Why Imposter Syndrome Hits Hardest When You're Winning

I've been there more times than I can count. You're at the peak of a career milestone - maybe landing that promotion you've hustled for, or closing a deal that everyone said was impossible. The room erupts in applause, emails flood in with congratulations, and yet, inside, a voice whispers that you've just gotten lucky. That you don't deserve it. That any second now, everyone will realize you're a fraud. Imposter syndrome doesn't care about your resume; it thrives when you're winning the most.

It's counterintuitive, right? You'd think self-doubt would hit during the slumps, when you're job hunting or facing rejection. But no, it often creeps in strongest right after a victory. Let me unpack why that happens, drawing from my own stumbles and climbs in the professional world.

The Spotlight Amplifies the Shadows

Success puts you under a microscope. When you're grinding away in the background, it's easy to hide your uncertainties. No one's watching closely enough to notice the gaps in your knowledge or the times you winged it. But win big, and suddenly all eyes are on you. Expectations skyrocket, and so does the pressure to maintain that image of competence.

I remember my first big client win early in my sales career. After months of pitches and follow-ups, we sealed the deal - a six-figure contract that boosted our team's quarterly targets. My boss pulled me aside for praise, and the news spread like wildfire. I should have been riding high, but instead, I spent the next week obsessing over what if they discover I only know half of what I pretended to? The promotion that followed felt like a setup for failure. Every meeting, I braced for the moment someone would call out my 'luck.'

Psychologists call this the 'imposter phenomenon,' and it's not just me. Studies show it affects high achievers disproportionately because success raises the stakes. You're no longer blending in; you're the example others measure against. That visibility turns every minor insecurity into a glaring flaw in your mind. It's like the brighter the light, the longer your shadow seems.

Success Redefines the Playing Field

When you win, the game changes. What was once a stretch goal becomes the new baseline. You start comparing yourself not to your past self, but to this elevated version that's impossible to sustain. Imposter syndrome feeds on that gap, convincing you that your wins were anomalies, not reflections of your ability.

Think about it in career terms. Say you're a developer who just led a project that went viral in your company. Peers are asking for your advice, managers are talking about your 'natural talent.' But deep down, you remember the late nights copying code from Stack Overflow or the mentor who basically wrote half your specs. That doubt doesn't vanish; it morphs into fear that you can't repeat the magic.

I saw this play out with a colleague in Lagos, a sharp project manager who'd orchestrated a flawless product launch for our startup. The event was a hit - media coverage, investor buzz, the works. She confided in me over jollof rice at a team lunch that she felt like an imposter because 'anyone could have done it with the right team.' Her win had shifted her role from contributor to leader, and suddenly, every decision felt like it could expose her. It's that redefinition that hits hard: success demands you level up faster than feels humanly possible.

The Cultural Layer in Our Wins

In places like Nigeria, where community and resilience are everything, imposter syndrome can feel even more acute during triumphs. We're raised on stories of underdogs who make it against the odds - think of the entrepreneurs bootstrapping from modest beginnings in Abuja or Lagos. But that same narrative can backfire. When you win, it doesn't just feel personal; it feels like you're carrying the hopes of family, friends, maybe even your entire network.

I felt this after negotiating my first international partnership. Coming from a background where opportunities were scarce, sealing that deal meant proving not just myself, but the path for others. The congratulations from relatives back home were overwhelming, but so was the inner voice saying, 'What if you mess this up and let everyone down?' Success here isn't solitary; it's communal, which intensifies the fear of falling short. It's why imposter syndrome strikes deepest when you're ascending - the higher you climb, the more eyes from below watch your footing.

Rewiring the Doubt into Drive

Understanding why this happens is one thing; dealing with it is another. The good news is that recognizing imposter syndrome as a byproduct of winning can turn it from a saboteur into a signal. It means you're pushing boundaries, growing, and that's where real careers are built.

Start by tracking your wins objectively. Keep a 'brag file' - not a boastful list, but a quiet record of achievements, feedback, and the effort behind them. When doubt hits after a success, pull it out. Remind yourself that luck doesn't sustain careers; preparation and persistence do. I started doing this after that sales win, jotting down the calls I made, the rejections I overcame. It grounded me, showing the win wasn't a fluke.

Talk it out, too. Share with a trusted mentor or peer - you'll likely hear they've felt the same. In my experience, normalizing it in conversations, maybe over a quick chat at a naija tech meetup, dissolves some of its power. And finally, embrace the learning curve. Use the post-win energy to skill up deliberately. Enroll in that course, seek feedback on your next project. Turn the syndrome's whisper into a question: 'What can I learn next to own this win fully?'

Imposter syndrome hitting hardest when you're winning isn't a sign to slow down; it's proof you're on the right track. Lean into it, and watch how it fuels even greater heights.