There Is Life After Being a Founder — I’m Joining Enjoy The Work!

I found a job that doesn’t feel like work. Here’s how…

I identify as an entrepreneur. I’ve been in the startup world since the 1990s, have started three very different companies, taken one public, and sold another. I’ve enjoyed inarguable successes and suffered painful failures. I even come from a family with entrepreneurial roots, including my dad, who was the first in his family to graduate from high school and started a tech company in the late 70s. Even when I was in an operating role in big companies, I felt like an entrepreneur — for better or worse, I never eased into the status quo of how things were done, always looking for more innovative methods and faster paths to outcomes.

What being an entrepreneur means to me is deciding to solve a problem that won’t stop nagging me and always looking for the shortest path to creative solutions to a constantly evolving set of challenges and problems. I get bored with repetition and sameness. As such, for my whole career, I’ve been climbing a steep learning curve — always a new industry, problem space, and new things I had to become an expert on quickly. I love learning, but because I always tackled new challenges, I began to believe that I was a jack of many trades and master of none, and at some point, this caused me some anxiety — what if I wanted the security of a big job that was not CEO and collect a big paycheck one day? Who would hire me, and for what?

Then, about ten years ago, founders started asking me for advice. I was invited to be an entrepreneur-in-residence at a venture firm and to give talks about how to build and run a startup, what I’d learned from my successes and failures, to help founders tackle their problems, and to take their independent board seats. These requests drew me in, and I said yes to them all.

What I learned when I leaned into being in service to other founders is that I knew more than I was giving myself credit for and that, in fact, I had achieved some level of mastery in this entrepreneurial craft. I got feedback from founders about how I helped them make better decisions, learn faster, achieve an outcome, and, most important to me, feel less alone. This work was always a side hustle to my main jobs but I absolutely loved it — it brought me so much energy. I called it “founder solidarity.”

Over the last year, I’ve given myself a break that I have never allowed myself before. I was suffering from some burnout and the Covid-induced zoom screen had taken its toll on my joy and health. So I continued to serve on five boards but otherwise determined not to start another company or take a full-time job until I figured out what would bring me joy. I spent a lot of time in nature, in the mountains, and even in ice-cold water. For the first time since I was a child, I allowed my mind to wander and dream of what might come next.

What happened is this: It became clear to me that much of my career to date had been about personal achievement. While this yielded results the world approved of, it fed my ego more than my happiness….I got clear on what I wanted…. I can sum it up in two words: Connection & Impact.

Connection is all about people — good people who care, are kind, and highly competent. The impact is about being in service to others to increase their chances of achieving their dreams and goals.

Just as I landed on this clarity, I was introduced to Leslie Fine and Jonathan Lowenhar from Enjoy The Work by a friend who happened to be a client of theirs. What I learned is that Jonathan and Leslie and their ten other partners have already been on the very journey I was beginning to imagine. For the past eight years, they’ve been helping dozens of founders grow, scale, and exit their startups.

The very name “Enjoy The Work” is an aspiration for themselves and their clients. When I spent time with the partners as a group, it became clear to me that the name is the reality of the culture they have created. I interviewed mutual contacts and clients and what they said sold me — the impact on them and their companies is immense.

There are so many wonderful advisors across the startup landscape. But nearly all of them are solo practitioners moonlighting until the next full-time gig grabs their attention. Part of what drew me to this unusual firm is the chance to collaborate with, contribute to and learn from this remarkable professional team of partners who have been CEO, CFO, CTO, CPO, CMO, and VCs.

I’m so proud and excited to be joining Enjoy The Work this month to help as many founders as we can to become the best possible operators and achieve the mastery that took me thirty years — in a much faster, less arduous, and less lonely way.

I’ll always give a founder in need an hour, so if you know one, feel free to send them my way.

Learn more about Kristen Hamilton here. 

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