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You don't have to suffer as a startup CEO
Every startup CEO knows the weight of the title, but does it have to come at the cost of personal suffering?
As a founder coach and ex-CEO of Makers myself, I've seen my clients suffer on the job in various ways and I have my own first-hand experience to share. Below I will share what I learned about one of the most common reasons why startup CEOs can feel miserable.
There's no question being a startup CEO (or a partner in a venture fund) is hard. Long hours? Yes. Difficult choices? Yes. Plenty of responsibility? Yes. High risks? Yes. Stress? You bet. Fear? Of course.
But feeling trapped, helpless, or turning to unhealthy coping mechanisms is optional.
Reasons startups CEOs may feel miserable
There are two big reasons why startup CEOs can be miserable: misunderstanding the job and being in the wrong job.
Being a CEO of a scaling startup is a counterintuitive job. We are learning to build a company that's building a product, instead of working directly on the product. We suffer because we try to do everything and firefight every problem. We are overwhelmed and often don't know what to do other than work harder. But we're already working at 110%, frequently sacrificing our family and social lives in the process. Secretly, we hope it won't lead to a divorce, but spoiler: it might.
To feel good as a CEO of a scaling startup, we need to have a good idea of what the job is, not only as an abstract framework (this one from Fred Wilson is a great place to start, though), but in the context of our own startup.
When I was in my second year as a CEO, a founder coach kept using a phrase "taking your seat as a CEO" without ever defining it. Eventually, the penny dropped: I had to understand it myself, through my own lived experience. And I did. There's no way to simply understand it intellectually, we have to live it.
But there's the second reason too. Sometimes we are doing a wrong job.
The job is hard enough if you love it. It's impossible if you don't.
It's important to be clear on whether you want to be a startup CEO for two reasons. First, running a successful startup all the way to an exit can easily take over a decade — a huge chunk of your life (an unsuccessful one will still take a few years and all your savings). Second, to be good at your job, to actually achieve what you want to achieve, you must want to do it. The job is hard enough if you love it. It's impossible if you don't.
Mistakes startup CEOs make
I notices that founder CEOs tend to make three big mistakes when their companies start to scale. First, they don't acknowledge how bad they feel, hoping the feelings will go away when they raise the next round, when they hire "one more executive", when they take a vacation or close a big client.
Second, they sit on the fence for too long after they notice doubts regarding whether they should be running their startups. This doesn't serve anyone. Reflection is important, but living with indecision for years damages wellbeing and undermines performance.
Third, if they do decide to step down, they don't plan it carefully and proactively, and this incredibly important and consequential transition doesn't get the attention it deserves.
Moreover, they tend to make three more mistakes thinking they are doing the right thing. First, they work harder, often making changes in the business instead of looking at their own psychology.
Second, they assume that being miserable is normal. After all, isn't it all part of The Struggle? Yes and no. We need to choose the right kind of struggle. If your body was born for running, but you signed up for a career in boxing, you will be neither a great boxer, nor a great runner. Yes, the Struggle is real, but we also need to choose the right kind of struggle for ourselves.
Third, they don't tell anyone about it. About a decade ago everyone was pretending they are killing it. Customers are piling in, investors are throwing money at them, and they are enjoying going from one conference to another flying business. Yeah, right. Eventually, startup founders started to open up and normalise being vulnerable in public. It's a long road, but it became a bit more acceptable to admit you're not always killing it. Hell, it actually feels like you're killing it for about 3 hours a year.
Many founders consider quitting at some point
Today, the open secret is that not every startup CEO is 110% committed to their job for life or at least until the exit. In the privacy of coaching conversations the reality is different. A lot of founders at some point of their journeys wonder if they should be running their businesses. It's ok. It's not a sign of failure or weakness. It's a perfectly good question to ask.
However, it's genuinely hard to even consider stepping down because it brings up big fears. What if I'm making an irreversible mistake? Who else can run my startup, if not me? What if I don't know what to do next with my career?
These fears are understandable. I went through each of them myself. I was afraid to acknowledge I wanted to step down as a CEO of my business. I naively thought that doing so is something to be ashamed of. I felt trapped and without options.
As a result, my wellbeing suffered more than I wanted to admit at the time. Company performance likely suffered too as I was distracted by my indecision.
Most of all, I was terrified to let others know I wasn't as committed as I pretended to be. I was terrified that the alternative to running the business was even worse.
What kept me trapped were my own thoughts.
However, once I started — or, rather, was forced by life — to face the situation and take action, I learned that I didn't have to suffer. That there is another way of life much more aligned with who I am deep inside. That there is a way to orchestrate a beautiful transition to another CEO.
Most of all, I learned that what kept me trapped were my own thoughts.
This is why today, as a founder coach, I help startup CEOs do two things. First, understand what the job is, to take their seat as a CEO and make it their own. Second, if they ever find themselves thinking if they should step down, make up their mind without sitting on the fence for years, feeling trapped in the prison of their imagination, and plan a graceful transition. There's a way out.
And that's why I say that there's no need to suffer as a startup CEO. Work hard, feel the pain, experience stress, bear responsibility — yes to all of that. But it's not the same as suffering.
Being a CEO doesn't mean enduring constant misery. By understanding our roles and seeking the right support, we can navigate challenges with resilience, not suffering.
Interested in diving deeper into CEO transitions? I'm writing a book on it and I’d love your insights. Become a beta reader and help shape the narrative. Contact me at email@example.com.