How to Know If You’re Ready for Your First 100 (or 200) Miler

If you’ve ever found yourself circling the question, “How do I know I’m ready to move up in distance?”—you’re not alone.

That question keeps a lot of runners stuck. They don’t know how to answer it, and because they can’t answer it with absolute certainty, they assume they’re not ready.

What they’re really trying to do is erase the risk. To find enough evidence to make the fear disappear. They think once they feel confident they’ll finish, then they’ll know it’s the right time.

But that moment doesn’t come. The fear doesn’t go away. The guarantee never shows up.

And so they keep waiting.

Let’s call this what it is: you’re not actually wondering if you’re ready. You’re wondering if you’re going to succeed. And the truth is, nothing can answer that for you. There’s no training plan, no amount of mileage, no coach, no expert who can guarantee your finish.

But here’s what I know from coaching ultrarunners for years:

If you’re asking this question, it’s because the opportunity is in front of you.

You’ve got some training under your belt. A race you’re eyeing. A moment where it would make sense. That’s why the question is even on your mind.

So let’s stop trying to erase the fear and start with something more powerful: a decision.

Not a decision about whether you can finish - a decision to go for it.

Because that’s the part you can control.

Once you decide to take the leap, you can get on with the real work: preparing, training, building belief, planning logistics, and shaping the kind of race experience you want to have.

It feels so much better to be moving forward—working toward a goal—than it does to stay stuck wondering endlessly whether you should go for it.

Waiting to feel ready wastes time. You can lose months—even years you can never get back—trying to out-think fear. And while you’re waiting, other runners are gaining experience, growing confidence, and stacking results… not because they were more ready, but because they said ‘yes.’

I know because I lived it.

I ran ultras for a couple of years before I ran my first 100. I always thought I’d do one eventually—but “eventually” has no timeline. Eventually can stretch out forever.

One June, after repeating the usual 50Ks and 50 milers, I ran a 40-mile race I’d also done before. When I finished, I had nothing on the calendar. I’d trained well. I’d finished the race. And now what? There wasn’t anything I was itching to do. I could keep running the same races, and that would be okay, but the next race was a few months away and I could fit something in between.

The idea was there before I could think it: What about 100 miles?

It didn’t feel like the “right” time. I hadn’t planned on it. I hadn’t picked this out as the year I was going to run my first 100 miles. I didn’t feel ready—didn’t even know what that would look like. But I was standing at a clear fork in the trail. This was an opportunity. I had enough base. I had enough time. I had the itch.

So I got honest with myself.

If I didn’t sign up, it wouldn’t be because it wasn’t the right time. That would be an excuse. It would really be because I was scared. And if I passed up this window, I’d always know I turned down a real chance. Maybe the best one I’d ever get. 

Passing this opportunity up would be saying I didn’t believe in myself and wasn’t willing to do what it takes to make my dreams a reality. If I went down that road, I could see becoming someone who talked about running 100 miles… but never actually did.

And that was the moment I made the decision.

Not because I was certain I’d finish.

But because I wanted the experience. I wanted to see what it was like. I was ready enough.

And I wasn’t about to let fear bully me. Not about this.

So I signed up. And then - I set about getting ready.

That’s how it works. Decision first. 

Then confidence. Then preparation. Then the race.

I finished that race. It wasn’t at all perfect by performance standards, but it was exactly what I needed it to be. And I’ve never once regretted grabbing the opportunity when I had it. In fact, my only regret is that I didn’t start sooner.

If you’re wondering whether you’re ready to make a leap in distance—whether it’s to your first 50, your first 100, or something else entirely—stop trying to find the perfect moment. Or wondering if you’re ready.

Look at the opportunity in front of you.

Decide if you’re going to take it.

That’s how you know you’re ready.

And once you do?

You’ll stop spinning in indecision.

You’ll start figuring out how you’ll do it.

You’ll start building confidence about it.

And a year from now, you won’t be wondering if you’re ready—you’ll be wondering why you waited so long.