When Success Doesn’t Feel Like Success

What one draining meeting taught me about authentic leadership and redefining success

I remember sitting in a sleek glass boardroom in Washington, DC, looking around at a table full of people who seemed impressed by me. I was thirty-four, a vice president, earning more money than I ever thought possible. Everyone in that room saw success.

But I didn’t feel it.

I felt tense by how quickly my team member’s idea had been dismissed. I felt frustrated by the amount of educating, navigating, and smoothing over I had to do with stakeholders just to keep the conversation moving. I felt tired from the constant balancing act of being strategic yet palatable, bold yet careful.

When the meeting ended, several colleagues told me how effectively I had handled it. How I’d redirected conflict, protected my team, and driven alignment. They meant it as praise. But instead of satisfaction, I felt drained.

I remember walking back to my hotel that evening thinking, Why doesn’t this feel good?
Others thrived in this kind of moment. The tension, the challenge, the politics. They left meetings like that feeling energized and successful. I left feeling flat, bored, and unfulfilled.

That was the day I began to suspect that the version of success I had worked so hard for might not be my own.

The Fear Behind the Drive

For much of my career, I thought I understood success. I worked relentlessly to build it: sharpening my business acumen, mastering strategy, leading global teams, and communicating with precision in rooms that were filled with men and big egos.

I built a resume that sparkled: Ivy League credentials, a decade in strategy consulting, and a vice-president title by age 34. Recruiters called weekly. My LinkedIn inbox was always full of “bigger and better” opportunities. On paper, I was the picture of achievement.

But privately, I was running on fear.

I grew up watching my single mother stretch every dollar. Financial insecurity was a constant companion. From an early age, I equated safety with performance. If I could just be impressive enough, indispensable enough, I’d never have to relive that instability.

That belief propelled me into elite spaces that once felt unreachable. But it also kept me in survival mode long after I was safe. My drive was fueled by anxiety and imposter syndrome; the sense that if I stopped proving myself, everything could vanish.

So I over-delivered. I worked through nights, took on extra projects, absorbed colleagues’ responsibilities, and perfected the art of the polished facade. My eldest-daughter instincts to please and protect translated seamlessly into corporate life.

And for a long time, I made that formula work.

The Burnout I Didn’t See Coming

After years of sprinting, I landed the “dream” job. I was the VP of strategy for a global organization with an impressive salary, travel perks, and a large, multi-layered team.

For the first time, I wasn’t constantly on planes or working until midnight. I had the space to breathe, to invest in my personal life, and to rediscover balance.

Except I didn’t feel balanced at all.

The burnout was quieter this time than it had been in the past - less frantic exhaustion, more hollow disconnection. I had achieved everything I was supposed to want, and still, something felt profoundly off. The title, the paycheck, and even the external validation no longer lit me up like it used to.

I remember sitting at my desk one morning thinking, Is this what success is supposed to feel like?

The Moment of Clarity

That question repeated quietly in my brain for months, until it finally cracked something open. I began to see that my definition of success had never actually been mine. It was an inheritance: a collection of expectations handed down by society, mentors, and well-meaning voices from my past.

When I started untangling those influences, I realized how little space I had ever given myself to imagine my own vision of success. My choices had been shaped by safety, not possibility. By fear, not authenticity.

The realization was disorienting, but also freeing. For the first time, I allowed myself to ask:

• What would my career look like if it were designed for joy, not survival?

• What does authentic leadership mean for me; not just the kind I model, but the kind I live?

• What if success wasn’t about external signs of achievement, but about feeling internal alignment and intrinsic satisfaction?

Those questions didn’t produce immediate answers. But they started a process. It was slow, and sometimes painful, but always clarifying, and led me towards personal reinvention.

Redefining Success

Over time, I began to notice patterns. The moments when I felt most alive weren’t during high-stakes presentations or after landing major contracts. They were in the quiet one-on-one conversations: mentoring younger women, helping colleagues find clarity in chaos, and coaching peers through transition.

I started truly listening to what energized me instead of what impressed others. That listening changed everything.

As I redefined success, my compass shifted from fear of losing to freedom to create. From building safety nets to building meaning. From playing roles to inhabiting my truth.

Eventually, that shift became impossible to ignore.

For me, this shift, really a series of small and large awakenings over time, felt radical. I had spent decades adapting to systems not built for me, contorting myself to fit structures that rewarded conformity over truth. Turning inward, tuning into my own compass, and choosing to act authentically in my work and leadership nudged me again and again to reverse that conditioning, to honor my intuition and center my values.

And yes, it took an incredible amount of courage. Not everyone embraced my authentic self right away, and some never did. But the beauty I found was that living and leading from authenticity allowed me to align with environments, teams, and organizations that do value who I am, and, for the first time, to feel truly and sustainably successful.

Full Circle

Sometimes I think back to that day in the boardroom and to how empty success felt while sitting in a room full of people who thought I had “made it.”

If I could go back and whisper something to that version of myself, it would be this: You are not here to perform success. You are here to define it.

That is what authentic leadership has come to mean for me: leading, living, and creating from truth rather than fear. There is nothing I love more than waking up each day and partnering with women who are beginning, or already deep into, their own journeys of transforming their lives and careers to be centered in authenticity.

Finally, my life and leadership feel like success.