Trust the Rule of 100

2.5 years ago I got a call from my buddy Ryan with a wild idea.

Do you want to paddle 23 miles across the Catalina Channel?

It was an insane question, mainly because I’d never paddled more than a mile or two while surfing.

But I said yes.

Because I’ve always believed in something I call the rule of 100.

I shared it a few weeks ago and a few thousand people resonated with it:

“Trust the rule of 100. If you want to become “good” at something, just go do it 100 times. Write 100 blog posts, make 100 videos, run 100 days in a row. Stop focusing on what you need to know before you begin, and just begin. By starting, experimenting, and iterating you will learn 100x more than 100 days of overthinking.”

I think it resonated because for most of us, it’s easy to overcomplicate things.

Overanalyzing, planning, strategizing, but failing to take action.

And that’s the cardinal sin.

Because without action you learn nothing.

There’s a story from the book Art & Fear that articulates this perfectly:

On the first day of class, a ceramics teacher split his students into two groups.

The first group would be graded purely on quantity.

50 pounds of pots gets an A, 40 pounds gets a B, and so on.

The second group would be graded on quality. They only had to make one pot, but it had to be perfect.

At the end of the semester, the best pots all came from the quantity group.

While they were cranking out pots and learning from every mistake, the quality group spent the semester theorizing about what perfect looked like, and had very little to show for it.

And this applies way beyond pottery.

I have a friend who set a goal to initiate 100 conversations with interesting people this year.

Whenever he’s at an event, a coffee shop, traveling, etc., he’s constantly looking for people he thinks fit his criteria.

He starts a conversation, sometimes tells them about his challenge (people laugh), and builds a relationship.

Sometimes the conversation goes nowhere.

But because of this challenge he’s found new customers, met his girlfriend, and built countless new friendships.

MrBeast, the biggest YouTuber in the world, uses the same idea as a filter.

He gets countless requests from people who want to “pick his brain” about YouTube, and he tells them all the same thing.

Go make 100 videos, and focus on making one thing better each time.

If someone’s not serious, they never do it.

If they are, and they actually go make 100 videos, they no longer need his advice because they’ve figured it out by doing.

The bar for “better than most people” is much lower than it feels.

Most people never start a given skill.

Of those who do, most quit early or practice casually without trying to improve.

Spend one hour a day on something for 100 days and you’ve put in 100 hours.

If those are deliberate hours (practicing with feedback, working on weak spots, studying people who are better), you’ve already passed nearly everyone.

Which brings me back to Catalina.

After I said yes to Ryan, I went out and bought a prone paddleboard (I didn’t even know these things existed), and a week later I was on a morning 4-mile paddle finding my groove.

I paddled 3-4 times a week.

100 days later, I paddled 23 miles across the channel, documented the whole thing with brands sponsoring it, and by that point was arguably in the top 1% of the world at this new “skill.”

I did the same with making videos online, with writing newsletters, and with making sales calls early in my career.

My current thing is a Q4 lock in doing daily 20-minute kettlebell AMRAP workouts.

Today is day 30 and I’ve almost doubled the amount I could do on day 1.

There’s something to be said for thinking less, and finding the simplest path to what you want.

The secret is starting and just not stopping.

Most people think it’s too simple, so they don’t believe it.

The rule of 100 can be applied to basically anything you want.

So if there’s something you’ve been wanting to get better at, I dare you to try it.

Shoot me a note and let me know how you’re going to use it.

Rooting for ya.

-Dodds

(P.S. In a few weeks I’ll be opening applications for my next in-person retreat in February 2027. This year I hosted one in San Diego and one in Norway. This next one will be in New Zealand. If you’re a founder who wants to spend a long weekend with a group of killers, you can get on the waitlist here.)