There's a throwaway line in the recent Chris Rock's Netflix special: "I'm rich... but I identify as poor. My pronoun is 'broke'."

That hit me. It's actually true of my internal compass. It's not a matter of choice, but psychologically I'm always on the verge of losing my shirt the next month.

It might be worth having a series around the theme of being broke as experienced by me. A kinda processing of this narrative (a story I tell myself about myself) where I go from rags to not-rags, a re-examination of its validity.

In my mind, all young men worthy of their hero's journey should go through at least one phase in their life where they are broke. It's the equivalent of ancient tribal traditions of throwing a boy into the lions den; eat or be eaten.

So I'll start with the time when I was broke as teen right out of secondary school. Technically this doesn't quite count because most boys are somewhat broke at this stage, only they don't think of it that because so are their friends. This tell you that poverty is relative.

However there were also a handful of peers driving souped up cars when I was riding buses. So I think I did qualify as being broke.

The primary question is: what should I have done differently at the time get hold of some money?

See, at the time Yahoo was just getting started. Running an online business in the bedroom was not a thing.

There was no real opportunity in the brick-n-mortar world for a boy who knew nothing. I remember signing up as a sales trainee, followed a saleswoman around the city selling some pointless widget to people on the street. I was horrible at it, hardly opened my mouth. This lasted one day.

I truly couldn't think of any opportunity that I could have exploited at the time to make money. I know of people who quit school to sell video games in the mall, that counted as opportunity. But I'm also fairly certain of the social class they end up in today.

So there was really not much to do except to take effort to prepare of opportunities that might surface in the far future. In doing that I took the most unimaginative of all beaten paths: studying hard.

Doing so involved sacrificing playing games, frequent parties and cigarettes (or anything that cost money). In fact studying hard was an approach so brute force it only serve to solidify my lack of talent as a fact.

But ultimately it worked, only because I was willing to sacrifice what others would not. With enough skills, opportunities came knocking eventually.

Thing is opportunities are only so if you are positioned for it. As a counter example, I am not positioned to go viral in TikTok even if I'm willing to work at it. I am simply ill equipped.

Had Bitcoin been invented a decade earlier, my trajectory would have changed dramatically. I highly suspect I would be well positioned to ride that wave.