Ryan Caldbeck recently stepped down as the CEO of CircleUp after leading the fintech company for almost nine years.
Leaving the best job I ever had — at the company I helped to create — was difficult and confusing. I wish I had found other stories about how the transition actually went and what it felt like. But I found surprisingly few first-hand accounts from founders or CEOs transitioning from their initial role, and even fewer that shared their full, authentic story of what really happened when they left and how they truly felt about the process.
For years I did a poor job of communicating the depth of my stress and exhaustion, a problem only compounded by the fact that, at times, I wasn't even sure of my own feelings. There were stretches of time where I felt horrible — lonely; terrified; depressed. Depression exacerbates exhaustion. But I tried to put on a brave face to make sure the board felt comfortable.The highs kept me going even though I knew the downs were unhealthy and untenable.
What she didn't know — and what most people didn't know — is that during that same 18-month window, I was also juggling personal challenges that were far more stressful than the hurdles at work. Two days later, I flew to a work conference in Anaheim, CA, while also trying to schedule further tests and treatment. In a 30-minute Uber ride, I told my story multiple times over the phone to multiple administrators at multiple hospitals .
The cancer diagnosis became even tougher to deal with because I mistakenly believed I shouldn't discuss it with others. CircleUp had just gone through our pivot and we were in the middle of raising that first fund and the parent company round. At the time, I worried that the team would use my diagnosis as an excuse to throw in the towel, that my health would become a distraction, cause the company to fail and make things that much worse.
By the end of 2017, I was completely worn out. Then, suddenly, the major professional challenges were done. I remember a top VC, who was not one of our investors, posted something very positive about me and CircleUp online. I read it on my phone and immediately said, "Damnit!" to my wife. I explained that he couldn't possibly know enough to mean these positive things, and his comments only made me wish that he genuinely did.I've eventually realized that for far too long, I wasn't clear — with myself or others — about what I wanted or needed.
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