What Will You Do on Monday Morning?

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Owners spend years getting ready to sell the business and almost no time getting ready to not own it. The money side gets all the attention. The part that actually decides whether you are happy afterward, what you will do and who you will be once the business is no longer the answer, is the part most owners never plan at all.

I have watched a lot of owners get right up to the finish line of a sale, with a good number on the table and the deal all but done, and freeze. Not because they had second thoughts about the price or the buyer, but because somewhere in the final stretch it lands on them that they have no real idea what Monday morning looks like once the business is gone. For thirty-plus years the business has been the first thing they thought about when they woke up, the thing that organized their days and told them who they were, and they have spent almost none of that time figuring out what takes its place.

This is the part of getting ready to exit that owners skip, and it is not a small part. The Exit Planning Institute’s State of Owner Readiness research has found that something like nine in ten owners have no written plan for the personal side of life after the business, and close to a third have not really thought about it at all. They will spend two years cleaning up the financials and tuning the company for a sale and not one afternoon on the question of what they are going to do with themselves afterward. They give the money a plan and leave the rest of it to sort itself out later.

The reason it matters is that for most owners the business is doing a lot more than producing income. It is where they are the person everyone calls when there is a problem and the name that means something in their industry and their town. When that goes away on a closing date, plenty of owners find they have gone from somebody everyone knew to a man with some money and an empty calendar, and the adjustment is harder and lonelier than anyone thought to warn them about. The ones I have seen come through it well are usually the ones who had somewhere to go, some next thing that actually mattered to them, lined up before they ever signed.

There is a version of this that looks fine for the first few months. The calendar clears, the trips finally happen, and then somewhere in the first year most people find that leisure on its own does not carry the weight they needed it to. I have heard the story more than once of the owner who went looking for a bigger boat or a second house to fill the space the business left, and found that none of it replaced the thing he actually missed, which was being needed by something. That is not a problem money solves, and having plenty of it can make the problem worse, because it takes away the excuse to not deal with it.

The practical side of this is a question I wish more owners asked themselves years earlier, which is what the business actually has to net them, after tax, to pay for whatever the next chapter turns out to be. You cannot answer that until you have given the next chapter some honest thought. An owner who knows what they want life to look like afterward can work backward to a real number, and then the business has a target to grow toward and the financial plan has something to aim at. An owner who has not done that thinking is guessing at a sale price with no way to know whether it is enough, because they do not yet know enough for what.

I am not suggesting anyone needs the whole rest of their life mapped out before they would ever sell. The owners who end up genuinely content afterward tend to be the ones who started asking these questions long before a sale was real, back when there was still time to try a few things, to step away from the business for a couple of weeks and see how it felt to not be there, to find out what they actually enjoy when the company is not filling every hour. None of that can be done in the ninety days between a letter of intent and a closing. It takes a running start.

This is why I keep coming back to the idea that exit planning is really just good planning for the owner as a whole person, not only for the company they built. Business readiness and financial readiness get most of the attention because they are easier to measure and easier to put on a checklist. The personal side is softer and slower, and it tends to be the one that decides whether an owner looks back on the sale as the best move they ever made or the one they wish they had handled differently. It is worth giving that side real thought while there is still plenty of time to act on what you find.

A note for the CPAs who refer clients to me

The personal side is not usually thought of as the accountant’s job, but you are often the one an owner trusts enough to raise it with, and you are the one who can connect what the owner wants their life to look like to what the sale actually has to produce after tax. Helping a client see that the number they need is a function of the life they are planning, rather than the other way around, is a conversation that benefits from your seat at the table, and it is a natural place to bring me in alongside you.

A note for the wealth advisors who refer clients to me

This sits close to the heart of what you do, because the question of what an owner will retire to is inseparable from whether their money will support it. You are well positioned to start the non-financial conversation early, the one about purpose and the next chapter, because an owner will have it with someone they already trust on the financial side. The clients who do that work with you years ahead tend to make better decisions about the business and about the sale when the time finally comes.