I remember trying to explain the job to a friend.

This was around 2016. We were six years into Key Digital and I’d just taken on someone whose role, as far as I could describe it, was to look after our online presence — the website, the data, the email marketing, building the kind of digital footprint that I sensed was going to matter even though I couldn’t have told you exactly why in precise terms.

My friend was a business owner. Sharp, experienced, running a decent operation in a different market. He looked at me the way you look at someone who’s just said something that doesn’t quite parse.

“So what does she actually do?” he said.

I tried again. Something about search, something about data, something about where customers were going to be looking for us in five years’ time.

He nodded slowly in the way that means he’d moved on.

I don’t tell that story to make myself look clever. I got plenty wrong in those years. But I’d sensed something was shifting, and I’d acted on the instinct before I could fully articulate it. The job title that confused him in 2016 is now on every business’s hiring list. The question is just whether you hired early or late.

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We set Key Digital up in 2010. From day one we ran on an IP phone system with digital numbers, and a CRM that tracked every customer interaction we had. I know how unremarkable that sounds now. In 2010, most of our competitors were running on fixed legacy systems — phones tied to a building, customer data living in someone’s head or a spreadsheet nobody could find.

We could work from anywhere. We could route calls without employing a receptionist. We were building and owning our data at a point when plenty of people in our market were still sending postal mailshots.

We weren’t geniuses. We just paid attention to where things were heading and didn’t wait until the direction was obvious to everyone.

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A few weeks after my bowel resection I helped carry a photocopier up a flight of stairs.

Still had my stitches in. There was a job on, the customer needed it done, and I was there. So I picked up my end and we went up the stairs.

I’m not telling you that as a badge of honour. I’m telling you because it’s the clearest illustration I have of something that took me a long time to properly understand — that when you’ve decided the business comes first, you will talk yourself into almost anything. And you won’t even notice you’re doing it.

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The Crohn’s had been building for years before it got serious. Managed on painkillers, worked around, never quite dealt with properly because there was always something more pressing. By 2016 I was on a liquid diet — solid food simply wouldn’t pass. I ran the business on nutritional drinks and kept going because stopping didn’t feel like an option.

The surgery that year removed a metre of bowel. Two days in ICU. Catherine was there, and I won’t speak for what she was carrying in those hours, but I know what I saw in her face.

I’ve never had a Crohn’s symptom since. Whatever they took out, they took the problem with it.

But within weeks I was on a staircase with a photocopier and a fresh set of stitches.

Because the job needed doing.

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There’s a question worth sitting with here — and I’d ask you to resist the urge to answer it too quickly.

**What are you currently managing, minimising, or pushing through that your body has been telling you about for longer than you’d care to admit?**

Not a dramatic question. Not an accusation. Just an honest one.

Because in my experience, entrepreneurs are remarkably good at two things: building businesses and ignoring warning signs. The same qualities that make you effective — the ability to push through discomfort, to defer gratification, to keep moving when everything in you wants to stop — those qualities do not distinguish between a difficult quarter and a serious health problem. They just push.

The business doesn’t know the difference either. It will take whatever you give it.

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Gary always wanted to be successful.

I don’t say that to damn him. I say it because it’s the most important thing about him, and because wanting to be successful is not the same thing as building something that lasts. That distinction cost Gary everything, and I watched it happen slowly enough that I could see every stage of it.

We worked together years before either of us had a business — same large company, same industry, same starting point. He was good. Understood the product, understood the market, had the kind of energy that makes you think someone’s going to do well. When we both eventually left to set up on our own, I wasn’t surprised he went the same way. He had ambition. You could see it from across the room.

What I didn’t know then was what kind of ambition it was.

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The sports car came first. Then the house — big place, proper money, the kind that ends up in Lancashire Life with a photo spread and a quote about vision. The office looked the part. The talk was confident. From the outside, Gary was doing it.

From slightly closer in, the picture was different.

He’d had four businesses by the time our paths crossed properly. The names changed. The story was always broadly the same. Things would build, things would stretch, the credit would run out, and then somehow there’d be a new vehicle, a fresh start, the same energy pointed at the same horizon.

I didn’t judge him for it at the time. I’m not sure I fully understood it.

What I did understand was why, every so often, Gary would ring up needing parts. Cash, with an invoice, collected in person.

By then none of his suppliers would touch him. Credit maxed, trust spent. But he still needed stock to keep moving, and I had what he needed.

I supplied him. Not because it was good business — it wasn’t, particularly — but because I knew why he was asking and I wanted to help. He wasn’t a crook. He never took money he didn’t intend to pay back. He just couldn’t quite get the foundations right, and I think somewhere underneath it all he knew that, even if he’d never have said it.

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Every Easter, I did the stocktake alone.

It wasn’t a decision I made once and revisited. It just became the thing. Catherine would have a few days that looked something like a normal holiday — catching up on the house, seeing family, breathing — and I’d be in the warehouse with a clipboard and a cold coffee, counting stock.

It took most of the long weekend. And I’ll be honest with you: I didn’t entirely hate it.

There was something satisfying about getting a proper handle on the numbers. Easter stocktake meant we went into our year end — end of May — with clean data, fewer surprises, a business that felt briefly under control. I knew where we stood. That mattered.

But there was always a moment, usually sometime on the Saturday afternoon, when the other feeling arrived.

We shouldn’t need to do it like this.

Twelve months in and we were still catching up with ourselves at Easter. Then thirteen months. Then further down the line than I’d care to admit. The satisfaction of getting on top of it and the quiet embarrassment of still needing to — those two things coexisted every single year.

That tension, I’ve come to think, is one of the most honest feelings in business.

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The operating model, for most of those thirteen years, was simple enough.

I worked weekends. Catherine did the admin in the evenings, in front of the TV. That was the rhythm — not a crisis, not a temporary arrangement, just the shape of the thing. It’s what building a business on your own terms actually looks like from the inside, and I’m not going to dress it up as something more glamorous than it was.

We got better over time. Found our version of flow. The systems improved, the team grew, the Easter stocktake got less painful. What had taken a full long weekend in year two took a day and a half in year eight. That’s not nothing — that’s compounding, applied to operations rather than money.

But here’s the thing I’d want you to sit with.

The one week we properly switched off — fully, completely, without the business needing something — was Christmas. Because the business was closed. Not because we’d built something that ran without us. Because the doors were physically shut.

Every other break had an asterisk.

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Every Easter, I did the stocktake alone.

It wasn’t a decision I made once and revisited. It just became the thing. Catherine would have a few days that looked something like a normal holiday — catching up on the house, seeing family, breathing — and I’d be in the warehouse with a clipboard and a cold coffee, counting stock.

It took most of the long weekend. And I’ll be honest with you: I didn’t entirely hate it.

There was something satisfying about getting a proper handle on the numbers. Easter stocktake meant we went into our year end — end of May — with clean data, fewer surprises, a business that felt briefly under control. I knew where we stood. That mattered.

But there was always a moment, usually sometime on the Saturday afternoon, when the other feeling arrived.

We shouldn’t need to do it like this.

Twelve months in and we were still catching up with ourselves at Easter. Then thirteen months. Then further down the line than I’d care to admit. The satisfaction of getting on top of it and the quiet embarrassment of still needing to — those two things coexisted every single year.

That tension, I’ve come to think, is one of the most honest feelings in business.

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The operating model, for most of those thirteen years, was simple enough.

I worked weekends. Catherine did the admin in the evenings, in front of the TV. That was the rhythm — not a crisis, not a temporary arrangement, just the shape of the thing. It’s what building a business on your own terms actually looks like from the inside, and I’m not going to dress it up as something more glamorous than it was.

We got better over time. Found our version of flow. The systems improved, the team grew, the Easter stocktake got less painful. What had taken a full long weekend in year two took a day and a half in year eight. That’s not nothing — that’s compounding, applied to operations rather than money.

But here’s the thing I’d want you to sit with.

The one week we properly switched off — fully, completely, without the business needing something — was Christmas. Because the business was closed. Not because we’d built something that ran without us. Because the doors were physically shut.

Every other break had an asterisk.

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By 2014 I was on a liquid-only diet.

Not a choice. A necessity. Years of Crohn’s disease, decades of symptoms I’d pushed through, managed, minimised — and eventually the bill came due. Strictures had formed. The inflammation had done its work quietly, patiently, while I’d done mine. Painkillers had kept me functional. Kept me working. Kept me from having to stop and deal with what my body had been trying to tell me for a very long time.

We’d started Key Digital three years earlier. The business was growing. There was always a reason to keep going.

There’s always a reason to keep going.

The surgery was a bowel resection. I spent two days in ICU afterwards. Catherine was there. We both thought — and we’ve talked about this since, in the way you only talk about things once they’re safely in the past — that I might not come home.

I did come home.

And somewhere in the recovery, something shifted. Not a dramatic conversion. Not a moment of clarity on a hospital bed. More of a quiet recalibration. An acknowledgement that I had spent years treating my body as something to be overridden rather than maintained. That I had applied discipline and rigour and long-game thinking to the business and almost none of it to myself.

I started running not long after. Tentatively at first — you don’t bounce back from major abdominal surgery — and then with increasing commitment. And what I found, over months and then years, was that the running didn’t just make me physically stronger. It made me a better operator. Clearer thinking. More patient. Better at absorbing pressure without it accumulating somewhere it would eventually cause damage.

I hadn’t expected that. I’d thought I was just going for a run.

Here’s what I’ve come to understand about entrepreneurial health, having learned it the hard way.

The body keeps score. It doesn’t send invoices. It doesn’t schedule meetings to discuss your arrears. It just accumulates the debt quietly, in the background, while you focus on everything else — until the debt becomes a demand and the demand becomes a crisis.

Most founders I’ve known are meticulous about risk in the business. They’d never ignore a structural problem in their finances or their operations for years at a stretch. They’d never take painkillers for a recurring system failure and just keep running the machine.

But they’ll do exactly that to themselves.

Because the business feels urgent and the body doesn’t. Until it does.

You are the asset. The one that can’t be replaced, can’t be insured against, and has no redundancy built in. The business can survive a bad quarter. It can survive losing a client or a key member of staff. There are versions of most business problems that you can recover from.

There is only one version of you.

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I met a man at a business event a few years ago. He’d just sold his company. Twelve years of work, a clean exit, a number that would have made most people in that room go quiet.

Someone asked him what he was going to do next.

He looked genuinely startled. Not overwhelmed. Not emotional. Just... blank. Like the question had never occurred to him.

“I don’t know,” he said. “I suppose I’ll start another one.”

He wasn’t being humble. He wasn’t deflecting. He meant it. The business had been the answer for so long that he’d forgotten what the question was.

I’ve thought about that moment a lot.

There’s a version of entrepreneurial ambition that’s really just forward motion dressed up as purpose. You’re working hard, building something real, hitting milestones — and it all feels meaningful because it’s difficult and consuming and the numbers are going in the right direction.

But difficult isn’t the same as purposeful. Consuming isn’t the same as fulfilling. And a number going in the right direction is only useful if you know what you’re pointing it at.

Most entrepreneurs I’ve known — and I include my earlier self in this — can answer the what without hesitation. What are you building? A technology business. A services firm. A brand. A team. Fine. Good. All accurate.

Ask them what for and the answer gets murkier.

“Financial security.” Okay — but what does that look like on a Tuesday afternoon when you’re sixty?

“To prove something.” To whom? And once it’s proved, then what?

“Because I love the challenge.” That’s a personality trait. It’s not a destination.

None of these are wrong answers. But they’re not complete ones either. And if you’re spending ten or fifteen years of your finite life building something, incomplete probably isn’t good enough.

Here’s what I’ve come to think.

The business isn’t the point. It never was.

The business is the vehicle. It’s the thing that generates the resources — financial, but also experiential, relational, psychological — to fund the life you actually want. And if you haven’t defined that life with any clarity, then you’re essentially building a very sophisticated machine with no idea what you’re manufacturing.

You can do that for years. Decades, even. The machine will keep running. You’ll keep feeding it. And one day someone will ask you what you’re going to do next, and you’ll look startled, because the machine was always the answer and you forgot to write down the question.

I’m not telling you to stop building. I’m asking you to run both things in parallel — the business and the life you’re building it for. Not sequentially. Not “I’ll figure out what I want once I’ve exited.” Now. With the same rigour you’d apply to a revenue target or a hiring decision.

Because here’s the uncomfortable truth: the clearer you are about what you’re building for, the better the business decisions get. You stop chasing contracts that pay well but cost you everything else. You stop building teams in a shape that serves the business but not the exit. You start making choices that compound towards something you’ve actually chosen, rather than defaulting to whatever’s in front of you.

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I used to know a founder — good business, sound fundamentals, the kind of slow-build story that actually works — who made a decision that cost him two years.

A competitor landed a big contract. The kind that gets talked about. And within six weeks, this founder had restructured his team, expanded his pitch, and started going after work that was too big, too soon, for a business that wasn’t ready to deliver it properly.

Not because his strategy was wrong. Not because the market had changed. Because someone else had gone past him looking comfortable, and he couldn’t help but respond.

Two years of strain, two years of overreach, two years of being somewhere he hadn’t planned to be. He recovered. But it cost him more than time.

I’ve thought about that a lot over the years. Because the pull he felt — the instinct to respond to someone else’s pace — is almost impossible to suppress entirely. I’ve felt it myself, in business and in running. Eighty-odd marathons and ultras and I still catch myself doing it. Someone goes past you at mile eighteen looking fresh, and before you’ve thought about it, you’ve picked up your pace to match theirs. Two miles later you’re hanging on. Four miles later the wheels have come off completely.

The problem is that you never have the full picture. You see their stride. You don’t see their race plan.

I watched it happen to entrepreneurs around me for thirteen years at Key Digital. Someone would be building something solid — patient, consistent, good work compounding quietly over time. Then a competitor would land a big client, or someone in their network would open a flashy new office, or they’d read about a business in their sector raising a round of funding.

And just like that, they’d change course. Start sprinting. Hire too fast. Pitch too wide. Stretch into territory they weren’t ready for.

Not because the fundamentals had changed. Because someone else had gone past them looking comfortable.

There was one year — probably year seven or eight — when a competitor won a contract that stung a little. Bigger than anything we were chasing at the time. There was pressure, unspoken but felt, to respond. To go after larger work faster than we were ready to deliver it properly.

I remember sitting at the kitchen table with Catherine going through it. All the reasons we should react. All the logic that made response feel like strategy.

She listened to all of it. And then she said: “They’re not us, though.”

Not a question. Not a debate. Just four words that cut straight through the noise.

They’re not us. Different margins, different overheads, different pressures, different definition of a good outcome. Maybe they needed that contract in a way we didn’t. Maybe they were buying revenue to paper over something else. Maybe they’d timed it right and got lucky. We had no idea. What we knew was our race. Our plan. The number we were building towards, and the kind of business we wanted to be when we got there.

We didn't change course. We stayed at our pace. And a few years later, Catherine and I walked away with our number.

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Stephen Covey said it thirty years ago and every business leader nodded along.

Begin with the end in mind.

They wrote it in their notebooks. They applied it to the next negotiation, the next product launch, the next quarterly target. They got very good at beginning specific projects with the end in mind.

And then they went back to building a business with no defined finish line.

Most entrepreneurs I know have never written the number down.

Not the revenue target. Not the EBITDA multiple. Not the profit target. The number. The one that means you never have to take a meeting you don’t want, a client you don’t like, or a job you don’t need. The number that means the business has done its job and you can get on with living.

Covey’s principle is taught in boardrooms and MBA programmes around the world. It gets applied to projects, negotiations, and five-year plans.

Almost nobody applies it to their business exit. Their career. Their life.

And that absence — that single unanswered question — is quietly running in the background of every decision they make.

Here’s what makes it harder.

The number isn’t just a figure. It’s a decision about what enough actually means. And most people avoid that decision for their entire career, because answering it honestly requires you to look past the image of success and ask what you actually need.

Not what sounds good at a networking event. Not what impresses people who don’t know your margins. What you genuinely need to live the life you want, on your terms, without the business consuming every waking hour until there’s nothing left to spend the money on.

That’s a harder question than it looks.

And then there’s lifestyle creep. The thing that makes the number a moving target for people who never pinned it down.

Here’s where entrepreneurs specifically get caught. It’s not a salary increase that does it — entrepreneurs don’t get pay rises. What happens is subtler. The business does well. The draws get bigger. The reinvestment decisions get more comfortable. The house gets better, the car gets better, the holidays get better. None of it feels excessive in the moment. Each decision feels like a fair reward for what you’ve built.

But nobody stops to count the cost in time.

That’s the calculation most people never make.

This is The Long Run Mindset for Entrepreneurs — a paid newsletter about the long game. Exits, financial freedom, and what comes next. If you’ve landed here for the first time, you might also enjoy our free Tuesday newsletter — The Long Run Mindset for a Life Worth Living — which is available to all subscribers and covers the bigger picture: running, health, mindset, and life after the exit.

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Business class to New York is a genuine pleasure. I’m not suggesting you shouldn’t have it. But what does it actually cost in time? In years of your working life? If your business needs to be worth an extra £200,000 at exit to fund a decade of business class travel, is that trade worth making? One more year building? Two? Five?

Only you can answer that. But you can only answer it honestly if you’ve defined what enough looks like first.

The same question applies to everything. The second home. The watches, the cars, the restaurants. Every upgrade to the lifestyle is a decision about how long you’re prepared to keep building. Most people make those decisions without ever doing that maths.

I’m not arguing against living well. Quite the opposite.

The point is that improving your life and wasting the years you have left are not always different things — and without a clear number, you can’t tell which one you’re doing.

I’ve watched people build for twenty-five years who could have walked away at fifteen with everything they actually needed. The extra decade bought them a bigger house and a better car and cost them the retirement they’d promised themselves.

They didn’t know what enough was. So they never stopped.

Catherine and I wrote our number down early. Not as a wish. As a target.

It shaped every decision we made for thirteen years. What we reinvested. What we drew. What we refused to do. When we almost walked away in 2013 and chose instead to go all in one last time. When a broker called while I was isolating in bed with Covid two weeks before our wedding — and I actually listened, because we were close enough to our number to make the conversation worth having.

We didn’t deprive ourselves. We made deliberate choices about what was worth having now and what we were prepared to wait for. We knew the cost of every upgrade in time, not just money.

When we eventually walked away with our number, it wasn’t luck. It was the result of beginning with the end in mind — not for a project, but for the business and the life.

Covey was right.

Begin with the end in mind.

He just didn’t say it loudly enough about the things that matter most.

If you’re building something right now and you haven’t written the number down — not just the exit target, but the life it needs to fund and what that life is genuinely worth in years — that’s the most important thing you’ll do this week.

Not the sales call. Not the strategy deck. Not the LinkedIn post.

The number. What it funds. What it costs in time.

Because a business without a finish line isn’t a vehicle.

It’s a treadmill.

Andy Ratcliffe writes about the long game — exits, financial freedom, and what comes next.

In June 1986, Andrew Ridgeley walked away from one of the most successful pop acts in the world.

Wham! had sold over 30 million records. Six UK number ones. Sellout tours. A concert in China — the first Western pop group to play there. They were at the height of their fame, not the end of it. Nobody was forcing the decision.

Ridgeley made it anyway.

Years later he was asked about the split. He corrected the interviewer. It wasn't a split, he said. They brought Wham! to a close in a manner of their own choosing. He knew George's future lay outside the band. He knew his own future did too. So they finished it properly — a farewell concert at Wembley Stadium in front of 72,000 people — and walked away on their own terms.

Ridgeley moved to Cornwall. Quiet life. Out of the spotlight.

George Michael stayed in the game. More albums, more tours, more headlines — the brilliant and troubled solo career of one of the greatest voices of his generation.

George Michael died on Christmas Day 2016. He was 53.

I'm not drawing a simple moral from that. George Michael's life was his own and the reasons for how it ended are complex and not mine to reduce to a business lesson.

What I am saying is this.

One of them knew when. He made the decision himself, while the choice was still his to make, and built a life on the other side of it. The other stayed in the game until the game ended it for him.

The question this newsletter exists to ask is a simple one.

Will you know when?

Most entrepreneurs I know have a vague idea of when they want to exit.

Fifty-five. Sixty. When it feels right.

What they don't have is a plan for recognising the moment when it actually arrives. And that gap — between the intention and the ability to act on it clearly, at the right time, for the right reasons — is where a lot of very good exits go wrong.

The moment doesn't announce itself. It doesn't arrive with a fanfare or a sign that says *this is it, you're done, you can go now.* It arrives quietly — in a broker call you nearly didn't answer, in a morning when the answer to a question you've been asking yourself for years is finally different from what it's always been.

And if you haven't done the work to recognise it, you'll miss it. Or worse — you'll feel it and talk yourself out of it, because there's always one more year that would make the business worth a little more, one more thing to fix before it goes to market, one more reason why now isn't quite right.

I know this from my own experience.

The broker called while I was isolating in bed with Covid, two weeks before our wedding. I nearly didn't answer. Something made me pick up — and I've thought about what that something was many times since. It wasn't desperation. It wasn't exhaustion. It was readiness. A quiet, settled sense that we were close enough to our number to make the conversation worth having. For the first time in thirteen years of building, I could hear the question “have you considered selling?” without the automatic internal response that said “not yet, not now, too much still to do.”

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