Quit: The Power of Knowing When to Walk Away

Ron Conway is one of the greatest angel investors of all time, yet only 10% of his investments succeed. When he detects that a founder needs to pull the plug, he asks where they will be a few months down the road. He then revisits the matter in a few months and asks if the agreed-upon benchmarks have been reached. He may have to do this again before he convinces the founder to quit.
Many founders keep going when they shouldn’t because they do not want to hurt the feelings of their workers. In reality, they will suffer less if the boss quits sooner as they can move on to something that might succeed. Everyone should have a quitting coach. This is someone who sees the project from the outside and has permission to tell the boss what he or she doesn’t want to hear. Note that being optimistic will only make you stick with something longer. You need something to temper your optimism. Try to have different people evaluate a continue decision from those who made the start decision.

Here, we encounter the exploit/explore dichotomy. While it’s important to exploit good things we discover, we also need to devote some fraction of our time exploring for new things with expected positive values. You never know when a good thing you are exploiting will no longer be available. Never stop exploring.

When Annie was nearing the end of her graduate work, she faced a stomach illness that forced her to step away. When her brother asked if she wanted to attend a poker tournament where he was competing, she jumped at the chance. It wasn’t long before she, too, was a professional poker player. She loved how she could choose the times and places where she played along with making good money and being able to choose when to quit for the day.
You never know when change will be thrust upon you so you should always be exploring other options. Think of it as diversifying your work portfolio like you would diversify your financial portfolio. The analogy here comes from the behavior of ants who have a pretty amazing survival record. While most ants fall in line to harvest food from a known source, some ants explore for new sources as it’s just a matter of time until the known source dries up.

There are many stories of marathoners who break a leg or a foot and still finish the race. Most goals have a finish line, which turns them into pass-fail situations. If we set kill criteria at the same time we set a goal and evaluate our progress from time to time, we can avoid pursuing goals that are no longer worth our efforts. Grit isn’t always a virtue. It’s good for getting you to stick to worthwhile goals. It’s also good at getting you to stick to things that are no longer worthwhile.
Fear of falling short also makes us not want to start. Once we start a goal with a finish line, we are in a losing situation until we finish and often fail to see progress as a good thing. As you pursue a goal, be sure to look for accomplishments along the way. Goals can make us myopic to other opportunities. We fail to quit as we see that quitting would waste money, time, and effort already spent (sunk cost). If you quit something that is no longer worthwhile, that is a success. Therefore, we need to redefine failure and waste. A successful path is going to involve a lot of quitting as, contrary to popular opinion, winners quit a lot.

Amy won over $4 million as a professional poker player. She left the game in 2012. She is now a corporate speaker and consultant in the decision-making space. She is co-founder of The Alliance for Decision Education and author of the best-selling books Thinking in Bets and How to Decide. Her website is annieduke.com where you can also contact her. Follow her on Twitter (X) @AnnieDuke

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