I felt like a failure as a woman despite external success - here's what was really missing

I was thirty-six years old, sitting in my corner office overlooking downtown, when I realized I had become exactly what I was supposed to be. And I hated myself for it.

The promotion had just come through. Senior Financial Analyst. Six figures. The kind of title that made my parents beam with pride when they told their friends. I should have felt triumphant. Instead, I felt like I was suffocating.

Because here's what nobody tells you about checking all the boxes: sometimes the boxes aren't even yours.

For nearly two decades, I'd been climbing what I thought was the ladder to success. I worked seventy-hour weeks. I sacrificed relationships, hobbies, sleep. I became the person who could read a balance sheet like poetry but couldn't remember the last time I'd laughed until my stomach hurt. And through it all, I carried this persistent, gnawing feeling that I was failing at the most important thing.

Being a woman.

Not in the obvious ways people talk about. I wasn't failing to "lean in" or smash any glass ceilings. My failure felt more fundamental than that. I was failing to feel fulfilled. Failing to feel whole. Failing to recognize myself in the mirror.

The achievement trap

Looking back, I can see how I built my own cage.

Growing up with high-achieving parents who measured success in degrees and promotions, I learned early that your worth was something you had to earn. Being labeled "gifted" in elementary school only made it worse. Suddenly, being smart wasn't just something I was but something I had to keep proving.

So I did. I proved it through perfect grades, through my economics degree, through my acceptance into a competitive MBA program. I proved it by being the first one in the office and the last one to leave. I proved it by outperforming my male colleagues, even when they got the promotions I deserved.

But here's the thing about building your identity on achievements: you're never done achieving. The goalpost keeps moving. And at some point, you realize you've been running so hard toward someone else's finish line that you forgot to ask where you actually wanted to go.

The research backs this up too. Studies show that perfectionism among young people has increased significantly over recent decades, particularly the kind that's tied to external validation. We're raising generations who believe their value is contingent on constant achievement. And women, who already face impossible standards from every direction, often feel this pressure most acutely.

What I was really measuring

The breakdown came quietly. Not a dramatic collapse, but a slow erosion.

I started having panic attacks in the bathroom at work. I'd stand there, gripping the sink, trying to breathe, wondering why success felt like drowning. My body was keeping score of all the stress my spreadsheets never showed. Sleep became impossible. My relationship with my partner suffered because I was always distracted, always thinking about the next deal, the next report, the next thing I needed to do to prove I deserved my place.

A friend convinced me to try therapy. I went reluctantly, still believing I could logic my way out of feeling terrible.

My therapist asked me a question in our third session that I couldn't answer: "What does success mean to you?"

Not to my parents. Not to my company. To me.

I sat there, silent, feeling exposed in a way no boardroom presentation had ever made me feel. Because I genuinely didn't know. I'd spent so long chasing other people's definitions that I'd never stopped to define my own.

That's when I started journaling. At first, it felt forced and awkward. But gradually, patterns emerged. Page after page, I wrote about feeling trapped. About missing the parts of myself I'd sacrificed. About how my definition of "successful woman" had somehow become "woman who succeeds like a man in a man's world."

The guilt of wanting something different

Deciding to leave finance wasn't a light bulb moment. It was months of wrestling with guilt.

I felt guilty for "throwing away" two decades of hard work. Guilty for letting down the women I'd mentored who saw me as proof that we could make it. Guilty for the financial privilege that made such a choice even possible when so many women don't have that option.

Most of all, I felt guilty for admitting that everything I'd worked for hadn't made me happy.

We don't talk enough about this particular kind of failure: the failure of success itself. When you achieve what you're supposed to want and discover it isn't enough, it can feel like a personal defect. Like everyone else figured out how to feel fulfilled by their accomplishments, but you're broken somehow.

Research on what's called the "failure schema" shows that many successful people carry a hidden belief that they're fundamentally inadequate, no matter what they achieve externally. This pattern often starts in childhood with overly critical parents or impossibly high standards. You learn that nothing you do is quite good enough, so you keep pushing, keep achieving, keep trying to finally feel worthy.

Sound familiar?

Learning to measure differently

The first year after I left my corporate job was terrifying. I was living off savings, trying to build a writing career, and feeling like I'd destroyed everything I'd built.

My parents didn't understand. "After everything you accomplished?" my mother kept saying, her disappointment palpable. Former colleagues thought I was having some kind of crisis. A few friends quietly distanced themselves, as if my choice to step off the achievement treadmill was somehow contagious.

But something interesting happened as I started writing about psychology and human behavior. I began to understand my own behavior. I saw how I'd used achievement as armor against feeling anything too deeply. How I'd believed that if I could just be successful enough, impressive enough, accomplished enough, I'd finally feel like I was enough.

The irony is that stepping away from external markers of success was the first time I actually felt successful. Not because I was making money or impressing anyone, but because I was finally living according to my own values.

I started running trails in the early morning, something I'd always dismissed as a waste of time that could be spent working. I discovered that physical exhaustion from a long run felt completely different from the soul exhaustion of corporate burnout. I started gardening, getting my hands dirty, watching things grow on a timeline I couldn't control or optimize.

I went vegan after years of knowing intellectually that factory farming was wrong but being too busy to change my habits. I started volunteering at farmers' markets, having real conversations with real people instead of networking for strategic advantage.

What was actually missing

It took almost two years before I could articulate what had been missing all those years I felt like a failure despite my success.

It wasn't another promotion or a bigger salary or finally getting the recognition I deserved. It was authenticity. Connection. The feeling that my life reflected my actual values instead of someone else's expectations.

In my finance days, I'd had a demanding female boss who was brilliant and ruthless. She taught me that to succeed as a woman in that world, you had to be tougher than the men. More aggressive. Less emotional. I watched her work herself into the ground, snapping at her kids on the phone, popping antacids like candy, and I remember thinking: is this what winning looks like?

The framework I'd been operating under was fundamentally flawed. I'd been trying to win a game where the rules were designed by people who didn't value what I valued. Where success was defined by metrics that had nothing to do with meaning or fulfillment or joy.

Understanding this didn't make everything magically better. I still struggle with the internalized belief that my worth is tied to productivity. I still catch myself dismissing accomplishments or minimizing things I've done well. Old patterns die hard.

But now I can recognize those patterns. I can catch myself when I start falling into the trap of measuring my life against external benchmarks that don't actually matter to me.

Redefining success on your own terms

If you're reading this and something resonates, here's what I wish someone had told me years ago.

That feeling of failure you carry despite doing everything "right"? It's not a personal defect. It's a signal that you're measuring yourself against the wrong standards.

The definitions of success we inherit often have nothing to do with what actually makes us feel fulfilled. They're based on what impresses other people, what looks good from the outside, what fits into neat categories that make sense on a resume.

But fulfillment rarely fits on a resume.

Start asking yourself what actually matters to you. Not what should matter, not what matters to your parents or your partner or society at large. What genuinely lights you up? What makes you lose track of time? What would you do even if no one ever knew about it or congratulated you for it?

These answers might surprise you. They might not look like what you expected. They might not impress anyone else. And that's exactly the point.

The ongoing work

I still have moments where I question whether I made the right choice. When I see LinkedIn updates about former colleagues' promotions, there's still a small voice that whispers I threw away something valuable.

But then I go for a long trail run on a Sunday morning, my mind quiet except for the rhythm of my feet and my breath. Or I spend an afternoon in my garden, hands in the soil, watching bees work the flowers I planted. Or I write something that helps someone see their own situation more clearly.

And I know, in a way I never knew in those corner office days, that I'm finally measuring the right things.

The transformation from feeling like a failure to feeling genuinely fulfilled doesn't happen overnight. It's not a single decision or realization. It's a daily practice of choosing your own values over external validation. Of checking in with yourself instead of checking boxes. Of building a life that feels right from the inside instead of looks right from the outside.

If therapy is accessible to you, I can't recommend it enough for this work. A good therapist can help you untangle the beliefs you've inherited from the ones you actually hold. They can help you see the patterns you're stuck in and imagine different possibilities.

And if you're in a place where you can't make major life changes right now, start small. Start noticing what makes you feel alive versus what makes you feel accomplished. Start questioning whose voice is in your head when you judge yourself. Start building tiny moments into your life that reflect who you actually are, not who you think you should be.

Because here's what I learned: you're not failing at being a woman, or at being successful, or at being enough. You're just trying to thrive in a framework that was never designed for your thriving. And recognizing that is the first step toward building something better.

Something that's actually yours.