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Leadership tour 2019

Scott Downes
Feb 18, 2021
Butter Pecan
Chocolate Chip
Rocky Road

Making a change

After 3 years as the CTO of a venture-backed startup, I had reached a new pinnacle of success. We'd raised over $30 million dollars in a Series C fundraise, and a large part of our story was how technology was transforming our industry. The build-out of that tech platform had been the center of my life work for years, and I felt immense pride in the accomplishments of my team. In fact, the team that we'd put together in product, engineering, and design was world class and could rival similarly sized teams anywhere.

On top of that, we'd raised more money than any other startup had ever done in the scrappy underdog tech hub of Chattanooga. So why was I so unhappy?

When we no longer feel connected to the mission of our employer and we aren't in alignment with its values, there's no amount of external success that can make up for that. No paycheck is large enough. Not even the camaraderie and loyalty of a great team is enough.

I was talking to the CEO of another startup the very day that we announced our Series C, and she asked me how excited I was about the news. She was clearly expecting to hear me reflect back some enthusiasm, and I just couldn't fake it. When I heard the flat empty tone of my own voice, I knew that a major change was coming for me and I needed it to come quickly.

What next?

At the end of the day, we are all our own boss. We are responsible for managing our own wellness, and we set our own direction. I knew that I was going to need a pause before leaping into a new CTO role at another startup, But at the same time, some of those conversations had already begun, and I knew that the path of least resistance led inexorably to a similar role as my prior one. Would it be the right step for me to leap from one high stakes leadership role directly into another? Obviously not!

I knew that a focus on my own health was long overdue, and I'd already picked up a three-day-a-week running routine. I took the moment as an opportunity to push myself into new habits and channeled my hyperactive mind into setting new personal bests. I also re-devoted myself to a meditation practice that's long been a key to my self-care regimen.

And yet, I knew that there was still something missing. That I needed to re-connect with my passions. Why is it that I love building software? Why is it that I love building teams? And how can I best develop myself and avoid repeating the same stories that I've lived in the past.

The Tour

My deepest love is connecting with people. And I am especially inspired by entrepeneurs.

People who fundamentally reject the idea of Working for The Man. People who are trying to design their own lives where they can pursue their passions and be true to themselves. Notably, this was exactly what I felt I'd drifted from in my own life.

In the last few months, I've spent time meeting with:

* a former startup CEO who's focused on helping people who are experiencing burnout

* a former teacher starting a program to bring mindfulness meditation to elementary schools

* a serial entrepreneur who's making waves with a new approach to wine sales

* a founder and CEO whose own deep curiosity and knowledge led him to invent a brand new type of musical instrument (of which he's sold thousands)

* a CTO for a heavily hyped tech company who's overwhelmed by his company's success and reaching out for help in every direction

* a designer who's built her own business creating concert posters for some pretty famous musicians

* a CEO trying to handle a high pressure job with a newborn baby and a wife living in another city thousands of miles away

What I've realized throughout the process is that not only do these folks energize and inspire me, but I can give the same back to them. What I thought of as a way to restore my own energy has helped to light the fire in many of them, and I'm excited to continue this process. As a matter of fact, I turned this passion into a coaching business which is probably why you're on this site right now :)

More to come

The tour continues, and I have no intention of allowing it to end. There's not a week that's passed without a host of new opportunities presenting themselves and new fascinating people to meet. In fact, I feel guilty for not mentioning the other folks I've met with recently, but the list was getting too long!

As I prepare to accept the CTO role with an exciting early-stage startup, I've committed myself to continuing this practice.

Scott Downes

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