Knowing When to Quit: Sometimes You Have to Move On

One of my favorite movies is You’ve Got Mail” starring Meg Ryan as a small children’s bookstore shopkeeper & Tom Hanks as her big chain bookstore businessman & nemesis. It’s such a classic movie showing the glory of New York City in all its 4 seasons. It’s also a great story full of great characters.

There is this scene when the character Meg Ryan plays decides she needs to close up her store because she can’t stay in business any longer due to the bruising competition. Her older & wiser friend tells her:

“Closing the store is the brave thing to do. You are daring to imagine that you could have a different life.

Oh I know it doesn’t feel like that. You feel like a big fat failure now. But you are not. You are marching into the great unknown with nothing.”

There is something to this. A brand new start. A blank canvas to paint on. A blank piece of paper to start over.

I’ve had so many conversations with startup founders talking about when to quit and shut down the company. Startups are really really hard & most usually don’t work out. It can be challenging and difficult to know when or whether to do so. To quit. You can’t think straight and usually need an outsider to help you look at the situation coldly. To talk through it.

The reason for this is “sunk costs fallacy”: this is when you continue with the behavior or in an initiative or project as a result of previously invested resources. Source:

Sunk costs are hard to overcome especially when you have spent so much of your own time, money and life into something. This is the same with marriage and long romantic relationships too.

But there comes to a point when things aren’t getting better. Where there is limited or no progress despite your efforts. Or maybe it’s getting worse. Sometimes things just don’t work out for whatever reason. Timing. Business model doesn’t work. Trends moving against you. Or maybe you are just plain tired and exhausted.

Change is hard. But it’s better to go out on your own terms. It’s okay to quit. If you have done your best and given your all, then you should have no regret. If you are a startup founder, make sure you take care of your employees. Be as generous with severance as possible, be a good reference for them and make whatever intros you can. Transition your customers well too. Die with Honor as they say.

Sometimes there are circumstances where it’s better to move on. Take the lessons you learned, treasure the good memories and step bravely into your new future.

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Marvin Liao

Ever curious: Tsundoku, Reader, Aspiring Shokunin, World traveller, Investor & Tech/Media exec interested in almost everything!