A younger business owner recently asked me about self-doubt. He wanted to know how I deal with it. I told him the truth: I don’t always deal with it well. There are moments, usually quiet ones, weekends mostly, when my mind goes into overdrive. That voice shows up. The one that says this is too much. You can’t do this. Who do you think you are?

I used to think that voice was the enemy. I’ve come to realise it’s actually fuel. It’s the reason I keep working as hard as I do. Every single day I go to work trying to prove it wrong. I’m not sure that ever fully stops — and I’m not sure it’s supposed to.

The World Has Changed. The Benchmark Hasn’t.

Think about what it used to mean to be the best barber or butcher in town. If you were one of three or four, being the best locally wasn’t that difficult. Your world was your town. But now? There are thousands all over the internet, some genuinely doing well, some absolutely faking it. The comparison pool has gone from your street to the entire world, and most of it is a highlight reel.

That’s what we’re up against. And it’s not just one specific industry or career. It’s every industry, every business, every life. How do you feel successful, feel enough, in that world?

The Highlight Reel Lie

I travel a lot, and I’ll put my hands up, I share the stunning views, the sunsets, the idyllic moments. What I rarely share is the hire car that went wrong, the delayed flight, the 12-hour journey trying to keep a five-year-old entertained, or the Airbnb that had a brothel operating downstairs.

You see the best bits because that’s what people share. And that curated version of someone else’s life is quietly convincing you that you’re falling short. As I wrote in an earlier piece on compounding, everything compounds — even when you pretend it doesn’t. The comparisons compound too. Every scroll, every comparison, every moment of telling yourself you’re not enough, they all stack up.

We Suffer More in Our Minds Than in Reality

The Stoics talked about this. We imagine the worst and live in that imagined version of events far longer than the event itself lasts. I know this better than most because of my dog.

He got cancer at 14. From the moment I found out, I knew I’d eventually have to make that call to the vet. And I spent days, weeks, dreading it. All I could think about was how he used to be. All I could feel was the loss that hadn’t happened yet.

Then it hit me: he was still here. Right in front of me. And I was choosing to live in a future that hadn’t arrived instead of being present in the moment I actually had.

Those final days, I sat outside with him under the pagoda in the summer sun. He’d been with me for almost every day of his life, sat in the office as I built this business, often just me and him for years. Those last days were some of the most present I’ve ever been. I’m grateful for that.

What I regret is the four years before that, from the moment he turned ten — that I spent quietly grieving something I hadn’t lost yet. I should have just enjoyed him.

There Is No Destination

I know it’s been said a million times, but sit with it for a second: the numbers can always be bigger. You can always be more. There is always more you could do. There will never be a moment where you arrive and think, right, that’s it, I’ve made it. It’s a myth. The only place you fully arrive at is the end.

A very successful friend of mine, someone who has built a business ten times the size of mine, and who is just over a decade older, told me recently to stop and smell the roses more. He said he wished he had done that earlier. That landed with me. One of the reasons I write these blogs is because I’ve realised how much you can learn from the journeys of people a little further down the road than you.

You Actually Build “Enough” It Doesn’t Just Appear

Everyone will tell you that you are enough. The difference is whether you believe it, and that belief won’t come from standing in front of a mirror shouting affirmations.

It comes from keeping promises to yourself. From having integrity, not just with others but with yourself. I once told my wife she never needed to worry about me being unfaithful. She said, thanks, I think. I told her it wasn’t really for her, even if I knew with absolute certainty I could get away with it, I’d have to look at myself in the mirror knowing I had no integrity. That matters to me more than anything.

As I wrote in a previous blog, The Truth About Confidence No One Talks About. Keep the promises you make to yourself. Do what you say you’ll do. Then you start to actually like the person you see in the mirror. From there, it becomes acceptance — accepting there will always be more, but getting excited about that rather than using it as a weapon against yourself.

Give Yourself Permission to Enjoy It

Most ambitious people are terrified to enjoy their lives in case it kills their hunger. I used to be the same. Then I read something that changed the way I thought about it. If you go to an amazing restaurant, have the best meal of your life, does that make you think, that’s enough, I’ll never eat out again? Or does it make you want to come back for more?

Enjoying your life fuels you. It doesn’t make you soft. Don’t become someone who works relentlessly and never lets themselves feel anything from it, that’s not ambition, it’s a treadmill with no off switch.

The word that matters here is feel. You control how you feel. You choose what you consume. You choose how you talk to yourself. You choose whether the voice that says you’re not enough is the thing that breaks you or the thing that drives you.

The Real Truth

I can’t tell you why most people never feel enough. I’m not a therapist or a counsellor. But I can tell you this: I feel it too. The difference is I’m good with it. I use it. I get excited by it. Because if there’s always more, more to achieve, more to experience, more to do, more to become, then what a life is still ahead. That’s the reason I get up every day at 5am!

Each day isn’t just another day. It’s one closer to the end. Give yourself permission to enjoy it.