How you know when it's time to leave
👋Hi! I'm Molly. This is where I share the lessons I’ve learned from building fast-moving, messy, ambitious companies. For more from me, you can also find me on the WorkLife Podcast, on LinkedIn, and in Glue Club, a community for leaders who care about building great companies.
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 3 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.


