How to Avoid Being Rich and Miserable As You Exit Your Business

Our most treasured family activity is traveling in our RV. Each year, I turn off my computer, put my phone on do-not-disturb, and we hit the open road. After days of interstate travel, my favorite part is coasting up or down an off-ramp. 

Whether my children are sleeping, playing video games or simply bothering each other, the deceleration changes the mood in the RV. Faces press against windows. Excitement builds.  

That excitement builds because we’ve spent months planning the trip, hyping up the destination.  

Imagine if we hadn’t. 

Imagine if we had just thrown clothes in a duffel bag, not knowing if we’re headed to the desert or the mountains. 

Imagine if we had three kids in the back, not knowing whether they had days of stream exploration or history museums ahead of them. 

Imagine if we arrived at a destination, planning to eat out, only to find the nearest restaurant is a gas station/diner combo 40 miles away. 

While there’s a great deal of excitement that can be gained from hitting the open road and not knowing what comes next, there’s an even higher risk that you won’t like what you find on the other side. Without the proper planning — and communication — the kids in the back of the RV can quickly become your biggest critics. 

If you’re a business owner, that interstate off-ramp is your business exit. It’s not your destination, but with proper planning, you can be excited enough to press your face up against the glass and anticipate what comes next. 

You can’t exit your business until you exit your identity 

There are three areas of readiness that you must pay attention to when planning for your eventual exit. 

You are likely spending almost all of your time on business readiness. As a business owner, that’s the easiest one: driving value in your business so you’re building something someone will eventually want to buy.  

If you’re finding success, you’re likely spending your remaining time on the second area: financial readiness. You’re building the resources to fund your post-exit life. You’ve got a financial advisor, and maybe you even have a “magic number” that tells you an exit will be financially comfortable for you and your family. 

The forgotten area is arguably the most important: personal readiness. Like the big moment of arriving at your destination with excitement, anticipation, and preparation, personal readiness often determines whether an exit feels successful. 

The problem is that, as business owners, we believe our identity is our business. We become so deeply connected to our title, influence, and routine that they become who we are. 

So when the phone stops ringing, weekly touchbases disappear from our calendar, and the business moves on with a new owner, we don’t have any sense of self. 

Cliches are cliches for a reason 

“The journey is the destination.” 

You have to start your personal plan now in order to have a sense of fulfillment post-exit. Whether you believe your exit to be five, 10, or 20 years down the road, a personal plan takes time to execute while you are still in the owner’s seat.  

A personal plan isn’t just how you’ll spend your time post-exit. It’s about identifying your purpose, determining ways to execute it, and planning how you’ll find fulfillment post-exit. 

Wealth can fund your future. 

Golf can be fun. 

But neither can create meaning. 

Invest in what matters 

You wouldn’t start funding your retirement account at 60. 

So why are you investing in yourself so late? 

Here’s how to get started: 

1. Define Purpose: What’s the unique impact you make on the world? How can you use your position as a business owner to start making that impact intentionally?  

2. Cast Vision: Name the ways that you want to fulfill that purpose outside of your business, post-exit. 

3. Take Baby Steps: Get outside of your business now and try out those new destinations. It’s not just a great test of your post-exit life—decentralizing yourself from your business also builds value in it. A potential buyer wants to know that your business isn’t a one-person show. 

4. Enjoy The Compound Interest: Just as small, early investments can compound, taking small steps towards your post-exit fulfillment now can create excitement for your next stage and help you truly identify what makes you feel fulfilled—and what doesn’t. 

5. Don’t Go Solo: Personal plans are complicated, and we’re not always honest with ourselves. Find an advisor—with a Certified Exit Planning Advisor (CEPA^®) credential—to help you build your plan. 

Always keep your face pressed up against the glass 

According to PwC, 75% of business owners deeply regret exiting their business within a year of the transaction. And, according to our own research at Exit Planning Institute, only 59% of owners have a written personal plan. 

That means most business owners don’t know their destination, and even more won’t like what they find when they get there. 

Just like my kids when they are fully prepared and hyped for our epic RV trip, we’re more excited when we know the destination is truly what we want. Investing your time and energy into making sure your destination is the correct one — and planning for that — is the only way we’ll get that “face pressed up against the glass” feeling in our post-exit life. 

Our most treasured family activity is traveling in our RV. Each year, I turn off my computer, put my phone on do-not-disturb, and we hit the open road. After days of interstate travel, my favorite part is coasting up or down an off-ramp. 

Whether my children are sleeping, playing video games or simply bothering each other, the deceleration changes the mood in the RV. Faces press against windows. Excitement builds.  

That excitement builds because we’ve spent months planning the trip, hyping up the destination.