The Wave They're Riding and the One That Often Breaks

There’s a conversation I have often with leaders in transition.

It usually starts with momentum.

An interview process moving quickly.
A promising recruiter call.
A sense that this one might finally be the answer.

And then comes the pause.

“Let me ride this out a little longer.”
“I just want to see where this goes.”
“I think I need to try this on my own for a bit.”

This month, I had one of those conversations again.

A thoughtful, capable executive shared that he was actively interviewing for a role that felt exciting and validating. He’d shifted his energy away from endless applications and toward something that had historically been uncomfortable for him: asking his network for help. That shift alone was already paying dividends—new conversations, referrals, momentum.

And yet, he hesitated.

Not because he didn’t see the value of coaching.
Not because he didn’t understand the strategy.
But because he was in the middle of a wave and part of him wanted to believe that this wave might carry him all the way to shore.

This is the moment I see repeatedly.

When momentum returns, people often feel they should wait.
When things feel uncertain, they’re more willing to ask for support.

Ironically, it’s often the opposite of what serves them best.

What I know—because I’ve walked alongside hundreds of leaders through these transitions—is that relying on a single opportunity is rarely a strategy. It’s hope. Sometimes hope works. Often, it doesn’t.

And when that one opportunity doesn’t materialize—as many don’t—people come back.

They come back tired.
They come back frustrated.
They come back saying, “I wish I had started sooner.”

I feel that with them.

I wish I could help them see it while they’re still in it—that this moment of momentum is actually the best time to build multiple flywheels, not pause the work. That support doesn’t replace their effort; it amplifies it. Having someone on their team doesn’t mean the wave will break—it means they won’t be stranded if it does.

And still, I remind myself of something essential:

This is their journey.
I am not here to push.
I am here to guide.

Every leader must feel ready. Safe. Aligned in their own body and timing. My role is to ask the questions that help them reflect—not to force the answer.

Some will move forward immediately.
Some will circle back later.
And when they do, the work begins exactly where it needs to.

If you find yourself riding a promising wave right now, ask yourself this:

What’s the risk of doing nothing differently?
And what’s the risk of building support before you need it?

There’s no right or wrong answer—only the one that’s honest for where you are.

And when you’re ready, I’ll be here.

— Gwen