Life After Exit: Why Every Entrepreneur Needs a Comprehensive Post-Sale Strategy

By Anne-Wallis Droter, EO Global Staff Writer

As an entrepreneur who lives and breathes the business you’ve built, it can feel strange to think about life after you sell or “exit” that business. But research indicates that exiting without a plan can lead to an identity crisis of epic proportions, so it’s a question worth considering: What will your life look like after you exit?

To help EO members understand the importance of planning for life beyond the exit, Noah Rosenfarb (EO South Florida) interviewed John Rood, an EO Chicago elumni, exited entrepreneur, and author of Beyond The Exit. After interviewing 70+ founders who sold their businesses, Rood uncovered key insights and shared them to benefit EO members. If you missed it, you can watch the replay of Beyond The Exit: Learnings from 70 Exited Founders on EO’s Learning Platform. 

Why Entrepreneurs Need a Plan Before Selling Their Business

As author Beau Burlingham reminds us in Finishing Big: “You're going to leave your business someday, one way or another — even if it's in a body bag.”

That’s why having a plan for life beyond your business isn’t just a smart idea—it’s essential.

Did you know that exiting without a solid plan can be one of the most challenging chapters of entrepreneurial life? It can feel like you fell off a cliff. You go from being incredibly busy to basically sitting at your desk with no deadlines or meetings — the exact opposite of entrepreneurship as we know it. 

“I Thought Life After My Exit Would Be Perfect”

Rood was once in the majority of entrepreneurs who didn’t think about what he might do after his business exit. Before he sold, he thought that after working so hard to build his business, life after selling would be perfect.

But that was not the case. 

“The period after selling my business was one of the hardest in my life,” he admitted. He experienced health problems, marital stress, and a complete loss of direction. And his 200+ interviews with exited entrepreneurs confirm that similar struggles are common. In fact, a startling number of entrepreneurs divorce shortly after their exit.

4 Reasons Life After Exit Feels Harder Than You’d Think

So, why is life after exit often more challenging than expected?

1. Selling your business can be extremely stressful. By the time the deal closes, you’re often exhausted mentally, physically, and emotionally.

2. Consulting or staying involved in your business doesn’t turn out as you imagined. Why? “As entrepreneurs, we want to be the boss,” Rood explained. “The vast majority of entrepreneurs enjoy working in their company after they have sold it far less than they expected.”

3. Life downshifts from 100mph to 1mph overnight. The phone stops ringing and your high-energy daily schedule vanishes, leaving many thinking, “Now what?”

4. It’s hard to find support. Though EO members have a solid basis for support, most of your friends, neighbors, and even family won’t understand why selling may result in an identity crisis.

Why Few Entrepreneurs Plan for Life After Exit

“The vast majority of entrepreneurs don’t think about what they’re going to do with their life after they sell,” Rood said. “I absolutely didn’t.”

As an entrepreneur who thinks of yourself as the business, it’s hard to imagine life without that aspect of your identity.

But, Rood noted, “The happiest people were those who started thinking about what post-exit life would look like before their exit.”

Start Planning for Life Beyond the Exit Before You Sell

The best time to plan your post-exit life is before you engage a business broker. Once the sales process starts, it’s like a boulder rolling downhill: It accelerates quickly.

Your post-exit plan also can (and should) inform the type of exit you pursue – whether it’s a clean break with a potentially lower selling price or the option to stay involved with a buyer who values your ongoing role.

In both scenarios, the key is thinking about it early, often, and in a relaxed mental space.

What Most Entrepreneurs Do Post-Exit

Rood shared that most entrepreneurs he interviewed explored three activities – often with unwelcome outcomes that caused more frustration than satisfaction:

1. Angel Investing. It seems like a natural fit, but many startups go bankrupt, and it can feel like a waste of time and energy.
2.  Advising Startups. Despite your extensive expertise, young founders sometimes ignore advice and stop returning phone calls.
3. Serving on Nonprofit Boards. You may hope to offer experience and guidance, but many nonprofits just want you to cut a large check and attend their annual gala.

Pitfalls of Starting Your Next Venture Too Soon

“The most miserable post-exit entrepreneurs were those who sold their businesses and then almost immediately started a second business,” Rood shared. 

Without a post-exit strategy, entrepreneurs can get bored, panic, and start a new business that is as close to the first one as their non-compete allows. Though it seems like logical, they realize anew that growing a business eats up your finite time and energy — and with a healthy post-exit bank account, they no longer have the motivation for late nights and business trips that drive success.

“It gets a lot harder to justify that sacrifice to yourself, your family, and your health,” Rood said.
After all: If you really wanted to be running a business so badly, why did you sell the one that you had?

Tools to Help Plan Your Post-Exit Strategy

1. Wheel of Life. EO members may be familiar with the Wheel of Life, which ranks your satisfaction in areas including spiritual, emotional, intellectual, health, and relationships. It’s a valuable self-assessment tool to identify and rebalance life priorities.
2. Revisit Childhood Interests. What hobbies made your heart sing at age 10 or 12? Did you like woodworking or mixed martial arts? Did you dream of helping kids? Finding an activity in those same arenas may still delight and fulfill you.
3. Ask Strategic Questions to Tease Out Ideas. Another method of envisioning life beyond business is to ask questions that help pinpoint your meaningful pursuits.
   •    What would you do if you could never start another business?
   •    What would you do if you weren't afraid?
   •    What would you do to make the biggest impact?
   •    At age 13, what did you think was the coolest thing you could possibly do as an adult?
   •    What could you do to maximize your growth? Your creativity?
   •    If you won the lottery today, what things you would start doing? What would you stop doing? Who would you spend more time with? Who would you spend less time with?

The Post-Exit Bottom Line

While a business exit might feel like the finish line, it’s really just another starting point.

If you’re contemplating an exit, start strategizing your post-exit life now. EO is ready to help with its newest Executive Education program, Navigating Your Exit with Harvard Business School, where Harvard faculty will share frameworks on how to maximize value and align your exit strategy with your goals to make your next phase the best ever.

Registration is now open for the inaugural class of Navigating Your Exit, 2–5 September 2025 in Boston, Massachusetts. Just 80 spots are available; register today!