There’s more to a business sale than crunching numbers. For thoughtful, successful people like you, it’s not just a transaction—it’s a transition. One that intersects with your identity, your future vision, and the legacy you leave behind. You’ve built something meaningful. Now you’re wondering: Is it time to let go? Here’s how to think through that decision with the clarity and intentionality it deserves.

Just because you’ve sold your business doesn’t mean your life is over. To the contrary, it means the opposite. Owning and operating a business is a time-consuming endeavor, and now that you’ve transitioned away from it, there are endless ways to fill your time after you cashed in. Your lifestyle may have changed, but you still need enough cash to meet your living expenses.

Entrepreneurs and business owners often approach risk differently than most, especially when it comes to their comfort with uncertainty. As one founder put it, “The risks are endless…they never go away when you’re an entrepreneur.” This is the reality business owners face daily as they strive for growth and earnings. Managing risk becomes even more complex when balancing a business with personal financial health.

How should you be paid for a thriving business? This guide will walk you through the earnout structure and guide your decision-making.

As a business owner, your professional and personal lives are intertwined and inherently connected to your business. With their identity largely tied to what they do professionally, many owners face confusing and conflicting emotions when leaving their company. Selling a business can be one of the most significant decisions of your life. The first step to planning for your exit is finding mental readiness.

In the game of entrepreneurship sometimes the market throws a curveball, and your business valuation is less than what you had expected. Instead of striking out, have a contingency plan in place. It’s good to hope for the best but be prepared to adjust your expectations downward if the valuation of your business comes in lower than expected.

Business owners are on the hook for a lot: the full 15.3% self-employment tax, the cost of healthcare, building your own nest egg without the matching employer contributions to retirement plans often referred to as “free money” for employees. It’s no wonder that investing for retirement isn’t a top priority for some business owners who are busy trying to grow their business’ value.

*The following article was contributed by Greg Maddox, Senior Business and Exit Advisor at Cultivate Advisors Every business owner will exit at some point, and we all hope it will be on our own terms and timeline. However, only 20% of those who try to sell actually do. Well, why is that? Most business owners aren’t actually preparing their business for a sale.