The Upside of Endings

Challenge your perspective, and reframe dead ends as data points.

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Quitting can be incredibly empowering. It’s a reminder that you control the situation and can leave whenever you like. You don’t have to be your own prison guard, keeping yourself locked up in a place that isn’t ever going to work. But that doesn’t mean quitting is easy.

We’re taught that quitting is a sign of weakness, although in many circumstances it’s just the opposite. Sometimes quitting is the bravest alternative. Quitting allows you to start over with a clean slate. And if you take the time to evaluate what happened, quitting can be an invaluable learning experience.

Because even great ideas require a tremendous amount of work to reach a successful outcome, it’s incredibly hard to know when to keep pushing on a problem, hoping for a breakthrough, and when to walk away. We all know that persistence is to be admired, but when does it become foolish to continue working on something that’s never going to fly? Gil Penchina, a serial entrepreneur and venture capitalist, describes the dilemma wonderfully in an interview: “If you throw gasoline on a log, all you get is a wet log. But if you throw gasoline on a small flame, you get an inferno.”

It’s worth evaluating how you spend your time, optimizing for both the short and long term.

That is, it’s important to know whether you’re putting energy into something that has the potential to pay off. This is one of life’s biggest challenges. We often stay in dead-end situations way too long. This occurs when companies commit to a doomed product or project, or when individuals stay with jobs or in relationships that make them miserable, hoping the situation will improve. As Phil Knight, founder of Nike, writes in his recent memoir, Shoe Dog, “Those who urge entrepreneurs to never give up are charlatans.  Sometimes you have to give up. Sometimes knowing when to give up, when to try something else, is genius. Giving up doesn’t mean stopping. Don’t ever stop.”

So, what do you quit?

One place to start is looking at your priorities. Life is a huge buffet of enticing platters of possibilities, but putting too much on your plate just leads to indigestion. Just like a real buffet, in life you can do it all, just not at the same time. In fact, no matter your age, prioritizing is hard work. But as Greg McKeown says, “If you don’t prioritize your life, someone else will.”

The problem is that many of us grow up with a mindset of scarcity and end up in a world of abundance. As a result, when opportunities became more abundant, we gorge ourselves at the buffet, taking on much more than we can chew. One approach is to pick three priorities at any one time, knowing that these will change as your life changes. This concept is not new. In fact, the US Marine Corps and other military services use the Rule of Three as a general principle.

Through years of trial and error, they’ve found that most people can track only three things at once. As a result, the entire military system is designed to reflect this. A squad leader is in charge of three fire team leaders, a platoon leader is in charge of three squad leaders, and each company consists of three platoons. The military experimented with a Rule of Four, and effectiveness dropped precipitously.

In order to pick the things you need to quit, consider whether they are things that you need to do and want to do. I like to imagine a 2×2 grid with need as the horizontal axis and want as the vertical axis, and then organize opportunities into four quadrants.

  • It should be easy to say yes to the things you both need and want to do.
  • It should be easy to say no to the things you neither want nor need to do.
  • You have to say yes to the things you need to do but don’t want to do.
  • The most challenging quadrant includes the things that you want to do but don’t need to do. In some cases the opportunity is so tempting that you may ultimately say yes, even though you are going to have to manufacture time to make it work.

It is important to train yourself to say no when you know deep down that you don’t have the time, no matter how attractive the opportunity. It’s also helpful to consider what percentage of time you spend doing things that you want to do versus those that you don’t want to do, and how much time you spend doing things you have to do versus things you don’t have to do.

If most of your time is spent on things you don’t want to do, then it’s time to reconsider your role. And if you spend most of your time doing things you don’t need to do, perhaps you should reconsider your priorities. The sweet spot is doing the things you both need and want to do. Of course, we often do things we don’t want to do in the short run – like studying for an exam or cleaning the house – because they will lead to long-term benefits. It’s worth evaluating how you spend your time, optimizing for both the short and long term.

Quitting allows you to start over with a clean slate. And if you take the time to evaluate what happened, quitting can be an invaluable learning experience.

In the recent LEAP! podcast episode “The Upside of Endings,” I discuss giving up on commitments with two young alumni from Stanford University, Konstantine Buhler of Meritech Capital Partners and John Melas-Kyriazi of Spark Capital, both of whom have great insights on this powerful topic.

Questions to consider:

  • What is something you have quit in the past that has provided a great relief, and an opportunity to start fresh?
  • Is everything you are doing now worth your effort? Would you be better off removing some things in order to take on something new?
  • How much time do you spend doing things that you neither want nor need to do? Are these things you can quit?

Instead of looking at false starts and dead ends with regret, I suggest that you look at each as a source of “data.” Scientists do this all the time. They know that each experiment may lead to unexpected results. And the unexpected results can and should be a source of great inspiration.


This article includes edited excerpts from the 2019 edition of What I Wish I Knew When I Was 20 by Tina Seelig.

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