Hard Decisions Don't Come With A Manual

I’ve got a theory: Life decisions are never objective.

As a result the most important skill in life might be training your intuition.

It’s why the pros & cons list never feel right. It’s why flipping a coin is a good way to make decisions: “You’ll know the answer you wanted before the coin hits the table.” It’s why you can’t spreadsheet your way to a life you love.

Take buying a house.

We just bought a new one. Before selling the old one. With a market situation that could charitably be called rude.

The math says: this is going to sting. Potential double mortgages. Temporary liquidity crunch. Short-term pain.

But none of that really matters long term. We looked at each other and said, This feels like home.

And that was that.

It’s not that we ignored the numbers. It’s that we knew the numbers were only part of the picture. Just make sure not to put yourself in a situation where you can multiply by zero.

The spreadsheet couldn’t factor in the neighbourhood vibe, the quiet in the backyard, the sense of rightness that’s hard to fake.

Which brings me to the real question:

How do you train your intuition?

“Follow your intuition” is great advice right up until your intuition turns out to be an untrained golden retriever chasing shiny things.

Your gut is not irrational. It’s built on everything you’ve ever paid attention to. Everything you’ve read, endured, watched, regretted. It’s your subconscious connecting dots faster than your conscious mind can name them.

Here’s what’s helped me:

• Expose it to wisdom. Not viral content, longform thought. Books. Deep conversations. Mistakes you’ve owned.

• Let it speak. Clarity often comes in quiet moments. Long runs. Shower thoughts. Driving without a podcast. Let your mind roam and see where it lands.

• Run small experiments. You don’t build trust in your gut by waiting for life-changing crossroads. You build it by making tiny bets and watching what happens. Order the weird thing on the menu. Try the side project. Trust yourself in low-stakes ways.

• Do post-game reviews. After each decision, ask: what did I feel? What did I choose? How did it go? That’s the calibration process.

Don’t abandon reason. There’s value in research, planning and asking for advice.

But, when the path ahead is muddy, the stakes are high and your heart might know something your head hasn’t yet articulated…

Listen.

That’s a skill no one taught us in school: How to feel our way forward without a guarantee.

And yet — almost every meaningful decision in life requires exactly that feel. It’s time we start treating intuition not as a last resort, but as one of the most important tools we have.

Words I Wish I Wrote

Links & Learnings

• We bought a new house last week, I’m gonna use ChatGPT as an interior designer.

• If you’re not already, you should probably become a generalist.

• Adler’s Theory of Life Tasks: The theory of “life tasks” was developed by the Jungian psychologist Alfred Adler, who offers additional information that may help you identify your life tasks. Adler specifies that there are three types of life tasks: 1) work tasks, which are acts that benefit the community (regardless of monetary reward), 2) social tasks, which connect with others and foster altruism and empathy, and 3) love tasks, which center on finding love in intimate relationships. Later psychologists also added two types: 1) self tasks, which uncover your authentic self, and 2) spiritual tasks, which focus on understanding existence and the meaning of life.

Psst… DSTLLD has a podcast now, too. I know — like the world needs another podcast, right? But here’s the thing: if you can tolerate my written rambles, you’ll probably find my in-person yammering… well, moderately tolerable. It’s basically me and a guest chatting about the same offbeat stuff you read here, except now you get to hear me stumble over big words in real time. I’m not saying it’s the greatest thing in the universe (trust me, I’ve listened to it), but if you like DSTLLD, there’s a good chance you won’t hate it. Win-win! Subscribe or follow on your favourite podcast platform:

• Youtube

• Spotify

• Apple

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