The terrifying taboo you should stare down and conquer

You, as a business professional and/or business owner, undoubtedly have business advisors who you work and talk with about a wide variety of topics — taxes, contracts, investment allocations, wealth planning, and so on. These conversations are informative and helpful in guiding your decision-making and other actions. Sometimes, the discussion dives deeply into various areas of your life and family. Your advisors are your go-to resources and support systems.

For all the topics you and your advisor discuss, how many of them cut right to the chase relative to your emotions surrounding the matrix that makes up our lives — that overlap of our family, business, business ownership, and, most importantly, you? When do you talk about how to best take care of yourself as a person, with emotions, aspirations, and needs? Regardless of your or your advisors’ gender, chances are that conversations do not stray into these personal and emotional territories very often. When they do stray, one or the other person often yanks on the leash to bring the stray back to the path. It’s as if we all, advisors, owners, and professionals alike, have this code that we follow about what we do and do not talk about in polite, professional company — sex, politics, religion, and all things emotional.

From my perspective, this attitude needs to change and change quickly. Let’s face it — business ownership is a very lonely road to walk. As owners, we carry a weighty load in terms of pressure, sensitive knowledge, and challenging dynamics that may or may not have an outlet for discussion. We have worries that we keep to ourselves. We are the leader. Showing cracks in the armor is dangerous territory. Talk about emotions or about what’s really going through our minds? Are you kidding?

A few weeks back, I was at a presentation at the Wisconsin Chapter of the Exit Planning Institute, where a panel of private equity fund managers was discussing what advisors should prioritize as topics or ways to help their business-owning clients. What is the “one thing we as advisors can do to prepare companies for an exit?” The normal response to this question surrounds managing the value expectation, largely because owners usually have overly optimistic ideas as to how the market values the business. However, that wasn’t the response.

On this day, the panel — comprised of four different private-equity guys — was unanimous:

  • “Help business owners prepare for their life after owning the business.”
  • “It’s emotional and life-changing for them.”
  • “They aren’t prepared for this, what to do or who to be — who they ‘are.’”
  • “Fear creeps in and many often sabotage their own transaction because of it.”

Amen! Hallelujah! I was both stunned and happy to hear this response from the panel. We aren’t talking about this transformative change in our lives in meaningful or constructive ways. We live in denial — kind of like in the old days where if we didn’t talk about sex, maybe nobody would get pregnant.

The reality is that human lives are being impacted here. It’s not merely a transaction, which is often what gets all the attention. Advisors need to broaden their view and care for their whole client — the person, their family, and their future. To effectively advise a business owner in transitioning their company to its next owner, we must talk and explore the personal and emotional aspects impacting the owner and his or her family.



Several years ago, a survey was done to ask business owners about how happy they were about selling their business 12 months after the sale. Three-quarters of the respondents stated that they “profoundly regretted” selling their business. Seventy-five percent! That’s stunning and heartbreaking, yet definitely avoidable with proper conversations and preparation.

There were two primary reasons driving this level of dissatisfaction. First, many cited that the transaction didn’t meet their expectations in terms of value, structure, etc. Second, and the more profound and prevalent reason cited, was that they had no idea what to do next. These business owners had not dedicated time in the years leading up to their transition and retirement to think, plan, or build a foundation for daily life as a former business owner. For example:

  • What activities outside of your business feed your intellectual curiosity and engagement?
  • Who do you spend time with outside of the business? Who would you like to spend more time with? What would you do together? How will you shift and build your new social web?
  • What activities will fill your day? Where will you hang out? What projects or meaningful causes will you pursue?
  • What steps should you start taking now to ensure that you’ve built the bridge to the above before the “big day”? Have you researched how to get involved in that cause or project? Have you met people already involved?
  • Have you talked with anyone, in earnest, about it? Who can help you move through your fears and anxiety to create your plan? Who can be your champion to hold you accountable and cheer you along?

How many times have you heard someone say, “I’ll never retire. I have no idea what I’d do if I weren’t working!” Maybe you’ve actually said this yourself. That’s emotion and fear popping up, hidden behind those words. That statement conveys deep denial. We’re not talking about the real deal, that fourth taboo topic in polite, professional company — our emotions and our own needs. Let’s change that.

Be a rebel. Find someone you trust and talk about it. You’ll feel better and have much better outcomes.

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