Why Staying Humble Is the Most Underrated Skill in Business and Life Day 2028

Day 2028. I laced up my Vibram FiveFingers, stepped out the door, and did what I do every single day — ran. Barefoot style. Come rain, come shine, come whatever. Today's run gave me space to think about something I've been sitting with for a while. Humility. Specifically, what happens when people lose it.

I've been running this streak for 2028 consecutive days now. That's 20,280km towards a target of 40,075km — a full lap of the world — raising £1 million for children's causes including Great Ormond Street and BBC Children in Need. I'm just under halfway on the distance. I'm nowhere near halfway on the lesson count. Because every single day I'm out there, I'm learning something.

Today's lesson was this: the bigger they are, the harder they fall. And that phrase only means something if you've seen it happen up close.

I have.

Over the years I've been fortunate enough to experience some real highs in business. I've also been around people who achieved genuinely remarkable things — people I knew when they were starting out, when they had nothing, when they were grinding just like everyone else. And then something shifted. Not in their business. In them. Success changed how they carried themselves. And not always for the better.

I want to be careful here, because I'm not pointing fingers. I understand it. When everything is going well, when the numbers are moving in the right direction and the recognition starts coming in, it's genuinely difficult to stay grounded. There's a pull toward reinvention. You start mixing in different circles. You start measuring yourself against new people. And sometimes, quietly and almost without noticing, you start distancing yourself from where you came from.

That's the bit that costs people, often years down the line.

Because here's what I've observed. When things go wrong — and they do, for everyone eventually, regardless of how much success they've accumulated — it's not your new network that picks you up. It's your old one. It's the people who knew you before. The ones who've seen you at your most unpolished. The ones you perhaps stopped calling when you got busy with success. Those are the people with genuine loyalty. And if you've burned those bridges while climbing, you'll find yourself in a very isolated place when you need support the most.

I've tried throughout my career to stay grounded. I don't always get it right. But I'm aware of the risk. Complacency is one of the quieter dangers of success. When things are going well, you scrutinise less. You question yourself less. You're less likely to do the hard work of reflection that you're forced to do when things are going badly. And ironically, it's during the difficult periods that you often do your best thinking, make your most honest assessments, and come out the other side sharper.

Rebuilding something teaches you what building it in the first place couldn't. That's not a comfortable truth, but it's an honest one.

There's also something worth saying about the people around you. I've always believed that surrounding yourself with loyal, decent, trustworthy people matters far more than surrounding yourself with impressive ones. I'd rather have someone in my corner who's going to tell me the truth than someone who reflects well in a photograph. The people who will be there at 2am when something has gone wrong — those are the ones worth keeping close.

And the flip side of that is making sure I'm that person for others too. Not because I expect reciprocity. But because it's the right thing to do. I think if you help people because you're quietly banking favour, you've missed the point entirely. You help because it aligns with what you believe. And if you're lucky, that same spirit comes back to you when you need it — but that can't be the motivation.

This mission — 40,075km, 2028 days and counting, fundraising for children who need it — is built entirely on that principle. I'm not doing this to impress anyone. I run every day because the commitment is real, the cause is real, and the children we're raising money for need real support. There's no vanity in this. It's just consistency, discipline, and staying true to what I said I would do.

That's what humility looks like in practice, to me. It's not self-deprecation. It's not playing small. It's simply not forgetting where you came from, not treating people as though they're beneath you because your circumstances have changed, and staying honest with yourself about the work still to be done.

I've still got 19,795km left to run. I've still got a long way to go to reach £1 million. Every morning I get up and go out, not because I feel heroic, but because that's what the commitment looks like. Some days it's easy. Some days it really isn't. But the streak doesn't care about how I feel. And neither does the mission.

Success, whatever form it takes, will test who you are. Not because it's designed to, but because it creates conditions where it becomes easy to stop checking yourself. The antidote, as far as I can tell, is to keep the people around you who'll tell you when you've drifted. And to stay humble enough to listen when they do.

Don't forget where you came from. You never know when you're going to need it.

If this resonated with you, follow along on the journey. Subscribe to the channel, drop a comment, and if you'd like to support the mission for children's causes, the links are in the description. I'll be back tomorrow. Day 2029.