How Do You Know When It’s Time to Quit?

How do you know when it’s time to find a new job?

I’ve worked at the same company for thirteen years now. The only place I’ve worked since graduation. And it’s a question I’ve considered many times. It’s one that I’m considering right now, even as you’re reading this.

When is the right time to find a new job? How do you decide that everything you’ve invested in your current company is no longer worth the future gains and it’s time to start over?

I don’t know if most people struggle with this. Recent statistics show that the average worker will have 11.7 jobs over the course of their career, so at least some percentage of the workforce doesn’t have these same qualms.

But 70% of people are also unhappy with their jobs. So is all of this job-hopping actually helping people to be more engaged at work? Or are we convincing people to simply jump ship when things become difficult? And things will always become difficult.

So when is it time to leave, and when is it time to buckle down and push through the difficulties?

Difficulty Isn’t the Problem

Psychologist and winner of the most-difficult-to-spell-last-name, Mihaly Csikszentmihalyi developed the concept of flow as a means of showing how people enjoy their work.

In his book, aptly titled Flow, he found that we operate in a flow state when we’re in a situation of both high skill and high challenge.

He also showed that we’re able to progress from bordering situations of control (medium challenge, high skill) and arousal (high challenge, medium skill) into flow by further stretching ourselves or building new skills.

Difficulty isn’t the opposite of achieving a fulfilling career. It’s a key component of working in a flow state. The opposite of fulfillment, the opposite of flow, then becomes apathy (low challenge, low skill). And this is what we need to be on guard for.

But things really aren’t that bad…

“Pure hell forces action, but anything less can be endured with enough clever rationalization.” — Tim Ferriss, The 4-Hour Workweek

Difficulty and challenge inspire us. It’s what drives us to respond with our highest quality work. Apathy, on the other hand, drains us. It leads to complacency, which promotes inaction.

A friend of mine has been talking about finding a new job. Each month, she says she’ll finally get that resume together. And we all know that she’ll still be saying this next month, and next year, and for the rest of her career.

She’s complacent with her job. So she’s become comfortable with inaction.

Another friend recently quit his job before he could start receiving a significant bonus. He was on track to become a senior manager and start collecting a sizable raise.

Except he didn’t like his job. And those senior managers didn’t like theirs. But they were too comfortable with the bonuses to give it up. So he quit before he could fall into that trap. He quit to avoid sliding too far into a void of complacency.

It’s this sense of complacency that keeps people saying, “I’ll start looking soon, I’m just too busy now.”

And then, “I suppose this job is okay for now, I can put up with it for a couple months.

With the eventual, “I guess this isn’t so bad. I mean, no one really likes their job, right?

How do we recognize this situation? How do we differentiate from a bad day and a bad job?

In my experience, it comes down to five questions.

Do You Still Believe in the Mission?

“We do better in cultures in which we are good fits. We do better in places that reflect our own values and beliefs.” — Simon Sinek, Start with Why

Every job will have difficulties. People will be unreasonable. Projects will struggle. Efforts will fail.

That these issues will happen is inevitable. Any job worth doing will bring comparable challenges.

In these instances, what gives us the conviction to carry through? What gives us the energy and the stamina to take on these obstacles and be stronger for it?

We persist through these challenges when we’re driven by a mission larger than ourselves. When we can think of our contribution and we’re proud to be a part of something greater.

We’ve seen too many wealthy, yet miserable, workaholics to not yet realize that money and status, without a guiding mission, are not sufficient for a fulfilling career.

When we stop associating with a mission, then money and status become our drivers. We pick up these rationalizations to justify our time and continued efforts.

But they aren’t genuine. When we choose to pursue something we don’t consider to be worthwhile, we eventually resent it. When we align ourselves to a mission that we don’t believe in, we start settling.

Do you still believe in the mission? Or have you started settling?

Are You Better Today Than You Were Yesterday?

“This is a fundamental truth about any sort of practice: If you never push yourself beyond your comfort zone, you will never improve.” — Anders Ericsson, Peak

Stanford psychology professor Carol Dweck has spent many years studying different mindsets and their relative impact on learning. She’s largely found two groups of people: those with a growth mindset and those with a fixed mindset.

The different perspectives became more clear as students were faced with difficulties. Growth mindset students sought improvement. They pursued more challenging work and when they made mistakes, they engaged with and learned from them. In contrast, fixed mindset students ran from these challenges. They felt as though their intelligence was up for judgment and they preferred to handle safer problems, ones that would guarantee a good grade today.

Growth mindset students lived with the “power of yet” while fixed mindset students were gripped in the “tyranny of now.”

Through multiple studies, Dweck has demonstrated that when we can create an environment that encourages a growth mindset, learning rapidly accelerates. When we can celebrate tomorrow’s development over today’s success, people are more engaged in future challenges and more likely to persevere through difficulties.

In most jobs, it’s easy to become comfortable with our responsibilities. We demonstrate competence in our role and are rewarded with easier versions of success. And without realizing it, we’re slowly adopting a fixed mindset. We’re prioritizing immediate results over our long-term development.

Once we lose our growth mindset, learning decelerates. We become proficient at our daily tasks, but often those daily tasks don’t present us with the opportunity to truly distinguish ourselves.

In these instances, we need to find new ways to stretch ourselves. Similar to Ericsson’s theory of deliberate practice, we need to find opportunities to push us out of our comfort zone and develop skills that let us distinguish ourselves.

Good companies will encourage this behavior. They’ll support new projects and new responsibilities. They’ll encourage challenge as a means of developing new capabilities. Because they understand that the long-term benefit of a growth mindset will more than make up for any short-term difficulties as people extend beyond their comfort zone.

But there’s also plenty of companies who discourage this behavior. They see the cost and liability of an inexperienced operator as an unnecessary risk. They prefer today’s success and are comfortable with the status quo.

If a company doesn’t support these behaviors, it’s a sign that they’re not invested in career development.

Are you allowed outside your comfort zone? Are you better today than you were yesterday?

Are You Free to Make a Difference?

“I didn’t tell my kids, ‘You have to play viola, and you have to play piano.’ They chose those things on their own, and I don’t think we have to give kids every choice, but we do have to give them some choice because that autonomy is crucial for fostering passion.” — Angela Duckworth

I once reviewed a company’s manufacturing plant. And in the age of automated machining centers, the technicians had less and less involvement with actually machining a part. Yet morale and engagement were at an all-time high.

They let people redefine how they wanted to make an impact. Machinists were encouraged to use their skills to improve designs. Others helped restructure the manufacturing flow to increase throughout. Or they optimized machining codes to reduce stoppages. As one role decreased, the company gave people the opportunity to make a difference in new areas. And people seized these chances.

We all want to pursue something worthwhile. That’s why it’s important to believe in a mission. But more than participating in something worthwhile, we want to contribute to something worthwhile.

We want to feel as though our contributions are making a noticeable difference. It’s this tendency that lets us appreciate our work. It makes it unique. And hence, valuable.

Amy Wrzeszniewski and Jane Dutton demonstrated this practice through their theory of jobcrafting. They showed high levels of engagement with workers who modified their responsibilities to instill a greater sense of meaning in their work. From hospital cleaners to engineers, nurses to hairdressers, people considered their work more valuable and more critical. And in addition to having a deeper sense of fulfillment, they delivered more value to the organization.

When we’re free to deliver unique value, we feel uniquely valued. Does your job let you make a unique contribution? Are you free to make a difference?

What Opportunity Are You Passing On?

“Because it is so much easier for me to remember the past than to generate new possibilities, I will tend to compare the present with the past even when I ought to be comparing it with the possible.” — Daniel Gilbert, Stumbling on Happiness

It’s easy to get stuck in that rut of comparing each day to the one before. We’re conditioned to adapt to incremental changes. Which is why it’s easy to adjust to the steadily increasing volume of a car radio. We don’t notice how ridiculously loud it is until we start our car the next time.

We often don’t notice magnitudes. We notice relative changes.

So as a job becomes slightly more monotonous, we compare today’s monotony to yesterday’s. This minute difference is largely unnoticeable and over time we adjust to the magnitude of these new conditions.

The relative incremental change doesn’t set off any alarm bells. Until we eventually find ourselves in a role that we wouldn’t ever choose.

We need to consciously pull ourselves out of this default mode. We need to evaluate our current condition not with yesterday’s, but with the other opportunities that we’re passing up.

That pulls us away from comparing the present with the past. And let’s us compare the present with the possible.

What are you giving up by staying where you are? What opportunities could you be pursuing?

Are You in a Dead-End?

“Strategic quitting is the secret of successful organizations. Reactive quitting and serial quitting are the bane of those that strive (and fail) to get what they want. And most people do just that. They quit when it’s painful and stick when they can’t be bothered to quit.” — Seth Godin, The Dip

Most of us were raised with the mentality that “winners never quit and quitters never win.”

A mindset that is still preached by overzealous coaches, parents, and conservative talk-show hosts.

Would they tell a smoker to keep at it. That quitting is for losers. That when they first started smoking, they made a commitment to see this through to the end. All the way to emphysema and lung cancer. Don’t quit now.

If something is no longer an effective use of our time, why is quitting not the optimal solution?

The truth is that winners quit things all the time. They recognize which investments are no longer worthwhile and choose to apply their resources in a more effective way.

The problem is that we often give more consideration to short-term pain than the long-term benefits. We have some difficulties and panic. Self-doubt creeps in and we lose sight of the long-term investment. And we’re compelled to quit.

But we need to understand whether we’re quitting because of that short-term pain or if we’ve finally realized that this just isn’t worth it anymore.

We need to understand whether things will improve or if we’re just going to keep banging our head against a wall. Are we reacting to an immediate disappointment and losing sight of the long-term strategy? Have recent developments changed our fundamental assumptions and beliefs?

Or said another way, if we knew then what we know today, would we still do this?

The answer often tells us whether we’re facing a worthwhile challenge, or whether we’re barreling down a dead-end. Because to paraphrase Henry Ford, obstacles are what we see when we take our eyes off our goal.

Be Mindful. Decide. And Find Meaning.

“I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn’t make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.”- Sylvia Plath, The Bell Jar

The best time to look for a job is when we don’t need one. And the best time to improve our current job is before it becomes unbearable.

Most of us spend over forty hours a week at work. With a significant portion of our life invested in this area, why would we not want that time to be spent in a job that gives us meaning, helps us grow, and lets us make worthwhile contributions.

As Steve Jobs said in his famous 2005 Stanford Commencement Address, “Your work is going to fill a large part of your life and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.”

You owe it to yourself to do something that you find meaningful. You owe it to the world to make that kind of a difference. If you’re not there now, keep looking. Don’t settle. You’ll find it.

If you enjoyed this or have any suggestions, please let me know your thoughts. I’d love to hear from you. And if you found this helpful, I’d appreciate if you could clap it up 👏 and help me share with more people. Cheers!


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