The fear of failing again is a different animal than ordinary fear. It isn’t stage fright, and it isn’t impostor syndrome in the usual sense. It’s the specific dread you carry when the thing you’re considering has already gone badly once — and you have the scar tissue to prove it. I spent most of last year stuck there. Here’s how I kept moving forward when the fear wouldn’t go away.
The fear won’t go away and neither does imposter syndrome
This past week some high school students hosted me on their podcast. I have a sweet spot for high school students and always have. It’s such an impressionable age, and I had some really great mentors who kept me directed in a way that even my parents sometimes struggled to. So I believe in paying it forward.
I’m sharing parts of that conversation here because the questions they asked are the same ones I hear from people with ten to twenty five years of experience. And honestly, they are questions I’ve had to revisit over the past year as I’ve restarted my business.
One of them asked whether I’d ever experienced impostor syndrome. My answer was immediate: all the time. It’s not something that goes away.
I had it as a college freshman, convinced someone in the admissions office had made a mistake. While we were building and exiting Mint. I had it at Apple, surrounded by brilliant people. And I have it now restarting my business.
What I told them is that the goal was never to get rid of it. The goal is to dial it down enough to do the work someone already decided you were capable of doing.
The goal was never to get rid of it. The goal is to dial it down enough to do the work.
The sentence I couldn’t say out loud for a year
Honestly, this is something I struggled with as recently as a year ago. I wanted to restart my business and had been planning to for years. But the conversation I was having with myself was about how badly I had failed in my second startup, BizeeBee. I didn’t have the luxury of failing now — I was a mom of three, thinking about college savings and a mortgage.
What actually happened at BizeeBee
I had a moment of catharsis back in March, when a good friend from college and I planned a weekend away together. She asked me what happened, and I told her everything.
I had put my entire life savings into building BizeeBee — the money I made from the Mint.com acquisition. I bootstrapped it the first year, plus sustained myself for three. Then I raised a round of angel investment, around $500K.
Just as we were launching our second product, we got hammered by scammers who were using it for money laundering. I came clean with my investors and my teammates. I couldn’t make payroll, and I couldn’t raise another round — we simply didn’t have the traction we needed. And I felt personally liable. I was eventually able to return the money we owed the people who’d been defrauded, coincidentally by teaching product development courses through Femgineer.
Yes, I pulled myself out of a hole. But I had the luxury of time, no kids, and no real commitments.
What if something like that happened this time around?
Why the fear won’t go away: it’s working from an outdated file
The fear was holding me back. As I told my friend the story, I also started sharing how I’d built Femgineer, and everything I’d learned in seven years at Apple. She told me I wasn’t giving myself enough credit. I had learned and grown a lot.
So I realized the fear of failing again was genuinely holding me back, and that I needed to keep it in check instead. I could use it as a gauge when making decisions that have a lot at stake. Even my husband — a security expert who works on the payment platform at his company — has told me he won’t let me build a tool with next-day payouts. It’s just too risky.
I needed to keep the fear in check — use it as a gauge when making decisions that have a lot at stake.
The thing that keeps people stuck when the fear won’t go away
The students also asked what I see people struggle with most when I coach them.
It’s almost never the how. The how can usually be taught pretty quickly. It’s that they get in their own way and second-guess themselves. For anyone restarting, the fear of failing again is usually the loudest version of that voice. They arrive with a real vision, then stall out on the inner critic. This is the same pattern I see in engineers who think they need to master a whole new field before they start — something I wrote about in just-in-time learning.
I gave the students that answer, and then had to sit with the fact that I’d spent a year doing exactly that to myself.
Will I make new mistakes? For sure. But maybe this time I have better safeguards, and supportive people around to bounce ideas off of. I had to tell myself I made the best decisions I could my first time around as a founder.
I’d also mapped out a two-to-three-year trajectory for my restart. A month before resigning, the only thing holding me back was me. Fortunately, I had another great friend who became my accountability buddy. She kept checking in to make sure I stayed on track, and gave me healthy reminders of why I couldn’t stay. I was burnt out.
Three months into making the leap, I do feel better. Has the business taken off? Not completely — I’ve got coaching clients and I’m working on expanding my offerings. And that’s enough, because this is also supposed to be a period of rest and reinvention.
It’s almost never the how. The how can be taught pretty quickly.
What resilience looks like when the fear won’t go away
I don’t think resilience is a personality trait you either have or don’t.
When the students asked what makes an effective leader, my answer was pretty unglamorous. You wake up every day knowing there are probably a thousand problems. You’ll solve one, maybe two. Or you’ll make some progress. Or you’ll figure out how to distribute the other 999.
Entrepreneurship taught me the same thing in a harsher way. You hit the milestone — first customer, first revenue, a launch — and you’re thrilled for about a day. Then there are more problems.
Engineering works identically. You fix the bug, you ship it, everyone’s happy, and tomorrow something else breaks. That’s not a sign something’s wrong. That’s the job.
So the wins don’t mean you’ve arrived, and the losses don’t mean you’re finished. Both just pass through.
What’s kept me steady this time
- I’m constantly learning things I didn’t have the time or energy to learn while working a full-time job.
- I can put myself out there in a way that would have required permission from multiple layers of management.
- I’m rebuilding a network with a diverse group of people. Before, I was often limited to a single product line by time and urgency.
Am I scared? Every day. But in spite of that fear, I keep turning down opportunities. I really want to focus on my own thing, at least for the next two years.
In fact, I’m kind of an idea-generating machine at the moment. I have to tell myself to stay focused and disciplined, especially since I have limited hours to work this summer and want to maximize my time with my kids.
A thousand problems. You’ll solve one, maybe two, or distribute the other 999.
How to move forward when the fear won’t go away
The last thing I told those students was that you don’t get one shot. If something goes badly — you shut the business down, you walk away, you move on. Yes, it’s an incredibly hard phase, but you will come out on the other end. You will get multiple chances. The whole thing is showing up, being consistent, and doing the work.
I said it to a room of sixteen-year-olds who mostly haven’t failed at anything expensive yet. But I think it lands harder for those of us who have.
So here’s what I want to ask you. Is there a change you’ve been circling? A job you’ve been meaning to leave. A business you’ve been meaning to restart. A conversation, a move, a pitch, a hard no.
And more specifically: what exactly are you scared of?
Not the vague dread. The actual sentence. Mine was I can’t afford to fail again, I have three kids and a mortgage. It took me a year to say that out loud to someone. About ten minutes after I did, a friend pointed out that I’d left the last seven years of evidence out of my own accounting.
That’s usually how it goes. The fear isn’t irrational — mine wasn’t, I really did lose everything once. But it’s almost always working from an outdated file. It knows what happened. It doesn’t know who you’ve become since.
One thing to do this week
Write the sentence down. Then ask what safeguards you have now that you didn’t have then, and who you’d call when it gets hard.
The fear knows what happened. It doesn’t know who you’ve become since.
You don’t have to be over the fear to start. I certainly wasn’t — I’m still not.
Everything I make is, in its own way, about updating that outdated file. Three doors, depending on which change you’re circling:
- 📖 Ghosted — if it’s a job search. It’s about uncovering the expertise your resume misses and communicating your value in interviews and beyond. The book isn’t out yet, but you can get a sneak peek at some of the lessons now. (If you’re deep in it right now, I also wrote about how to navigate a brutal job market.)
- 🔍 Uncover — if you’d rather not wait for the book. It’s the free companion tool, it takes a few minutes, and you can start right now. Run it on yourself and see what it surfaces.
- 🚀 Ship It — if it involves building something. The introductory series is about what building and shipping actually take end to end: scoping the problem, making the thing, getting it in front of real people, and owning every step in between. That holds whether you’re standing up a proof of concept inside your company or building a prototype product for yourself.
Whichever door you pick — or none of them — tell me in the comments: what’s your sentence? I read every one.
