Hi,
I asked 100 CEOs this question, and here are the top 6 answers:
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Doug McNamee, Founder and CEO of JOLT, the Australian-founded global EV-charging company expanding fast-charging infrastructure to accelerate a zero-emissions future. |
“The boldest risk I took was following an idea everyone told me was impossible.
In 2019, I bought an electric car and realised home charging would cost almost as much as the car itself. But there was a problem with the only alternative: public charging. Sydney had just two public chargers for five million people.
My solution was simple:
Public chargers with ad screens, offering drivers free daily power funded by ad revenue.
The reaction was unanimous: it wouldn’t work.
“Advertisers won’t pay.”
“The economics don’t make sense.”
“You can’t solve two problems at once.”
But I’d spent a decade in media. I knew EV drivers spent over half an hour at a charger - a captive, high-intent audience no billboard could match.
So I backed the idea.
Our first charger had queues within hours and the model proved itself almost immediately. Today the network covers multiple countries and continues to grow.
It's a reminder that sometimes the boldest risk is trusting an insight no one else believes in yet.”
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Helen Millar, Founder of Heart Healer Ltd, an international speaker, coach, and transformation expert to CEOs and visionary leaders. |
“I invested over half my life savings on myself, when everyone would have called it reckless.
When both my parents died and I had no family to lean on I realised I had to start making major decisions by myself. There was no one to soundboard with.
After years working in coaching programmes, I was offered an opportunity to get one-on-one coaching from someone I thought was brilliant. The cost? More than 50% of everything I had saved as a solopreneur.
No backup plan, no mortgage, still renting.
Saying yes meant letting go of everything I’d put aside for six months’ sick pay, maternity pay, pension, and a house deposit.
I didn’t tell anyone. I knew they’d think I was mad. I knew they’d try to talk me out of it. But something in me knew it was the right move. So I transferred the funds.
Within a year, I grew my business by 360%.
I invested in a second year of coaching, then doubled down again to work with Tony Robbins in his inner circle.
What I’ve learned is simple: investing in yourself is always the highest ROI. Surround yourself with people who set a higher standard, and your life can only rise to meet it.
It looked like madness from the outside. But if you don’t want an ordinary life, don’t follow ordinary logic.”
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Jessica Walsh, Founder of &Walsh Creative Agency; designer, art director, illustrator and educator. |
“The boldest risk I’ve taken was choosing to spend my most valuable resource, my time, over one tiny detail instead of moving on to everything else demanding my attention.
When I started my own agency, &Walsh, it was a pivotal moment in my career and I wanted the branding for the studio to set the tone for the kind of work we wanted to create.
Designing the right ampersand for our name became something of an obsession for me. We sketched more than 1,200 variations of the ampersand before landing on the final one. I probably drove a few people a little nuts during the process, but I just kept pushing and pushing. For me, it wasn’t just about creating something beautiful. It was about finding that one defining element that could carry the entire brand and represent who we are.
A lot of people didn’t understand why I was spending so much time on something so small. But I’ve always believed that excellent creative work isn’t just about the big idea. It’s about pushing for that one better detail that makes people stop, feel something, and really remember it.
In the end, that ampersand was so much more than just a design choice. It became a symbol of everything I stand for: pushing boundaries and never settling for safe.
Sometimes the boldest risk is obsessing over the little things, and caring deeply enough to keep going when everyone else thinks you’re done.”
If you’re someone who pushes for that one better detail too, the One Better Guide was made with you in mind.
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Rupal Patel, Founder & CEO of The Global Leadership Lab and best-selling author of "From CIA to CEO". |
“The boldest risk I took was ignoring my family’s insistence to get a “safe job” that would look good on my resume and starting my business straight out of my MBA.
In 2013, my siblings sat me down for what was basically an intervention. They were convinced I was throwing away my degree, my career, and financial safety net. Their argument made sense and I felt every bit of the fear they were projecting. Part of me wondered if they were right.
But I knew they were giving advice based on their own anxieties, not my ambitions. They loved the version of me that was safe.
So I backed myself. I built backup plans, prepared for things to go wrong, and committed fully to the business. Those first months were rough, their doubts echoed in my head on the bad days. But I kept going, and within 18 months I’d replaced my post-MBA salary and proved that the risk was worth it.
Two things I now look for when I get advice:
1) Are they qualified to give the advice? AKA Have they done what we are trying to do successfully?
2) Do they have the same values as we do?
What that whole experience taught me is that not everyone is worth listening to, no matter how much they love us. Not everyone is qualified to have an opinion, no matter how long they've been in our lives. The people closest to you can care about you and still be completely wrong about what you should do next.
Sometimes the real risk is listening to everyone else. The bold one is trusting the direction you know you need to go.”
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Prof. James Logan, CEO at Arctech Innovation, developing AI-enabled, nature-inspired technologies that detect pests and diseases to help predict and prevent global health threats. |
“The boldest risk I took was walking away from the safety of academia to build a company nobody believed could work.
At the time, I was doing research with huge potential for public health, but it kept getting trapped in the slow, traditional publishing process. We were making discoveries that could genuinely help people, yet they weren’t reaching the real world fast enough.
Academia and industry were traditionally kept separate and that gap was stopping good science becoming useful. I could see the bridge that needed to be built, but when I said I wanted to launch a company from inside a research institution, almost everyone thought it was the wrong move. It hadn’t been done at our university.
But what I believed then and still believe now is that research only matters if it makes a difference. And sometimes the right decision is the one that looks completely wrong in that moment.
So I trusted my instinct, even when hardly anyone else saw the vision.
Today, the tools we’ve built are used globally across public health and agriculture to predict, protect, and prevent disease faster.
And it all started with the decision to build the bridge nobody else could see, and create something that didn’t exist yet.”
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Talk soon,
Steven