Take the Plunge – Sell Your Business While You’re on Top

man taking a leap of faith and jumping into the ocean

Take the Plunge – Sell Your Business While You’re on Top

If you’re a business owner who still loves what you do, brims with ideas to grow your company, and leaps out of bed each morning excited to work, then this article isn’t for you. Keep doing what you love, and don’t even think about selling.

But if you’re like many business owners I meet—those who’ve been in the game for years, feel less excited about the day-to-day grind, and frequently find yourself thinking about exiting—selling your business should be a priority.

Most of the business owners I work with are Baby Boomers who’ve built successful companies but now sit on the proverbial fence about selling. When asked when they plan to sell, the most common response is, “Probably in 3–5 years.” Yet, with the youngest Baby Boomers turning 65 by 2030, the clock is ticking.

Some owners tell me they’d rather hold on to their business for another few years, confident they can earn as much by staying as they would by selling now. My response? If you’re content coasting and maintaining the status quo—and willing to bet your business value won’t decline—then maybe holding off is right for you.

I personally sold the business I owned and operated for 29 years in my mid-50s—not because I was ready to retire but because I needed a change. On paper, it didn’t make sense; the business was thriving financially with significant growth potential. But I was ready for the next chapter.

As a business owner, walking away from a profitable company is never easy. But if you want to sell at a premium, you need to exit while you’re on top. If you’re uncertain, here are a few factors to consider:

Selling Is a Financial Win—Maximize It

If your business generates annual profits comparable to its potential sale price in 3–4 years, you’re likely sitting on a highly valuable asset. Selling now could mean walking away with a significant sum to invest.

With guidance from a financial professional, you could grow this “large pot” of money far beyond what you could have achieved while still running the business. The stock market, for example, has delivered strong returns for many sellers over the past decade. If handled wisely, selling your business can be the start of an exciting new financial chapter.

The Future Is Unpredictable

Your business might be thriving now, but what about 3–5 years from today? As a business owner, you’re no stranger to risk. Yet many Boomers I talk to—having weathered 9/11, the Great Recession, and the pandemic—admit they’re burned out.

After retirement, the second most common reason owners sell is burn out. Many tell me they simply don’t have the energy to navigate another major challenge. Holding on too long can put your financial future at risk. When a business becomes stagnant, its value often declines, making it less attractive to buyers.

Selling Can Propel Personal Growth

Selling your business isn’t just a financial decision—it’s a chance to reinvent yourself.

One option many owners explore is holding on to the real estate, leasing it to the buyer, and then building a real estate portfolio. Others dive into new careers, volunteer in their communities, or simply spend more time with loved ones.

The common thread? Growth and fulfillment. The clients I’ve stayed in touch with overwhelmingly tell me that selling was one of the best decisions they made. Retirement or reinvention—it’s been good to them.

In Conclusion

If you’ve built a successful, financially strong business but find your passion for growth waning, now might be the right time to sell. Life is unpredictable, and waiting could mean missing out on opportunities to maximize your business value.

Selling allows you to pass the torch to someone with fresh ideas and energy while opening the door to a new and rewarding chapter in your life.

Life’s too short—take the plunge!