How do I know I'm making the right choice?

I’ve been thinking about something since I wrote Part 1 (in case you missed it linked here) . We spend so much time trying to make the right decision.

The right time to leave.

The right business idea.

The right amount of money in the bank.

The right next chapter.

And I get it. At this stage of life, decisions can feel like they carry more weight.

We have mortgages, kids, college, aging parents, careers we’ve spent decades building, financial responsibilities...there’s more at stake.

But I see something happen when women become so focused on getting it right.

They stop choosing at all. They stay in the job another year. Keep thinking about the idea. Wait until things settle down. Research a little more.

And meanwhile, time keeps moving.

I know this one personally. When I was rebuilding my life after my divorce, I desperately wanted to know that the decisions I was making were the right ones.

Where to live. How to support myself and my boys. What I was going to do with my career. What kind of life I was actually building now.

There was no one standing there saying, Yep Lucy, this is definitely going to work out.

I had to make decisions without knowing. Some worked. Some led me somewhere completely different. Some I changed my mind about (including dating!).

And some eventually led me here, doing work I absolutely love, in a life I couldn't have mapped out back then.

That experience changed the way I make decisions.

I’ve become way more open at exploring directions with the information I have (and no bullet proof plan), listening to what I know about myself, and trusting that I can adjust if I need to.

That’s a very different way to live.

Why This Matters

I work with incredibly capable women.

Women who have made big decisions their entire lives.

Yet when the decision is about themselves and what they want next, suddenly the stakes can feel enormous.

Because underneath “What if I make the wrong decision?” is often something much bigger:

What if I regret it?

What if I lose the security I've worked so hard for?

What if everyone else thinks I've lost my mind?

What if I discover I'm actually not capable of doing this?

So we look for certainty.

Except certainty isn't usually available at the beginning.

You build trust in yourself by seeing that you can choose, respond, adjust and choose again.

A decision doesn't have to dictate the next ten years of your life.

It can simply be the best next choice for the woman you are now.

You can make a good decision and still feel uncertain about it.

I wish I’d understood that earlier. The nerves don’t automatically mean don’t go. The questions don’t mean you’re making a mistake. And changing your mind later doesn’t mean you got it wrong.

We put so much pressure on ourselves to know. But sometimes you make the best choice you can with what you know today...and trust yourself with tomorrow.

With you in it,

P.S. If your “what now?” feels bigger than one decision and you want someone beside you to help get underneath it, that’s exactly what we do in my Next Chapter Roadmap Intensive.

- 90 minutes intensive

- 30-minute follow-up

- your personalized Roadmap to turn all that noise into something you can actually work with.

Book your Next Chapter Roadmap Intensive

Lucy Regan

18 Bayview Avenue
Mill Valley, CA 94941, United States