Hi [FIRST NAME GOES HERE],

I asked 100 CEOs this exact question for you...

Here are the six standout answers.

Steven Bartlett - Founder of FlightStory, serial investor, dragon on Dragons' Den, and host of Diary Of A CEO podcast.

The game we should all be focused on is the game of self-awareness; It's about tuning out what society, Instagram, motivational speakers, our parents, or newsletters like this tell us, and tuning into that profound yet often ignored signal which asks, "How do you feel inside?”.

Whenever you're trying to solve a problem, you need to go to the first principles of that problem. In this case, instead of trying to decide between a 9-5 job or entrepreneurship - which are just paths - get clear on where you want to go - the destination.

Write out the core components you want in your professional life in order to feel great every day: challenge, freedom, a sense of forward motion, a supportive group of colleagues, meaningful work. Then design a life via a 9-to-5 OR entrepreneurship that will give you exactly that.
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Do not ask other people for their opinions; nobody else can truly give you advice on matters of the heart.

It doesn't really matter if you choose a 9-to-5 or entrepreneurship, because the risk is not in the path you take, the risk is in the price you’ll pay if you end up in the wrong place.

Codie Sanchez - Investor, NYT bestselling author & founder of Contrarian Thinking, the newsletter empowering millions to embrace the power of entrepreneurship.

Most people assume (stable job) = (security) - which is wrong. Your salary is a ceiling, not a foundation. And betting your entire financial future on one company that could replace you tomorrow? That’s the real risk.

Starting something new isn’t the scary part - blindly trusting a system you can’t control is. Not that entrepreneurship is EASIER. But employment is hard, startups are hard, acquisitions are hard. So choose your hard, diversify your income streams, and build wealth on your own terms.

Dom Maskell - Co-founder and CEO of running coaching app Runna; growing in under four years to a team of >100 and millions of users worldwide. Forbes 30 Under 30 entrepreneur.

Entrepreneurship isn’t just tough - it’s brutal. It takes more than hard work; it demands obsession, resilience, and a high tolerance for risk. Most people aren’t wired for it.

A 9-to-5 might mean missing out on something unique - control over your time, the thrill of building something from nothing. But let’s not romanticise the alternative. Stability has its perks, and great jobs exist with great upside - without the 24/7 stress.

Ask yourself: Do I thrive in uncertainty, or do I need structure to do my best work? Am I obsessed with solving a problem no one else is tackling?

Eric Partaker - Founder of The CEO Accelerator, which coaches CEOs how to scale themselves & their companies.

Here’s the truth: both paths are incredibly important. Just like in ancient hunter-gatherer societies, where some took high-risk hunting roles while others ensured survival through gathering. Both are essential.

A 9-5 isn’t a trap; it can be a launchpad! It provides stability, skills, and income, giving you the space to build something on the side or ease into entrepreneurship.

You don’t need to start a company to think like an entrepreneur. Look at Microsoft's CEO, Satya Nadella - he worked his way up from within, and with a 2024 estimated compensation of nearly $80 million, I think that’s pretty exceptional!

There’s no right or wrong path. The real question isn’t which route is riskier - it’s whether your risk tolerance and ambition align with what you’re doing.

Murvah Iqbal - Co-founder and CEO of HIVED, a London-based climate and logistics startup.

Starting a business isn’t just risky - it’s a mental endurance test. The highs are euphoric, but the lows can break you. Not everyone is wired for that, and there’s nothing wrong with choosing stability.

For me, there was never a question - I was going to start a business. I had job offers in consultancy after university, but the idea of a traditional career felt more like a slow gamble than a safe bet.

I grew up in an entrepreneurial family, so the thought of building something of my own wasn’t just exciting - it felt like the only path where I’d truly thrive. The real risk, for me, was waking up every day feeling unfulfilled.

But if you can stomach the uncertainty, fight through setbacks, and push through when most would quit - the fulfilment of creating something from nothing is unmatched.

Richard Chambers - Founder & CEO of Get A Drip, UK's leading longevity clinic.

Security isn’t the opposite of risk - stagnation is. In a 9-to-5, the real danger is staying in a role that doesn’t push you to grow while entrepreneurship flips that trade. You give up security for the chance to build something real and allow yourself to grow in ways you never expected!

I don't think success is about labels. The people who step up, own their work, and push beyond what’s expected thrive in all types of environments - whether they’re employees, founders, or something in between.

Remember: initiative, adaptability and problem-solving will always be in high demand.

I read every single message and your input shapes this - click the button below to let me know.

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Talk soon,

Steven

73 Cornhill, London, EC3V 3QQ
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