Ryan Caldbeck's site

I stepped down as CEO in October 2020 after nine years at CircleUp. I will be a CEO again. There were parts of the role I loved and it was the best job I ever had. During my transition, I’ve had time to reflect on my experience. On Twitter and in real life I hear others – VCs, teammates, pundits – give their views. I can safely say that if you haven’t done the job, you can’t know what it’s like. You can see some of the activity, but the emotional rollercoaster is, in my opinion, wholly unique to the role. 

Loneliness- This is probably the most obvious of the emotions and the easiest for those not in the seat to recognize. I felt lonely every day – maybe not constantly, but definitely every day for 9+ years. I haven’t talked to a CEO who didn’t feel extreme loneliness. For the first time in my life I didn’t feel like I could be friends, even work friends, with anyone else on the team. That might have been my own baggage or a consequence of struggling to bring my whole self to work. The loneliness driver I’ve heard of most from other CEOs is the inability to talk with people about the emotional rollercoaster that’s inherent to the role. So few people have experienced it, and those that have are rarely willing or able to be vulnerable and talk about the difficulties they faced. That lack of vulnerability and connection leads to increased loneliness. 

Adrenaline- At all times there are 100 fire drills, but only time to address 2 or 3. The best CEOs can focus on the ones that matter most and tune out the other 97 – all while helping their team do the same. There are constantly reasons to feel adrenaline. Those could be great things (an investor is open to investing in 2 weeks, time to sprint) or really bad things (a horrible HR issue; a board member who wants to sell; a major disagreement with a co-founder; whatever). Almost every day I felt adrenaline. You get hooked on it, like a drug, but it also drives stress. Adrenaline elevates your heart rate and blood pressure. Long-term activation of adrenaline disrupts your body’s natural functions. It causes headaches, digestive problems, anxiety, sleep problems, weight gain, memory issues and depression. 

Constant information flow- It’s not uncommon to get 300-500 emails a day, even for startups that haven’t hit escape velocity. Add to that your company’s dashboard of KPIs; meetings every day where you are usually expected to provide your thoughts along with news about the community, competitors, customers and macro issues, and it’s a constant barrage of information. Frankly I loved it, and it is exhilarating. But it also helps to drive the aforementioned adrenaline. If you don’t like constantly ingesting information, it may not be for you. 

Feelings of inadequacy- I don’t think all CEOs feel this, but I did and I know many (particularly great ones) who did. Inadequacy about my performance, the performance of the company and every other part of the job. Even though you know that the best companies have 100 fire drills at all times, it is still so easy to believe that your own indicate a dumpster fire at the core. “Just because I’m paranoid doesn’t mean I’m wrong” was a thought that would creep into my head too frequently. I found talking with other vulnerable CEOs and my management coach really helped here, and I wish I had done so more.

Arrogance- I was more arrogant when I was CEO than at any other time. I have confidence, but most of my life I don’t think I’ve demonstrated much arrogance (others may disagree). When I was CEO there were times when I felt arrogance creep in and I regret that. I think the feelings of inadequacy helped to drive the arrogance much more so than true confidence.  By trying to offset an overwhelming feeling of inadequacy, I overcompensated to the other end of the spectrum and it became arrogance.  

Jealousy- I think this is the least acknowledged emotion, but I’m confident it’s common. Until I became a CEO, it was unfamiliar territory to me. If someone got a better grade than I did in school or was better in sports, I assumed they deserved it and I wanted to work harder. But as the founder and CEO of a technology company, I felt jealousy every day. Jealous of another company’s growth, or technology, or team, or valuation, or board, or impact on the world, or anything. I could always come up with a reason. A fellow CEO once told me: “If you don’t enjoy the journey, the only thing that matters is the destination. If all that matters is the scoreboard, then it’s easier to be jealous.” I think I felt more jealousy because I wasn’t focusing enough on enjoying the ride. 

Secret desire to leave- I’ve been a part of a few CEO support groups, and 90% of their participants – regardless of company performance – have at one time or another talked openly about their fantasy of leaving. This is something that few investors I’ve talked to believe exists, but I think this desire is rampant. As a CEO, you feel dramatically less in control of your life than you would imagine. You’re always answering to customers, the team, the board, and others. I remember one CEO raising a $40m growth round for a startup that seemed to be doing really well. The day after the announcement, he told me: “I so desperately just want to leave. I don’t want to be the CEO anymore.” To be clear, I think those emotions, including for me, are periodic and rarely constant. But few non-CEOs recognize that these emotions exist and are common.  

Not knowing when the pain will end- Studies have shown that people can handle a lot of pain, as long as they know when it will end. If there’s no end in sight, it is much more likely to cause depression. Learned helplessness is a phenomenon that I think many CEOs, including myself, have experienced. The company could be doing well – great, even – and yet an exit is many years away. The CEO could feel depressed for all of the other reasons listed here, regardless of performance. But the CEO can’t leave – and that’s key to understanding why so many CEOs experience this learned helplessness. Just outright leaving is complicated for lots of reasons. Investors and employees joined the journey in part because of you. Other stakeholders including potential partners or major customers could be rattled. It could create a negative halo around the company. It typically takes a lot of planning for a CEO to leave and it is extremely difficult unless the CEO is fired. For me it was years in the making. 

Pride- I was more proud of what we built at CircleUp than any other professional achievement by a large margin. Seeing teammates grow, watching the product develop, seeing others strive for our mission, witnessing the impact on customers (in our case other founders) and the world around us. Nothing quite prepares you for the pride you will likely feel as a CEO. It is a really special experience.