Quit summary

Stewart Butterfield’s big goal was to create a successful online computer game. What he ended up building was an enormously profitable communications tool. But he was only able to do this because he had the wisdom to quit. 

Butterfield’s company, Tiny Speck, was armed with millions in investment capital. It had created a game called “Glitch” that attracted rave reviews and a small but passionate fan base. 

Imagine you’re offered a ticket to an outdoor concert, but the weather is going to be terrible. Even if you love the band, a free ticket probably won’t be enough to entice you to suffer through it. But what if you’ve already bought the ticket? You’ll be tempted to go so you don’t waste the money. 

Of course, it shouldn’t matter if the ticket was free or cost money. You’ll be miserable either way. But still, you think of the two situations differently.

Sears was a colossal retail powerhouse. It built an extremely successful mail order business in the 1800s, delivering goods to rural residents. Later, with the rise of retail stores, Sears continued building its empire by switching to that model. But with stiffer competition and a changing market, Sears began a long, inexorable decline. 

The company had a potential way out. Along with retail, it had built up a lucrative financial services branch, which included Allstate Insurance, Discover Card, and Coldwell Banker real estate brokers. But it didn’t choose that path. Instead of shifting out of a losing market, Sears sold these successful businesses to finance its retail operation and keep the core of its identity. You can probably guess how this all ended: bankruptcy. 

We’ve talked a lot about how hard it is to quit when we should. Research has shown it’s almost impossible to avoid these mental hangups. But we haven’t discussed the incredible juggling monkey yet. Wait . . . what?! Let’s explain.

Eric “Astro” Teller, an entrepreneur and academic who helped lead Alphabet’s X branch, is a quitting specialist. His company focuses on big ideas – ones that can change the world – and clearly doesn’t waste much time on creative company names. Because they invest so much money, they have to be willing to ditch ideas that aren’t working and use that money on better ones. If they can’t bring an idea to market and make it profitable in five to ten years, they aren’t interested. 

Believe it or not, more than one marathon runner has broken a bone and finished the race – in excruciating pain – anyway. 

Goals can be incredibly helpful in motivating us to accomplish difficult things. But they also come with a big downside – they can blind us to circumstances, make us inflexible, and actually keep us in negative situations. Like worsening an injury by running with a broken bone.