I’ve been thinking a lot about waiting lately.
How much time I’ve wasted sitting on decisions, convincing myself that I needed just a little more time, a little more certainty. Like there was some magical moment coming where everything would fall into place, and I’d finally feel ready to take the leap. Spoiler: it never came.
It’s funny how convincing those arguments are when you’re inside them. “Let me save up a little more.” “I’ll wait until the kids are older.” “I’ll just finish this project first, and then I’ll have time.” And you believe it, because it sounds so reasonable. So logical. But if I’m honest, it was never about needing more time. It was fear, every single time.
I remember this one decision—I was debating whether to leave a stable job for something risky, something I wasn’t even sure I could pull off. It was all-consuming. I made pro/con lists. I had endless conversations with friends, with my wife. I Googled, researched, stared at the ceiling in the middle of the night running through worst-case scenarios. Weeks of this. Maybe months. And then one night, my wife just looked at me and said, “What are you so scared of?”
And I didn’t have an answer.
I mean, I could’ve said failure. Or regret. Or humiliation. Or some long-winded excuse about how the timing wasn’t right. But none of it felt real in that moment. Because what I was actually scared of was the part nobody talks about: what if I succeed?
Seriously. What if I actually pulled it off? What if it worked? That’s terrifying in its own way, isn’t it? Succeeding means change. It means new problems, new responsibilities, new expectations. And I think, deep down, I wasn’t sure if I was ready for that.
The irony is, I did it anyway. Wrote the resignation letter, walked into my boss’s office, and quit. Not because I had a sudden burst of courage, but because I realized I wasn’t going to feel ready no matter how long I waited. So why not now?
It wasn’t a graceful leap, by the way. I was a mess—sweating, second-guessing, fighting the urge to backtrack. I wish I could say it felt like freedom, but it didn’t. Not at first. It felt like chaos. And yet, looking back, it was one of the best decisions I ever made.
Not because it worked out. It didn’t, not exactly. But because I finally got out of my own way. I stopped waiting for life to hand me permission, and I just started.
That’s the part nobody tells you. Starting isn’t some epic, Hollywood moment where the music swells and the hero takes a dramatic first step. It’s awkward. It’s clunky. It’s half-baked ideas and stumbling and sheer panic. But it’s also the only way to get anywhere.
I think about all the people I know who are waiting. Waiting for the right time to ask for a raise. Waiting to start the business they’ve been dreaming about. Waiting for the perfect idea, the perfect opportunity, the perfect excuse to finally take themselves seriously.
They tell themselves it’s not the right time yet. That they’ll know when it is. But will they? Or will they still be sitting there five years from now, telling themselves the same story?
Here’s the thing: I’ve never met anyone who felt ready. Not really. Every person I’ve ever known who did something bold or scary or transformative has said the same thing. “I wasn’t ready, but I did it anyway.”
And you know what? They were fine.
Actually, they were more than fine. They were better for it. Not because everything worked out perfectly—because it rarely does—but because they started.
I don’t know who needs to hear this, but maybe it’s time to stop waiting. To stop rehearsing the story of why you can’t or shouldn’t or don’t have time. To just write the resignation letter, or buy the guitar, or start the thing you’ve been dreaming about for years.
What’s the worst that could happen?
You fail? You pivot? You make a fool of yourself and learn something in the process? Sounds like a pretty good deal to me.
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