For many business owners, the journey of building, growing, and ultimately selling their business is a defining part of their life. But what happens after the sale? What comes next when the company you poured years—perhaps even decades—into is no longer yours? The reality is, the vast majority of business owners regret selling their business within a year of the sale.
Why does this happen? Because selling a business isn’t just about the financial transaction—it’s about identity, purpose, and planning for the next chapter.
The Identity Crisis of Selling Your Business
For so many entrepreneurs, their identity is deeply intertwined with their business. It’s not just what they do—it’s who they are. When the business is gone, they find themselves asking, Who am I now?
I’ve spoken with exit planning experts, Mergers Acquisitions professionals, and business coaches, and they all say the same thing: The biggest barrier to a successful exit is the business owner failing to plan for what they would do with the rest of their life once they were done.
This lack of preparation can manifest in different ways:
- Owners turning down reasonable offers because they aren’t truly ready to let go.
- Struggling to fill the newfound free time with meaningful activities.
- Watching their business change under new ownership and feeling a sense of loss or regret.
Planning for the Afterlife: Your Next Chapter
What happens when you suddenly have all those extra hours back in a day, a week, a year? If you don’t have a plan, you might find yourself in a post-sale slump, unsure of what to do next.
Retirement, travel, and spending time with family may sound wonderful, but for many former business owners, it’s not enough. Business owners thrive on challenge, vision, and creation. Without something to work toward, life can feel stagnant. In some cases, people even face severe depression or health challenges post-sale because their sense of purpose is lost.
So, how do you avoid this fate? Here are some key considerations:
- Define Your New Purpose: What excites you beyond your business? Is it philanthropy, mentoring, consulting, writing a book, or even starting a new venture? The possibilities are endless, but you need to start exploring them before you sell.
- Structure Your Time: Having complete freedom sounds great, but structure is what keeps us grounded. Think about how you will spend your days, and make a list of activities that bring you joy and fulfillment.
- Build a Support System: Surround yourself with other retired entrepreneurs, advisors, or coaches who have navigated this transition successfully. They can help you adjust to your new reality.
Lessons from the Business World
Many business owners struggle to let go. Take, for instance, the owner of an engineering firm who, at 87 years old, still controlled every decision. His children were ready to retire, employees were frustrated with stagnation, and the business faced an uncertain future because he couldn’t step aside.
Contrast that with an Ohio farm family that has perfected the art of generational transition. By the time each new generation reaches 35, they step into leadership roles, and the older generation transitions into advisory positions. The result? A thriving, sustainable business model that has lasted for over a century.
Will You Have Enough?
Another major concern for business owners is financial security. Many have most of their wealth tied up in their business. When they sell, they need to turn those assets into a sustainable income stream for retirement. But questions linger:
- Will the proceeds be enough to fund my lifestyle?
- How should I invest for long-term security?
- What are the tax implications of my exit strategy?
Working with financial and exit planning professionals well in advance can help you navigate these concerns with confidence.
Embracing Change and Letting Go
Change is hard, but it’s necessary. Just as you adapted and evolved to build a successful business, you must now embrace the transition into the next phase of your life. Don’t fall into the trap of clinging to control because you fear the unknown. Instead, take proactive steps to design a post-business life that excites you.
Your legacy doesn’t disappear when you sell—it evolves. Whether through mentoring the next generation, philanthropy, or a new venture, you can continue to have a meaningful impact.
The key takeaway? Don’t wait until after you sell to think about what’s next. Plan for your afterlife now, so when the time comes, you’re not left wondering, What do I do now? Instead, you can step confidently into your next adventure, knowing that your best years may still be ahead of you.
Final Thoughts
Business exit planning is more than a procedural necessity—it is a strategic, reflective, and transformative process. By approaching it with the same passion and thoroughness, business owners can create a plan that safeguards their legacy and opens doors to new possibilities. Ultimately, the journey of exit planning is about taking control of your future, ensuring that when the time comes, you exit on your own terms and with confidence.
A well-executed exit plan isn’t just about leaving—it’s about leaving on your terms. Whether your goal is financial security, business legacy, or a stress-free transition, the right planning ensures you exit with confidence.
Want expert guidance for your business exit? Contact us today for a personalized consultation
