Retire to Something, Not From Something
A Guide to Life Beyond Your Business
You need to retire to something, not from something.
Succession planning isn’t just about transitioning a business—it’s about preparing the business owner. While crafting a solid transition plan is crucial, it’s equally important to start with the person at the heart of the process: the business owner. That’s where my philosophy begins, in the Business Owner Readiness phase.
For many business owners, selling or transitioning their business is a deeply emotional journey. This business isn’t just a livelihood—it’s often their legacy. Owners invest their time, energy, and heart into nurturing their business, navigating tough times, and sharing pivotal life moments with employees and customers. It’s no surprise that without careful planning, many find themselves regretting their decision to exit, wondering, “Why did I leave when I have nothing better to do?”
Two Key Considerations Before Transition
Before considering the mechanics of a business transition, every owner must answer two critical questions:
What will I do with my newfound time?
Can I afford the lifestyle I desire?
This article focuses on the first question—how business owners can prepare for life outside their business.
The Challenge of Identity Beyond the Business
For many business owners, their identity is intertwined with their business. Their days, routines, and sense of purpose are rooted in their role as a business owner. When the day-to-day hustle is gone, they may experience a void, feeling aimless without the structure their business provided.
A lack of balance between personal and professional life makes this transition even harder. It’s not uncommon for owners to focus so heavily on financial outcomes that they neglect to explore their personal aspirations, hobbies, or goals.
Creating a Plan for What’s Next
Transitioning out of business ownership is highly personal, but it doesn’t have to be done alone. Trusted friends, family members, and advisors can provide valuable perspective and support as you explore what life looks like post-business.
Do you have a passion project waiting in the wings?
Is there a charitable cause that inspires you?
What are the hobbies or goals you’ve put on hold?
Engaging in these discussions early can shift the focus from loss to excitement for the next phase. With a clear plan, the prospect of life beyond the business becomes an exhilarating new chapter rather than a daunting unknown.
Questions Every Business Owner Should Ask
To get started on your personal readiness plan, reflect on these core questions:
Why do I want to exit the business?
What do I plan to do after leaving the business?
How personally attached am I to the business?
Do I have a fulfilling life outside of the business?
Resources to Support Your Journey
Several tools and resources can help you prepare for the next phase:
“The Master Plan” by Peter G. Christman
This book outlines three pillars every business owner must balance when planning their exit strategy.“The Exit Checklist eBook” by Value Builder. This eBook addresses the considerations of why the business owner is exiting the business. This eBook is available upon request. Contact — BOSS -- Business Owners Strategic Solutions
Complete your What is your Endgame? Business Owner Readiness Assessment located at Value Enhancement — BOSS -- Business Owners Strategic Solutions.
What’s Next?
The next article in this series will tackle the second consideration for business owners: Freedom of Choice—whether you’re financially ready to maintain the lifestyle you desire after leaving your business.
Start planning your next chapter today—because retirement should be about moving to something meaningful, not running away from something familiar.
For personalized support in planning your transition, reach out to BOSS – Business Owners Strategic Solutions. We’re here to help you turn the next phase of life into your best chapter yet.