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Welcome to The Ascend Archives Friday Edition where I share insights from the brightest minds in business and life and how I'm applying them to my life.

Ascend Archives is centered around everyone climbing their own mountains (i.e., pursuing accomplishments) across all aspects of life: career, relationships, and health.

In my welcome email, I talk about the importance of “taking action” and “putting in the work” to climb our mountains. But I never mentioned the importance of choosing the right mountain to climb. Or better yet, knowing when it’s time to climb down the mountain (even if we haven’t reached the top).

In her book, Quit, Annie Duke, a former professional poker player and PhD in Cognitive Psychology, made me realize I needed to add these critical details to my mountain climbing analogy.

Annie shared new perspectives on quitting that I have already started using in my day-to-day decision making. Today I want to share 3 things to keep in mind next time you think:

Should I stick or quit?

3 Quitting Lessons from Annie Duke

1. Success lies in picking the right thing to stick to and quitting the rest

By definition, anybody who has succeeded at something has stuck with it.

They persevered, they had grit, they gave it their all. They never quit. But consider the inverse of that statement…

Anybody who sticks to something will succeed at it.

Life doesn’t work that way. A 60 year-old who practices gymnastics every day for one year is not going to make the Olympics. This is an extreme example, but it reminds us that we will not succeed at everything we try.

Annie encourages us to look at our pursuits through the eyes of a scientist with an experimental lens. Try a lot of things, knowing that most of them won’t work out and when something looks promising, double down on it.

2. Quitting keeps us wondering, so we don’t quit

We all want to know what happens at the end of the story.

The only way to find out is to not quit before the story ends. Even when all the signs are screaming to turn around, to leave, to quit, we as humans don’t like the feeling of wondering what would have happened if we stayed.

People love the phrase “better the devil I know than the one I don’t”. Is that really true? Even when the devil you know is destined for misery, hard aches, or even death?

Annie explains that it’s easy for people to wrap their heads around what they could miss out on in their current situation if they quit. It’s harder for people to assess what they are missing out on by not quitting.

Here’s a simple example:

Have you ever read 25% of a book, realized that you didn’t like it, but ended up finishing the entire book anyways?

Why is that?

Most people tell themselves, “The book will get better” or “I started it so I have to finish it”.

But when we look at it logically none of those answers make sense.

If you are 25% into a book you don’t like, there is a high probability you won’t like the rest of it. So you’re better off putting that book down and picking up a new one. But the new book could suck too, right?

Sure, it could. Or it could be the best book you ever read.

Chances are the current book you don’t like isn’t going to turn into your favorite book ever. But let’s say you select the new one based on a friend’s recommendation and reading the summary, there’s a real chance this one could be great.

Deciding to finish a book is a pretty low stakes, but this same logic can be applied in all areas of life. Even when the stakes are high like whether to stay at your job.

If the same job has sucked for 6 years, why do we stay? Because it’s familiar to us. We can see that a promotion could be right around the corner.

It’s more difficult to see that you could quit right now, find another job that gives you a raise and allows you to work on something you enjoy. Just because it’s more difficult to see, doesn’t mean it’s more difficult to achieve if we go looking for it.

3. Just because you are close to the top, doesn’t mean you are on solid ground

Stories about Mt. Everest are either the heroic climbers that summitted the mountain or the tragic situation that led to death.

What we don’t hear about, but should celebrate, are the climbers that turn around when the conditions are not right and live to fight another day. Annie tells the story of 6 climbers who spent thousands of dollars and months of their lives training to summit Everest. They were only a few hours from the top, but missed the cutoff time at their checkpoint. It was too dangerous to move on. But if the climbers didn’t keep going now, they would have to wait an entire year to try again.

Do they continue or turn around?

In the book, Annie explains the importance of establishing “Kill Criteria” before starting any new pursuit. These criteria let us know when we should quit. Setting them prior to starting a pursuit allows us to stay objective because we all know that objectivity goes out the door when we are “in the moment”.

Every kill criteria must have 2 things:

1. State: objective condition the project is in

2. Date: a specific time

So in our story, the climber’s kill criteria was if they didn’t reach Checkmark X by 1:30 PM they had to turn around.

Only 2 of the climbers stuck to the kill criteria. The others got lost in the moment and continued climbing to the top.

The climbers that turned around had failed to summit Everest after all that sacrifice and returned home without achieving their goal.

The climbers that continued made it to the top and achieved their goal. However, because of the delayed summit, they did not make it back to camp in the dark. They died on the descent.

Who are the winners here? The ones who quit but survived or the ones who persevered to their death. I know which one I’d choose.

Final Thoughts

Quitting shouldn’t have a negative connotation.

“I’m not a quitter” is a very common phrase.

It’s meant to portray strength, determination, and perseverance. All traits of a successful person, accomplishing big things. People with grit are celebrated.

Where’s the context?

If that non-quitter is the founder of a failing startup, in a toxic relationship, or owner of a losing stock, should they still never quit?

Life is one long game. When we zoom out and optimize for the long run, it’s easier to think of quitting a project, an activity, a job, or a relationship as just one of many experiments that didn’t work out. Not thinking of it as a failure.

Much easier said than done.

As someone who quit their 6 figure job last year, I’m eager to build a business that gets me back making the income I’m used to while doing work I enjoy. This week I sent a proposal to a potential client. He countered asking to reduce my fees in half. I was staring at the devil I knew. I had someone willing to pay me $1,000/month to do work that I was sort of interested in. Money that would get me closer to my goals in the short term.

But I turned him down. I stuck to my number and opted for the devil I don’t know. There is someone else out there who will pay me my value for work that I’m fired up to do.

All I need to do is keep experimenting.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew