Bruce Helmer and Peg Webb are financial advisors at Wealth Enhancement  and co-hosts of “Your Money” on WCCO AM 830 on Sunday mornings. Email Bruce and Peg at yourmoney@wealthenhancement.com. Advisory services offered through Wealth Enhancement Advisory Services, LLC, a registered investment advisor and affiliate of Wealth Enhancement Group®. 

For many successful entrepreneurs, longtime employees with stock options, or heirs to a family business, the biggest financial decision of their life is often not how to grow their wealth, but how to unlock it. 

At Wealth Enhancement, we often work with clients who have spent decades building value in a privately held business or have accumulated significant equity through an employee stock ownership plan (ESOP), incentive stock options or inheritance. For these clients, the decision to sell the business or diversify out of a concentrated equity position is not just financial—it can be highly emotional. And when it’s handled without foresight, it can lead to profound regret. 

The emotional complexity of selling 

Here’s a surprising statistic: 76% of business owners regret selling their business within one year of the sale, according to research by the Exit Planning Institute. That’s not because the sale went poorly. In many cases, it’s because the seller didn’t know what they wanted after the sale. They lacked a plan for what was next in life, or what to do with the money. 

That regret isn’t limited to business owners. It also shows up in long-tenured employees who’ve accumulated large company stock positions and in individuals who inherit ownership in a family enterprise. When you’ve spent years (or generations) identifying with the company you’ve built, worked for, or inherited, the exit can feel like losing part of your identity. 

So how do you avoid that sense of loss? How do you ensure that what could be a once-in-a-lifetime liquidity even leads to opportunity, not uncertainty? 

Begin with the end in mind 

One of the most powerful tools in successful transitions is a concept borrowed from the late Stephen Covey: Begin with the end in mind (One of The 7 Habits of Highly Effective People). 

Start by clarifying your “wealth mission”—a statement of your goals, values, and vision for what you want this money to accomplish. Whether you hope to retire, support a cause, invest in a new venture, or pass wealth down to future generations, this mission can help guide your decisions from a place of purpose, not just numbers. 

Ten keys to a no-regrets exit 

Our colleague Paul Brahim, CFP®, CEPA®, a specialist in advising company leaders and wealthy families on business exit strategies, has identified 10 key strategies to help business owners, employees with equity and inheritors plan for a confident and regret-free transition: 

1. Start early and define your why. Ask yourself: “What’s next?” Whether it’s more time with family or launching a nonprofit, the clarity of that vision will shape every decision that follows.
2. Get the timing right. Don’t wait for perfect market conditions, but don’t rush, either. Review your financials, align with personal goals, and assess buyer interest or vesting schedules.
3. Know your numbers. Understand what a buyer sees in your company. Get professional help to assess your financials and valuation.
4. Get a formal valuation. Use multiple approaches (asset-based, income-based, and market-based) to determine a fair range.
5. Build a strong leadership team. Whether you’re selling or stepping away, continuity matters. Buyers and boards want to see that the business can run without you.
6. Prepare emotionally. Selling or stepping back can be surprisingly difficult. Be honest about the emotional impact and plan for it.
7. Assemble the right advisory team. You’ll likely need a CPA, financial advisor, estate attorney, and possibly a business broker or transaction expert.
8. Communicate clearly. Whether it's employees, family members or co-owners, manage expectations with transparency and empathy.
9. Focus on transferable value. Strengthen operations, reduce owner dependence, protect intellectual property, and increase recurring revenue to boost valuation.
10. Plan for life after the sale. A large liquidity event is not the finish line—it’s the starting point of the next chapter. Work with a financial advisor to map out how to invest, diversify and sustain income for the long run. 

Considerations for equity-rich employees and heirs 

If you’ve built up company stock through an ESOP or options over a long career, now could be the time to plan. Diversification becomes especially critical as retirement nears. Similarly, if you’ve inherited a stake in a family business, it’s essential to clarify ownership rights, valuation and long-term governance with your advisors. 

In both cases, too much of your financial future may be riding on one company. It’s wise to consider tax-smart strategies to gradually diversify your holdings. 

Life transitions require reflection, and sometimes advice 

Exiting a business or unwinding from a concentrated equity position is not a simple transaction. It’s a life transition. The difference between regret and confidence often comes down to planning early, asking the right questions, and surrounding yourself with the right people. 

So if you’re thinking about making a move—whether it’s selling the company, exercising options, or passing ownership to the next generation—recognize that you don’t need to go it alone. There are professionals who do this work each day and who can bring great insight and experience to the process. 

Read the full article here.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. 

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