How to Know When to Quit

We sample new ventures, projects, and types of work to see what we may like, but later, we need to quit most of them. Most of new things won’t end up replacing one of our favorites, and we get worse results in all areas of work and life when we spread ourselves too thin. The trick then is knowing when to quit.

When we’re kids, we’re told by well-meaning adults that we ought to finish what we start. Supposedly, this builds character. Kids aren’t sure what character is, but giving in to a mother or father with stronger will is easier than fighting them, especially when parents can bestow or withhold ice cream.

And once kids become adults themselves, they know not to take what their own kids say too seriously because half the time kids forget what they said they disliked once they’re in the middle of it. After adults force kids to do what laziness, insecurity, or fear of embarrassment would otherwise make them avoid, kids see for themselves that the spelling bee, orange chicken, or Little League baseball season wasn’t so bad.

I was ready to quit Tee Ball after a couple of games, but my parents made me finish the season. That parent-imposed perseverance probably did fill some vacant nook in my character cabinet. Perseverance is useful later in life.

And once we’re grown, perseverance comes with an opportunity cost. The “I’m not a quitter” mindset has driven me to finish things that consumed lots of time, attention, and resources. If I had quit those things sooner, I could have diverted resources elsewhere and seen a higher return of enjoyment, money, or opportunities.

What management expert Peter Drucker said about stupid efficiency also applies to stupid perseverance:

“There's nothing so useless as doing efficiently that which should not be done at all.”

Quitting can be more valuable as gumption. Quitting can be a sign of maturity and wisdom, not of a character defect.

So if no one will give you an award for exploring the last inches of a dead end, how do you recognize dead ends earlier? How do you know when you’ve seen and learned enough to quit?

I will share four ways to know when to quit.

Quit when you don’t enjoy it.

The first way to know when to quit is to assess your own enjoyment, with one important caveat called the law. I don’t enjoy filing my taxes, but I keep doing it because I don’t want to go to jail. A whole category of required but unpleasant obligations exists. Here I’m not referring to that category but to a second bucket of unnecessary and unpleasant things that we can quit at any time.

Why we don’t empty that second bucket more often is complicated, and it’s worth taking a few moments to examine the reasons.

Being a good friend, partner, parent, citizen, and member of a faith community means that we accumulate commitments. We voluntarily tangle ourselves in many strings of roles, meetings, favors, social norms, peer pressures, and other time sucks that seem like a good idea at the time.

One such idea I had was to serve on a nonprofit board. The executive director was a friend, and I believed in the Christian ministry that she led. So far, so good. As the months passed, I came to dread the meetings. Sweet, well-intentioned people discussed the same issues ad nauseam, and each time we reconvened, nothing had happened. For someone with my bias toward action, the meetings were drowning in honey.

As funny as it sounds, my wife had to remind me that I could resign, and when I told my friend that’s what I wanted to do, she was confused and said, “It’s only one meeting a month.” True, and my willingness to have the awkward conversation and snip the string of that small obligation produced an outsized amount of joy and relief.

If you want more simplicity and joy in your life, be willing to quit more commitments that you’ve come to resent or dislike, for whatever reason—even if quitting requires an awkward conversations.

Quitting what you dislike automatically makes more room for what you do like. Duh.

Quit when it hurts your health.

The second way to know when to quit is to be honest about your health by asking questions with that framing:

• Does this hurt my relationships or body?
• Does this make me feel heavy, gray, and pessimistic?
• Does this make it harder to enjoy the simple, good things I already have?

I’m not suggesting that we oversimplify health in its various dimensions, including physical, mental, sexual, emotional, relational, social, financial, and spiritual. I’m also not suggesting that we ignore the reality of chemical imbalances, disease, substance abuse, and addiction or pretend that it’s easy to quit things that harm us.

Rather, I’m suggesting that “health,” despite being a broad and multi-faceted concept, provides a simple, intuitive measuring stick for our less complicated attachments and choices:

• Does this make me healthier?
• Is this additive or subtractive?
• Does it get me more than it costs me?

The Apple News app wasn’t reliably giving me the news, but it did reliably make me feel lousy. When I recognized that fact, I couldn’t help but think of Dr. Phil’s question: “How’s that working for you?” Um, not well. That app hurts my health.

On the other hand, regular exercise makes my life less comfortable while also making me feel better, not worse. The same goes for being a part of my church when I’d rather sleep in on Sundays and saving money when we could have spent it. I don’t always enjoy frugality, but it contributes to my health.

On balance, we need more difficult things that add to our health and fewer easy things that subtract from it.

A simple exercise will help you decide what is additive and subtractive:

1. Take inventory. Write down every obligation and commitment, running meeting and regular appointment. List every role, responsibility, and demand on your time and attention. List every habit without judging it good or bad just yet.
2. Ask, “Does this add to health? If I were to keep doing it for months and years, will it enhance my ability to get and keep what I want most?”
3. If the answer is no, then ask, “Am I okay with that?”
4. If the answer is no, then ask, “What is my new commitment?”

Health as a metric or magnifying glass may reveal you that you are too quick and free with your yeses and have a near-pathological tendency to refill your calendar as soon as you’ve cleared it. No may need to be your default answer for six months.

You may see that your current habits will keep producing your current results, and that you can’t reasonably expect different results until you form new ones. James Clear’s Atomic Habits is a bestseller for a reason.

You may see that you need better rules, such as no alcohol on weeknights, no iPhones in the bedroom, and no inbox before 11:00am.

Though I can’t tell you exactly what or how to quit, I can tell you when to quit. Quit when there’s no denying that whatever it is costs you more than it gains you.

You’ll be more satisfied with your life if you replace old, automatic commitments with new ones that improve one or more dimension of your health. The inverse is also true—if you don’t quit the things that hurt your health, you’ll be less satisfied with your life.

You will know it’s time to quit when you tell yourself you can’t. Fear hides open doors.

Quit when you want it less.

The third way to know when to quit is to get clear on what you want more, and you gain clarity by exposing the tradeoffs you’ve been making.

I’ll share an example from my marriage. For years my wife and I didn’t keep a budget or categorize our monthly expenses. All of our spending was rolled into one multicolored ball of Play-Dough, and without any real visibility into where the money was going, all we could say at the end of the month was “Geez, we need to get our spending under control!”

That realization didn’t do much except start arguments, and we didn’t experience meaningful change (and fewer fights) until we started categorizing certain transactions as utilities, entertainment, or dining out.

Categorizing expenses showed us where our money was going, and then the cause-and-effect connections and tradeoffs became painfully obvious. We dined out more often than we could afford because we didn’t make a meal plan and go grocery shopping. If we kept spending money on burritos and sushi, then our credit card balance would keep growing. If we racked up more debt, then we wouldn’t be buying a house anytime soon.

What I learned is that it’s much easier to make a meal plan and cook a cheap spaghetti dinner at home when I can say between bites, “I want to buy a house.”

Discipline is easier when you make the tradeoffs as obvious and jarring as potholes.

Discipline is easier if you clarify what you want more—house more than burrito, exercise-fueled health more than a self-indulgent diet, good sleep more than whiskey, wholesome simplicity more than chaotic excitement.

Discipline can be intermittent too. Sometimes the tradeoff is worth it. When I ate at Uchi in Austin, Texas, I spent too much on Bluefin Chutoro, Tasmanian Ocean Trout, and Hama Chili. My aim isn’t perfect performance but conscious compromise.

Quit when that allows you to produce more.

The fourth way to know when to quit is to take an honest look at how you’re spending your time and make the changes required to spend more time on what you care about most.

We collect claims on our time and attention because we aren’t clear on what we want and because we mistakenly believe that more irons in the fire equals more lottery tickets. You just never know, right?

Paul Graham’s advice in “How to Do What You Love” strikes me as the better bet: “Always produce.”

Instead of trying to find success or fulfillment through a mishmash of commitments, zero in on the thing you think you want and produce more in that area.

Is the thing being a novelist? Write one thousand words a day. Being a musician? Write two songs a week. Full-time nonprofit work? Mentor one kid on Saturdays. Always produce.

If you aren’t sure what your one thing is, then ask questions that will help you come at it sideways:

• What would you start doing more of if you assumed that your big break was never going to come?
• What would you start doing right away if you knew the timing was always going to be terrible?
• If you didn’t need money, how would you spend your time?

If you still don’t have a clue about what to produce, then read Anne-Laure Le Cunff’s book Tiny Experiments. Running experiments is one way to produce more.

Producing more takes you from wishful thinking to reality. You thought you wanted more short stories, songs, or at-risk kids in your life, but now that you are producing more, do you like your life more?

A measurable commitment to what we think we want brings clarity—and strips us of our fantasies. Only after you’ve produced for six or twelve or twenty-four months will you know if you need to quit that too.

Don’t quit until you’ve answered yes to these three questions.

Some people quit before they make a clear commitment to producing or before they finish that commitment. They can’t really say that they sampled the thing, and thus they don’t have a true process of elimination. These serial quitters just walk away when the thing gets hard.

To avoid becoming a serial quitter—meaning, to avoid quitting too early—you ask yourself, “Am I proud of my progress or the milestone I’ve reached?”

You don’t quit until you can quit with your head held high.

You also ask, “Is quitting right now fair?”

You don’t quit until you believe that you have left other people and the situation or shared goal in better shape than you found them. You don’t screw people because screwing people will screw you eventually.

Finally, you ask, “Have I gained more intelligence?”

By “intelligence” I mean insight into what you like, what you’re good at, what reliably causes joy and flow, and what you ought to try next or avoid.

If we slow down to consider what question we’re trying to answer or what we’re trying to learn about ourselves, then it becomes obvious when it’s time to move on—or when it’s time to renegotiate the commitment so that we can gain new intelligence.

Knowing when to quit comes down to discovering what is most important to you, being brave enough to pursue that, and accepting yourself.