The Hard, Liberating Work of Figuring Out What Makes You Happy

Happiness is not something ready-made. It comes from your own actions.
— Dalai Lama

Let’s get one thing straight: you get to decide what makes you happy.

Not your parents. Not your boss. Not Instagram influencers.

You can choose: hustle or slow mornings; minimalism or maximalism; adventure or deep roots; wealth or freedom or both.

But – and this is the brutal part – most people never find out what makes them happy. They drift. They settle. They wake up one day and wonder how they ended up living someone else’s version of happiness.

Why?

Because figuring it out is hard. It means sitting with yourself. Asking uncomfortable questions. Maybe even losing people who don’t understand the new you.

The good news? Once you know what makes you happy, the rest gets easier. Decisions become clear. Distractions fade. You stop wasting time on things that don’t matter.

If you don’t design your happiness, someone else will.

Ready to start?

Happiness Isn’t One-Size-Fits-All

Some people thrive in fast-paced careers. Others find joy in quiet, simple lives. Some love big social circles. Others prefer deep one-on-one connections.

There’s no "right" way to be happy. But we often judge ourselves for wanting what we want.

  • You love your high-pressure job, but feel guilty for not wanting kids.

  • You dream of living off-grid, but worry people will think you’ve “given up.”

  • You’d rather earn less and work less, but fear being called “lazy.”

First step: Stop apologising.

Then, ask:

  • What’s one thing I love that I’ve been hiding because it’s "weird" or "unacceptable"?

  • Who do I secretly admire – not for their success, but for their lifestyle?

  • If no one would judge me, what would I do differently tomorrow?

What makes you happy is personal. Stop comparing.

Why Knowing What Makes You Happy Everything

Imagine two people:

  • Person A vaguely wants “to be happy.” They say yes to everything – good jobs, nice trips, random hobbies. They’re busy but unfulfilled.

  • Person B knows they need three things: creative work, long walks, and deep friendships. They turn down promotions that demand overtime. They plan weekends around hiking, not brunches. They’re specific.

Who do you think feels better about their life?

When you know what makes you happy:

  • You spend money on what matters (and stop wasting it on what doesn’t).

  • You say no without guilt (no more "maybe" to things you dread).

  • Small choices add up (reading instead of scrolling, calling a friend instead of binge-watching).

Why Most People Never Figure Out What Makes Them Happy

Three big reasons:

A. Autopilot Feels Safe

It’s easier to keep doing what you’ve always done. Same job. Same routine. Same friends. Even if it’s not great, it’s familiar.

Question: “If I keep living exactly like this, where will I be in five years?”

B. “Shoulds” Steal Your Freedom

  • “You should want marriage and kids.”

  • “You should care about promotions.”

  • “You should like travelling.”

What if you don’t?

C. Fear of Rocking the Boat

What happens if you change?

  • Friends might drift away.

  • Family might worry.

  • Colleagues might gossip.

But ask yourself: “If these people don’t want the real me, why am I fighting to keep them?”

How to Find Out What Makes You Happy

1. Track Your Energy

For a week, note:

  • High-energy moments: What were you doing? Who were you with?

  • Low-energy moments: What drained you? Was it the task or the people?

2. Learn from People Who Radiate Freedom

Who inspires you not just by their success, but by their lifestyle?

Ask:

  • What do I admire about this person? Freedom? Creativity? Calm?

  • What could I do to feel that way in my current life?

3. Design Your Ideal Day

No limits. No rules.

  • Wake up when?

  • Spend the day doing what?

  • See who?

  • Go to bed feeling how?

Warning: This might piss you off. If your ideal day looks nothing like your real life, that’s a clue.

4. Figure Out Your Core Values

Rank these from most to least important:

  • Security (stable income, safety)

  • Freedom (flexibility, no boss)

  • Creativity (making things, expressing ideas)

  • Connection (deep relationships, community)

  • Impact (helping others, leaving a mark)

Now check: Does your life match your top three?

5. Write Your Eulogy

Not your resume. Not your social media.

How do you want to be remembered? As someone who…

  • Loved fiercely?

  • Built something meaningful?

  • Lived boldly?

Then work backwards.

Act As If You’re Already Happy (Even If You’re Not Yet)

Sounds fake, but it works.

Your “future happy self”:

  • Wears what? (Start wearing it now.)

  • Spends mornings how? (Do one thing they’d do.)

  • Talks about what? (Drop topics that bore you.)

Small actions rewire your brain.

What If You Had One Year Left?

Morbid but clarifying.

Ask:

  • What would I stop tolerating immediately?

  • Who would I see more? Less?

  • What would I finally try?

The answers aren’t about bucket lists. They’re about daily life.

Maybe you’d:

  • Quit the committee you hate.

  • Call your sister every week.

  • Start writing that book.

Why wait?

Cut What Doesn’t Spark Joy

Freedom starts with subtraction. This week:

  • Delete one app that drains you.

  • Cancel one obligation you dread.

  • Use page 7 of the Freedom Workbook to identify your "non-negotiables".

Happiness Is a Practice, Not a Destination

You’ll change. Your wants will shift. That’s normal.

Today’s assignment:

Pick one thing from above. Do it before bed.

Then notice how it feels.

That’s how you start figuring out what makes you happy.

Joanne Tai

An adventurer, and former seafarer.

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