What Successful Entrepreneurs Actually Have in Common (It's Not What You'd Guess)

A while back, I set out to answer a question that had been bothering me: what do genuinely successful entrepreneurs actually have in common? Not the surface stuff — not "hard work" or "vision" or any of the words that show up on a motivational poster. The actual, underlying thing.

So I did what an NLP modeller does. I found people who were operating at a level I wanted to understand, and I interviewed them — not about their businesses, but about their minds. I asked them to think back to moments when they were launching something new, and I wanted to know what was actually going on inside their heads at that moment.

The mountain climber

The first person I spoke to ran a global conference business. I asked him about launching new projects. Without missing a beat, he started telling me about mountain climbing — where he places his hooks, how he sets his lines, how he manages the risk of the ascent.

I'll be honest, I wasn't sure what this had to do with my question. I let him keep going.

Eventually he circled back to business, and started using the mountain as a direct metaphor for what he does as an entrepreneur. Risky. You put safety lines in place so that if you fall, you're not destroyed by it. But you climb anyway.

The skydiver

The second person had built and sold a telecommunications company for several million pounds. I asked him the same question. He didn't talk about business plans or market research. He talked about skydiving. Parachuting. Surfing.

Two completely different people, two completely different industries, and both of them — unprompted — answered a question about entrepreneurship by talking about physically risky hobbies.

The pattern

I kept going. I spoke to a third person, highly effective in her field, and the same thread kept showing up: comfort with risk, comfort with not knowing exactly what happens next, and — critically — genuine enjoyment of that uncertainty rather than white-knuckled tolerance of it.

Once I noticed the pattern, I went looking for it in the research, and it turns out this isn't just anecdotal. It's a documented, commonly observed characteristic among people who build things successfully: a comfortable, even enthusiastic relationship with risk and uncertainty.

That's the golden thread. Not intelligence. Not work ethic, though that matters too. A trained-up relationship with risk.

What this actually means for you

Here's the useful part. If you're sitting in a comfort zone right now, feeling the pull toward doing something entrepreneurial but held back, this gives you something concrete to work on. It's not about magically becoming fearless. None of the people I spoke to described themselves as fearless. It's about building your relationship with risk and uncertainty the same way you'd build any other skill — deliberately, and in smaller doses before the big ones.

If you already have a place in your life where you enjoy uncertainty — a physical hobby, a creative pursuit, anything where you don't know exactly how it'll turn out but you do it anyway and it's rewarding — that's not irrelevant to your business ambitions. It's actually a working model of the exact muscle you need. The question worth asking yourself is: where do I already trust myself with uncertainty, and how do I bring that same trust to my business decisions?

Being an entrepreneur is, at its core, about being alright with not knowing exactly what's going to happen next, and doing the thing anyway.

I dig into questions like this live every week in Breakfast with Champions on Clubhouse — real investigation, not motivational talk. If you want to keep exploring this, you can find upcoming sessions and get on my list at ravingworld.co.uk/bwc.

---

If you want your message noticed, understood and remembered, Precision Communication is your practical next step.

Browse everything else in the DSNLP store.