Have you ever built more confidence after a setback than you ever built by playing it safe?
Confidence after a setback doesn’t usually feel like confidence while it’s happening. It feels like the floor dropping out. It’s less about what just happened, and more about what you next that matters.
I found that out the hard way years ago, when I was let go from a teaching job I’d had for a decade. It was the hardest thing that ever happened to me — and it’s also, without question, one of the best things that ever happened.
Key Takeaways
If you’ve ever wondered whether you have to feel ready before you do something big, here’s what I’d tell you.
- Confidence after a setback often gets built without warning, in the middle of a plan falling apart — not in some calm moment of preparation.
- Being pushed out of a stable path can open space for ideas you’d never have let yourself seriously consider otherwise.
- Choosing what matters most over what feels safest can look like a step backward in the moment, and turn out to be the opening you needed.
- The confidence to try something big usually isn’t there before you start. It gets built by doing it anyway.
The Job I Didn’t Choose to Leave
I had been a high school English teacher for ten years when my husband got a six-month project in Australia. We decided to take our kids out of school and go as a family — new place, new adventure, the kind of thing you don’t get many chances to do.
When I asked my school for family leave, I was told: if there’s a job when you come back, you can apply for it.
We all say “family first.” Sometimes, it’s easier to say than it is to live. At the end of the day, it was a clear choice for me. I could always find another job. I definitely wasn’t going to get another family. So I left — and something I didn’t expect happened next.
What Opened Up When the Plan Fell Apart
Finding myself in a new country and a blank slate, my mind opened to possibilities I hadn’t let myself consider before. If I didn’t have a job waiting for me, what was I actually going to do with myself? I had six months to meet new people and have new experiences — anything felt possible in a way it hadn’t in years.
By the time we came back, it was clear. I had become obsessed with reusable grocery bags. The product didn’t exist in the US market yet, and I’d been an environmentalist for a long time. My research showed the product had been a spectacular success everywhere it had launched — Australia, Ireland, Bangladesh, everywhere. It seemed obvious someone was eventually going to bring this product to the US.
And the next thought was: maybe that someone could be me.
A Big, Hairy, Audacious Idea for a High School English Teacher
That’s exactly what it was — a big, hairy, audacious idea for a high school English teacher with zero business background. And if my job hadn’t threatened to disappear out from under me, I honestly don’t think I’d have let myself think it on my own.
But sometimes the worst moment is what opens you to the best one just around the corner. I actually did get my teaching job back, but by the time classes started that fall, I had already started up a company.
Entrepreneurship turned out to be the best adventure I could have hoped for. I quit my job a year later and within a few years, I was flying to China for supplier trips, giving keynote speeches at networking events and even a university, and selling more bags than I’d ever dreamed of — over 10 million in the first three years alone.
Over the next 12 years, I did what I set out to do: changed the way Americans shopped. And along the way, I built the skills and the confidence I now help others build.
That’s what confidence after a setback actually looks like up close. Not composure. Not a plan. Just moving before you feel ready, and letting the confidence catch up to you afterward.
I didn’t have any of that confidence on the day I found out I might not have a job to come back to. It showed up later, built one uncertain decision at a time — the same way it shows up for almost every leader I coach today.
Keep Learning
Stop Second Guessing Yourself: A Confidence Webinar — live today at 3:30 PM ET.
Find out more about the framework here.
FAQ
Did you know the reusable bag business would work when you started it?
Not at all. In fact, people told me it would never work in the US. But I had a strong hunch, based on what I’d seen happen in other countries and what my friends were telling me, and no guarantee. Confidence after a setback rarely comes with guarantees — it comes with deciding to try anyway.
Is this the same story from your book?
Yes — this is a shorter version of a story I tell in more detail in my book. The short version here is the same core truth: the setback came first, and the confidence came after.
What if my situation isn’t as dramatic as getting fired?
It doesn’t need to be. The pattern holds at any scale — a passed-over promotion, a canceled project, a hard conversation you didn’t choose to have. Confidence after a setback isn’t about the size of the setback. It’s about what you do in the space it opens up.
How does today’s webinar build on this?
We’ll go deeper into exactly this — not how to avoid the moments that knock you off your plan, but how to build the confidence to move anyway, before you feel fully ready.
