11 Fears of CEOs in Transition

Our fears are many but so are the ways to work with them.

Every CEO considering stepping down has at least a few fears. Having interviewed dozens of CEOs in transition for my upcoming book Startup CEO Succession: A Founder’s Guide to Leadership Transition and reflecting on my own experience, I identified 11 distinct fears that often stop founders from taking action. The last one surprised me and, I’m sure, will surprise you!

In this essay, I’ll briefly outline each of them, alongside how I think about approaching each of them.

1. What if I’m making a mistake?

This was my biggest fear when preparing to step down as CEO of Makers. What if I was trying to address the wrong problem? What if, two months later, I regret it?

After all, I was running a successful startup that is making the tech industry a better place by training incredible developers who regularly describe their experience as life-changing.

Antidote: I found it helpful to accept that I won’t know if I was solving the right problem, and it’s okay because I can trust my ability to face the consequences of my decision. If I’m going to wait until I have certainty, I might be waiting for a very long time, paralysed by fear. If I move ahead with a sense of trust in being able to navigate what life will offer me, I can continue to make progress.

2. What if I don’t know what to do next?

Another big fear for me was the fear of the unknown. What do I want to do next professionally? Sure, I’ve been telling my friends and coaches for years that I want to train as a coach one day, but what if I’m no good or don’t like the work?

Antidote: While I can’t know what it will be like after I step down as a CEO, it’s not a reason not to do it for two reasons. First, it’s a separate question from whether I need to step down. If it’s the right thing to do, it’s the right thing to do regardless. Second, I am fully capable of facing life as it presents itself.

The fear of not knowing what to do next is the fear of being unable to handle the uncertainty. It’s the fear that life is so scary and unpredictable that we need the safety of our current position to be okay.

3. Who am I if I’m not a founder?

Running your startup can feel like a rollercoaster because it feels like your identity is inseparable from the business. If the company is doing well, we feel we’re on top of the world. If the business is struggling, it can feel nauseating.

It is very understandable that losing the founder's identity may feel scary. This is how our friends know us and how we thought about ourselves for years.

Antidote: The way to befriend this fear is to remember to trust your ability to find and build a new identity. As founders, when we step down as CEOs, we never go back to our old identity that we had before starting the business. Instead, we lean into the future and build a new one, trusting that the new identity will feel even more comfortable, even if we can’t see it yet.

Not being able to see that new identity is normal because it doesn’t exist yet. But it doesn’t mean that it can’t exist or won’t exist. Trust your ability to build it.

4. Will others still respect me?

Another of my fears was around status. Having a “founder and CEO” business card was cool, especially because many people in the UK tech community knew Makers because of the thousands of developers we trained. My mum was proud that her son was running a business. As much as I liked to pretend that it didn’t matter to me, it did.

Ultimately, the fear of losing status is a different way to describe an illusion (or delusion) that we’re not lovable and acceptable just as we are. The truth is that we don’t need our startup or the founder status to feel ok. An even harder truth is that trying to hide behind status never works well or for a long time: a part of us will still feel like we need to hide.

Antidote: The way to work with this fear is not to keep hiding and not to find another thing to hide it behind, but to realise that we don’t need to hide in the first place — that we’re okay as we are and are unconditionally human.

There is no simple recipe or checklist for getting in touch with that deep sense inside you that tells you that you’re okay as you are.

As founders, we are often driven to build and achieve by some chip on our shoulder, looking to prove to someone, real or imaginary, that we deserve to be loved and accepted. Eventually, we realise that we can’t prove it and that no proof was ever required in the first place. Only once we drop this weight do we realise how much we might have been carrying our entire lives.

5. What if I will have nothing to do?

The fear of an empty calendar may sound unusual or even unreasonable. After all, aren’t we founding startups precisely so that we could be in charge of our time and, after leaving the business, have the freedom to do or not do anything at all?

An empty calendar can be scary because a part of us knows that there are essential questions we aren’t answering when running too fast. We don’t know what we’ll discover when we slow down. What if there are more fears there? What if it’s overwhelming?

Antidote: My invitation to any founder who fears that they’ll step down and won’t know what to do with their days is to treat this as an exceptional opportunity to discover what they need to face. Uncertainty tends to be uncomfortable but abundant with lessons about where we are still stuck and what we need to work on.

James Hollis ' audiobook Through the Dark Wood is a great place to start exploring what needs to be faced. This book is about transitioning from the first to the second half of life. It might be that the fear of an empty calendar is coming up for those founders who sense that how they’ve been living their life up until now isn’t working anymore, and they are called to do some inner work to discover what their second half of life will be.

6. What if I’m unemployable?

This fear is usually shared as a joke: “I have been working for myself for so long, no one will ever hire me”, but there’s both a grain of truth and a grain of fear in it.

The grain of truth is that startup founders are in a weird spot regarding employability. On the one hand, they possess various beautiful qualities and skills: resilience, tenacity, business acumen, resourcefulness and many others. On the other hand, they usually aren’t professional CEOs with a track record of taking over someone else’s company and taking it to the next level. Therefore, founder are afraid it’ll be hard to find their next job.

Antidote: Remember that the grain of fear in this is misguided. I've yet to come across an example of a founder CEO unable to figure out what’s next for them. It may take time or effort, but if you have what it takes to build a startup, you have what it takes to land on your feet after leaving it.

7. What will my investors think of me?

Yet another fear is that of letting down your investors. Contrary to another stereotype, according to which it’s easy for startup founders to be spending someone else’s money building their unicorns, most founders I know have a deep sense of responsibility towards the investors they raised from and respect for the faith their investors put in them.

This respect is healthy. However,  professional venture capitalists are grown-ups who account for the risk of a founder stepping down and, therefore, price it in by offering terms that take this risk into account.

Just as importantly, stepping down might be in the investors’ interests. If another CEO takes over with new ideas and energy, it may increase the chances of the company delivering a great return on the investment. Therefore, it would be misguided for founders to avoid stepping down out of a sense of obligation to stay until an exit.

Antidote: Remember that our job as CEOs is not to last in our seats for as long as we can. Our job is to make the business successful. If replacing ourselves with another CEO will likely make the business more successful, the right thing to do is to discuss it with the board. Feelings of guilt that may accompany this conversation are natural and understandable, but they aren’t a reason to stay in a job we should otherwise leave.

8. What if I won’t be able to raise again?

A related fear is that stepping down will prevent founders from raising money again.

What matters is how it’s done, not whether you ever left your position as a founder CEO. If the business was handed over to a new CEO, who took it to new heights after realising that, for example, your skill set lies in navigating the early years until finding the product-market fit, congratulations! It’s a mark of success to take the business to the point when it’s ready for the next growth stage under a new leader, not a failure.

Antidote: Remember that your ability to raise money depends on the results you deliver and how you face difficulties. If you work hard as a founder, show self-awareness, treat others with respect, face challenges head-on, welcome difficult conversations and behave with integrity, that’s what will influence your chances of raising again, not how long you managed to stay in your job past the point when it made sense to do so.

9. How will I pay the bills without my CEO salary?

Another fear that occasionally stops founder CEOs from considering stepping down is not knowing how to cover their expenses while navigating this transition. Contrary to a stereotype held by those who never started a business, founders aren't flush with cash, particularly those who haven’t had a big exit before.

The company may be doing well, and the CEO's salary may be comfortable. But that’s different from being able to afford to take several months or more unpaid while they are figuring out what to do next, especially if they have children.

As I argue in the book, it’s pragmatic for the business to give the outgoing founder financial certainty, as this will make the transition easier and increase the chances of business success.

Antidote: Take charge of the conversation with the board. Although they may be very open to giving you financial certainty for practical reasons, it’s unlikely to be on top of their concerns unless you raise it yourself.

10. What if the new CEO screws up?

If you’re the only person who ever ran your business, it can be hard to imagine that someone else could do your job, let alone do it far better than you. It can be easy to focus on worst-case scenarios of the new CEO failing your business.

A slightly related fear is that the new CEO will make the company financially successful but will sacrifice its culture or violate its values to make it happen, ruining what you worked so hard to build.

Antidote: The way to approach this fear is to ask yourself whether you haven’t found the right candidate yet or assume you’ll never find a candidate you can trust.

If you’re having doubts about a specific person you’ve considered your successor, it’s worth going deep into these concerns. You’ll never have perfect certainty that they’re the best person, but you should be certain enough.

However, if you struggle to imagine anyone possibly doing a great job, look inside and work with your own fear.

What is it exactly that you’re afraid of? How does it feel in the body? Can you stay with it? Can you relax into it? What happens if you write those fears down on a piece of paper? What if you explain it to a trusted friend, coach or therapist who will listen and help you make sense of the fear?

A new CEO may indeed fail at their job, but it’s not a reason to never trust anyone.

11. What if my successor smashes it?

This fear surprised me because I never had it myself. A founder I know captured it this way:

So you know, all this work we've done to get ready to be this amazingly successful business? And then the new guy takes over and this thing flies! Suddenly he’s a superstar? And I'm like, fuck, I can't do that.

That’s how our ego can set us up for failure by putting us in a double bind. The ego says, If we hire the wrong CEO and they ruin the company, we’ll feel like we’ve failed.

And the ego continues: What does it say about us if we hire the right CEO and the company becomes vastly more successful? We couldn’t have done it ourselves? We left at the wrong time? Were we the problem to begin with?

Antidote: Recognise two things. One is that the new CEO’s success is exactly what you aim for if you leave. There might be a part of you that feels a bit insecure about that, and it’s ok to have it. We can notice this insecurity and let it be, simply noticing it as a pattern of thoughts and feelings.

The other thing to remember is that the business's success doesn’t define our success in life or our worth. You don’t become a better person when you IPO your business, and you don’t become a worse person when you call in the administrators.

Final thoughts

The goal is not to banish or ignore the fears that come up for founders considering stepping down. If we try to do that, the fears will find a way to sabotage our lives. Instead, we need to get to know them, to listen to them, to see what they have to say and what they are trying to teach us, and treat them with respect and even gratitude because each fear is trying to protect us from something.

Paradoxically, the more you work with your fears, the more of them you might discover, but they will feel less scary as you grow in your confidence to face each of them.

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PS: Where can you buy the book? Not yet; it’s still in the final pre-publication stages! But you’ll certainly hear from me when it’s out.