How to Make Big Life Decisions

Hi there,

I just got back to London after being away for the past few months. Something about flying, being in that nowhere space between places, always gives me unusual clarity. No WhatsApp notifications. No laundry or dishes to do. Just altitude and quiet.

Up there, life feels far enough away to finally start making some sense.
And my life lately has turned completely upside down.

In the last six months, I’ve quit my job, moved across the world, started over in a new field, and taken more terrifying leaps than I ever thought I had in me.

All because of the start of the year, I made one promise to myself:

Take the bigger risk.

I decided that would be directional compass for me this year because as a professional overthinker, I’ve stayed in relationships, jobs, and cities longer than I should have because I was playing it safe.

And that’s exactly what kept me stuck.

It sounds noble, right? Wanting to have all the puzzle pieces figured out to make the “right” decision.

But I’ve learned (sometimes, the hard way) that chasing happiness is a terrible GPS.
It’s foggy, glitchy, and panics every time the terrain gets uncertain.

Happiness, as a metric, is too easily hijacked by fear.

It favors comfort.
It rewards familiarity.
It hates disruption.
But growth loves disruption.

And growth, unlike happiness, is trustworthy. It’s measurable. It has receipts.
How do I know? Because you feel growth in your bones.

Ask anyone who’s ever left something safe and good-ish to pursue something uncertain and meaningful. It rarely felt “happy” in the moment. If they’re honest, they’d tell you it felt like a panic attack in a parking lot. Because it does.

The truth is that we’re terrible at predicting what will make us happy.

You think staying will bring peace. It brings resentment.
You think leaving will ruin you. When in reality, it gives you space to grow.

A friend recently asked me if she should leave a job that paid well, gave her prestige, but made her feel dead and numb inside.

I asked her one question:

“Are you shrinking or expanding there?”

(She quit 2 weeks later.)

If you're wired to be high-functioning, emotionally intelligent, self-aware, a good thinker, you’re also probably good at disguising fear as logic.

It sounds like:

• “I just want to be sure I’m making the right decision.”

• “I’m still trying to understand my feelings.”

• “Let me think about it a little more.”

But the harsh truth is that you’re not thinking. You’re delaying.
And you’re not gathering insight. You’re gathering excuses.

And guess what? Your nervous system is eating it up because staying stuck feels safer than the unknown of action.

There’s this belief that if we think enough, journal enough, or therapize enough, we’ll finally hit the jackpot of certainty… and then we’ll act.

But most people don’t suffer from lack of insight.
They suffer from insight constipation.

Too much reflection. Too much awareness. Not enough action.

You don’t become braver by intellectualizing fear.
You become braver by doing the thing scared, badly, awkwardly and surviving it.

No amount of analyzing prepares your body like a single real rep of experience.

So, forget chasing happiness. Ask instead: Will this decision expand me, or shrink me?

This question has carried me through career pivots, endings, and new beginnings. It cuts through the noise of anxiety and analysis paralysis every time.

In life, we’re told to “keep doors open.” To be “rational.” To “think it through.”

But here’s a weird psychological truth:

Irreversible decisions tend to make us more satisfied.

Why?

Because once there’s no turning back, your mind stops scanning for exits and starts scanning for opportunities.

You stop second-guessing and start adapting.

Burning the bridge isn't reckless. Sometimes it's the most clarifying thing you can do.

TL;DR – If you’re stuck:

Don’t ask:

• Will this make me happy?

• Will this make me more liked?

• Will this make sense to other people?

Ask:

• Will this make me larger or smaller?

• Am I choosing comfort over growth?

• If I removed fear from the equation, what would I choose?

Then make the choice that scares you just enough to mean you're still alive in there.

READER POLL

Final Thought

Most of the best decisions I’ve ever made didn’t look wise on paper.

They didn’t look safe. They looked like jumping off cliffs in bad weather, with no parachute. Just faith and a gut feeling.

But they made me bigger. And allowed me to take up more space.

So if you’re waiting for the perfect timing, the green light, the guarantee, you’ll wait forever.

Real life doesn’t come with clarity in advance. It comes with clarity in motion.

So forget chasing happiness or comfort.

Chase the thing that asks more of you.

That stretches your edges. That scares you just enough to prove you’re not sleepwalking through your one wild and precious life.

If you’ve been looking for a sign, this is it.

Your nudge.
Your invitation.
Your moment.

Say yes to the leap you’ve been thinking about.

And let who you become on the other side astonish you.

See you next week,

Shakila

P.S. Here’s the results of last week’s poll.