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Ryan Caldbeck @ryan_caldbeck
, 21 tweets, 4 min read Read on Twitter
1/ I believe there are things that CEOs almost universally feel, but are afraid to talk about, making this journey as a CEO lonelier and less healthy. I recently had an amazing dialogue with some other CEOs about these topics. I wanted to broaden the conversation publicly.
2/ People may make up stories about my intentions. Call me weak, brave, etc. Mental health is a vital topic that doesn’t get enough attention- esp amongst leaders. This isn’t a sign that I’m burnt out or that CircleUp is in a rough spot. Far from it. It’s me sharing how I feel:
3/ I feel the soul crushing stress and pressure of being a venture backed CEO. In the worst moments – missing a goal, letting a team member go, pivoting - it is almost unbearable. In best moments -just closed round, hired someone amazing, hit big goal- I feel pressure about next.
4/ I feel all consumed. All the time. It's hard for me to feel present in non-work conversations. On my Friday date night with my wife, I often struggle to focus on us- my mind slips to work. I hate that. I’m embarrassed to admit it. I actively work on it. But I feel all consumed
5/ I feel incredibly lonely. As CEO it’s hard to fully open up about my company and it’s hard to find other CEOs who are willing to be vulnerable and talk honestly about the hard things. The “we’re crushing it” CEO just makes me close down more.
6/ I feel tired- mentally and physically – constantly. I sleep less well than I ever have in my life- and almost never am able to catch up on sleep. Not because I’m so busy, but because my mind races and refuses to rest. This has been my reality for 6 years.
7/ I feel scared. The fear has increased with time and I had thought it would decrease. Fear that I will disappoint people, fear that our effort will be wasted, scared that new team members won’t want to join or that our best will leave.
8/ I feel worried that I don’t know what to do. Experts call this Imposter Syndrome. Some of the best leaders I’ve ever seen still have it deep down inside. @bhorowitz THTAHT Chapter 7: How to Lead Even When You Don't Know Where You are Going. (Book I most identify with)....
9/ ….a quote from Howard Schultz I really like: “One of the fundamental aspects of leadership, I realized more and more, is the ability to instill confidence in others when you yourself are feeling insecure.”
10/ I often feel like I can’t be my whole self. I’m honest and hardworking. That’s easy. But sharing more of myself - what I like/don’t like outside of work- is hard for me because I’m worried I will alienate others. I try to be authentic but it is hard to be all of me.
11/ I feel jealous almost every time I talk to another entrepreneur. They always seem to be better than me or us at something, anything. Shows like Silicon Valley are not fun for me - my mind just spins about things we could be doing better. Or reminds me of painful failures.
12/ I feel all these things every day and I know many other CEOs do too - wherever they live, whatever type of co/org/team they lead. Fear, self-doubt, and fatigue…. But it’s really really hard to say it out loud. Especially in Silicon Valley where there is So. Much. Posturing.
13/ But just because it’s damn hard doesn’t mean I’m over it. We just had the best six months we’ve had in our history - by far. And I’m all in.
14/ It’s the hard things about being a CEO that make the joys that much sweeter. When a team member proudly releases a technical blog or shares an update about something they’ve been working on. When a career develops right before your eyes and someone grows to have a big impact
15/ Those moments, and the journey overall, give me so much energy. Because we’re creating something. And the chance to have an impact on others, to help entrepreneurs to thrive, gets me more passionate than I could have ever imagined at work.
16/ I feel so lucky that I have the opportunity to try. To try to build something that matters. To be a part of something bigger than myself. To live in a place and a time where this is possible. To have the resources and support system to be able to give this a real shot.
17/ This isn’t about the hindsight of the success story. We still don’t know what will happen here. It’s about the process of getting to that success, with every fumble and pivot and sleepless night along the way.
18/ I’m not done. Nowhere near it. But I feel compelled to share this today. The benefit of doing it now – and not waiting until the CircleUp story has been fully written - is so that other CEOs might feel more comfortable expressing themselves, and we can all lead happier lives.
19/ I’m also writing this to hopefully create empathy. Empathy amongst entrepreneurs, teammates they build with every day, VCs that fund them, friends and families that support their journey. I’m hopeful that this empathy will create safe spaces for others to share their journey.
20/ It's ok to be scared. It's ok to be worried. It's ok to be tired. If we can talk about it, and build bridges to support & encourage each other the system overall will be more inclusive, more reassuring, more open. Everyone is on their own journey - now you know part of mine.
21/ To open this dialogue, we need to be willing to talk about it. If this made you feel something - better, more connected, more understood, etc. Or if you just feel some of the same feelings, I would love to hear from you and I think others would too. Share your feelings.
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