Chapter 29: How to Use Discomfort to Change Your Life

In ancient cultures, before boys became men they were sent into the wilderness.

Spartans. Samurais. Native Americans.

Each had a rite of passage.

To hunt. To survive.

To face the unknown and return transformed.

But today?

No one sends you into the wild.

There’s no ceremony. No fire. No final test.

So most people drift through life.

Mindlessly scrolling. Waiting for clarity.

Never living up to their potential.

If you’re reading this, you’re not most people.

But you still might need your own rite of passage.

Today, we’ll walk through how to do it.

The Death Before the Rebirth

Real transformation requires a death.

Not physical — but identity-based.

A letting go of the old version of you:

The comfort seeker. The people pleaser. The one who plays it safe.

Joseph Campbell said it best:

But no one’s forcing you in.

If you want to become who you’re meant to be — you have to choose the path yourself.

To leave comfort behind. To face the unknown.

To go into the wilderness and bury the old version of yourself — so the real one can rise.

Why We Crave Hard Things

This is why discomfort is magnetic.

Why sports teams bond in brutal preseason.

Why the military forges identity through shared suffering.

Why startups weld people together — one all-in day at a time.

Because doing hard things changes who you are.

It draws a line between who you used to be and who you're becoming.

Before the Ironman. After the Ironman.

Before I quit drinking. After I quit drinking.

Before the leap. After the leap.

Without that line, there’s no story.

No tension. No transformation.

And no pride in who you’ve become.

The Modern Rite of Passage

I’m not saying you need to go full Bear Grylls.

But you do need a challenge that recalibrates your identity.

Something that demands effort. Intention. Sacrifice.

Whether it’s:

• Learning a new skill

• Leaving your hometown

• Running your first marathon

• Building a business from scratch

• Doing 75 Hard — and finishing it

The challenge matters less than the decision:

To enter the unknown.

To choose discomfort.

To bet on yourself.

Because in a world built to keep us numb…

Discomfort is a portal.

And the ones who walk through it?

They don’t just change their life — they become who they were always meant to be.

Try This Today

1. Name the Cave.

   Write down the challenge you keep avoiding — the thing that scares you, excites you, or keeps tapping you on the shoulder. That’s your portal.

2. Set a Date.

   Give yourself 72 hours to commit. Sign up. Book the flight. Tell someone. Make it real.

3. Create the Constraint.

   Block the time. Get an accountability partner. Go public. Discomfort needs a container.

4. Document the Journey.

   Use voice notes, short videos, or a journal. Reflection turns effort into meaning.

5. Return With the Lesson.

   When you finish, write down what changed. What did you let go of? What did you gain? Who did you become?

Because rites of passage aren’t about trophies.

They’re about proof. To yourself first, then the world — that you can go into the wilderness, brave the unknown, and come out transformed.

P.S.

This idea — using story, challenge, and identity change — is the core of what I’ve built my life around.

If you’re a founder and want to go through a transformation like this, I’m opening up 5 spots for July to work 1-on-1 with me.

You’ll choose a challenge and go through StorySchool — my accelerator for founders who want to grow their business by leveraging story and the modern media playbook.

Reply here if you want to discuss — or join the waitlist [here].

Rooting for you,

—Dodds