Crippled CEO Blog #182: The Gap Between “Not Ready” and “Too Late”

Crippled CEO Blog #182:

There’s this weird little gap in life. You’ve probably noticed it. It’s the chasm that exists between feeling like you’re “not ready” and realizing it’s “too late.”

It’s sneaky, too, because it’s almost never an actual timeline. It’s a feeling. A mindset. A story we tell ourselves. And if you’re like most people, you’ve probably stood in that gap, stuck, more times than you’d like to admit.

The gap shows up in all kinds of places.

You’re not ready to start the new project, the new relationship, or the new habit… until one day, you look back and think, “I missed my chance.”

You’re not ready to speak up in a meeting, pitch your idea, or apply for the job you really want… until someone else does, and the opportunity is gone.

You’re not ready to reach out to someone you miss, someone you love, someone who hurt you… until they’re gone for good, and it’s too late.

This gap is where dreams go to die. It’s where regret sets up camp.

And the thing is, the gap is almost always imaginary. That “not ready” feeling? It’s rarely true. You’ve probably been ready for a while now—you just haven’t given yourself permission to act. And that “too late” realization? More often than not, it’s just your brain being dramatic.

The reality is that most of the time, you’re as ready as you’re ever going to be.

Let me tell you a story.

When I was in my early twenties, I wasn’t ready to run Life Saver Pool Fence. My dad had retired, and suddenly, this entire company was on my shoulders. People were looking at me like I knew what I was doing, but I didn’t. I felt like a fraud. I wasn’t ready.

But guess what? No one cared if I was ready. The business didn’t care. The employees didn’t care. The customers didn’t care. Ready or not, it was time to go.

So I figured it out. I stumbled. I made mistakes. Some of those mistakes were really stupid, like “what-the-hell-was-I-thinking” stupid. But I kept going. And somewhere along the way, I became ready.

Here’s the thing: readiness is a lie. It’s a mirage. It’s the procrastinator’s best friend and the perfectionist’s excuse. If you’re waiting to feel ready, you’ll be waiting forever.

Now, don’t get me wrong—there are actual deadlines in life. There are moments when opportunities really do expire. That’s why I’m writing this. Because the only way to bridge the gap between “not ready” and “too late” is to stop waiting for readiness and start doing something. Anything.

Feeling unprepared? Start small. Start messy. Start scared. Just start.

The best things in life happen when you step into the gap and act before you feel ready. When you stop overthinking, stop hesitating, and stop worrying about all the ways it might go wrong.

If I can run a company while feeling like a clueless kid who had no business being in charge, you can take the next step toward whatever you’re hesitating on.

And if you’re worried it’s too late, let me remind you: my dad didn’t start winning until he was 40. You’ve got time.

Just don’t waste it standing in the gap.

(Do you know who never hesitates? Your mom. She was ready last night, and she didn’t waste a single second. Your mom also gets a text from me every Sunday with a link to the latest blog post. Send a text to 561-726-1567 with the word CRIP as the message to get a link to the blog as soon as it’s up.)