Why Choosing A Path In Life Is Hard

And how we can overcome this frustrating psychological hangup.

Choosing a path in life is bloody difficult for the same reason we keep swiping on dating apps when we’re already talking to someone cool — fear of missing out.

Every time we struggle to make big life decisions, it’s not actually about whether we want to do the thing or not; it’s about what we could be doing instead.

Because in our minds, saying “Yes!” to Option A means saying “No!” to options B through Z.

So instead of picking an option, a path in life, we either try to do everything at once and burn out, or we don’t choose anything and get upset for not moving forward.

It’s a simple fact: We want a lot of things, but we don’t like choosing.

And whether we’re trying to get a hole-in-one by analyzing all 99 options or we’re trying to do everything at once, it all just leads to a form of paralysis.

In reality, this is just a jail we’ve built for ourselves.

We don’t need to keep telling ourselves that we need to choose. Because its complete fiction, it’s not true.

And if we built this fiction, this jail, we can also break out of it — that’s the part where we need to convince ourselves of the reality.

And It’s Simple

It doesn’t matter how we do it, but we need to understand and internalize that trial and error is the way to find our path in life — not “one-try-no-errors.”

It’s iterative.

That’s how startups do it, it’s now how companies do it, and it’s also how designers do it — it’s solving a problem by trying again and again while learning through iterations.

Because sure, we all want to get a hole-in-one or climb the right peak, but the fact is that there are too many options out there to choose the “right” one effectively.

We need to try that corporate gig, business idea, or travel dream.

We need to try that relationship, philanthropic endeavor, or sport.

We need to try things we think will be fulfilling.

And here’s a “bandaid ripping” moment for you; there will be a lot that goes incredibly wrong.

But the parts that go wrong, the paths that turn out to not be for us, and the feeling of “wasted time” during the process — that’s a life well-lived.

That’s a life with no regrets.

Here’s The Thing About Regrets

I think back to all the bad times I’ve had trying things, and I can’t say I have any regrets.

Bad decisions make good memories, and adventures have conflict. And honestly, I struggle to find other people that have many (if any) regrets — so it’s not just me.

But you know what I tend to find a lot of?

Older people regretting not doing a thing.

Every failure, every path you try, one at a time —it’s prescribed; it’s not optional.

And understanding that saying yes to A does not mean saying no to B through Z is how you make finding a path in life easy.

That’s how you take away the pressure. B, C, D, and E are all coming, but first, you want to give A a good try.

And that’s how you rack up experiences and stories.

The destination isn’t the cool part.

Mordor sucked in Lord of The Rings. It was a shitty volcano thing. The adventure, the path — that was the cool part.

And I’d say multiple paths tried one after the other in the pursuit of fulfillment is the story I want to hear. The story with zero regrets.

Not one where someone does the same things for 30 years.

So don’t worry about what’s “optimal.” Start with your interests and try different things. Two-week experiments and six-month projects is a great framework to start.

And in 2–3 years, you would have lived infinitely more “life” than someone trying to figure out a path and standing still while doing it.

Good luck, my friend.

✌ Sah

I hope you enjoyed that one. Keep up with my shenanigans here; I post maybe 2–3 times a week. And hey, if you want something deeper than this article, I’ve written a small book on sorting the mess that life-decision pressure can cause — enjoy!

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