Confidence is on the Other Side
Taking the Leap Before You Are Ready
I was standing in front of fifty women at a recruiting event, sharing my story about returning to work after a five-year career break. My voice was steady. My message was clear. I looked confident.
And I was. In that moment.
But as I looked out at their faces, hopeful but uncertain, eager but scared, I saw myself years earlier. When I was exactly where they were. Desperate to return to work but convinced I’d never pull it off. Watching other women do it and thinking they were superwomen while I was... just me.
Here’s the cruel irony: the confidence I had in that moment, standing on that stage telling my story? I didn’t have any of it when I actually needed it. When I was in the thick of it, sending out resumes and wondering if anyone would take a chance on someone with a five-year gap. When I was trying to explain why I left, and why I wanted to come back without sounding apologetic or over-explaining my choices.
Confidence, I’ve learned, doesn’t show up when you need it most. It shows up after. On the other side of the thing you’re terrified to do.
The Messy Middle
Last week, I wrote about playing your own game—defining success on your terms instead of running someone else’s race. But here’s what I didn’t say: even when you know what game you want to play, actually playing it requires moving forward before you feel ready.
There’s this phase called the “messy middle.” It’s when you’ve made a decision to change — careers, companies, direction — but you haven’t yet proven you can pull it off. You’re in transition. Everything feels uncertain. You don’t have the story yet because you’re still figuring it out.
And in that messy middle? Confidence is nowhere to be found.
I’ve been in the messy middle more times than I can count. But the one that taught me the most about this was my return to work after staying home with my kids.
The Superwoman I Wasn’t
For most of my early career, I had what I call a “CEO or bust” mentality. Not literally. I wasn’t naive enough to think everyone becomes a CEO. But I was completely bought into the idea that career success meant climbing the ladder. One level to the next. Each title a notch on the belt. Manager. Senior Manager. Director. Senior Director. VP. That was the game, and I was playing it hard.
Then I had three kids in five years. And somewhere in the chaos of maternity leaves and childcare logistics and trying to maintain some semblance of my pre-kids life, something shifted.
I made a decision that felt impossible at the time: I left the workforce entirely to be home with my kids.
It felt like career suicide. I’d invested years building my career in tech, and I was just... walking away. But I also knew, somewhere deep down, that I wanted to return at some point. I just had no idea how. Or when. Each year away felt like my value was depreciating like a used car—exponential and irreversible. Would anyone give me a chance after so much time away?
During that time at home, I thought often about a woman I’d admired from afar at my former company. She was a VP. Successful, respected. Exactly who I wanted to be. And she’d done something remarkable: she’d left the workforce, come back, and rebuilt her career to that VP level.
I thought she was amazing. A superwoman, really.
But I never thought of myself in the same category. She had something I didn’t have. Some special quality, some superpower, some magic that made her capable of pulling off what seemed impossible.
When I finally started searching for jobs, polishing my resume, crafting cover letters, going to interviews, I thought of her. But I still saw her as exceptional. And myself as... not.
Faking It Through the Door
I landed a job. Somehow, despite my fears and my resume gap and my certainty that no one would want me, I landed a role back in corporate tech.
And not just any role—I landed a position focused on women in tech initiatives, where I could define and launch a return-to-work program. A returnship program, modeled after college internships, designed to bridge the gap between talented women who’d left the workforce for caregiving and companies building new pipelines for tech talent.
Suddenly, I was the person other women looked to. The success story. The one who’d done it.
As part of the role, I became a spokesperson. I was speaking at Grace Hopper (the largest conference for women in tech) sharing my return-to-work story. I led roundtable discussions, spoke at recruiting events, met with returnship candidates who were exactly where I’d been just months earlier. Women who’d left their careers and were trying to find their way back. Women who lacked confidence. Who wondered if they could really do this.
And there I was, telling them my story. Confidently.
That’s when it hit me: the confidence I had standing in front of them—sharing how I’d navigated the career break, found my way back, proved I could succeed in this new chapter—was nowhere near the confidence I’d had when I was actually going through it.
When I was in it? My confidence meter was on empty.
Now, looking at their uncertain faces? It was full.
If only I could have sent some of that confidence back to my earlier self. The one who thought that VP was a superwoman and I was just... ordinary. The one who almost didn’t apply because I was sure I wouldn’t get it. The one who spent the first six months back at work waiting for someone to realize they’d made a mistake hiring me.
The Phenomenon That Repeats
Here’s the frustrating truth: this isn’t a one-time thing.
Every time you take on a new challenge, every career change, every leadership transformation, the pattern repeats. When you’re in the messy middle, you don’t have the confidence. You’re just trying to survive, to figure it out, to prove you can do it.
The confidence comes after. When you’ve made it through. When you can look back and say, “I did that.”
But by then, you’re facing the next challenge. And the confidence from the last win doesn’t automatically transfer. You’re back in the messy middle again, feeling like you did before.
It’s maddening. And it’s universal.
Moving Forward Without Confidence
So what do you do when you’re in that messy middle? When you know what you want to do but you don’t feel confident enough to do it?
You move anyway.
You borrow confidence from your past. Look back at other hard things you’ve done. Other times you felt uncertain and did it anyway. You’ve been in the messy middle before. You got through it. You can do it again.
You reframe “faking it.” People say “fake it till you make it” like it’s dishonest. But here’s the truth: acting confident when you don’t feel confident isn’t lying. It’s practicing. It’s showing up as the person you’re becoming before you fully believe you are that person. That’s not fake, that’s courage.
You trust the process. Have faith that you’ll get through this messy middle just like you’ve gotten through others. The confidence will come. It always does. It’s just waiting for you on the other side.
You give yourself the grace you’d give a friend. If your best friend came to you in the messy middle, uncertain and scared, you wouldn’t tell her she’s not ready or not good enough. You’d remind her of everything she’s accomplished. You’d tell her she can do hard things. Talk to yourself that way.
You stop waiting to feel ready. Because here’s the secret: you’ll never feel fully ready for the big, transformative things. The confidence comes from doing them, not before doing them. You have to take the leap to build the wings.
You remember: they’re not superwomen either. That person you’re looking at who seems so confident, so capable? They were in the messy middle too. They just got to the other side. They’re not special. They’re just a few steps ahead. And that means you can get there too.
What I Know Now
I look back at that VP I admired—the one I thought was a superwoman—and I realize she probably felt exactly how I felt when I was trying to return to work. Uncertain. Scared. Wondering if she could really pull it off.
She just did it anyway.
And now, when I stand in front of women who are in their own messy middles, I see the same look I once had. They see me as the superwoman. The one who figured it out. The exception.
But I’m not exceptional. I’m just on the other side.
And the only way I got here was by moving forward when I didn’t feel confident. By taking the leap before I felt ready. By trusting that the confidence would come once I proved to myself I could do it.
It did. And it will for you too.
Your Messy Middle
Whatever challenge you’re facing right now—the career change, the big leap, the transformation that feels too big—you’re probably in your messy middle. You’re probably waiting to feel more confident before you take the next step.
But confidence isn’t a prerequisite. It’s what comes after.
You don’t need to feel confident to start. You just need to start. The confidence will meet you on the other side.
So take the leap. Apply for the role you think you’re not qualified for. Make the career change that scares you. Start the thing you’ve been putting off until you feel ready.
You won’t feel ready. Do it anyway.
The confidence you’re looking for? It’s waiting for you. On the other side.
I’m Tracy Stone, a leadership coach who helps women leaders navigate career challenges and step into their full potential. If you’re in your messy middle and need support moving forward before you feel ready, reach out.
Next week, we’ll talk about taking risks and stepping off the slopes of self-doubt—because playing it safe is actually the riskiest move of all. Until then, keep carving your path.