on me. And you can read all the fucking philosophy and all that, but the only way out is just doing shit.
  8. That said, reading gives you hope on bad days. Two recommendations: The Making of Prince of Persia and Masters of Doom. I love reading competence porn. I love reading how someone is torturing themselves to greatness. Like give me stories of someone making an impossible thing happen. It’s kinda sorta reassuring to know that even the best of the best  just figured it out along the way rather than having a straight path. 
  9. Journaling is a great way to deal with the ebbs. I was in a rut for the last three months, so like every other techbro, I went to Claude, fed it my journal entries and asked it to tell me what ideas have I discarded in my journals. One of the ideas was a cafe map in Indiranagar.  So I decided to build it on a whim, and it gave me enough dopamine to survive for the week.
  10. A sabbatical is an exercise of pursuing excellence of your own kind. 
  11. You either can work on something very niche, very cute, which will cater to hundreds of fans. Or you work on something so big that it should seem intimidating to you as well. Because mid-curving is not an option, at least at this age.)
  12. There are two types of sabbaticals. One is where you get a fifteen to twenty-five LPA jump. And the second is you want a fifteen to like a sixty jump. The first is simpler. You take a break for six months, study something, and you can figure out a way to get there. But to the other type of jump, I think you just need to become a whole different version of yourself. So it's like you're like, "Cool. I've tried this one life. Now I just want to change my life altogether." I think about this a lot: in the next one year, I could be living a very different life. I could just take up a job. I could move to New York. And that's a very different life. 
  13. We need to be audacious. We are ambitious, but ambition and audacity are two very different things. The stillness of a sabbatical is a great time to figure out a way to match the frequency of one with another.
  14. The Peter Pan syndrome is a real thing. Take your audacious bets when you’re young and have little to lose. Before you reach a certain stage in career, it's okay to like fuck around and find out a lot. But I'm assuming when I'm thirty-one, this phase of FAFO can't happen, because priorities change.
  15. That does not mean you’re building all the time. You can’t be ‘high agency’ all the time. Treat your sabbatical as a period of constant side quests – today, I’m working on a hackathon idea. Yesterday, I spent the entire day on Pinterest. The day before, I was doomscrolling on Instagram. Months and years, not hours and days. 

You’re always ~6 months away from living a completely different life.