Imagine spending decades building your roofing company only to sell it and wake up a year later feeling seller's remorse, regret, doubt, and emptiness.

An Exit Planning Institute (EPI) study and other sources have consistently reported this 75% statistic. The regret is usually not due to the financial outcome but because of the personal and emotional aftermath of the sale.

I personally understood this dilemma when I sold my company, which is why I started Beacon Exit Planning. I was only 62 and wanted to bridge the emotional gap caused by the lack of daily engagement that comes with running a business. I also wanted to help other business owners navigate the complex exit process without being clobbered by taxes.

Owners have a strong identity tied to their business and have not really planned for the absence of the day-to-day mental and intellectual challenge of running a business.

This statistic emphasizes that a successful exit isn’t solely about the money. It’s about planning carefully—emotionally, financially, and strategically.

A professionally developed and executed exit plan emphasizes personal, financial, and business planning, including for life after the sale. This includes succession planning, where we recommend owners eventually take longer vacations to enjoy life outside the business and allow the management team to work together to run the company without them.

If you’re thinking about selling your company someday, here’s what you need to know and how to prepare so you won’t become one of the regrettable statistics.

What Drives Exit Regret?

1. Loss of identity: The business is more than just what we do; it's who we are. For many owners, the business is their life's work and a core part of their identity. Without the daily challenges and purpose that come with running the company, they can experience a deep sense of loss and grief.
2. Lack of personal or post-exit planning: Many owners focus solely on business valuation and tax optimization—but skip planning for life after the business. This sudden loss of routine, identity, and purpose can leave them feeling disoriented and without purpose.
3. Post-sale boredom: Absence from a rigorous work schedule can quickly turn into boredom. Many entrepreneurs thrive on the daily intellectual challenges of running a business but miss the stimulation it provides.
4. Unrealistic expectations: Some owners may hold unrealistic expectations about the sale price, the speed of the transaction, or the role they will play post-exit. When these expectations are not met, disappointment and regret can set in.
5. Lack of buyer fit or cultural/vision misalignment: When you sell, you lose control. Your values, culture, and strategic direction may conflict with what you've built and go against your expectations with the new ownership. The seller may feel guilt or sadness if the new buyer treats employees differently or dismantles the company culture they've created. 
6. Tax, structure, and cash flow surprises: Your final offer structure should consider taxes, working capital, and earn-out clauses, or much of your windfall can disappear. Poor planning can make your “big payday” feel disappointing.

That’s why a successful exit is not just financial. It must integrate your personal life, relationships, values, and future vision.

How to Exit Without Regret: A 5-Step Framework

Here’s a proven roadmap to minimize regret and maximize fulfillment after your exit.

1. Define Holistic Success Beyond Just Dollars

Start by defining what success means across several areas.

• Financial goals: Financial independence with after-tax proceeds
• Personal & lifestyle goals: What does life look like in retirement with family, friends, employees, hobbies, and community?
• Business: What will your legacy and business become?

If your exit strategy focuses only on valuation and multiples, you’ll probably overlook the emotional and lifestyle factors many owners regret missing.

2. Build a Pre-Exit Runway (3-5+ Years)

Begin preparing long before you list your business:

• Implement succession by decentralizing your role—establish systems and teams that can operate independently, allowing you to step back from daily involvement.
• Gradually take extended vacations to allow the management team to work together independently of your day-to-day oversight.
• Begin shifting your identity to life and interests outside the business.
• Build relationships, projects, or hobbies that provide you with meaning.

The earlier the owner starts, the more likely they will transition gracefully and avoid the shock of an abrupt change.

3. Get a Realistic Valuation & Understand Value Drivers (5-Year out)

Don’t estimate the value. Hire a licensed appraiser to:

• Determine your business’s current worth that can be defended
• Identify levers that create value (e.g., recurring revenue, margin stability, systems)
• Show what detracts from value (e.g., owner dependence, risk, lack of diversification)
• Modelling different sales structures, tax strategies, and outcomes

This insight is critical in setting expectations and negotiating effectively. Without it, you risk walking away from real value.

4. Structure the Deal to Align with Your Goals

With clarity about your goals and value, tailor the deal structure to your needs:

• Full sale versus partial sale (keeping some ownership or control)
• Upfront cash versus earn-outs or seller financing
• Retention or advisory roles post-exit
• Tax-efficient structuring (e.g., asset sale vs. stock sale, S‑Corp vs. C‑Corp implications)
• Transition support and knowledge transfer agreements

A structure aligned with your holistic goals—not just headline multiples—is key to long-term satisfaction.

5. Create Post‑Exit Support & Accountability

Don’t disappear once the deal closes. Create a post-exit personal plan to envision life after the exit. Consider new hobbies, passions, and activities to fill the void that your business once filled.

• Consider a multi-year phased exit where you stay in an advisory role to help ease the emotional transition.
• Maintain close relationships with financial, tax, and wealth advisors to monitor your budget and lifestyle requirements.
• Join peer groups or networks of exited business owners
• Engage in philanthropic, mentoring, consulting, or passion projects
• Communicate and plan with your family or personal support circle

Having a plan and network to support your next chapter dramatically reduces regret and uncertainty.

It’s Not Just a Sale, It’s Your Life

The EPI research and related studies tell a sobering truth: successfully selling your business is insufficient. You must also architect your life after the sale. For 75% of owners to feel regret, many exits were rushed, incomplete, or built on assumptions.

Don’t let that be your story.

Start planning early with a professional exit plan. Make emotional and lifestyle planning as important as financial strategy. Surround yourself with advisors who understand that exit planning is about your life, not just your company. Create a structured transition and intentionally design your next chapter before the ink dries.

That’s how you’ll exit your business with confidence and not regret.