[Photo: Our Skoda Octavia — one last look]

I took this photograph on the day we said goodbye.

It sounds dramatic, I know. It’s a car. A Skoda Octavia Estate, silver, five years old, reliable as the sunrise. But as I stood there on the drive looking at it one last time, I felt something I hadn’t quite expected. A genuine pang. The kind that catches you off guard and makes you wonder when exactly you got so attached to an inanimate object.

The answer, of course, is that it was never really just a car.

It was five years of life. Motorway miles and school runs. Holidays packed to the roof. The quiet companionship of a thing that always started, always performed, never let us down. We bought it new with the intention of keeping it for years, and we did. It became part of the furniture. Part of the family, almost.

And then the numbers changed.

We’d been watching the electric vehicle market for a while, quietly, without any urgency. We weren’t looking to replace the Octavia; we liked the Octavia. But gradually, almost without noticing, the case became impossible to ignore. The running costs. The environmental argument. The technology. The numbers, quite simply, became too compelling to dismiss.

So after much soul searching, we made the decision. New electric car ordered. Octavia gone.

Here’s what struck me about the whole experience though, and why I think it’s worth sharing with anyone running or building a family business. The hardest decisions are rarely the ones where the answer is unclear. They’re the ones where the answer is obvious, but letting go is painful.

In business, as in life, we form attachments. To a supplier we’ve worked with for decades. To a product line that defined our early years. To a process, a system, a way of doing things that feels like part of our identity. And sometimes, often, those attachments are worth honouring. Loyalty and continuity are real values.

But sometimes the numbers change. The market moves. The technology shifts. And the most important skill isn’t knowing how to hold on; it’s knowing when, with gratitude and without guilt, to let go.

The Octavia deserved a proper goodbye. It got one. And whatever comes next, I’ll be a little more ready for it.

Onwards.

When It’s Time to Sell: The Human Side of One of the Biggest Decisions a Family Business Will Ever Make

This week I wrote about saying goodbye to our Skoda Octavia, and the unexpected emotion of letting go of something that had simply become part of life. Several people have messaged to say it resonated. Which didn’t entirely surprise me. Because the feeling I was describing, that mix of clarity and grief, of knowing the right answer but still finding it hard, is one I’ve sat with dozens of times in my work. Except the stakes are usually considerably higher than a five-year-old car. Selling a family business is unlike selling almost anything else.

Yes, there is a transaction. There are advisers and valuations and heads of terms and due diligence. There are spreadsheets, and lawyers, and a completion date. All of that is real, and all of it matters. But underneath it, running alongside the entire process from the first conversation to the moment the money hits the account, is something the spreadsheets can’t capture.

The business was never just a business.

It was the thing your father built.

Or the thing you built, with your own hands, in the early years when there was no salary and no certainty and you kept going anyway. It became the structure around which your family organised itself: school fees, holidays, the house you live in, the conversations at the dinner table.

Other family members work in it, depend on it, have shaped their own identities around it. It is, in ways that are difficult to articulate but impossible to ignore, part of who you are.

And now someone is asking you to put a number on it and hand over the keys.
 

Why the human dimension is where most deals go wrong

I’ve been involved in enough family business sales to know that the deals which fall apart rarely fail for financial reasons.

The numbers are usually resolvable. What’s harder to resolve is the human dimension: the unspoken disagreements within the family about whether to sell at all, the founder who says yes but means maybe, the next generation who feel the decision is being made without them, the spouse who has sacrificed alongside the business for decades and has never been properly included in the conversation.

These dynamics don’t show up in the information memorandum. But they derail deals. They slow processes. They create friction with buyers who can sense that the sellers aren’t fully aligned, even when no-one has said so explicitly.

The most common mistake families make when selling is treating it as a financial event with some emotional inconvenience attached. It is the other way around. It is a profound human transition, one of the biggest a family will navigate together, that happens to involve a financial transaction.
 

The three conversations most families avoid — until they can’t

In my experience, there are three conversations that determine whether a family business sale goes well or badly. None of them are with lawyers or accountants. All of them happen within the family itself.

The first is the why conversation.

Why are we selling, really? Not the official answer, the one you’d give a journalist or a buyer. The honest one. Are you selling because it’s the right time strategically? Because you’re tired? Because you want to release capital for the next generation?

The why matters enormously, because if different family members have different answers, that tension will surface somewhere in the process. Better to surface it early, in a room with people who trust each other, than late, in a room with people who don’t.

The second is the after conversation.

What happens next? This is the one founders find hardest.

The business has provided structure, purpose, identity, routine, status, and income, often simultaneously, for decades.

Selling doesn’t just change the financial picture. It changes who you are on a Monday morning. I have seen founders complete sales they’d worked toward for years and find themselves, within months, profoundly lost. Not because the deal was wrong. Because no-one had helped them think seriously about what came after it.

The third is the fairness conversation.

Within almost every family business, there are people who have contributed in ways that the formal ownership structure doesn’t fully reflect.

A spouse who kept the family together during the hard years. A sibling who chose a different path but who has always felt the business’s shadow.

These conversations are uncomfortable.

They are also necessary.
 

What good looks like

The family business sales I’ve seen go well, where the financial outcome was good, the relationships survived intact, and the founder looked genuinely at peace on completion day, shared a few things in common.

They started early.

Not the formal sale process, but the internal conversations.

The family had been talking openly about the future for long enough that by the time the decision was made, it felt like a conclusion rather than a shock.

They involved the right people. Not just the founder and the lead adviser.

The people who had skin in the game, emotionally, financially, practically, were included in conversations at the right time, in the right way.

And they took the after seriously. The founder had a genuine answer to the question of what came next. Not a vague plan, but something real, a purpose, a project, a role, a way of spending time that would give the next chapter its own meaning. Saying goodbye to the Skoda, I felt something I hadn’t expected. A genuine pang. The kind you get when you realise that what you thought was just a useful object had become something more.
I imagine that feeling, multiplied considerably, is part of what every family business owner carries on the day they sign.
The numbers matter. But they’re rarely the hardest part.

If your family is beginning to think about succession or sale, even at an early stage, even just as a conversation, I’m happy to have a quiet, confidential chat. There’s no process, no pitch, just a direct conversation about where you are and what might help.

peter@familybusinessman.com