You Sold Your Business. Now What?
It’s Monday morning. You don't have to go to work.
That probably sounds pretty great. Until you think about Tuesday. And Wednesday. And the next 20 years.
For decades, you’ve had somewhere to be. It’s your routine. Going into the office five (or more) days a week. People need you. Your calendar is full. You make big decisions, solve problems, talk with customers, work with your leadership team and strategize about what the business needs next.
Then, you sell the business. It’s time to relax and enjoy your well-earned retirement…right?
But what will you do when Monday morning comes?
I think that question is a bigger part of exit planning than business owners give it credit for.
The Business May Be Ready Before the Owner Is
We spend a lot of time with owners preparing their businesses for an eventual transition. We work on building the leadership team, improving financial performance, documenting processes and reducing the company’s dependence on the owner. All of that helps create a more valuable and transferable business.
But we’ve also seen owners get stuck because they haven’t spent nearly as much time thinking about themselves.
They know they don’t want to work forever. They may have a general timeframe in mind for selling their business. Financially, they may even be in a position to do it.
But when you’ve spent 20, 30 or 40 years building a business, it can be hard to picture your life without it.
What Does Your Next Chapter Actually Look Like?
If you sold your business tomorrow and money were not an issue, how would you spend the next three years?
I’m not sure “retirement” is even the right word for a lot of business owners.
Most of the owners I know aren’t looking forward to sitting around and doing nothing. They still want to contribute. They like solving problems. They have decades of experience and relationships that don’t suddenly disappear when they sell a company.
We have a client right now who is preparing for his own transition and getting ready to invest in one of his children’s businesses. He’s looking forward to being involved as an investor and an outside advisor when needed, without being responsible for running the business every day.
He isn’t retiring from being useful. He’s changing how he uses his time and experience.
For someone else, it could be serving on a board, mentoring other business owners, investing in businesses or real estate, or staying involved in the current company in a smaller advisory role for a while. There may be a nonprofit or community organization that would love to have your experience.
And yes, there can be plenty of room for travel, time at the lake, golf, grandkids or escaping the Wisconsin cold for part of the winter.
The point is to start picturing it.
Start Testing Your Next Chapter Before You Exit
You don’t need a 10-year strategic plan for retirement. That sounds like a good way to take all the fun out of it.
Start smaller.
Try something you think you might enjoy. Join a board. Mentor someone. Explore an investment opportunity. Get involved with an organization you care about.
You can also start testing what it feels like to be less involved in your own business.
Take the two-week vacation instead of the long weekend. Let someone else handle the customer issue. Stop sitting in on a meeting where you really don’t need to be. Give your leadership team room to make some decisions that you would normally make.
Some of that may feel uncomfortable. That’s useful information, too.
It gives you a chance to see where the business is still dependent on you, and it gives you some practice figuring out who you are when you aren’t involved in every decision.
Don’t Let “Next Year” Become Five Years
This is where owners can get caught.
You tell yourself you’ll think about planning for your exit next year. There’s a big project to finish first. The market isn’t quite right. You need to get one more person in place. You’d like one more strong year under your belt.
Those may all be legitimate reasons to wait. But then another year goes by.
If selling or transitioning your business could be part of your next 5 to 10 years, start planning for your transition at the same time you’re planning for the business.
You don’t need to have it all figured out. Instead, give yourself a few things to do over the next 30 days:
Write down five things you would want more time for if you weren't running the business every day.
Identify one role or responsibility you can begin stepping away from and give someone else the opportunity to own it.
Test one idea for your next chapter: attend a board meeting, mentor another owner, explore an investment, volunteer with an organization or simply take a longer stretch of time away from the business.
Talk with your spouse, family or someone you trust about what you want life after the business to look like, not just financially, but personally.
Put a date on the calendar six months from now to ask yourself: Am I any closer to being ready for the business to operate without me, and am I any clearer about what I want to move toward?
Exit planning shouldn't only answer, “How do I successfully leave my business?”
It should also answer, “What am I excited to move toward?”
Because someday, there really will be a Monday morning when you don’t have to go to work.
The goal is to make sure you have somewhere you’re excited to go instead.
If a business transition may be in your future, start by asking two questions: Is the business ready to operate without me, and am I ready to move on from the business? At Journey Consulting, we help owners work through both sides of that equation as part of the exit planning process.
You’ve Sold Your Business: Common Questions
How far in advance should I start planning for life after selling my business?
Ideally, you should start thinking about life after the business several years before you plan to sell or transition. That gives you time to explore what you might want next while also preparing the company to operate without you.
Good business exit planning considers both sides of the transition: whether the business is ready and whether you are ready to move on.
What should my immediate plan be after selling my business?
Give yourself some room before filling your calendar again. After years of running a business, it can be tempting to jump straight into the next investment, board role or project. Instead, use the first few months to adjust to having more control over your time. Reconnect with the people and activities you may have put on the back burner, explore a few interests without making long-term commitments, and pay attention to what gives you energy.
You don’t need to have your entire next chapter figured out on day one. The immediate goal is to create enough space to decide what you actually want next, rather than simply replacing one full calendar with another.
What should my spouse or family know before I sell my business?
Talk about more than the money. Selling a business can change your schedule, where you live, how you spend your time and even how much time you and your spouse suddenly spend together. Your family may have a very different picture of retirement than you do. Those conversations are worth having before the sale, not the Monday morning after it.
What if I sell my business and realize I miss working?
Selling your business doesn’t mean you have to stop working altogether. You may discover that what you miss is solving problems, leading people or building something, rather than the responsibility of owning and operating a company every day. That can lead to a board role, mentoring, investing, consulting, another business venture or something you haven’t considered yet.
The goal isn’t necessarily to stop working. It’s to have more choice over what work looks like.
How do I know if I’m personally ready to sell my business?
Financial readiness is only one part of it. Ask yourself whether you can picture a fulfilling life that doesn’t revolve around the company, whether you trust other people to make decisions without you and whether you’re genuinely willing to give up control. If those questions make you uncomfortable, that doesn’t necessarily mean you shouldn’t sell. It may mean the personal side of your exit plan needs more attention.
Katie Busch, Value Advisor, draws on deep experience in executive leadership, operations, and human resources. With firsthand insight into fast-paced growth across multiple industries, she helps business owners identify opportunities that strengthen value, improve profitability, and free up time for what matters most.
Journey Consulting is focused on providing business owners and their businesses with strategic planning, exit planning, financial expertise, and organizational improvement. We use a holistic approach within all of our services by aligning leadership with business strategy and outcomes.
