Nobody prepares you for life after selling a business, especially the first Monday morning after the deal is done.
The process leading up to it can be stressful and there isn’t really any time to think about what comes next. There’s a lot of time spent with advisers, in negotiations, fielding due diligence requests, reviewing legal documents, having conversations with the team, and even the odd sleepless night. And then, it’s suddenly done, the paperwork is signed, the announcement goes out, and…that’s it!
And then the first Monday comes, and you’ve nothing in the diary.
For some owners, life after selling a business is the moment they hoped for. A clean break, a sense of completion, and the beginning of a new chapter in their lives. Most owners find that the moment is surprisingly hard. Not because the sale was a mistake, but because they hadn’t thought to prepare for it.
The conversation nobody has
The exit conversation in business is almost entirely financial and operational. What’s the business valuation? How is the deal going to be structured? What does an earn-out look like? How long is the handover period going to last? These are important questions and they take up your attention.
But there’s a conversation that gets forgotten about. What does life after selling a business look like? Who are you when the business is no longer the answer to that question?
Most people don’t have an answer for this. Perhaps they haven’t thought about it, but because for a long time, the business has been a key part of their identity and they can’t imagine life without it. It’s not just a place they spent their time, it’s what they talk about at dinner, it’s their status with their friends, and it’s the thing that gave their days structure.
Life after selling a business doesn’t just change the bank balance, it changes who you are and that’s a hard thing to face without any preparation.
Four questions before you exit
These questions don’t have right or wrong answers. Think about these, ideally well before a deal is on the table, because thinking is harder to do once everything else is in motion.
What do I want the first year after the exit to look like?
I don’t mean “travel more” or “spend time with the family”. Where will you be, what will you be doing, what will a typical Tuesday feel like?
The more specific you can be with your answer, the better.
What have I told myself I’d do when I had more time?
Is what I said still true, or was it just something I only thought I wanted? You might discover that what you thought you wanted, is no longer of interest.
Do I want to have a role in the business post-sale?
Would you like to stay involved, or would you prefer a clean break? Know which one you want, and communicate it clearly during the deal process. An earn-out that keeps you involved for three years when you wanted to be done in one, is very different from something you agreed to with open eyes.
Who am I outside of this business?
Not who you were before it, and not who you’ll become afterwards. Who are you now, separate from the business? When you’ve spent the best part of their working life building something, the answer is uncertain. That’s not a problem, but it’s better to know this before the deal closes, instead of discovering it on the Monday morning after.
Can your business work without you?
Take the Business Dependency Test.
It takes less than 3 minutes and will give you a clear answer.
Sellers Remorse
Most owners are glad they sold their business. The relief, the freedom, the financial security, these are the things that are talked about.
Post-exit regret, or what I call Sellers Remorse, is more common. Not having regrets about selling, but about not having a plan for what’s next. The owners who struggle after an exit, aren’t the ones who got a bad deal. They’re the ones who got a great deal but still found it hard. They were focused on getting out of the business, that they never thought about what they were getting into.
The first six months tends to be fine. There’s decompression, travel, time with family, things that were postponed for years. Around month seven or eight, something changes and the novelty wears off. They miss the structure that the business had provided, the daily rhythm, the decisions, the problems to solve, and the people to lead. All of it is gone and life after sellign a business can feel surprisingly empty.
That’s the part that doesn’t come up in the meetings with your accountant or financial adviser.
What the owners who transition well have in common
They have a clear sense of what they’re moving towards, and not just what they’re leaving behind them. They’ve spoken to people who’ve been through it before, not just their lawyers and accountants. They’ve thought about how they’ll spend their newly found free time and allowed themselves to find it strange at first.
Some stay connected to the business in some form. This can be in an advisory role or by sitting on a board. Others decide they want to mentor other business owners. Not because they can’t let go, but because they enjoy the work, have experience to share, and want to stay busy, without the responsibility of running something day to day.
Other people decide to step away entirely and build a different kind of life. That works too.
The common thread isn’t what they chose to do, it’s that they chose it deliberately.
The personal preparation is part of the exit
Everything that has been covered in this series has been about preparing the business. Removing the bottleneck, building systems developing the team, cleaning up the financials, and reducing owner dependency.
The business preparation and the personal preparation are not separate, but are connected. The owners who get the most from an exit are the ones who planned for both. They built a business worth selling, and thought carefully about what selling would mean for them.
Is It Too Late To Sell My Business covers the timing of the business preparation, but the timing of the personal preparation is different. You can’t start it too early. Most owners start it too late, or not at all.
You’ve spent years building something worth selling. It deserves a proper ending and a proper beginning of whatever comes next.
The financial preparation and the operational preparation matters. But so does working out what you want from life after selling a business, what you want the next chapter of your life to look like, and what you’re moving towards when the deal is done.