Whether you are a business owner, a professional manager, an advisor, or anyone engaged in an enterprise for an extended time – how do you know when it is time to go?

“Nothing is forever,” the saying goes, and yet sometimes, perhaps even frequently, we stay too long. We watch professional athletes stay past their prime, and we participate in the debate about term limits for our congress. Yet, when it comes to our own engagements, how often do we look inward and debate our own need for term limits?

When I was negotiating my exit from the corporate world years ago, I remember a conversation I had with a friend. My friend asked, “What are you going to do if you don’t get the deal you want?” My answer was, “I guess I will stay one more year.” Her response, “How many more years are you going to say, one more year?” At that moment, I realized it was time for me to go, regardless of the negotiation outcome. And… because I had made my decision to exit, I, of course, handled the negotiation more effectively.

While this topic comes up for most leaders now and then, it typically surfaces in a time of frustration. I wonder if it might serve us to ask ourselves this question as part of our annual strategic planning instead. What if, as part of strategic planning, every business owner or executive answered the following five questions:

  1. What did I give to the business, other than my time, this past year?
  2. What did I get, other than $$, from my engagement in the business?
  3. How do my answers to #1 and #2 compare to previous years?
  4. If my give/get has declined, what do I need to do to change this, and do I have the passion and skillset to do it?
  5. If I didn’t lead or own this business, what would I be doing instead?

If you have asked these questions in the past and have stopped asking them, you may already know that it is time to go.  

Share this story