It Took Me Years to Let Go (Issue 996)

In which we are reminded to ask questions that help friends and clients disentangle themselves from their businesses.

“It took me years to step away from the business that financially ruined me.”

A small business owner friend was describing his transition out of his first business, an online retailer in the early days of online retailing.

“What do you mean?”, I asked, feeling a little shocked by his revelation.

“It wasn’t going well. But I kept thinking, ‘If I do this or if I do that, THEN the business will be successful’ …… When I finally stopped, I had inventory. I owed money.  It was a mess.”

“So, you meant, ‘I should have stopped sooner’?”

“Yes, I should have stopped sooner and, after I stopped, it took me years to let it go, finally to make peace with it.”

I wondered and did not ask, “What would have helped you, at the time, to make peace?” That ship, I thought, had sailed.

Sometimes, friends or clients conflate their personal and business identities. Their feelings of worth rise and fall with their business performance. Highs are incredible. Failures trigger deep survival, tunnel vision that obscures relationships and opportunities.

When we sense that, we can share, heartfelt, “I am concerned about you”, and ask, however gently we must, questions like “What would tell you that you could make a change?” or “…that it’s  time to make a change?” and “What would you need in order to step away from this and move to the next?” and “What would help you feel whole…?” and “How could that happen?”

With these and similar questions, we can prompt friends and clients to consider, at least, conditions that might open their doors to peace and steps required to reach them so that they don’t need years afterward to step away.

Nick Miller is President of Clarity Advantage based in Concord, MA. He trains banks and bankers to attract and develop deeper relationships with small businesses. Many more Sales Thoughts like this and a host of other articles and resources at

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