Hi,
I asked 100 CEOs this question, and here are the top 5 answers:
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Tom Eggemeier is CEO of Zendesk, a tech company providing software-as-a-service (SaaS) to customer support and sales |
“Here’s what I’d say to my younger self: You are so fixated on the horizon that you are completely missing the view right in front of you. At 16 years-old, you have this constant, buzzing anxiety that life only truly starts once you hit the next big goal. But the brutal reality is that there is no magic arrival point where everything finally feels complete.
Those quiet nights in with your friends in Ohio or the long, boring walks home are not just background noise, they are the actual substance of your life. If you spend every day waiting for the weekend or the next milestone, you are effectively wishing your life away. Learn to breathe and be where your feet are. Success is hollow if you never learned how to inhabit the present.
As for school, stop worrying about whether you’ll ever need that specific chemistry equation later in life. Turns out, you probably won’t. The real value is not in the facts you are cramming into your head for a test. It is in the grit it takes to wrap your mind around something difficult. You are essentially training your brain to be a flexible tool. In a world reshaped by AI, the specific things you know today will likely be outdated by tomorrow. Your only real superpower is the ability to learn anything from scratch. Focus less on being the smartest person in the room and more on being the most curious. If you can do that, you will never be left behind.”
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Alessandro Frau is CEO of Treatwell, Europe’s biggest wellness and beauty booking app |
“If I could give my 16-year-old self one piece of advice, it would be to not confuse talent with trajectory.
At 16, a lot of things came easily. School didn’t feel too difficult, I picked things up quickly, and I was used to being told I was “good” at things. I built an identity around that, thinking that being capable meant I was already on the right path.
What I didn’t see back then was how comfort can become a ceiling. When you’re praised for your natural ability, you tend to avoid situations that might expose what you don’t know. I definitely did. I shied away from things that made me feel average. I didn’t ask enough questions, and I mistook confidence for self-awareness.
The older me can see clearly that growth starts the moment you stop trying to protect the image of being talented and start being willing to be a beginner again. Have the humility to work harder than you think you need to, to learn and improve. Even when I became a CEO, I was a beginner again.
If I could go back, I’d tell myself that talent is overrated; in the long run, hard work always beats talent. But even hard work isn’t enough on its own. To maximise your chances of success, you need direction. People who challenge you, guide you, and tell you the truth when you need it. Mentors matter more than you think. I wish I’d realised this sooner. Mentors have steered me, and not just opened doors, but shown me which are worth entering. To this day I rely on mentors. When you find the right one, whatever you do, feed that relationship!
If I could go back, I wouldn’t tell myself to be smarter or tougher. I’d tell myself to stay open, stay curious, and let myself be stretched. Talent opens the door. Humility and effort decide how far you walk through it.”
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Chano Fernandez is co-CEO at Klaviyo, an email and SMS marketing platform
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"I’d tell myself that there’s no substitute for kindness, empathy, and hard work. Be someone others want to work with, trust, and learn from. Be an all-in team player.
Don’t be afraid to place some bets and take risks. Many of them won’t work out, and that’s OK. The learnings you gain from those moments are often far more valuable than the wins themselves. Growth doesn’t come from playing it safe all the time.
Most importantly of all, life is short. It’s important to be honest with yourself about what you truly care about. Try to build a life and career around things you have a real passion for and always question yourself along the way. Ask yourself if you’re doing the right things for your family, your friends, your team, your customers, your investors, and all the people who trust and depend on you. That self-reflection matters more than you think.”
“That there’s no way to fast-track experience. At 16, I was convinced I wanted to be a journalist. I’d wanted it since childhood – so much so that ITV Meridian News once did a bulletin on me reporting on a fire on my Nan’s road and giving my class the “inside scoop”.
I fell into PR entirely by accident – someone walked into the pub I was working in and offered me a short-term job to fill a gap. Twenty years later, I run a seven-figure agency.
When studying or starting out at work, I wanted to be good at things quickly. What I didn’t understand then is that there’s something both exhilarating and awful about learning on the job. The lows when you have no idea what you’re doing. The highs when you finally get something right.
I’ve never been comfortable with not being good at what I do. But by the time you reach my age (40), you realise you can’t rush competence. The only way to be truly good at something is to give it time – to make mistakes, take the wins, and learn through lived experience. The skills I value most in myself weren’t learned quickly, they were earned over time.
I try to explain this when nurturing new talent: my expectation isn’t that they know how to do something immediately, but that they’re willing to experience it and learn how to do it best. Most people want to fast-track success and achievement. I’ve learned that until enough time has been invested, that isn’t always possible.”
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Dan Rogers is CEO at Asana, a work management system allowing teams to coordinate and automate tasks
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“I’d tell my teenage self that environment – the combination of company, industry and location – matters more than most people think.
Rocket ships don't launch everywhere, they concentrate where talent, capital, and ambition collide. I eventually gravitated to Silicon Valley because I wanted to be around that intensity and innovation.
But proximity alone isn't enough. Rocket ships don't wait for you to be ready. So while working your way there, deliberately build the capabilities you'll need – learn strategy, understand how to build and ship products, develop skills to drive revenue. Take roles that don't look glamorous but teach you fundamentals.
It's the combination that creates opportunity. Get into the right environment where ambitious people solve hard problems. Then build the skills that will matter when the rocket ship appears.
Once on board, let the velocity pull you forward. Your growth accelerates with every iteration because you're moving at the same speed as everything around you. The opportunity compounds quickly. When that rare moment appears, be ready to jump on – because it may not come twice."
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Talk soon,
Steven