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Did you know that 50% of businesses are sold under duress? These sales often stem from the "5Ds": distress, divorce, disagreement, disability, or death. When unplanned, these situations can lead to selling at a deep discount, stripping businesses of their true value. In this blog post, we unpack why exit planning is crucial—not just for financial optimization but also for emotional well-being—through the lens of Nate Collins, a Certified Exit Planning Adviser and former CEO who successfully navigated a mid-8 figure business exit.

The 5Ds Trap: Duress, Discounts, and Regrets

When it comes to Exit Planning, there’s a harsh reality that too many business owners discover too late: about half of all business sales happen under duress. These are not the well-orchestrated, strategic exits we all hope for. Instead, they are forced by what I call the “5Ds”—distress, divorce, disagreement, disability, or death. These five factors are the leading causes of rushed business transitions, and they almost always result in a business sale at a deep discount.

The 5Ds: The Unwelcome Triggers of a Business Sale

• Distress: Financial hardship or operational crises can force a sale when the business is at its weakest.
• Divorce: Personal relationships unravel, and suddenly, the business becomes a bargaining chip or casualty.
• Disagreement: Partner disputes can escalate quickly, leading to a forced exit for one or more parties.
• Disability: A sudden illness or accident can leave an owner unable to continue, with no plan in place.
• Death: The most final of the 5Ds, leaving families and partners scrambling to figure out next steps.

These events rarely give owners the luxury of time. Instead, they create a sense of urgency that puts sellers at a disadvantage. The result is often a rushed, sub-optimal deal that leaves significant value on the table.

Discounts: The Hidden Cost of Selling Under Pressure

One of the most painful lessons I’ve witnessed in Exit Strategy is how much value is lost in a forced sale. When a business owner is caught off guard by one of the 5Ds, the sale is typically rushed. Buyers know this. They sense the urgency and negotiate hard, often resulting in a sale price that is 20-50% below the business’s true value.

“Typically 50% of businesses are sold under duress, right? Because of distress, divorce, disagreement, disability, or death. What we call the 5Ds. When that happens, you end up selling typically at a deep discount to what the true value is.”

Imagine building a business for decades, only to be forced to sell it for half of what it’s worth because you didn’t have a plan. It’s a scenario that plays out far too often. In fact, studies show that only 20-30% of small businesses that go to market actually sell, and a big reason is inadequate exit planning. Even among those that do sell, many owners walk away with less than they expected—or needed.

Regrets: The Emotional Toll of a Rushed Business Transition

Beyond the financial hit, there’s an emotional cost to selling under the gun. I’ve seen it firsthand. A close friend of mine, after years of building a successful company, found himself in a sudden partner dispute. The disagreement escalated quickly, and with no exit plan in place, he was forced to sell his share of the business almost overnight. The sale price was far below what he’d hoped for, and the process left him with more questions than answers. He told me later, “I wish I’d been ready. I wish I’d had a plan.”

This kind of regret is common. According to research, as many as 74% of business owners don’t have an exit strategy. That means most are unprepared for the unexpected, and when the 5Ds strike, they’re left scrambling. The result is not just a financial loss, but a sense of unfinished business and missed opportunity.

Why Proactive Exit Planning Matters

The numbers are clear:

• 50% of business sales are triggered by the 5Ds.
• Business value loss from a rushed exit: often 20-50% below true value.
• 74% of owners lack a formal Exit Strategy.
• Only 20-30% of small businesses that are listed actually sell.

Without proactive Exit Planning, business owners are at the mercy of events beyond their control. The 5Ds can strike at any time, and when they do, the lack of preparation almost always leads to discounted sales and lasting regrets. The lesson is simple: don’t wait for a crisis to force your hand. Start planning your Business Transition now, before the 5Ds come calling.

Beyond the Bank Account: The Emotional Aftershocks of a Business Exit

When most people think about selling a business, the focus is almost always on the numbers. Financial freedom, a big payday, and the chance to finally relax—these are the dreams that drive many business owners to the exit planning table. But the reality of life after business is rarely as simple as a bank balance. In fact, the emotional impact of a business exit is often far more significant than the financial outcome.

Financial Freedom Isn’t the Whole Story

For years, I believed that selling my company would be the ultimate achievement. I pictured myself with unlimited time, money, and the freedom to do whatever I wanted. But the truth is, financial freedom does not guarantee personal fulfillment. The initial excitement quickly faded, and I found myself feeling more lost than liberated. I wasn’t alone in this experience.

Why 75% of Business Owners Regret Selling

According to Forbes, a staggering 75% of business owners regret selling their business within just 12 months. This statistic is not just about missing out on a better deal or wishing for a higher sale price. In most cases, the regret comes from something deeper: a lack of preparation for life after business. The emotional impact of leaving behind a company you built is often underestimated in exit planning.

“You’d think they regret the transaction because they didn’t make enough on the sale. Maybe, but typically it’s because they haven’t prepared for life after exit.”

The ‘Liinal Period’: An Emotional No-Man’s Land

There’s a term for what many business owners experience after selling: the liinal period. This is a confusing, identity-shaking phase that can feel a lot like career postpartum depression. A South African study that followed CEOs after their exits found that most went through a period marked by:

• Uncertainty and loss of direction
• Depression and anxiety
• Regret and identity crisis
• Strained relationships and disrupted sleep

During this liinal period, everything that once provided structure—community, purpose, daily routine—is suddenly gone. Handing over your business doesn’t just mean a change in financial status; it often means losing the very things that defined who you are.

Personal Perspective: The Unexpected Toll

I’ve lived through this myself. After selling my business, I expected paradise: more time for family, travel, and relaxation. Instead, I found myself struggling with anxiety and a deep sense of emptiness. My relationships suffered. I lost sleep for years. The loss of structure and purpose left me more anxious than excited. I realized that, like many others, I had tied my identity and self-worth to my role as a business owner.

“I thought my goal was financial freedom. I thought, ‘Wow, this will be great. I’ll be able to afford anything I want. I will have time to sit on the beach.’ But I also found out that financial freedom does not lead to personal fulfillment. In fact, if anything, I felt more empty, worthless at times because I wasn’t needed. I didn’t have a purpose.”

It’s Not Just About the Money

One of the most important insights from research and real-life stories is that business owner regrets are rarely about the money. Even entrepreneurs who sell for tens or hundreds of millions of dollars often experience the same emotional aftershocks. The loss of routine, community, and a sense of being needed can be overwhelming. The emotional impact can last for years, affecting family life, health, and overall well-being.

Preparing for Life After Business: The Missing Piece in Exit Planning

Most exit planning focuses on maximizing value and negotiating the best deal. But preparing for the emotional transition is just as critical. The personal fallout of a business exit can be severe if you haven’t thought about what comes next. The data is clear: 75% of business owners regret selling within the first year, not because of the money, but because they weren’t ready for the emotional shift.

Understanding the emotional impact of selling a business—and planning for life after business—is essential. Without this preparation, the aftershocks can be stronger and longer-lasting than anyone expects.

Exit Planning Is Wellness Planning: Rebuilding Purpose and Health After the Sale

When I first sold my business, I thought I had everything figured out. I had a good job at a hedge fund, plenty to do, and a healthy bank account. But something was missing. I didn’t feel fulfilled, and I couldn’t quite put my finger on why. During this period, I had lunch with my old Vistage coach—a truly wonderful human being who could see I was struggling. He told me, “You’re missing personal well-being.” He explained that the secret recipe to personal well-being comes down to three things: purpose, community, and health. At the time, I didn’t realize how much these three pillars would shape my journey after the sale.

It’s easy to assume that once the deal is done and the money is in the bank, happiness and success will follow. But for many business owners, the reality is more complex. The transition out of your business is not just a financial transaction; it’s a personal transformation. This is where the role of a Certified Exit Planning Advisor becomes so valuable. These professionals do more than manage the logistics of your exit—they help you plan for your life beyond the boardroom, focusing on your overall well-being and personal fulfillment.

My Vistage coach’s advice stuck with me. I spent months reflecting on how to rebuild my sense of purpose, reconnect with my community, and prioritize my health. I set three goals: first, to share my experiences with others, which gave me a renewed sense of purpose. Second, to be a role model for my children—my immediate community. And third, to find a career that aligned with these values. That’s how I became a financial adviser, working with other entrepreneurs and executives to help them navigate their own transitions and find personal well-being after the sale.

One story that stands out is a client who, after selling his company, tried his hand at trading stocks. Despite the financial rewards, he felt restless and disconnected. It wasn’t until he started leading local business workshops that he found real joy again. By sharing his knowledge and mentoring others, he rediscovered his purpose and built new connections in his community. His health improved, too—he was less stressed and more energized. This experience reinforced what I had learned: post-exit success is about more than money; it’s about meaning, connection, and growth outside of the boardroom.

Research backs this up. A Dutch study found a direct correlation between entrepreneur well-being and business success. In fact, the well-being of the business owner had a stronger impact on the success of the company than the other way around. This means that investing in your personal well-being isn’t just good for you—it’s good for your business, your relationships, and your future endeavors. Networks like the Vistage CEO Network and educational webinars provide not just peer support and advice, but also a sense of belonging and shared experience. These resources are invaluable as you navigate the emotional and practical challenges of exit planning.

As you consider your own exit—whether it’s on the horizon or just a distant thought—remember that exit planning is wellness planning. It’s about creating a post-exit plan that includes sharing your story, reconnecting with family or your community, and setting new goals that stretch you beyond your previous role. The most successful transitions I’ve seen are those where business owners embrace growth in all areas of life, not just financially. Advisory teams and Certified Exit Planning Advisors can help bridge the gap between strategy and well-being, ensuring that you don’t just survive the transition, but thrive in your new chapter.

In the end, the real measure of success after selling your business isn’t the size of your bank account, but the depth of your purpose, the strength of your community, and the quality of your health. Building a support network and focusing on your well-being are as strategic as any financial move you’ll make. If you’re planning your exit, or even just thinking about it, start with your personal fulfillment. Because beyond the sale, that’s what truly matters.

TL;DR: Most business exit guides talk numbers, but the real story is what happens to your sense of self, community, and purpose after you sell. Plan for the next chapter—not just the sale.