The Steepest Slope

A recruiter once told me I didn’t have a cohesive career. He was wrong.

There are people who take a straight path through their career. They go to business school, get a degree in accounting, and march forward. Then there are people who take a winding path, trying different things, finding their way eventually. And then there’s me. I often joke that I went to the steepest part of the steepest mountain and started bushwhacking my way up it. I don’t know that I’d recommend my path. But it’s mine.

What makes this even more surprising is where I started. In college I was a music major. I played five instruments, was a classically trained singer, played in bands, and had roles in musicals. Not exactly the obvious origin story for someone who would eventually become a COO and now works as an organizational strategist who coaches and advises CEOs and CPOs.

Here’s what I didn’t know then. Music taught me something that would turn out to be foundational. How to be part of a system. How to listen for where you fit in an ensemble. How to follow and lead at the same time. I just didn’t have that language for it yet.

I sang alto — a harmonizing part. Not the melody, not the spotlight. Altos don’t have main character energy. We make everything else sound better. It turns out playing in an ensemble, being one part of something larger, learning to hear how the parts fit together was systems thinking before I had a name for it.

Eventually I changed my major to social and IO psychology with a minor in sociology. Back when I graduated, I could practically hear people say “good luck finding a job with those degrees.” I briefly looked for work and could only find one job — as an assistant manager at Enterprise Rent-A-Car. Knowing I did not want to get into the car rental industry, I went back to school, eventually getting two masters degrees focused on organization development, leadership development, and community organizing.

When I graduated I started my career by finding roles wherever I could. I worked for the Girl Scouts managing two cities, responsible for recruiting and managing 500 adult volunteers. None of those volunteers had to listen to me. I had to figure out how to get them to get on board and trust me. I did a stint in a buying office at the headquarters of Banana Republic, then found my way to project management at an interactive agency where I eventually became manager of the project management department. That’s when I discovered coaching. It opened a whole new world. I became a consultant at Gallup focused on leadership development and StrengthsFinder coaching, then took my first official job in the people world as director of career development at a health tech company. Later I became a COO, including leading the people function at a growing startup.

I was also laid off six times.

Rejected by a system that decided my work wasn't necessary. It didn’t always feel like I was climbing toward something. More often it felt like I was scrambling to find my footing. I once went to an external recruiter. Nice suit, nice office. I watched him look at my resume, practically throw it in the air, and say “there’s no story here. How am I supposed to sell this to a client?”

Turns out that steep slope had some loose rocks on it.

People often ask me why I chose to work for myself. The honest answer is that in the beginning, it mostly wasn't a choice. It was survival. Being laid off that many times does something to you. I felt like my expertise wasn't valued. Some days I wondered if it actually was. Most days I decided others just couldn't see it. After my fifth layoff, I gave it up. I took any kind of work I could do in order to make a living.

It was fine.

But I never felt fully engaged in the work. I constantly felt like I couldn’t find my footing. Like I was just surviving. But I never stopped wanting to have better organizations that supported people and were good for the business.

I never saw them as separate things.

From the outside I imagine it looked like a bold move. A bet on myself. And maybe eventually it became that. But in the beginning I just wanted to make a living doing work I was good at and thought mattered.

I suspect I’m not the only one who got here that way.

Then something unexpected happened. A CEO asked me to be a COO. My genuine reaction was to look around the room and say — me? Do you mean me? I’d never pictured myself in a C-Suite role. Not because I doubted my abilities, but because nothing about my path had ever pointed there. I never had a five year plan. I just kept putting one foot in front of the other, trying to do meaningful work that I was good at. That CEO connected the dots before I did.

Looking back, it wasn’t chaos. It just looked that way from the outside. Sometimes it felt that way from the inside too. Family dinners trying to explain my career choices felt like leading a press conference.

Here’s what connected all of it. Influence was never optional for me. I rarely had the authority to fall back on. Girl Scout volunteers don’t have to listen to you. Neither do the 30 people across various functions and outside vendors you’re herding toward a deadline as a project manager. Peer executives when you’re COO aren’t any different. Never having the luxury of just telling people what to do and instead having to bring them along — it turns out that was handy preparation for the work I do today.

The recruiter who threw my resume in the air saw no story. But it was always there. Even though those jobs didn't look connected on paper, every single one required me to navigate people and organizational systems. I just had to live it long enough to see it myself.