In 2007, my husband and I left a stable, senior role in advertising and moved across the country, to start something of our own. The timing, by any rational standard, was questionable, as the economy was showing signs of, to put it mildly(!), strain. We had a mortgage, and no roadmap for what was next. And yet—I felt oddly calm.

The people around me were more nervous than I was. Friends, family, and former colleagues couldn’t understand why I’d leave when I was “at the top of my game,” and when I had an actual paying job when people were starting to lose theirs. But the truth was, I knew it was time. Not because the conditions were perfect, but because something in me had shifted. I was ready to build something different.

We like to think there’s an ideal moment to begin—a green-light feeling that says “go now.” But more often, what we’re actually waiting for is a sense of certainty.

Certainty that we won’t fail.
Certainty that it will be worth it.
Certainty that people will understand (and not judge us).

But certainty is rarely part of the equation at the beginning. Especially when what you're considering feels deeply personal—starting a company, making a pivot, or reimagining your business. As I wrote in The Real Reason You Fell Stuck, we often label these hesitations as being “stuck,” when what’s really going on is a negotiation between our desire for clarity and our fear of risk.

In When, Daniel Pink explores how we misread timing by focusing too much on external cues—fiscal calendars, market cycles, school years—and not enough on internal timing: that flicker of misalignment, the quiet urgency to grow, the sense that your current path no longer fits. Those signals may be soft, but they’re not wrong. They’re valuable information.

The challenge is that even when you know something’s off, it’s easy to convince yourself you need more clarity before taking action. But as we explored in my recent post, The Power of Clarity, clarity isn’t the end state—it’s the foundation. It sharpens through movement, not before it.

And movement doesn’t have to be bold or irreversible.

In Tiny Experiments: How to Live Freely in a Goal-Obsessed World, Anne-Laure Le Cunff invites us to treat personal and professional growth like a series of small experiments designed to be low-stakes, curiosity-led, and rich in feedback. When you stop trying to prove something and start trying to learn something, the pressure changes. The path opens up.

So if you’ve been waiting for the perfect time to act, you’re not alone. But what if instead of waiting, you made a move? Not a leap. Just a test. One that helps you listen more closely to the part of you that already knows what it’s time for.

Reflection Prompt

What are you postponing because the timing doesn’t feel ideal? What internal signals are you tuning out?

Mini Exercise: Redefine Readiness

Write down three things you believe you need before you can take your next step. Now ask yourself:

Are these prerequisites or just protection?
What’s one small, low-stakes action I could take this week to test the waters?

If you’ve been waiting for the right moment, I’d be glad to help you figure out what’s actually holding you back. Sometimes all it takes is a grounded conversation to turn hesitation into momentum—and help you take that first step with intention. Let’s talk!