Chapter 59: The 3 Phases Of Every Breakthrough

January 2025 was the darkest period of my life.

I’d blown up my life, sold 80% of my things, and moved to Portugal with the thought I'd be surfing every day and living my best life. Boy was I wrong.

Instead, it was pouring rain for weeks at a time, and I was trapped in what felt like a cement jail cell.

On top of that, I had no income, no community, and no structure.

Oh, and I'd fucked up my visa process.

At the end of March, I would have to leave the country.

I spent most of January overthinking and wondering if I'd made a massive mistake.

The path in front of me wasn't clear, and the uncertainty was suffocating.

But something shifted the first week of February.

I got so fed up with my lack of progress that I looked in the mirror and snapped.

I said "fuck it" and booked a last-minute flight to New York. I went for 48 hours to attend a visa appointment that might (might) give me a shot at staying.

And on that trip, I committed to The Daily Experiment: telling 30 stories in 30 days.

While I'd committed to building this new skillset of short form video, I didn't know if I actually enjoyed it.

And the first two months of creating did not inspire confidence. I was making videos every 2-3 days (and not growing at all).

So I knew something needed to change — and fast.

This decision kicked off a seven-month period of obsession. I posted 97% of days and started growing my audience by 100+ people per day.

I fell in love with the process. It became a game and I could see myself leveling up in real time.

I said no to tens of brand deals and remained focused on building towards my own products and businesses.

The real skill I cared about was learning to create, communicate ideas, and build trust online.

Short-term money didn't matter.

I committed to the identity of being a creator. Nothing else mattered as long as I created something I was proud of every day.

This started with short-form content, but I knew it would lead to my own products and businesses.

I spent 1000+ hours studying the game. Watching podcasts, going through courses, and reverse engineering what worked and what didn't.

I pursued this new path with ruthless abandon.

And three days before I would've had to leave Portugal, my visa got approved.

Booyah. The show goes on.

After five months of doing this ~7 days a week, I could feel the burnout creeping in.

I was making progress, but the pace was unsustainable

So I started to shift.

I launched a second email list for my content products. Then secured my first high-ticket consulting client.

Next, I launched Story30, a cohort for founders and brand builders who wanted to grow their audience and business using content. (get on the waitlist for the next one here)

As I entered fall of last year, I realized I'd accomplished what I set out to do in the beginning of the year.

The obsession phase worked, but it wasn't sustainable.

I knew I needed to systemize and enter my next chapter.

So I stripped it down to three things: writing, coaching/consulting, and a new software project.

I also decided to wrap up the Portugal chapter. I wanted to be closer to family and be in a city of ambition, so I decided to head to San Francisco for the next year.

Phase 3 was about working smarter. I built structure around what mattered and let everything else fall away

I didn't see the pattern until it was over. But looking back, every breakthrough in my life has followed the same three phases:

Phase 1: Feeling Lost

You're overthinking, anxious, and questioning the point of it all.

You're trying to make progress, but you're in the unknown and the path in front of you isn't clear.

Phase 2: Becoming Obsessed

After weeks or months of feeling lost, you finally snap.

You put on the blinders. You work hard, long hours, and can't pull yourself away. You start to see progress and become addicted to it. This is where breakthroughs happen, but it's not sustainable.

Phase 3: Building Structure

By this point, you figure out what works.

So you begin to build systems.

You strip it down to the 2-3 things that create momentum and recalibrate for the next chapter.

Then, you repeat.

You aim for the next level, feel lost, become obsessed, and build structure again.

This is the natural cycle.

The thing most people don't understand is that the snap doesn't happen when you feel ready.

It happens when staying stuck becomes more painful than changing.

I didn't fly to New York and commit to The Daily Experiment because I knew it would work.

I did it because it was the only thing I could see that would give me a chance to make this path work. I reached a breaking point and couldn't tolerate the lack of progress anymore.

Action (any action) was better than the suffocation of uncertainty.

And when I reflect, it's the same trigger that has kickstarted all the best periods of my life.

When the pain of staying still becomes greater than the fear of the unknown, you snap. And that decision, the decision to act with ruthless conviction, changes everything.

If you're stuck right now, you might be closer to a snap than you think.

The people who make insane leaps aren't the ones who never feel stuck.

They're the ones who get so fed up that they snap and take relentless action toward what they want.

I now look back at that seven-month period as one of the best periods of my life.

Not because it was easy, but because it forced me to become who I needed to be. And now I'm aiming for the next level. Which meant in December I was right back in Phase 1, moving back across the world, and feeling lost all over again.

But, over the past two weeks, I’ve entered a new period of obsession, and I can’t wait to see where I am 6-12 months from now.

The cycle never ends (and that's the entire point.)

I hope this helps.

Rooting for ya,

—Dodds