Skip to content
When Success Becomes a Trap: Why Leaders Need to Get Uncomfortable artwork

When Success Becomes a Trap: Why Leaders Need to Get Uncomfortable

Morning Drive

October 5, 2026

Success can be the goal, but what happens when it becomes the comfort zone? For some business leaders, past achievements can make taking risks harder and create a sense of stagnation.

Speakers Ollie Ollerton

TopicsInvestingBusinessManagement

SPEAKER_1 (0:00)

This is Mira Business FM, it's the Morning Drive, tooking success now, which can be a goal, but what happens when it becomes the comfort zone? When it just becomes normal? Some business leaders' past achievements can make taking risks harder and create a sense of stagnation. So what we want to do next is look at why pushing beyond what feels comfortable could be key to staying ambitious and focused and effective and all those good things in business. Our guest is a former UK Special Forces operative. He's an entrepreneur. He's a best-selling author, TV personality. Based now in Dubai, he was one of the founding stars of the hugely successful TV show SAS Who Dares Wins. He is an experienced, sought-after international inspirational speaker. I'm running out of breath here.

But what's really interesting to us, I think, for this interview, he's the founder of BreakPoint, which is an academy, and it's all about unlocking potential and maximizing performance. Ollie Ollerton, good morning.

Ollie Ollerton (1:02)

Good morning, sir.

SPEAKER_1 (1:04)

Good to meet you. Thanks for coming in.

One of the things, I'm going to jump straight in actually, because one of the things about being successful in business is, specifically, I think, is once you've had some success, it's very easy to think, I'm there now. This is me. I'm just going to go up and up and up. So how can business leaders tell when they think they're successful, but that success is maybe a little bit of complacency. It's kind of creeping in.

Ollie Ollerton (1:33)

Yeah, it's a really good question. And it's something I recently learned, actually, about my own achievements. And the fact is, I think all you simply have to do, right, look in your diary. Is there anything in your diary that would scare you and excite you at the same time, or is it just maintenance?

SPEAKER_1 (1:49)

That's such a good question. Yeah. Okay. So you need to look in your diary and think, oh, that's a bit of a test.

Ollie Ollerton (1:54)

Yeah, but the thing is, let me take this radio interview, this interview as an example for myself, right? So the weekend or Friday or whatever, I looked at my diary, realized Monday morning, I've got an interview with yourself.

SPEAKER_1 (2:06)

Right.

Ollie Ollerton (2:07)

Amazing. What an opportunity to be able to speak to you in the wider world in Dubai.

But then there's that thing that goes, oh, but I've got so much to do. This is such a pain.

So, no, honestly, but the thing is that all those things in my head there is, I've got to maintain everything. There's so much I've got to do to maintain, whereas this is an opportunity to grow. This is an opportunity to put yourself in the firing line where you can lean into the wind. And really, if anyone just takes a look into their diary and just goes, what have I got my diary? Is there anything that gets the heart racing just a little bit? Or is it just maintenance? Am I just not wanting to upset the status quo? Or do I want to push the boundaries a bit? Because we all should have at least one thing, at least one thing every week, that gets that heart pumping in and scares us, but excites us at the same time.

SPEAKER_1 (2:59)

Yeah, no, I know exactly what you mean. There are times when there are particular interviews, in this job, for example, it's relatively run of the mill. I'll do four or five interviews a day, really. And most of them, if I prep, I know I can handle them. But every now and again, there'll be somebody that I just think, I don't know enough about this, or I don't really understand this, and I have to think a bit harder. So it's the test stuff.

I suppose, though, for lots of entrepreneurs, it's got to be really difficult to admit to yourself if things aren't right, or you're not testing yourself enough. You're not pushing those boundaries, right? So, because it's your company, it's your idea, it's your thing, isn't it? So you're right about everything that you do in your head. So how do you admit that you've maybe lost your way a little, things weren't what they were? How do you do that?

Ollie Ollerton (3:46)

I think really that's something that we all know internally, don't we? We just know if we're sort of cruising or we're not. You know, we've got to feel that sense of pressure. I really do. You know, there's a lot of talk in the world today, obviously, about mental health. Now, my message to someone struggling with mental health is no different to someone that is doing really well. We have always got to be leaning into the wind. We've always got to be pushing against some level of resistance. We've always got to be feeling the pressure of life. Getting the balances right, of course, but really, I think the answer to a lot of people's issues is the fact that we should always be aiming for something bigger. That is the mechanism. This operating system that we've got, which is amazing, that probably 90% of the people on this in humanity don't understand is the fact that it needs to feel a sense of progress. And even when you're doing well, you know, this is the perception as well. A lot of people think, well, I've got the family, I've got the car, the business is doing well. All these things are so externalized, we are so fixated on the external. You know, when we look around us, we look outside of us and we go, yeah, I've got everything, but why is there something missing? Why is there this void? Why do I still think I need more? And then we go and buy something else. We go and aim to go on a holiday. We do something. We want to get the shiny thing that then becomes very unshiny within a week.

25 more minutes of transcript below

Thousands of transcripts fetched by people building searchable podcast archives

Fetch the whole transcript

The demo key returns a sample episode in full, no card needed:

request
curl -H "x-api-key: pt_demo" \
  https://spoken.md/transcripts/1000651996090

Markdown with the speakers named, for your notes, your knowledge base, or anything that makes HTTP calls.

From $0.10 per transcript. No subscription. Credits never expire. Prices exclude VAT, added at checkout for EU customers. Not what you expected? Email us within 14 days with 20 or fewer credits used and we refund the pack in full.

Using your own key:

request
curl -H "x-api-key: YOUR_KEY" \
  https://spoken.md/transcripts/1000793196235