A wise man once said: regretting is just imagining that the alternatives could’ve been better.
But in reality… the alternatives could’ve been way worse.
That wise man is none other than me.
See, regret is just a feeling. And like any feeling, it’s slippery, subjective.
Yes, if you gamble your house away, regret will sit on your chest like a boulder.
But I’ve also seen men lose their ancestral wealth in extinct businesses… and still raise a glass of champagne to celebrate “the risk.”
So what really is regret? And how do we make sure it doesn’t eat us alive?
Let me tell you what happened to me.
I always knew I wasn’t meant for a 9–5. That life never sat well with me.
But after enough failures; real bruises, not motivational-poster failures, I caved in.
Still, my stubborn brain wouldn’t let me walk into just any cubicle job.
So I found an opening with a fitness influencer- a guy who made funny skits around gym myths.
And before I even applied, I had already mapped it all out in my head:
the funnels I’d build, the automations I’d set up, the systems, the CRMs, everything.
I even made a pitch timeline.
Three days into my first ever job, I walked in with the audacity of a man twice my experience.
I pitched. Boldly.
And it bombed.
He didn’t see me as a problem-solver. He saw me as a threat.
The man even threatened to sue me on nonsense grounds.
I came home with my head spinning:
Did I jump the gun too early? Was I too blunt? Did he feel played?
Every angle of doubt replayed like a broken record.
But then something clicked. My conscience - that inner mirror you can’t lie to; kept asking me one thing:
What’s the alternative?
Stay in a place where incompetence is the culture?
Stay under an authority that values obedience over contribution?
Stay in a cult where ideology matters more than ideas?
If there are a hundred ways to do something, and the tie gets cut after your first attempt, then you’ve only got a 1% chance anyway.
So is it really worth regretting? Or should you be proud that you at least tried?
That’s when I realized: regret is only heavy if you keep judging yourself after the fact.
If you stop over-judging and start owning your attempts, even your “failures” make you a better human.
And maybe that’s the only way to keep regret from consuming you.