The Night I Mapped Three Versions of My Life

I almost skipped it.

It was late. Long day of calls. A few decisions I wasn’t fully happy with. The usual pile of things that quietly move to tomorrow’s list.

Then I saw Daniel Pink’s post about the Odyssey Plan. A Stanford exercise. Twenty minutes. Three versions of your next five years.

I almost scrolled past it.

But something about it wouldn’t let me.

So I did something I almost never do. I put the phone down, found a pen, found paper, and sat with it.

Path 1: Stay Exactly Where You Are

The first question was simple. What does your life look like in five years if nothing changes?

Same job. Same routine. Same direction.

I sat with that. Then I wrote it down honestly.

Brainium at year 18. Same clients in the UK, US, Australia. Same team of around 150 people. Products like LeadFlow and Diamond Picks still finding their footing. Revenue steady. No dramatic leap forward. No dramatic fall either.

Just steadiness.

Then the uncomfortable part. When I wrote “what does Monday morning look like?” the answer was almost identical to today. Early calls across time zones. Internal reviews. Some writing if I’m lucky. A lot of problem-solving that never fully ends.

That picture sat heavy.

Not because it’s a bad life. It isn’t. But because steadiness is another word for stagnation when you’re capable of more.

Path 2: Take the Risk

The second question asked me to imagine the version of my life where I actually took the leap.

This one came faster.

Path 2 Sourav makes a serious pivot. Products over services. A few energetic new hires who bring fire into a team that has gotten comfortable. Real risk put behind the ideas that have been sitting in planning documents for too long.

By 2031 in this version, things look different. Brainium’s products have found markets. The business has momentum that Path 1 never could.

Monday morning feels different too. Busy. A little chaotic. The kind of chaos that comes from growth.

I liked that picture.

But I also noticed something as I wrote it. The thing stopping Path 1 from becoming Path 2 wasn’t opportunity. It wasn’t resources. It was appetite for risk. The willingness to move faster than feels comfortable. To stop waiting for the right moment and accept that the right moment is probably now.

Path 3: If Nothing Was Stopping You

No money pressure. No one else’s opinion. No constraints. What do you actually build?

I expected this one to be dramatic. A fantasy I’d never really pursue.

Instead, what came out was quiet.

Reading. A lot of it. The kind of deep, unhurried reading I used to do before the business got big enough to consume every hour.

Writing. Books, specifically. I’ve written two already, The Diamond Way and The 12th Man. In Path 3, there are more.

Stock market investing. Not as a hobby but as a serious craft. The kind that requires patience and time to think rather than react.

Sales talks. Speaking at events, mentoring founders, sharing what I’ve learned in 13 years of running a bootstrapped business.

Slower days. More intentional. Less firefighting.

I looked at what I had written and felt something unexpected.

Relief.

Not because it was a fantasy. But because none of it was actually that far away.

The Thing That Surprised Me

Path 3 and Path 2 are not opposites.

The writing is already happening. You’re reading this right now. The books exist. Diamond Picks, our AI stock screening product, is already deep in the territory of investing and markets.

The “chilled out” version of my life and the “serious growth” version aren’t pulling in different directions. They’re pointing at the same place. The gap between them isn’t about what I want. It’s about the speed and courage with which I move toward it.

Path 1 is what happens when I let the days run me.

Path 2 is what happens when I decide to run the days.

Path 3 is proof that I already know what matters.

Try It Tonight

Twenty minutes. Pen and paper.

Three paths. Five years. Specific enough that you can see Monday morning in each one.

Then notice which path you avoid looking at too long. That’s probably the one with the real answer.

For me, it was Path 1.

I’m not going back there.