When to Back Yourself, or Back Away?

In 2019, I got on a plane to fly to the US with a knot in the pit of my stomach.

I was going to train in person with Brené Brown to become a Dare to Lead™ certified facilitator.

Dare to Lead was brand new then. Barely off the back of the book, no track record to point to, no long list of graduates I could ask, “Was it worth it?”

I couldn’t show anyone the results.

I couldn’t really explain what I was signing up for.

I just had a feeling that “trusting my gut” (as my dad used to say) that this was the work I was meant to be doing, and a fee on my credit card that said I’d decided to find out.

Reflecting on what that moment actually felt like makes me want to be honest with you.

I think we romanticise these decisions after the fact. It didn’t feel brave. It felt like a risk I couldn’t fully justify on paper. I was investing money I’d worked hard for, and time away from my business, in a program that was still finding its feet. Yes, it was built on research I believed in, taught by someone I trusted, but with absolutely no guarantee it would go anywhere.

There was a very reasonable version of me that stayed home. Waited a year. Watched what happened to the people who went first, and made a safer decision once there was evidence to back it up.

But I didn’t do that.

Something in me said this was the moment. Not next year, not once it was proven, right now. And I’ve spent time since trying to understand what let me hear that and act on it, because I don’t always.

I can point to plenty of other moments where I backed away, and it was exactly the right call.

That’s the part people leave out when they tell these stories. Backing yourself isn’t the answer every time. Sometimes backing away is the wise, grounded, self-respecting thing to do. The skill isn’t courage on demand — it’s telling the two apart.

What I’ve learned, six years and around 2,000 trained leaders later, is that the decision was never really about Brené, or the program, or even the plane ticket. It was about whether I trusted myself enough to move before I had paper proof. Since then, I’ve had to recertify — and I’ve watched roughly half the facilitators in any given cohort not make it through that bar. Not because they weren’t capable, but because staying sharp at this work takes more than the initial leap. The leap gets you in the room. What you do after is a different kind of daring altogether, and a quieter one; showing up, recommitting, doing the unglamorous work of staying good at something, year after year.

I think about that trip a lot, especially now, listening to people wrestle with their own version of it — a decision they’re not sure they should make, a path with no guarantees, the thing that would mean betting on themselves before anyone else has. I don’t have a formula for knowing which way to go. I just know the feeling of the decision, and I know it’s rarely as loud or as obvious as we want it to be.

So I’ll leave you with the question rather than an answer, because I think it’s a better use of your time than mine: when was the last time you stood at that fork in the road — back yourself, or back away — and what did you do? And looking back now, do you still think it was the right call?

It’s your time now!

Tammy x