Business Owners: How to Quit Without Regretting It

How to sell your business confidently, secure your retirement, and avoid common regrets.

Selling Your Business Is a Big Deal—Let’s Make Sure You Feel Good About It

If you’re like most small business owners, your company isn’t just your livelihood—it’s your life. It’s your legacy, your routine, your relationships, your sense of purpose. And when you’re ready to move on, it’s also your retirement plan.

But here’s the tough truth: three out of four business owners (75%!) regret how they exited their business within the first year. That regret usually comes down to one thing—lack of preparation.

Selling a business is not just a financial transaction. It’s a deeply personal transition. Here’s how to get ahead of the process, protect your future, and avoid retirement regrets.

Planning Ahead Is Power

The biggest mistake I see when business owners sell and retire? Waiting too long to start. Owners assume they’ll start planning once they find a buyer, but by then, you’re reacting instead of leading.

Ideally, you’re thinking about your exit at least three to five years before you want to walk away. That gives you time to strengthen your business, get your financial house in order, and explore different paths. Even if you’re not planning to sell soon, prepping your business now makes it stronger today and more valuable down the road.

Think of it this way: the more prepared you are, the more control you’ll have when it’s time to say yes (or no) to a purchase offer.

Know what your business is really worth

Spoiler alert: your business is probably not worth the same as what your golf buddy’s sold for. I’ve seen too many business owners latch onto an unrealistic number because “someone they know” got a big check.

In reality, every business is different. To know what your business may be worth, you need an objective, third-party valuation. Not only does a third-party valuation set realistic expectations, but it also helps uncover hidden risks or value-killers—like owner

dependence (the business can’t run without you) or inconsistent financials—that you can start fixing now.

If it turns out the value isn’t quite where you want it to be, that’s okay. Because you started planning early, you’ve got time to make improvements. And even small changes can make a big difference in your eventual sale price.

How to Make Your Business More Attractive to Buyers

Think like a buyer: would you want to buy a business that falls apart without its owner? Or one with no systems in place, no bench strength, and no visibility into the future?

What business buyers love:

• A strong leadership team that’s ready to run the show
• Documented systems and procedures
• Reliable, diversified revenue
• Clean books
• Recurring income (bonus points if it’s sticky revenue)

Identify your business’ strengths and weaknesses

I often recommend business owners who want to improve their business’ salability start with a SWOT analysis: strengths, weaknesses, opportunities, and threats. Then, bring in an accountability partner, like your financial planner, CPA, or business advisor, to help you stay focused on your goals.

The Deal Isn’t Just About the Dollar Amount

It’s easy to focus on the sale price, but for small business owners, the structure of the deal matters just as much. It’s important to know what you want, need, and are willing to do to make your business sale and retirement a success.

Some potential deal structures include:

Earn-out

In an earn-out deal, the buyer agrees to pay part of the sale price up front. The rest is paid later, but only if the business hits specific financial targets after the sale. This arrangement may require you to stay on for a while, and you risk not receiving the full purchase amount should the business underperform.

Lump Sum Payment

When the buyer pays the entire purchase upfront, you enjoy immediate access to your retirement funds, no strings attached. However, this approach could cause you to give a lot more of your proceeds to Uncle Sam and the state through extra-large (and potentially avoidable!) tax bills.

Installment Sale

When the buyer pays for your business over time (often monthly or annually) your business sale income can be spread over several tax years, reducing your total taxes owed. However, if your buyer defaults, you may be out of luck.

Each type of sale structure has different risks, benefits, and tax consequences. That’s why I strongly suggest you seek advice from your financial advisor and your CPA before proceeding with any sale agreement!

Don’t let taxes sneak up on you

You might sell your business for $2 million and think you’re set. But after taxes, fees, and other costs? That number could shrink fast.

Here’s what to be aware of:

• Federal capital gains tax (up to 20%)
• State capital gains tax (5% in MA, more in other states)
• Net Investment Income Tax for high earners
• Possible hikes to Medicare premiums due to increased income
• Millionaire’s Tax in Massachusetts on all income over $1 million

This is why, when we think about the sale of a business, we always focus on net proceeds, not just the top-line number. Knowing what you’ll keep from your sale after taxes is what really drives your retirement strategy.

Prepare for the emotional side of your exit

This is the part of retiring from your business that people don’t talk about enough. Letting go of your business can feel like losing a piece of yourself. I’ve seen clients wrestle with who they are without the title, without the daily responsibilities, without their team. The antidote? Start creating your “what’s next” before you hand over the keys so you’re retiring TO something, not FROM something.

• Grab a blank calendar and fill in what you want your days to look like. Travel? Time with grandkids? Mentorship? Consulting work? Volunteering? There’s no wrong answer—just make sure you have one.
• Consider your hobbies and passions. What will you do more of? What new opportunities will retirement present?
• Think about how you introduce yourself to people today, and how you want to be known tomorrow. Who will you be when you’re no longer “Owner and CEO” of your company?
• Do a practice run! Plan to take some time off – three weeks or more – and see how you feel. There’s a bonus benefit to this plan: you’re also testing your business’ ability to run without you.

Protect your legacy

A successful exit isn’t just about the numbers—it’s also about the people. The employees you care about. The clients you’ve served. The brand you’ve built.

Think about:

• How your buyer treats people
• Whether the new management is a cultural fit for the team you’ve developed
• How the changes planned by the buyers impact the brand you created
• Whether your most valued customers will continue to receive the level of service you think they deserve
• How you would feel if the business closed in 3, 5, or 10 years

After careful reflection, you might decide it’s worth taking a little less if it means protecting your team and your culture. After all, you only sell once. You don’t get to redo it.

Have a Plan B (and maybe a Plan C)

Deals fall through. Markets shift. Health changes. Life happens. Having a contingency plan protects your options—and your peace of mind – whether you’re planning to retire next year or in the next decade.

Here are a few ways to prepare:

• Buy-sell agreement: Crucial if you have a business partner. It outlines how your interest in the business will be handled if something unexpected happens.
• Contingency succession plan: This can be as simple as naming an interim leader or as formal as developing your successor.
• Liquidity cushion: Set aside funds to keep your personal finances afloat if your sale gets delayed.
• Multiple exit paths: Consider and evaluate options beyond an outright sale, such as:
  • Internal buyouts (selling to employees or management)
  • ESOPs (Employee Stock Ownership Plans)
  • Partial sales or staged exits
  • Gifting shares to family or charity (when it aligns with your goals)
• Business continuity playbook: Make sure your systems, vendors, key employees, and financial records are documented and accessible.

Unfortunately, about half of business exits are involuntary. This sort of advance planning gives you choices when your sale doesn’t go as planned and protects your family and business in the event of illness, injury, or death.

Turn your business sale into a retirement income

Once you successfully sell your business, how do you make that money last? Whether it’s a business sale, lottery winnings, or an inheritance, people everywhere struggle to manage a lump sum payment effectively. But the good news is, you don’t have to do this alone.

At Berkshire Money Management, your financial plan would include what we call the Paycheck Replacement Plan, which creates a predictable, tax-efficient stream of income in retirement. Your Paycheck Replacement Plan shows you where your retirement income will come from year after year, so you don’t have to worry about how you’ll pay your bills.

We’ll help you:

• Map out your expected income and expenses in retirement
• Factor in Social Security, savings, and investments
• Understand what your withdrawal strategy might look like over time

Retirement isn’t static. Some years you’ll spend more, some less. The key is to build a plan that gives you peace of mind and flexibility.

Client outcomes will vary based on individual circumstances. No plan or strategy should be construed as a guarantee of any level of performance or income.

You’ve Built Something Great—Now Let’s Build What Comes Next

Selling your business can feel overwhelming, but it doesn’t have to be. With the right plan, the right team, and the right mindset, you can exit with confidence—and without regrets.

Let’s make sure your hard work turns into the retirement you want. If you’re ready to start planning, I’m here to help.