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Decision making can be hard

Making decisions isn’t for the faint-hearted. Each choice has weight, some light as feathers and others as heavy as boulders. Navigate them, and you’re walking a tightrope strung between present and future, every step shadowed by the silent specter of regret.

Consider the mundane: to go out for a drink or not. Seems harmless, right? A fleeting choice. On one side, there’s the pull of camaraderie, the low hum of conversation, the possibility of that unexpected connection. Maybe tonight’s the night you run into someone who changes the course of your life. Or maybe it’s just a few hours of easy laughter.

On the flip side, there’s the stark contrast of the morning after. Sunlight piercing through blinds, a head that feels like a lead drum, and memories that blur around the edges. You’re left weighing the warmth of the previous night against the price paid in daylight.

Then come the decisions that feel like you’re holding the world on your shoulders: like whether to uproot your life and head cross-country. The promise of new horizons and the thrill of the unknown beckon. But in the rearview, there’s a familiar skyline, well-worn paths, and faces that have mapped out your life up until now. It’s the allure of tomorrow versus the comfort of yesterday.

The problem? Life doesn’t deal in previews or free trials. You can’t A/B test life. So, you make the choice and live with it. That’s how you collect regrets, the little and big tokens from every junction where you paused and wondered.

Choosing your Regrets

You probably cringed a little bit as you read the word, “regrets”. Regrets get a bad rap. Everyone wants to live with no regrets. How many “No Regrets” tattoos are out there?

What if regrets weren’t such a bad thing? What if they were actually an invaluable tool in your decision making toolbox?

I recently was introduced to this concept of Choosing your Regrets while listening to a podcast with Chris Williamson and Alex Hormozi. It’s a fascinating concept, and one that I will continue to use for the rest of my life.

We know that there will always be regrets with every decision we make. There will always be what-if’s. Instead of fearing them, use these potential regrets as indicators. When deciding what job to go with, think about what you’ll regret if you choose job A and what you’ll regret if you choose job B. Which regret would you rather live with? You can use this when ordering lunch today or when deciding who to marry.

Proactively choosing what we are willing to live with allows us to make bolder decisions. Looking to regrets in the eye and being okay with them is unbelievably freeing. Further, when those regrets do pop up, it’s in the form of a light summer rain, not a hurricane. They’re almost pleasant, because they remind us that we expected this, and that we stand by our decision.

Maybe I’ll get a “Choose your Regrets” tattoo…?


Think about the last decision you made. If you gauged the weight of potential regrets back then, would you have taken a different path?

A parable

I’ll leave you with this parable that’s admittedly only semi-related to this but nonetheless it’s a great one. I return to this whenever I’m facing adversity or things don’t go my way.

A farmer and his son had a beloved horse who helped the family earn a living. One day, the horse ran away and their neighbours exclaimed, “Your horse ran away, what terrible luck!” The farmer replied, “Maybe so, maybe not.”

A few days later, the horse returned home, leading a few wild horses back to the farm as well. The neighbours shouted out, “Your horse has returned, and brought several horses home with him. What great luck!” The farmer replied, “Maybe so, maybe not.”

Later that week, the farmer’s son was trying to break one of the horses and she threw him to the ground, breaking his leg. The neighbours cried, “Your son broke his leg, what terrible luck!” The farmer replied, “Maybe so, maybe not.”

A few weeks later, soldiers from the national army marched through town, recruiting all boys for the army. They did not take the farmer’s son, because he had a broken leg. The neighbours shouted, “Your boy is spared, what tremendous luck!” To which the farmer replied, “Maybe so, maybe not. We’ll see.”

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