Quitting Small

Sara Eshelman
Spero Ventures
Published in
3 min readJan 4, 2023

One of my all-time favorite Freakonomics episodes is called The Upside of Quitting. Steven Levitt and Stephen Dubner extol the benefits of quitting across industries, but their discussion of minor league baseball players — who have just an 11% chance of making it to the majors — has always stuck with me. They interview Sudhir Venkatesh (of Chicago gang economics fame) who evaluated the 10-year economic outcomes of the 2001 Draft Class against their peers who didn’t play baseball. The key finding is that quitting baseball to become a stockbroker or whatever is a superior strategy for most players, resulting in ~40% higher average earnings.

Annie Duke recently published Quit, which explores a new crop of examples. She talks about mountain climbers who pre-commit to quitting if they haven’t summitted after a certain time mark. Those who quit survive at higher rates than those who persevere. Startup founders who quit (or in sexier startup lingo, fail fast) when they can no longer create value for their shareholders and themselves ultimately fare better. Poker players like herself who fold if their hand is bad and competitors formidable win more money than those who continue to play. And better players fold more (up to a certain point).

Quitting baseball is one end of the spectrum — a BIG quit. Folding a poker hand is the other — a small quit. A poker player may fold a dozen times in a night. Each hand, the player assesses her odds and chooses to play or fold. It’s so small that it’s hard to even call it quitting. But some of the most powerful “quits” are small decisions that researchers would never even think to assess. Things like emails that go unresponded to, customers no longer pursued, tasks delegated, recurring meetings deleted, books or movies abandoned, or hobbies left behind.

Why don’t we quit more?

  1. Researchers are clear that we’re systematically terrible at quitting — big or small. Our reptile brains are hung up on sunk costs and overestimated probabilities of future success. It usually takes an outside impetus or sober observer with good data to see our situations clearly.
  2. Small quits’ value is often in time savings or stress reduction, not cost savings. Dollars not spent are a clean, measurable outcome, whereas time savings and stress avoidance are harder to evaluate honestly, especially when it’s our own time.

So what can we do to overcome these obstacles to more effectively quit small when the benefits no longer outweigh the costs (especially the opportunity cost of time):

  1. Create forcing functions. For example, design time commitments that expire after a year and have to be recommitted to; set up quarterly or annual reviews of your calendar and extra-curricular priorities to cull what’s no longer beneficial.
  2. Pre-commit to quitting if certain conditions are met (Duke calls these ‘kill criteria’). Like mountain climbers, pre-committing doesn’t necessarily mean you’ll actually quit, but it forces you to stop and re-assess conditions, asking questions like: did I get what I hoped to get from that? Did the ROI match my predictions? And if not, how far off was I and what will I do differently next time?
  3. Train yourself to update your assumptions constantly, similar to how you would a poker hand when a card is overturned. Notice what you spend time doing and thinking about every day and night. Do YOU really have to do this? Does it even need to get done at all?

At the beginning of a calendar year, we’re trained to think about new priorities we should take on. But choosing what not to do is as important as choosing what to do, and several small quits can be as important as one big quit.

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Sara Eshelman
Spero Ventures

Partner at Spero Ventures — venture capital for the things that make life worth living.