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I asked 100 CEOs this question, and here are the top 5 answers:
"No one told me how lonely this journey would be.When I started Airbnb, I started it with my friends. Then we hired people. They were employees, but they were also kind of our friends. I was the boss but we were all broke in a three-bedroom apartment, so what does it mean that I’m CEO? It was a meaningless title.
I felt very connected to them. We were more like a family than a business. But as we got successful, it became more of a corporation. There was a chain of command. There were more boundaries. We started hiring people who had families and people with families don’t hang out with you on nights and weekends. It became more formal.
That’s the moment your employees become your employees, and less your friends. It’s isolating. People start looking at you differently. You find yourself working more and more to live up to the responsibility, but you feel like you’re never working enough. You’re working 60 hours a week, then 80 hours, then 100 hours. You almost feel guilty any second you’re alive and not working.
When you’re lonely, you’re less empathetic. Your sense of vigilance is up. You don’t see problems clearly. You don’t have people to bounce ideas off of.
Lonely leaders are probably not the best leaders. The truth is, sometimes we need to step away from work. We need to be happy and to do that we need to have healthy relationships to make good decisions.” Listen to the full conversation here.
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Raquel Bouris, Founder & Creative Director of WHO IS ELIJAH, an Australian fragrance brand valued at $20M.
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“I’ve had moments where we had $0 in the bank account, but a million dollars owed to us by retailers.Those are the moments of building a business that rarely make it into glossy press releases or Instagram posts.
When I launched my fragrance brand, I didn’t come from a corporate background or have millions in funding behind me. I was hand-filling bottles in my garage while raising my newborn baby.Fast forward to today, we are a multi-million dollar global brand, stocked in major retailers across the UK, US, New Zealand and Australia. But that journey was bloody difficult, and still is!
What I feel is missing from most CEO and founder conversations is the truth of how they got to where they are. How they got through the bits they might be embarrassed of sharing.
- The nights you don’t sleep because you don’t know how you will make payroll.
- The wrong hires that hurt your business.
- The partnerships that fail.
- The product and supplier issues.
- The days where you feel like you may just lose everything.
There have been times when I questioned every decision up until that point, and have had so many realisations along the way of what I did wrong.
I have found it is in those messy, unfiltered moments that you grow as a leader. That’s where you learn resilience, creativity, and grit. That’s where you discover that being a CEO or founder isn’t about having all the answers - it’s about finding them fast, motivating your team when you’re running on empty, and staying committed to the vision even when everything around you feels uncertain.
I want other founders and future CEOs to know: if you feel overwhelmed, under-qualified, and like you’re barely keeping it together, it doesn’t mean you’re failing. It means you’re building.”
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Mark Baillie, CEO of Compare The Market, one of the UK’s biggest price comparison websites. |
"The surprising truth is that business isn’t always as dramatic or high-stakes as Hollywood would have you believe. Most movies about business feature visionary leaders making ‘make or break’ decisions which always pay off. In reality, those moments are rare. For most CEOs, they never come at all.
I used to want to be across every detail - every contract, every number. Now, I barely look at them. Not because I don’t care, but because I’ve built a team I trust completely. With thousands of decisions to be made, you’ll never have time to make them all personally, so you need a system built on trust and empowerment.
Business is a bit like gardening. You tend to it every day. The grass is mowed, the weeds are pulled. Maybe every few years you get to redesign a corner that’s starting to look a bit tired. It’s long-term, it’s careful, it’s disciplined, and it’s rarely headline-grabbing.
Maybe that’s why we don’t talk about this side of leadership much. It isn’t flashy - but it is quietly satisfying. Over time, it builds something truly remarkable.”
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Carl Hazeley, CEO of Finimize, an investment information platform with over 1M subscribers. |
“I'm constantly questioning whether I'm making the right decisions. That’s exactly what makes me good at my job - but I can't talk about it.
CEOs need to be (or at least be seen to be) completely certain. If you get things wrong, it has to come down to things out of your control, like market forces - not because you’ve fundamentally made the wrong call.
Any moment of uncertainty or wavering might be perceived as a weakness or a lack of conviction or belief in the company and its people. It could even result in the company failing to achieve its goals.
That feels wrong, and it’s strange we’re not willing to discuss it much, if at all. A CEO has the livelihoods and often the lives of an entire organisation's employees in their hands. Their fortunes depend on their decisions and leadership. It should be natural that you question, re-question, and question again what you’re doing.
Ultimately, you want and need to be able to make the tough decisions and stand firm in backing them, and leading the company and its people to deliver upon them.
But I think there’s room, at least in this little corner of the internet, to be honest, a bit more human, and admit that you’re not 100% sure all of the time. That could even be the key to being a responsible CEO.”
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Kiran Kachela, Founder & CEO of CI Projects, a business consultancy that works with the NHS, the Ministry of Justice, academic institutions, and private sector organisations. |
“Being a CEO means making unpopular decisions that impact the people you care about most.
People think being a CEO is just about pure, detached strategy. No one talks about the emotional isolation of making a decision you know is right for the business's survival, yet will be personally devastating to key members of your team. Over the years, I’ve faced countless decisions where the ‘right’ choice wasn’t necessarily the easiest.
One moment that stands out is when I had to say no to a major client contract because I could see early warning signs that their approach would impact our team’s wellbeing and clash with our values. It became apparent that women weren’t treated as equals. They were seen as administrative support rather than strategic contributors, and their voices weren’t given space in meetings or decision-making.
Walking away meant taking a financial hit. Several members of my team were out of project work for a few weeks. But they saw that integrity and culture always comes first.
The right decision is often clear. But you’re choosing the hard path for the health of the collective, and you’re the one person who cannot lean on a co-worker or a subordinate for comfort. There are moments when the self-doubt creeps in, when I question whether I’ve made the right call or whether I could have done more.
This weight ultimately sits with me as the CEO. I don’t want to transfer that burden onto my team. But I do share my vulnerabilities with them. I think it’s important that they see that I’m human too, and that learning comes from both successes and mistakes.”
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Talk soon,
Steven