How to know when to quit your job: The not so definitive guide to the modern career

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"How do I know when I should quit my job?"


I was recently asked this by a mentee and I did not know how to respond.

Everyone has had that period at work when things are incredibly frustrating. The feeling overpowers you on Sunday night as you dread returning to work or paralyzes you in bed as you avoid starting your day.

These moments suck, but they also give us valuable insight: if you focus on what’s driving that feeling you can determine what is “off” in your own career or life and then take action to address it. Is it the lack of support from your manager? Is it the type of work you are doing? Is it the speed of work? Is it the people? Do you not have enough stress-free time out of work? Or is everything off?

As I think back to leaving my first job after college, I didn’t ask myself these questions. I just knew I wanted out. That first job was in Cincinnati, where I joined an entry-level management rotational program. The program was prestigious and well-run by all accounts, but I felt like a fish out of water. I was desperate to be in a job I was more passionate about. I always promised myself I would not stay in a job that I did not enjoy, so I decided to take action. With or without a job, I was going to leave my job and move to Boston.

I committed to this 100% and started telling friends and family. For some reason, people have always had faith that things will be fine for me. I’ve always been relatively confident, but in this moment I had a lot of anxiety and worry. I was terrified of moving without a job. A month before my self-designated “quit date,” I got lucky: I landed a job in consulting, an industry I had been trying to break into for over two years.

To the outside world, this has always been seen as a good move for me. I moved from one good job to an arguably better one. I don’t have to spend much time selling people on why I left. Does that mean I knew what I was doing? Of course not.

I could have spent more time asking myself questions around why I was frustrated, but I was not thinking with a clear head. I was an emotional wreck — driven by a lack of interest in the work and uncertainty about where I would be living as well as a big dose of homesickness. My drive to take action was mostly to quell that feeling.

If you are feeling something similar, I’m not saying to quit your job tomorrow. Just because I landed a job I loved after leaving my first job doesn’t mean it was the right approach. I didn’t know how to enjoy the journey as much as I do now. Reading Robert Greene’s book Mastery I was stunned to find that some of the world’s greatest minds in history took years and decades to reach a level of mastery and find their “dream jobs.” I wanted my dream job at 22.

A good question to ask when deciding to leave your job is, “Can I get what I want in my current company?” A lot of people are surprised when the company desperately tries to keep them upon quitting. Just because you are incredibly frustrated and know you are not maximizing your potential does not mean you are seen as a low performer. A friend recently quit his law job and was surprised when they offered him a month’s paid leave and the opportunity to switch to a different practice area. He left anyway, but he was prepared for that counter offer. A good exercise is to put yourself in that situation. If the company would give you a counter-offer to retain you upon quitting, what would you be willing to accept? Why not ask for that?

We often think that things are out of our control in the workplace, that things are what they are. However, I’ve found that people in the workplace are usually much more empathetic than you would expect. Due to some outdated beliefs about how we are supposed to act in the workplace, we are scared to be vulnerable. However, when you have the courage to say to someone you trust, “I am struggling, this is not working for me” it often ends with an ally in your corner and a brainstorming session on what to do next. Early in my career, I was scared to share with others how I was feeling. It was much easier to go pursue something else.

The true challenge is being true to yourself. Most people will give you conservative advice when talking about your career: how to ruffle the least feathers and pursue paths that are seen as successful or safe by others. This makes sense. Nobody wants to see anyone else suffer or fail.

But that’s crap.

You have to realize that if you listen to what everyone else is saying, you will ultimately be miserable. Everyone has that friend that has been complaining about their job for years. Those people drain your energy. You don’t want to be that person.

The great thing about life is you make the rules. You don’t have to do what others expect for you. Have you ever seen someone’s eyes light up when they describe something they are working on? Something they would gladly do for free? Everyone deserves that — and I know everyone can find some form of it.

So is it time to leave your job?

Unfortunately, I don’t have that answer for you.

There is always going to be a rational approach for figuring these things out, but emotions are always going to claim a seat at the table. One of my recent clients was in a good job — but the endless hours and work culture were crushing his spirit. He decided he needed a job change to get some breathing room to figure out what he really wanted long-term. Sure, he could have tried to negotiate for a different role at work, but he had reached a point where he was done. He had to move on. This was the right decision for him, but every situation is unique.

There is no perfect career. In today’s world, there will be missteps, side steps and steps forward. The important thing is that you are learning and reflecting along your journey. The closer you get to something that you are passionate about and aligns with who you are, the better off you will be.

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  • Jeremy Pena

    I was ready to quit my job but a better work/life/business balance made all the difference. Now I consider it one step below passive income. 80% is just showing up.

  • Hey great article! I remember clearly when I wanted to quit my job and how long it took me before I had the courage to make it happen. Quitting a job is like breaking up it’s pretty scary but the opportunities are endless.