Chapter 27: F*ck Your 5 Year Plan. Go On A Side Quest.

One of my oldest friends just hit a milestone he’s been chasing for years.

He sold his first feature-length film script to a production company.

It’s huge.

He’s now saying things like “my agent” and “my lawyer.”

We were laughing about how surreal it feels.

Like he’s cosplaying as the guy in a Hollywood movie.

But he’s not.

He’s doing it.

He’s a writer. A producer. A storyteller in the arena.

And here’s the part most people miss:

This “overnight success” was 20+ years in the making.

How It Really Happened

Since we were teenagers, this guy’s been obsessed with movies.

Rewatching cult films. Quoting movies. Going to acting school in Paris.

None of it paid the bills. One could argue it didn’t make sense at the time.

But over the years, those late-night rabbit holes and unfinished projects added up to something real.

What felt like distractions?

They were the path.

Introducing: The Side Quest Mindset

If you ever played video games growing up, you know the deal:

Every game has a main quest.

But along the way? You take side quests.

You explore hidden alleys, learn new skills, & meet strange characters.

Sometimes those side quests give you the exact thing you need later on.

Other times, they’re just fun.

But they always make the game richer.

Real life works the same way.

My Life Is One Big Side Quest

At 18, I never would’ve guessed I’d be building a business around storytelling and content strategy.

But looking back, I…

• Hustled as a kid — from candy sales to dog walking

• Made travel videos in my early 20s

• Studied abroad and traveled through Europe, Asia, and Central America

• Spent 8 years in tech learning how to sell and build teams

• Got into endurance sports and became an Ironman

• Became obsessed with how the best brands built cult-like fan bases

• Took courses on media & content-led businesses, writing, and AI tools

• Started writing daily and learning from the world’s best thinkers

None of it looked connected at the time.

But now?

I see it clearly.

All these side quests laid the foundation for the life and career I’m building today.

The Steve Jobs Chapter Most People Miss

When Steve Jobs dropped out of college, he didn’t stop learning.

He sat in on classes that sparked his curiosity — like calligraphy.

Random, right?

But years later, that obsession with beautiful typography helped define Apple’s iconic design language.

Then, when he got pushed out of Apple?

He went on two side quests:

• He built NeXT, a computer company

• He acquired and scaled Pixar

Both wildly successful in their own right.

And when Apple brought him back?

He brought everything he learned with him.

Those side quests didn’t distract from the main quest — they defined it.

The Problem With Adults

When you’re a kid, you explore.

You fall, skin your knee, and try again.

That’s how you learn.

But somewhere along the way, we stop doing that.

We get obsessed with linear paths. With titles. With playing it safe.

We think every move needs a clear ROI.

And we forget the magic of doing something just because it lights us up.

So your job right now?

Keep collecting dots.

This Is Your Reminder:

You don’t need a perfect plan.

You don’t need to know what your life will look like 10 years from now.

You just need to follow the curiosity that keeps tapping you on the shoulder.

Pick up that camera. Take the course. Start the weird project.

Go on the side quest.

Because one day?

It might turn into the main one.

Try This Today:

If you’re feeling stuck, ask yourself:

• What am I curious about… but not giving myself permission to explore?

• What’s one tiny “quest” I could go on just for the fun of it?

• If I zoomed out 10 years, what might this chapter actually be preparing me for?

Don’t underestimate your detours.

They might be the most important thing you do.

Wrapping Up

So no — your path doesn’t need to make sense yet.

But it does need motion.

You learn by doing. You build momentum by exploring.

You discover what matters by getting lost a little.

Because one day soon…

You’ll look back and realize those side quests weren’t distractions.

They were training.

And you’re more ready than you think.

Rooting for ya,

—Dodds