How Do You Know It’s Time to Quit?

I just quit my full-time job. After months of agonizing over the decision, I finally decided it was time. It was absolutely the right thing to do and I’ve known for quite some time that I needed to do it. So why didn’t I act sooner?

It’s hard to step away from the status quo. We are all so busy living our lives that years can go by before we realized aspects of our life, largely lived on auto-pilot, are no longer serving us. So, how do we know when to quit and when to keep going? I’ve learned a few things as I’ve grappled with this decision that I hope will help you make the leap at the right time.

Weigh Expected Value

One of my favorite books on the subject of quitting is Annie Duke’s Quit: The Power of Knowing When to Walk Away. Annie is an ex-poker player and a pretty good one at that. Over the course of her career, she’s won over $4 million dollars. How? By getting really good at weighing the expected value of her hands.

Expected value has a complicated-looking math formula that I won’t even bother to replicate here. No one in their right mind would use it to actually figure out the expected value of certain things in their lives. It’s fairly easy to figure out expected value of something that has monetary or numerical value. For instance, a job’s monetary expected value might be your salary for as long as you keep that job.

But the reality is that even your job has other factors besides its monetary value and those should be weighed as well. If you’re thinking about quitting, for example, you also need to think about the opportunity cost of spending 40 hours or more per week working (what else could you do with that time?), its affects (good and bad) on your health and mental health, how it affects your relationships, how it helps you achieve (or doesn’t) life goals, etc. And it’s really difficult to weigh the expected value of better health against the clear monetary value of, say, keeping a job with a nice bonus structure.

While calculating expected value is a useful idea, a more practical one is likely to use a good old-fashioned pros and cons list. When your cons list is longer than your pros list, perhaps it’s time to quit?

Your Current Situation is Toxic

There’s one time that quitting becomes a no-brainer, though we don’t always act on it quickly enough. If your current situation is toxic, get out of there ASAP. When there’s physical violence involved, seek help and leave right this second. If you’re being emotionally abused, gaslit, and treated terribly, it’s also time to go. Who cares what anyone else thinks? Your safety and health are your #1 priority. Don’t think in this situation, just quit.

Quit When You First Think of Quitting

Annie Duke also points out that most of us quit way too late. It’s far better to quit while you’re ahead than to wait until you’re miserable. In hindsight, I’ve noticed that I would have been far happier in many situations if I’d quit when I first thought of quitting. For example, I wish I’d quit my first marriage years earlier when I started to think about it. I usually wish I’d fired underperforming employee faster too. Surprisingly, a good rule of thumb that Annie Duke shared is when you first think of quitting, do it.

A good rule of thumb is when you first think of quitting, do it.

Annie Duke, Quit: The Power of Knowing When to Walk away

You’re Not Learning / Challenged

I believe that every activity has a natural arc. With new jobs in particular you start out learning a ton, then you spend some time really performing at a high level, but then you plateau. At that point, it’s time to figure out what to do next. If you’re at the point in a job or situation where you’re no longer learning, growing, or feeling challenged (in a good way — being challenged by biases, discrimination, etc is a good sign you should go), it’s time to leave. Plan out your exit strategy and find something new to do.

You Feel Unhappy…A Lot

There’s an anecdote that Steve Jobs used to start every day by looking himself in the mirror and asking whether he was happy about how he was going to spend that day. When the answer was no too many times, he knew it was time for a change.

As I talked about in last week’s topic on Serendipity in Career Planning, most of what you are pursuing in life should be fun. If you’re not having fun, it’s time to look for ways to bring fun back into your life. Granted, there are a lot of ways to do that besides quitting. I highly recommend trying some of those first. With my current job, I tried to go to coffee with more people, play more board games at lunch, and plan more happy hours. But when your efforts to make your pursuits more fun fail, it might be time to quit.

Your Values No Longer Align

I’m here to tell you that it’s ok to leave a great job, relationship, volunteer position, etc if you feel that your trajectory and values no longer align. If you notice your boss making repeated bad decisions, or the company strategy goes in a direction you’re not on board with, it might be time to go. If your life partner wants kids and you don’t or wants to move to Alaska and you don’t, it’s OK not to stay and work it out. In the US especially we push people to “stick it out” and “work extra hard” as if quitting were a terrible move always. It’s not, sometimes quitting can make your life 1000% better. Life’s too short to do things that don’t align with your own values.

Is There a Third Option?

A lot of times we think about decisions as binary. Stay in a job or leave it? Travel to Italy or stay home? Get your MBA or continue working? However, in almost every situation, your choices are not limited to two. There is almost always a third, fourth, fifth, etc option — it might just take a little creativity to find! For example, I know plenty of people who were thinking of leaving jobs that ended up working part-time instead and then using their extra time to pursue other things. It may seem like you don’t have a lot of options, but if you’re already willing to quit, then you have an amazingly powerful bargaining chip. You may as well ask for exactly what you want first and if that doesn’t work out, then quit anyway!

Find a Friend, Mentor, or Coach

Have you ever noticed that when a friend comes to you with a big decision, it seems 100 times easier to give them advice than to figure things out in your own life? That’s because we get weighed down with factors that seem important, but may not be in the long run because we are too close to the problem (e.g. my parents are going to hate this). So, grab a friend and bounce your ideas off of them. Sometimes it’s important for us to hear from someone we trust “on the outside” that the right path is obvious.

Occasionally we hear our friends but continue to grapple with our decisions. If that’s the case, finding a trusted mentor in your field or a great life coach can be just what you need. Coaches especially give you the time and space to lay out all options and think through them. They are trained to ask you insightful questions that open up new opportunities. I’ve had great life coaches who have helped me through many, many decisions (one of them is my husband, who doesn’t technically coach me, but still asks really key questions at exactly the right times).

Regardless of how you’re approaching a big life decision, it can be really hard. Don’t worry about how indecisive you are. Keep working on gaining the data you need to make a decision and trust that you will make the right decision at the right time.

Good luck finding your way. I hope this article gives you a few more things to consider as you make that big decision!