You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.

— Steve Jobs

When I was 15, fresh into high school, I had my first business idea.

I would build a trivia website where people could participate to win mobile recharge. The site would host ads, and with enough participants, the ad revenue would outpace the recharge vouchers I’d give away.

Yes, mobile recharge was a big thing in 2010. If you’re a millennial, you probably remember the daily night-pack recharges that let you talk unlimited from 11 PM to 6 AM.

For this idea to work, I needed strong distribution. I had no money to spend out of pocket.

So I created a meme page on Facebook. It grew to 150,000 followers. Somewhere along the way, I ditched the trivia website for something better: smaller meme pages started reaching out to be promoted during our peak engagement hours (around 9-10 PM every day). I was making 500-2000 rupees a month from this.

As a 16-year-old, I was rich.

At 18, I started charging small businesses to build their websites.

Back in college, I visited my college souvenir store. I didn’t buy anything, but soon after, I started a merchandise business, selling directly to the college administration. Shortly after, I launched an e-commerce website where students could shop directly. In less than a year, I’d made enough to cover my college tuition.

After graduation, I built a platform for buying from local stores instead of ordering the smallest item from Amazon or Flipkart. After ten months of trying to make it work, I went broke. But I kept pushing. I took loans to keep the business afloat, until I realized I’d accumulated debt nearly the size of what even the best job would pay me in a year.

I quit the idea and found a job to pay back those debts. I worked as a software engineer, then a product manager, for about three years.

Once I cleared my debts and built some savings, I felt ready to try again.

I started a dev shop building software for fast-growing startups.

In October 2022, I shut it down after running it for over two years. While it was always profitable, I always had to be around to keep it that way.

For some profound (or utterly stupid) reason, I don’t want to spend the rest of my life working 8-12 hours a day running a business. I don’t think I’d enjoy that very much.

I spent two months on sabbatical. I treated it as a much-needed break to re-evaluate what’s important to me and what kind of life I want to build. My conclusion: there are much better ways to achieve my goals than running a large team for a service business.

I’ve decided to take a path that brings me the most joy: solving problems and building things. Creating a portfolio of profitable software businesses. Something that doesn’t require me to be around every waking hour.

Over the next 12-18 months, I’m experimenting with 4-6 ideas. Spending roughly 6-8 weeks to build and ship each one.

Before I kick any of this off, I need a strong playbook to ideate, validate, design, engineer, ship, and distribute a product.

I plan to spend the next four to six weeks building that playbook.

Do I know for sure if this will work? Absolutely not.

Will I have a lot of fun doing this? 100%.

Today, I’m grateful for the courage to experiment. And I intend to keep doing so.

Update (2026): This post marked a turning point. The reflection that started here eventually became LifeOS, a personal operating system for designing life with intention. The playbook I mentioned building? It evolved into something bigger: a framework for staying consistent with what matters across Joy, Money, and Impact. If you’re curious where this journey led, check out my 2026 manifesto.