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

Be honest with yourself about what you care about and what, deep down, you don’t. And rather than viewing quitting as an act of abandonment, consider it a way to reallocate your time and energy away from things that don’t matter and toward things that do. You can’t be gritty about what you care about most if you don’t have any energy left.

Early in our adult lives, we’re urged to try everything—to say yes to every opportunity, meet every new person, and take on a little more than is comfortable to build relationships and credibility. But demands on your time and energy grow steadily as you age, especially if you become a leader; every choice you make to invest those resources shuts off the possibility of doing something else that might serve you better.

This opportunity cost calculation is crucial. If you’re considering giving up on something but are afraid of being “a quitter,” figure out if there is a concrete way that the time, effort or money you’re investing in that thing can be better spent. If you reframe quitting as an opportunity to better use your time, it relieves your psychic burden and gives you the permission you need to move on.

Deciding To Quit

Of course, sometimes we struggle to evaluate whether we really care about something in the heat of the moment. Humans are prideful and stubborn, and people can often convince themselves that they want to stick with something when, deep down, they don’t. Knowing this, Annie Duke shares some strategies for forcing a quit decision proactively.