The Gamble Guide

Making Wise Choices

Olabanji Stephen
2 min readMar 21, 2022

The thing about gambling is that, to play, we have to be willing to lose. That’s what we put on the table — the willingness.

Not what we have, but what we are willing to stake. That’s the play.

It’s a trial, a guess… We want something back (tangible or intangible), so we put something on the table. We have to.

It pays to set aside what we consider as valuable, how much of it we are willing to stake, and for what.

How much of your time are you willing to let go? For what?

Would you rather save for your next degree or a trip to Bali for one year to experience life differently?

Would you rather get a job or show up in a field you believe you can make a change in, even if no one cares about it now?

It may be wise to decline the next boring zoom call to go plant some trees.

It may be wise to decline the next low-paid client project for a personal one.

We gamble every day when we deploy our time, our resources, our ideas, and our attention to a thing.

This or that…

Former President Obama declined invitations from reputable law firms (as a graduate of Harvard Law School) to organize people in small communities and lead political projects.

If it’s valuable, consider staking it for what you consider valuable as well and it’ll be worth it.

Tables remain tables, but the ability to choose what goes on it is a superpower… and it's ours.

… it's yours.



Olabanji Stephen

I see the world differently and attempt to interpret it in ways that inspire genius