Selling your business is the end of something; everyone understands that. But it’s also the beginning of something, and it should be a big consideration in when – or if – you sell.
I’ve spoken to owners who are concerned about losing their identity when they sell the company. They’ve been turning wrenches since they were an 18-year-old kid, and they’ve probably not had time over the past few years to do much else other than run their business.
So the question is not just “should I sell the business?” You also have to ask yourself, “If I do, what will I do with myself all day?”
I’ve pondered that myself. I have hobbies; I enjoy hunting, fishing, and working on my property. But are those activities enough to replace the hours I’ve put in after I retire from the business? The jury’s still out.
Here are some things to consider if you’re wondering the same thing:
Have a clear plan for what you’re retiring to. You’re probably not planning retirement in a vacuum. You might have a spouse with some definite ideas on what you could be doing more of together (and less of, like talking business at every meal). Your spouse might be working, maybe even working in the business, so selling it will have twice the impact on your partnership.
I know some people who have failed retirement. That is to say, they found themselves feeling lost after selling. They may even regret selling, no matter that the payout was everything they’d hoped. Some find themselves starting another business just to feel needed again. Spoiler alert: it’s much less stressful to keep running the one you have than it is to start a new one. Plus, non-compete agreements usually mean you’re also going into another industry. Doing everything or doing nothing are not the only two options.
Create a time budget and manage it like you do your financial budget. Many sellers have found that without the structure of their former business day, they tend to drift. Things they meant to get to “one day” never end up happening, whether it’s the to-do list of home repairs or planning that cruise to Europe.
Think of your days, months, or years like a pie chart. You can (and maybe should) have a visual chart that sets your intention. Exercise and productive activity for a set number of hours per day or per week. Quality time with family and/or friends every week. A certain number of weeks or months per year for travel or a change of pace. Diving deeper into hobbies or interests, or developing new ones. Creating a time budget helps you structure how you spend your days and helps hold you accountable for spending your time on what matters most.
Your plan helps you say no to things you don’t want to do. “Now that you have all this free time on your hands” is how people start deciding how you spend your time for you. Whether it’s committing to helping family, taking on big projects, or volunteer work, you need to take charge of what, when, and how much you invest. It can be easy to find yourself working almost as many hours a week as you did in the business (but without the income). Even if you truly enjoy the activity, whether it’s family or a good cause, you’ll need to set boundaries so you have control over your own time and can leave when you’re ready.
Your time budget is the most effective way to manage saying no gracefully: “I’d like to help out more, but I have just one day a week that I spend on community service.” Or, “I would love to pick the kids up from school on Fridays so you can have date night. But, as you know, I have (the other thing) that won’t allow me to do it more than once a week.”
Leaving your business is an emotional decision as well as a financial one. You can’t just turn off your management skills or creative energy like a spigot. Figuring out the best way to channel them into your next chapter is an important step to take before you close the deal.




