In 2006, San Antonio Spurs coach Greg Popovich went to his boss, owner Peter Holt, and asked to be fired.

As the story goes, Pop said to Holt, “I don’t think the guys are listening to me anymore. Maybe it is time for you to find yourself a new coach.”

It’s a good thing Holt refused to accept Pop’s resignation. A few months later the Spurs were World Champions.

Saturday night I checked one off of my bucket list by attending an NBA playoff game in the league’s loudest arena in Oklahoma City. Game 6 of the Western Conference Finals did not disappoint, and let’s just say the Spurs are still listening to their coach. They beat the Thunder in overtime and now move on to face the Miami Heat for a shot at a fifth NBA Title since 1999.


For Popovich, it clearly wasn’t time to go back in 2006. But the question remains for every leader; “How do I know when it is time to leave?”

Let me start by saying I have been thinking about this question for the past few months. In fact, Friday was my last day in a job I have been working for the past 18 years. I decided it was time to leave.

The following layers helped convince me to make the change. They should prove to serve you if you are ever contemplating a departure.

1. Am I being challenged by my work? To be honest, after 18 years the biggest challenge in my work was feeling challenged by my work. Increasingly, I felt the pain of routine and the numbing reality that it often stifles creativity. This is something every leader experiences at some point. It is no one else’s fault; but stay somewhere long enough, and you will eventually know all the answers to the test – whatever your test is. When that day happens you will be required to decide whether you want to make A’s or whether you want to stretch yourself with a harder class.

Great leaders continually reinvent themselves. The best ones never settle for easy. Answering the, “Do I feel challenged by my work,” question is a great way to know whether or not it is time to leave.

2. Am I being courageous? While this one is closely related to the challenge question, it goes much deeper. Challenge is based on your circumstances and tasks, while courage goes to your heart. A leader must choose … Comfort or Courage. The longer I lead, the more I am certain you cannot have both.

As a Bible reader, I can’t find the verse that says, “Be comfortable.” Trust me, I’ve looked for it. But over and over God encourages His people to “Be courageous.” I think He says Be Courageous so many times because He knows our default mode is to chase comfort.

Whether or not you are a person of faith, you need to know that one of the words associated with comfortable is the word unexceptional. They don’t tell stories about unexceptional people. No movies. No indebtedness. No impact. If you want to expand your territory, grow your influence, and experience an exceptional life, it will require courage.

3. Am I being true to who I am? Over the years my role as a leader in my workplace had morphed into several areas that from an energy standpoint were very draining to me. Like the stem of a rose, I needed some pruning. In my case, it was time to cut back the entire bush.

The writing of FINDING YOUR WAY was a big part of my process. I had to face the fact I literally wrote the book on living into your sweet spot, and yet I wasn’t totally living into mine. By definition, that is a lack of integrity. Could I have continued to do what I was doing? Sure, but that would not have been fair to my team, or healthy for me.

If you are trying to decide if you should leave, the first place to start is to pay attention to what brings you life. For me, it is encouraging leaders through my speaking, writing, and coaching. In my old job, a majority of my time was spent on other things. That disconnect made a difficult decision much easier.

The shift in my work has me very excited, and I am certain it was the right decision to make. However, making the move was also hard. Leaving a team of people I love, a meaningful mission I believe in, and work that had become second nature all tempted me to stay. But like leaving would have been a mistake for Pop, staying would have been one for me.

I will tell you more about my new work over the coming weeks. In the mean time, if you need to know if it is time to leave, start with the three questions that continually nudged me. Am I being challenged by my work? Am I being courageous? Am I being true to who I am? If the answer to all three is no, it is probably time to go.

Leadership Begins at Home,


What other questions can help a leader decide when it is time to leave?

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