Effective at Quitting While Ahead

Last week, as I watched the Champions League final, I was amazed by Toni Kroos' decision to retire at the top of his career. He could literally continue more years and make more money in lesser competitive teams, but he is not. Quitting while ahead is an important yet overlooked skill.

The Theory

In business and life, knowing when to quit is key. Success is usually associated with perseverance, yet there comes a point when continuing can lead to diminishing returns or even failure. Recognizing the right time to step away from a project, job, or career can ensure we preserve our legacies, prevent burnout, and even create new and better opportunities. People like Toni Kroos, Jacinda Ardern, and Jerry Seinfeld exemplify mastering the art of quitting at their peaks while potentially "leaving some things behind".

We need to constantly assess if "the juice is worth the squeeze". Seth Godin's "The Dip" emphasizes that temporary setbacks can be overcome with persistence, but it's essential to distinguish "dips" from "dead ends". To do so, it is important to assess if the current goals (the juice) are worth pursuing given the required resources (the squeeze). If the effort aligns with meaningful goals, persistence is justified. Recognizing a dead end early saves valuable resources to invest in other opportunities.

We are biased towards thinking we just need to "push through." Annie Duke's "Quit" highlights biases that lead to irrational persistence: forgetting we could be placing our efforts into other alternatives (opportunity costs), overestimating past investments (sunk cost fallacy), and a natural emotional attachment to projects. Additionally, adopting a small bet mentality to test alternatives can be game-changing, allowing for experimentation without having to make a huge jump. It is also important to place a bet on existing team members as part of a succession plan that ensures continuity for the team and a strong legacy for yourself.

My personal thoughts

I have been always conflicted by the theories recommending us to have grit (push through obstacles) and actually quit when we don't deem them worth it. In 2018, I faced a rough patch at work and reach out to five mentors for advice on what to do, expecting a pep talk about perseverance. Surprisingly, all five recommended quitting and finding another job. The main reason behind this unanimous recommendation was that I was going to need to put a lot of effort into something that wasn't aligned to my long-term career goal. In hindsight, this was great advice.

How to put this into practice

1. Regularly evaluate your progress and satisfaction with current project(s). Identify if challenges are temporary setbacks (dips) or persistent issues (dead ends). There's many ways to do this, journaling is one of the most popular ones.

2. Reassess goals and milestones. We sometimes divert from our original goals and don't even notice it. We need to track progress recurrently and see if we need to make adjustments.

3. Analyze Costs and Benefits (Is the juice worth the squeeze?). Compare the resources (time, money, energy) invested to the potential benefits received, and if the benefits are still aligned with your goals. If not, consider redirecting efforts.

4. Aim to reduce biases by seeking an unbiased perspective. This person will help you determine opportunity costs, recognize sunk costs, and detach from your emotions.

5. Develop a Quitting Strategy. Plan potential exits and experiment with small bets to test new opportunities. Include a succession plan for a smooth transition and a good legacy.

Realistically, this is challenging, but it happens frequently. The key is not to "push through" no matter what but to constantly evaluate if it's worth doing so. We all need to be evaluating our goals and challenges constantly, just as Toni Kroos did, recognizing that quitting is sometimes the wisest choice.

Quitting while I am ahead,

Jorge Luis Pando

“Knowing when to walk away is wisdom, being able to is courage, walking away with your head held high is dignity” - Ritu Ghatourey

Enjoying this newsletter? Share it with friends and colleagues who would benefit!