Fear of failing louder

I’ve been in startups, in some capacity or the other, for almost a decade. My first startup — also my current one — will complete 7 years next month.

If you are around me, I would’ve pushed you to startup at least once. More like badgered, if you are in the (un)lucky closer circle.

Saying that I love startups doesn’t convey how hell-bent I am on preaching the startup life. If I am a dictator of a country, everyone in that country would be starting up.

When I graduated, I believed every one in my batch of 100 should be starting up. If CPI is anything to go by, I was just a seven-pointer. And most of my batchmates were smarter, more capable. In my dream world, all the 100 created 100 startups and shared the equity with everyone else. Even with just a couple of unicorns, we all would’ve made at least as much money — if not more. Importantly, far higher impact than corporate jobs.

Seven years in, I am gearing up for my second venture.

But, fuck how am I still anxious?

How did it not get easier? Despite 7 years of experience.

For someone who is high on startup life, shouldn’t it be a breeze?

So I decided to unpack a bit of that anxiety.

As much as it hurt me to see my smarter friends “waste” their talent,

I was pushing everyone to startup because I wanted to feel safer.

If everyone took a career path similar to mine, my risk, my anxiety and my choices would feel more validated.

And I get to make my difficult journey easier by sharing it with everyone. That’s what my college life felt like. Hundreds of people taking similar risks.

A decade ago, I had little to lose. If I started up, failed and moved to another career path. The worst was that 3 people in my circle would know that I tried something and moved on.

But now, after simmering the belief that I am going to make it big in startups —

If I try now — and fail — it won’t just be a blip.

It could cost me important years.

And tens if not hundreds of people in my circle would know that I failed at something despite trying for half of my life.

I won’t be a “scrappy founder” — just that guy who wouldn’t give up even when the market clearly asked him to.

And given how likely it is that a startup will die, I was already lucky to have one good win the first time.

Second time? There’s a solid chance I come out of this story as a joke rather than a hero.

—

And that’s where I wrapped my voice note. I finished my walk around the Singapore waterfront. Looked at the transcript of what I thought. Felt good. Realized being a joke is not such a bad thing. As long as I make sure I am really excited by the journey. So I went back to dreaming the next big thing.

But this might be a better ending —

Bryan Johnson (The ‘Don’t Die’ guy) said this — "My biggest risk in life is irony. I'm the Don't Die guy. So it means, inevitably, I'm going to die by the most ridiculous means possible... So when I die by a bus or choking on broccoli, I give you permission to laugh"