Coaching and Therapy

Founding a company is hard and mentally taxing. There’s plenty of literature out there about entrepreneurship's emotional toll. Not only are the odds forever stacked against founders, but they deal with a seemingly insurmountable pile of problems: people problems, market problems, product problems, customer problems, etc. There are always fires.

One of the ways I learned to cope with the highs and lows of the roller coaster was to simply become numb to it all. I've had multiple board members share that I never seemed happy when things were going "up and to the right," and that I never seemed fazed when we were facing an existential cataclysmic meltdown. I don't particularly think this is a good thing - it's important to be emotionally present to acknowledge and celebrate wins (although I think I probably did an adequate job here since I was surrounded by people who were good at this). But I do think it's fine when dealing with the lows. I'd rather a steady hand in times of turmoil.

There are two tools I wished I used more frequently to better manage myself and improve as a leader: coaching and therapy. I look at them as two distinct practices, but sometimes one may use a single practitioner for both. I've engaged with a variety of executive coaches, but my favorite has been Jason Gore from Neuberg Gore. I even brought in multiple coaches to work with our leadership team at Fundera which was an excellent investment and something I recommend other founders do if they have the resources.

In my experience, what has made coaching work for me, and specifically my relationship with Jason, is focusing on very actionable situations. When I had to prepare for difficult conversations with teammates I'd rehearse them with Jason. When I had to figure out how to customize my management style, or even whether to adapt it to certain people, I'd workshop it with my coach. He equipped me with a variety of super effective tools that made my life easier as a leader and manager. And having that sounding board that could advise me every other week or so while being somewhat embedded in my management/leadership flow and cadence was super helpful. You have to make so many decisions as a founder; it's really comforting and useful to have someone to consistently dig into and help with the most important ones. In retrospect though, what makes for an effective coach, at least for me, is someone who can help me confidently do the things that I like least (i.e. having hard conversations, quickly) while strengthening the things I do well.

I never did therapy while building companies but I wish I had. I started around a year ago after a mentor I deeply admire recommended it. He had been doing it for decades. I asked him why and he said, "So I can understand why I feel the way I do, hone in on what makes me happy, and do more of that." I liked that so I took the plunge. It was really hard for me to get into for the first couple months. But then something clicked and I started to pay attention to my emotions (which I had spent the past decade attempting to suppress in the workplace for the sake of my mental health and operating capabilities). Identifying emotions is difficult, but now I am getting better at being able to do it in the moment. And when I can identify how I feel and why I feel that way, I can better understand my behaviors and proclivities. That alone is an extremely powerful tool to have as an entrepreneur - the ability to recognize how you feel in the moment and how that feeling may influence your behavior. I wish it was one I was able to to consciously use, or at the very least even be aware of, over the course of my early career.

If coaching is about doing, then therapy is about feeling.

Coaching and therapy are expensive, but I think the combination of the two is a powerful one for entrepreneurs. It's cliche to say you have to invest in yourself, but you really do. You just cannot do the job for an extended period of time without having a sound mind (and ideally a sound body, too), you will simply wither away and grow to resent the things that make life and building things beautiful and enjoyable. I'm grateful for having the opportunity to use these practices day to day. I think they make me better at what I do, happier, and a better person.

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