Why Quitters Always Win


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It’s a common misconception that quitting is easy.

In fact, quitting can be quite difficult due to how we view our investment of time. The more we put into something, the less likely we are to quit. Because if we quit then we feel as though those resources have been wasted.

It’s why people keep playing the lottery week after week, despite the fact that you’re more likely to be struck by lightning twice than win! Quitting comes with the constant paranoia that once you stop playing your numbers will come up. Isn’t that the worst feeling ever?

All that said — not only am I telling you it’s OK to quit, I’m also going to give you some tips on how to do it right:

Stop before you even start – I know it’s a crazy suggestion, but if something’s not going to work, there’s no point forcing it. The online shoe company Zappos famously offers new employees $2000 to quit. They believe this system works because it’s an incentive for those who might be having doubts to leave. Zappos believes that, after training, if an employee isn’t excited to work for the company it’s cheaper in the long run to cut them loose right away.

Likewise if you’re having doubts or you feel unsure about a new project, sometimes it’s best to avoid it altogether, before you even start to worry about ‘sunk costs’.

Stop while you’re ahead – It’s obvious to stop when something’s not worth it anymore, but knowing when that happens is the hard part. Do you know a couple that hates being together? Do you find yourself wondering why they stay in that doomed relationship? It’s difficult to let go of something when you focus on the past. People think, ‘we used to be so good together, why can’t we go back to that?’

Unfortunately what’s past is past. When considering whether to quit something — you need to focus primarily on the present and the future. Whether it’s a new business venture or an ill-fitting organizational system — sometimes it’s time to cut the cord. Don’t view the loss of time and money as being wasted on failure. But instead as well spent on a good learning opportunity.

It’s never too late! – Do you know someone who has worked the same job for decades, and then one day upped and quit? You might have thought they were crazy. However the reality is, we can enjoy something for years, and then we can just stop enjoying it and we become stagnant.

It’s okay to change things up every once in a while. If you find yourself desiring something new, be it a new job or a new city, go for it. If we don’t change we can’t move forward. I say this as someone who has huge trouble with change — but I’m pushing myself to be better with it.

When you haven’t got around to it yet – Is there an item on the bottom of your list that’s been there for months or years even? Give yourself permission to cross it off. We all know you never would have done it, and that’s okay. For example the book, Things to Bring, Sh#t to Do is a memoir written entirely in lists. The author Karen Rizzo had ‘learn Italian’ on her list for year before she finally let it go!

Still not sure if you should quit something? Here are some examples of famous quitters:

  • Oprah Winfrey – Oprah quit her job as a newscaster to go into acting.
  • Vera Wang – Wang was a figure skater before she gave it up to work in the fashion industry.
  • Mark Cuban – The billionaire owner of Dallas Mavericks, Mark quit several jobs in his twenties before he decided to start his own business.

So why do quitters win? When you give up and let go of all that nonsense, you’ll find you have more time. That’s free time (and possibly money) that can be spent doing the things that actually matter. You might find that these past projects were clouding your judgement or making you feel depressed. Quitting takes all that weight off your shoulders, giving you more time to daydream or observe the things around you. As well as renewing your energy for meeting new people and trying new experiences.

What do you need to quit to move forward?

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