How you know when it's time to leave

Feb 17, 2022

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There are three connected posts in this series. This one, Choosing your next job, and Taking time off. I hope they’re helpful to you!

Ever since I wrote the post on burn out, I’ve been wanting to write about how you know when it’s time to leave a job.

It’s a particular moment when I’ve seen a lot of friends and colleagues feel totally stuck or confused or lost, and I don’t think we talk about it enough. By “it” I mean, how do you tell the difference between issues or concerns that are solvable inside your current company and ones that aren’t?

Over the years of making my own decisions and helping friends, I developed a set of tools that really help me figure out how to piece apart what’s going on for me and what the right decision is.

Signs that it's time to start asking questions

When I was struggling with burn out at Facebook, I couldn't figure out what was wrong. A friend of mine pointed out that “your valleys are getting closer together” and it is a phrase that has stuck with me ever since.

Every job has low points — days where things are rough, weeks when you feel bored or unhappy, etc — but in a job where you are generally happy, those moments should be few and far between: lots of hills, few valleys and the valleys shouldn't last that long.

If you start to notice that you're unhappy more regularly or your unhappy periods are longer than your happy ones, it's time to start asking questions. If your valleys outnumber your hills or your valleys are particularly long, something isn't right.

The tools below are great for helping you figure out what's wrong and whether it's fixable, or whether it's time to leave.

Tool 1: The magic wand

This is my go-to tool to identify where your unhappiness is coming from and whether the issues are fixable.

Close your eyes and give yourself a magic wand. The magic wand can solve any problem, no matter how unsolvable it may feel. For the first part of this exercise, you have to suspend disbelief and pretend that everything is within your control.

I'll give you some examples for how it can work:

Let's pretend, for example, that you think the problem is that your learning curve has slowed down — that you're a little bored, you don't feel challenged, and it's causing you to feel drained by your day-to-day meetings and tasks. Everything just feels repetitive.

Pick up your magic wand and solve the problem piece by piece. Using the example above, the first and easiest thing is to give yourself a new job inside the company. Pretend that someone asked you to take on a huge new fun project adjacent to your current role or that someone asked you to move from support in to product management. Like I said, the magic wand requires suspending disbelief — just let the wand solve the problem.

Now sit with the idea that the problem is solve and imagine how it would feel: does your heart feel excited or still exhausted? Can you imagine feeling like you're skipping in to work every day? If yes, great! What are the properties of the new role that get you excited? What are the parts of your new day that you imagine looking forward to?

If you're still not excited, then ask why. What's causing the lack of excitement if it's not your role? Sometimes using the magic wand helps you discover that the problem isn't exactly what you thought it was. Or sometimes there's a secondary problem hiding underneath the first big one. For example, you might realize that you thought it was your learning curve slowing down but it turns out that you've also lost faith in the company or that you can't work for your manager anymore.

Whenever you discover a second-order problem, use the magic wand to solve that too. For example, let's say that you thought the problem was that you're an engineering manager but you've found managing people to be exhausting so you used the magic wand to switch back to being an IC. But then, as you tried that solution on, your gut was saying: “being an IC won't bring me energy if I have the same manager. I just can't learn from Frank anymore.” Ok! Frank is part of the problem! Let's use the magic wand so that Frank isn't your manager anymore. Suspend disbelief even if Frank is the only manager in the company -- just pretend he's not. Now how does your heart feel? What is your gut saying?

Using the magic wand and then doing a gut / heart check will help you unwind the tangled ball of what is making you feel unhappy. Keep using the wand until your heart or your gut says: yes, if the following things are true, I'd be psyched to come to work every day. You should be able to get to a set of statements that look like this:

I'm bored because my learning curve has slowed down in user support.
I really need to move to a different department because I just feel like I've learned everything I can in support.
Product management sounds like it would really spark joy but I really don't want to report to Sammy, the head of product. She doesn't seem like a good manager for me.
If I could work as a PM reporting to someone other than Sammy, I'd be really excited. I love what we are doing at Acme Co. and I would love to stay and continue to work on the mission — I just need a totally new challenge.
I tried the same exercise for every other department other than product management and none of them excite me. I know I want to work closer to product.

Look! You just created a set of bullets that will let you have a conversation with your manager or a mentor or a friend.

Sometimes the magic wand helps you create a template for a conversation with someone about what you need in order to stay, and sometimes it helps you create your “why I’m leaving” script. But if you use it well, it should always leave you with a complete and granular list of what you need in order to be happy.

This may be obvious but let me just emphasize that my other favorite thing about using this tool when you’re feeling unhappy in a job is that it gives you a list of what you’re looking for in your next job. You just have to figure out if that next job is inside your current company or somewhere new.

Alrighty, now that you’ve suspended disbelief while using the magic wand, it’s time to bring reality back in.

Tool 2: The Likelihood Meter

The likelihood meter lets you bring reality back in as you look at your bullets. For example, the magic wand told you that to be happy at work, you really need to relocate to New York where your family lives so that you can have more support for your kids and childcare help. So then you ask: how likely is it that I can move to New York and stay in my current role? The likelihood meter tells you that your company doesn't have an NYC office and doesn't support remote work.

My basic rule of thumb is that there are only three categories of “likely”:

Likely to be solvable
Don’t know
Unlikely to be solvable

The likelihood meter will help you figure out whether it is worth having a conversation to see if your needs and the company’s plans align or whether you just wrote your goodbye messages.

Often, you don’t know how likely it is that a problem can be solved — would they let me work from New York? Can I work in Product without reporting to Sammy? Will they pay me $20,000 more in this role?

For anything in either the “don’t know” or “likely” category, it is ALWAYS worth a conversation. You never know what's going on behind the scenes, what conversations are already underway, etc. There is almost never harm in asking for what you want before you quit. When in doubt, ask for what you need to be happy. The worst thing that will happen is that they will say no. And then you have more information that helps you make a decision.

The magic wand and the likelihood meter sometimes find unsolvable problems. For example - if the magic wand found that you are frustrated with your role because you don't like or trust your manager and you'd love your role if you didn't have to work for her, but the likelihood meter told you that she's the CEO and it's unlikely she's going to leave, then you're in a pickle. You can go to the board and discuss your issues with the CEO but that is obviously a gamble in many ways. Maybe it’s a gamble worth taking or maybe you just found an unsolvable problem: a job you love but a boss you can't work with.

The upside is that you just found the job description for your next role: your same job, but a different CEO.

Unsolvable problems are only solvable by leaving. It is ALWAYS worth questioning whether a problem is truly unsolvable, and when in doubt, I’d ask. I’ve seen everything under the sun in terms of companies trying to fix problems when high-value people make it clear that they’re unhappy. But sometimes, after picking the problem apart, it becomes clear that the only solution is to leave. And that’s ok too. At least the magic wand helped you create the beginning of a script that explains why you have to go and the beginning of your next job description.

Tool 3: “Listen for the answer”

Final tool that’s going to sound obvious but has been invaluable to me.

When I was deciding whether to take a new role at Google or leave and go to Facebook in 2008, I talked to a lot of people — people at both companies, friends and family outside, etc. I still felt confused. If anything, all the advice made me feel more confused because I was choosing between two good options. A very wise person said to me, “I think you have the answer inside of you, you just have to listen for it.”

So I went home, opened a beer and sat on my teeny tiny slightly sketch balcony in San Francisco and watched the sunset. At some point, a voice from my stomach just showed up and said, “I really want to go learn from the people at Facebook.” It was clear and certain.

After making a number of hard decisions, I’ve realized that I have a method that helps me make them:

1) collect data by talking to people involved in the options and also with people who are uninvolved that I trust
2) stop talking to people, let the dust settle, and listen to my gut

Both phases are important, but at some point phase 1 has to end and I need to go for a run, or a hike, or walk my dog and just listen to myself.

When I was deciding whether or not to leave Facebook in 2012, another very smart friend gave me an exercise: “go to bed and wake up tomorrow and pretend you’ve chosen one of the options. Live the day as if you’ve decided to stay at Facebook and see how your gut responds.” I did it and after waking up at 7:30am, my gut told me that staying at Facebook wasn't right by 8am. “Living a day as if” is another great tool for helping you connect with your gut.

The right decision-making process is not the same for everyone. Over time, you want to figure out how YOU make hard decisions. Careers (and life) are full of them. By hard decisions I mean the ones where there is no “right” answer and generally each option makes you feel like you are disappointing people you care about or closing doors that feel scary to close. (Put positively, each option has upsides and downsides.) Sometimes decisions are clear and sometimes they are genuinely not, but I have found, over and over, that if you learn to trust yourself and find a way to listen to that basic, instinctual part of yourself, you will always find the answer that’s right for you.

Ok, so now I’ve summarized advice that I’ve given to dozens and dozens (maybe hundreds?) of times. Next time you ask me what you should do, I’ll just annoyingly send you a link to this post.

For what it’s worth, I use these tools in making a lot of different hard decisions: picking between two good job options, deciding when to fire someone, helping someone on my team debug a thorny people issue, etc. They are great, particularly the magic wand / likelihood meter pair, at helping you reduce the noise and figure out the root of the issues.

Hope they help you!

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