When you quit on time, it feels like you're quitting early

Annie Duke in her recent book 'QUIT: The Power of Knowing When to Walk Away' shares the story of Stewart Butterfield.

Stewart was the co-founder of a growing startup that was doing very well when he made a perplexing decision. He quit. His calculations suggested that the startup wouldn't be a venture-scale company. As such, he felt morally obligated not to waste any further resources on it.

Here's a coda to the story with an important lesson. It is important to quit not only because the path you are pursuing isn't worthwhile anymore, but also because you are less likely to put your time, money, and intention in exploring other opportunities due to myopic path dependency. (Please read the last sentence again. Slowly. I agree that it is dense. I am not supremely proud of its construction, but it has a critical lesson).

As Stewart was freed up to look for his next opportunity, he realised that it was right under his nose all this time. (see the dense sentence above again for myopia). His company had developed a software for its own internal communication. They had called it “Searchable Log of All Conversations and Knowledge.” Today it’s known as Slack, which Salesforce bought for $27.7 billion.

Here's the cautionary tale though. The wrong lesson to draw from the story would be that quitting leads to success. (It doesn't). Just as dropping out of college to startup doesn't make you a billionaire (Gates, Zuck, et al).

The right lesson is to know what is 'hard but worthwhile' vs 'hard but not worthwhile.' The key skill is to discern the difference between the two. The success comes from showing grit for the former and quitting the latter.

Building the skill to know what to quit or when to quit is a hard one. It goes against our natural instincts and behaviour. That's why, as Annie says in the book, 'when you quit on time, it feels like you're quitting early.' When we are on a path, we tie our identity to it. We suffer from sunk cost fallacy as we believe we've invested too much into it and it would be foolish to move away. It potentially prevents us from having a bigger outcome in life.

I highly recommend the book. If you are like me, get it as an audiobook. Great companion while walking.