The Best Quitting Decision I Ever Made - Leadership Minute
When done right, quitting is a skill, not a weakness
I had never felt more stuck in my life.
It was the end of 2005, and I was working at a startup with toxic leadership, which left me feeling trapped and miserable. It was my fourth job in seven years, a job-hopping track record that’s normal now, but was not so enviable at the time and was a red flag for employers.
On a daily basis, I contemplated whether to quit that job. However, because I had a two-year-old child and a second on the way, I was determined to stick it out to add tenure and operational experience to my resume. One day, I poured out my frustration during a regular lunch with a good friend, Al Chase. I told him that I really wasn’t enjoying what I was doing but didn’t want to quit yet another job without having accomplished my goals. I told him, with regret, that the responsible choice was to stay put.
Al heard me out, then said something that changed my life. Unprompted, he looked at me and said: “my friend, I give you permission to leave.” He knew I was better off leaving and gave me the push I could not give myself.
I quit within a few months of that conversation. Almost 20 years later, I interviewed Annie Duke on the Elevate Podcast. Annie is a champion poker player and the bestselling author of Quit, which resonated with me for obvious reasons.
Annie wrote Quit because so many people end up in situations like the one I experienced in 2005. Our society glorifies perseverance and views quitting as failure, regardless of the context, your goals, or the opportunity cost of not quitting. Because of this, I had internalized that it was okay to struggle, as long as you don’t give up.
The past few years have been a real grind, and a lot of people are investing time and energy in things that aren’t working, personally or professionally. I recommend taking a literal page from Annie’s book and changing your point of view on quitting. The truth is, there is good quitting and bad quitting, and knowing the distinction makes all the difference.
Why Quit


