Top 10 Reasons to Sell Your Business (Especially If You're a Boomer)
If you’re a Baby Boomer business owner, chances are you’ve poured decades of sweat, time, and energy into building something meaningful. But when it comes to what’s next, the plan often gets a little fuzzy
Maybe you're thinking about retirement, slowing down, or simply doing something different—but you're not sure when or how to step away. You’re not alone. Many business owners struggle with timing their exit just right. The truth? There is a right time—and often, it’s sooner than you think.
Here are 10 compelling reasons why now might be the right time to sell your business:
1. 10,000 Baby Boomers Are Retiring Every Day
The wave is real. With this many people exiting the workforce daily, we’re heading into what economists call the Silver Tsunami. If you're planning to sell, getting ahead of the crowd can help you stand out in a soon-to-be flooded market.
2. Only 20-30% of Small Businesses That Go to Market Actually Sell
Most businesses don’t sell—not because they aren’t valuable, but because they aren’t prepared for sale. By planning your exit intentionally, you can be in the successful minority who actually make a deal.
3. It Can Take 6–12 Months (Or More) to Sell
Selling a business isn’t like selling a car—it’s a process. Between finding a buyer, negotiating, and transitioning ownership, it can take time. Starting early gives you flexibility and leverage.
4. The Market is Shifting to a Buyer’s Market
As more Boomers list their businesses for sale, supply will start to outpace demand. Waiting too long could mean you’re competing with dozens of similar businesses—and that can drive down your price.
5. Most Owners Overvalue Their Business
It’s natural to think your business is worth more than what the market says. But when it comes time to sell, the only value that counts is what a buyer will pay. Selling while your financials are strong can help you secure top dollar.
6. You May Already Know Your Ideal Buyer
Your buyer might not be a stranger—it could be an employee, competitor, vendor, or even a loyal customer. The sooner you start thinking about this, the more intentional your sale can be.
7. Buyers Want Systems, Not Just Stories
You’ve built a legacy, but to a buyer, systems matter more than sentiment. Selling your business forces you to streamline operations—something that makes it more valuable and easier to hand off.
Check out the free Small Business Automation Starter Guide.
8. Selling Can Fund Your Retirement
For many business owners, the sale of their business is their retirement plan. Done right, it can provide financial freedom and open the door to the next chapter—whatever that looks like for you.
9. Burnout is Real
Let’s be honest—owning a business is exhausting. If you’ve lost the spark, it might be time to pass the torch and reclaim your time, energy, and peace of mind.
10. You Don’t Want to Leave Your Family in a Bind
If something happened to you tomorrow, would your family know what to do with the business? Having a clear exit plan protects the people you care about and ensures your business legacy is handled the way you want.
Final Thought
Selling your business isn’t giving up—it’s moving forward. Whether you’re ready to retire, reinvent, or just relax, selling on your own terms is one of the most empowering moves you can make.
Start planning today—because “someday” isn’t a strategy.
Want help mapping out your business exit? Check out my free Business Broker Question Guide or sign up for early access to my course, The Confident Exit: A Proven guide to Sell Your Small Business Without Regret.
