On quitting

Modern culture glorifies perseverance and grit. While these qualities have obvious value, too much of anything can be detrimental. We also tend to stigmatize quitting and see it as a failure. However, quitting can sometimes be a wise choice.

As a startup founder, one of the most important skills you learn is knowing when to keep going and when to call it quits. Many startups fail because founders become attached to a particular idea or solution, even when evidence shows it won't succeed. They struggle to adapt and build something users really want because the sunk cost fallacy is hard to overcome.

It gets exponentially harder when founders are faced with a decision to leave or shut down their company entirely. After months or years of hard work and personal investment, making such a terminal decision can feel impossible. But stepping back to consider the opportunity cost and expected value of continuing versus pursuing something new can offer surprising clarity, despite the emotional challenges.

Our minds employ several tricks to prevent us from quitting, even when quitting is the right choice. One is the endowment effect, which causes us to overvalue what we already have compared to what we don't have yet. Another is when our identity becomes too tied to something external, making it hard to let go. Finally, goals are motivating but can also be harmful. They create a binary pass/fail choice and ignore the option of completing something partially.

When facing a difficult decision, think about what's holding you back. Is an unrealistic fear of failure preventing you from taking action that could lead to success more aligned with your values? Knowing when to quit a situation that’s no longer beneficial to you is an important yet overlooked skill. Rather than blindly persisting, it’s better to make an honest assessment and opt out if necessary.


This post was inspired by Annie Duke’s latest book, Quit. Check out my related post on regret minimization.