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There are few professional transitions that prepare you for the vacuum that is created when you step down as CEO. I’ve been fortunate to talk with 20+ CEOs about their transition and what life was like after they left their role. I found their experiences to be incredibly similar to one other and also my own. Most went on to do extraordinary things in their next act, but I was most curious about the transition itself. 

These are some of the emotions and experiences I have had during my transition. They are not in order and they are not MECE. A marketing person once told me to not talk about mental health issues publicly given the privilege that I have in life. If you agree with that, this post is not for you. 

Stress– Being CEO is an exceptionally stressful job, and the stress never dissipates. If the company is doing well, the CEO feels pressure to keep it going, to reward high-performing employees, and to get to the next milestone. If the company isn’t doing well there is obvious stress, only exacerbated by the need to put on a good face. 

Chronic stress leads to serious health consequences if not treated, including anxiety, feelings of helplessness, trouble sleeping, and depression. I felt more stress on the average day as CEO than I did on any day of my life before starting CircleUp. When I stopped being CEO, the stress went away almost immediately. There were a few occasions after I transitioned out when I double-checked whether I needed to engage with a certain topic, or when someone would (by habit) bring me into a conversation that I no longer needed to be a part of. But in general, the stress declined by about 95% in less than a week. 

Vacuum of information flow– As a CEO you are hooked up to an IV drip of constant information. The dashboard of the company, internal emails, external stakeholders, macro changes impacting your industry, etc. You’re on receive mode all the time. As CEO, my day began at 6am with 30-50 emails (mostly from East Coast) and typically ended after 300-500 emails throughout the day. Many weren’t things I needed to weigh in on, but it’s still a constant stream of information that most senders expect you to ingest (if not respond to). Sprinkle in a day full of meetings that need your presence and attention, and you can quickly see how the information flow adds up.

When I stepped down, that Matrix-style IV drip plugged into the back of my head was ripped out immediately. Within a few weeks my emails were down to 30-50 a day. I remember a few months ago I woke up and for the first time in a decade I literally didn’t have a single email waiting for me. 

This decrease helped lower my stress dramatically for a few reasons. The lack of fire drills I was ultimately responsible for made a huge difference, but I also rapidly realized the massive opportunity cost of constant, work-related communication. Not being at my desk responding to emails allowed more time for deep-thinking, more time with my kids, more time reading — the list goes on.
Yet despite these benefits, the dramatic shift also led to perhaps the strongest emotion that I and many other CEOs experienced during the transition phase: insecurity.  

Insecurity– In my research, which included talking with CEOs and reading blogs and books about transitions, the most common “advice” I got was to try and be comfortable living in “the nothingness”. “After you step down as CEO, just be ok saying you don’t know what you’ll do next and you’re taking time off.” That was the advice from effectively 100% of the people I talked to who had experienced a similar transition — whether it was the CEO of a Fortune 100 company, a startup CEO that sold the company for billions, or the CEO of a company that went under. After half a breath, everyone — Every Single Person — also talked about feeling wildly insecure in their transitional period. When you’re CEO, regardless of the company, others depend on you. At least in tech and Silicon Valley, there is a certain cache that comes with saying you’re CEO. The information flow previously mentioned led me to always feel “on” and “needed”. You get invited to dinners that seem fancy; dinners you never hear about and are entirely unaware of when you’re not a CEO. Then it stops.

The information and invitations dry up. When asked what you do, the answer “I’m taking time off” is suddenly met with “oh” instead of “oh wow”. I want to say that people don’t treat you differently, but they do. It’s hard to know how much of that was me presenting myself differently (perhaps demonstrating more insecurity) and how much of it was the other person. My honest gut feeling is more the latter, but I don’t know. 

“You will feel a crushing amount of insecurity,” said one exceptionally successful CEO who had stepped down. He was 100% right, and it came on very quickly. I lacked a sense of clarity about who I was, what I did, what I would do next, why I was impactful in the world. I loved spending more time with my kids, but that personal joy didn’t abate the professional insecurity I experience(d) during my “nothingness” phase. 

Offers and saying no– When I was planning on stepping down and talking to trusted advisors and friends, I was told by several other CEOs, “you’ll get offers on what to do next”. They recommended not even considering new opportunities and just “living in the nothingness” for at least 6-18 months. William Bridges recommends not putting a time limit on the “nothingness” period. Allow your mind to decompress and figure out what you really want to do, they said. I’ve since gotten a bunch of offers, and each time I decline I am confident, perhaps positive, that I won’t get another. Some are to be an investor, some are to be CEO, and some are to start something entirely new. Every time I say no and then immediately I break into a cold sweat, confident no one will ever call again. I’m not giving that information as a humble brag, I’m sharing so that when you go through something similar you’ll know you aren’t alone. There is no logic or data that can convince my emotions that another offer will come. 

Loneliness– I’m more lonely now. But that could be because of COVID, I’m not sure. Since transitioning, my human interaction has declined dramatically. I’m split between an introvert and an extrovert, and sometimes the interaction would exhaust me as CEO, but it’s also been tough to adapt to its absence. 

Regret– My management coach, Ed, asked if I might feel regret when I stepped down. It was a worry, but my experience has held very little regret. There are certainly things I miss — I absolutely loved being CEO of CircleUp and the time spent with our team — but I know stepping down was the right decision for me.

Those are the overriding emotions during this nothingness phase as of early August 2021, about 9 months into post-CEO life.