Why 75% of Founders Regret Their Exit — and How to Avoid It

For many, nothing says “I made it” like a superyacht. From the old Lifestyles of the Rich and Famous episodes to cable’s Below Deck, yachts have been positioned as more than just boats. 

They’re a message to everyone: I’ve unlocked the world. 

Imagine standing on the deck of your own custom-built superyacht. Twenty years ago, you started planning it: selecting engineers and builders, identifying the best staff, and picking out the finest details. You check your bank app and see a balance to cover more than all of this for decades. In the distance, you see your business—a business you have sold for more money than you thought possible.  

And then you realize:  

• You don’t know how to swim. 
• Your crew chief has things handled, and no one expects you to lead. 
• Your spouse has motion sickness. 
• You can’t spend time with your grandchildren from the South Pacific Ocean. 

Suddenly, everyone else’s idea of fulfillment makes you queasier than your spouse. And the great open water looks like an abyss. 

You didn’t need a status symbol. You needed a personal plan. 

According to PwC, 75% of business owners profoundly regret exiting their business within a year. It’s not because they didn’t have money, and it’s not because they didn’t try doing the things the world told them rich people do when they retire. It’s because they spent all of their time building a thing that wasn’t really for them.  

Achieving the real status symbol—post-exit fulfillment—takes much more work. And to accomplish that, you can’t treat your post-exit life like a vague retirement daydream. Instead, it’s a rigorous strategic roadmap. Like most business strategies, it comes with concrete, trackable metrics. 

So what is a personal plan? 

A personal plan sets goals to fulfill your legacy grounded on your unique purpose and identity. Despite its importance, many owners still fail to build one — and risk missing that legacy. 

Post-exit fulfillment is about meaning, not just filling free time. An effective plan includes:  

• Purpose: Your unique impact on the world, which guides your future activities and strengthens your current leadership.  

• Vision: Where you want to be in 10 years across all areas of life.  

• Goals: Measurable, one-year milestones moving you toward that vision.  

• Action: Immediate steps to take over the next 90 days to achieve your annual goals.  

According to the Exit Planning Institute’s State of Owner Readiness Report, only 44% of owners felt personally ready to exit, just 41% had a formal written plan, and only 35% had completed a personal readiness assessment. We are heading towards a crisis of personal fulfillment among exited business owners. 

Building the plan isn’t the only step, though. The real value comes from measuring it—and then adapting it — is where you’ll find the greatest value. Here are three ways to do that. 

#1: The checklist: An entry point 

According to the Exit Planning Institute, there’s a huge gap between the work people have done to prepare a personal plan and how ready they feel. Only 41% of owners nationwide have a formal written plan, and only 35% have completed any sort of readiness assessment. Meanwhile, 44% of owners believe they are best-in-class or perfect when it comes to personal planning.  

Two yes-or-no questions can help you start measuring your personal planning: Do I have a documented personal plan detailing my post-exit life? and Have I formally audited my personal readiness for a transition? 

#2: The assessment: A moment-in-time readiness score 

I’m fortunate, as president of Exit Planning Institute, to know plenty of advisors who are making great strides in exit planning — especially in the growing area of personal planning. We’re all realizing that business planning and financial planning cannot be the only types of planning owners experience on their path to exit. 

If you answered “no” to the question “Have I formally audited my personal readiness for a transition?” start that assessment—and revisit it often. One assessment I recommend is The Happiness Portfolio® created by Marianne Oehser and Susan Latremoille. They focus on eight critical areas of life: professional, primary relationship, family and friends, giving back, spiritual/emotional well-being, leisure, self-development and health.

The questions in their assessment can help you understand how ready you are to exit in each of those eight important arenas and how to make a plan to improve. Continuing to take the assessment can show your progress in specific areas — and which areas you need to focus on more. 

#3: The visual aid: The 21 time-slot audit 

Find a whiteboard and draw two 7×3 tables on it. The seven columns represent the days of the week, and the three rows represent the time of day: morning, afternoon and evening. 

Then, make a list of all the activities that make you feel fulfilled. Examples include mentoring other professionals, working out, spending time with your spouse, volunteering and attending non-profit board meetings. Give each activity — maybe narrow it down to the top five — a different colored marker or post-it. 

Then, audit your last week. Find the times when you engaged in those activities.  

Do you notice that some time slots are bare? 

Do you notice that some activities don’t make the board? 

Now, move to the other table you drew. Using only the activities that leave you feeling fulfilled, map out your ideal post-exit week. 

Let’s say your first table had only four of 21 time slots filled. Record that. And, looking at your ideal post-exit week, challenge yourself to fill one more timeslot the next week. Over time, you’ll make measurable progress to your post-exit life—all while continuing to own your business. 

Will you have the time to hit 21/21 as a business owner? Maybe not. But measuring your progress — and having an incentive to decentralize yourself from your business to achieve your personal goals — is a productive exercise. 

No measurement without a baseline 

There’s no point in measuring something that doesn’t have a baseline, and that’s why starting on your personal plan is so critical. You cannot wait until you’re standing on a yacht you won’t enjoy.

The good news? You don’t have to do this on your own: find an exit planning advisor near you who can guide you through the creation — and measurement — of a personal plan so you can find fulfillment in your post-exit life. 

For many, nothing says “I made it” like a superyacht. From the old Lifestyles of the Rich and Famous episodes to cable’s Below Deck, yachts have been positioned as more than just boats. 

They’re a message to everyone: I’ve unlocked the world. 

Imagine standing on the deck of your own custom-built superyacht. Twenty years ago, you started planning it: selecting engineers and builders, identifying the best staff, and picking out the finest details. You check your bank app and see a balance to cover more than all of this for decades. In the distance, you see your business—a business you have sold for more money than you thought possible.