How to Know if You Should Bail from your Design Job

A few years ago I peaked as a senior level product designer at Pivotal Labs. I was there for almost four years, so after weighing the pros and cons it felt natural to move on.

Last year I joined Strava. I was incredibly excited for the new opportunity. But after a few months I was having a really hard time. So I obsessively explored every option I had, all the while refining my own process for bailing or staying. I confidently decided to quit a few months later.

Here is my decision making process for leaving your current design job (or any job really) or for deciding to keep at it. I hope this helps you with one of the harder career decisions you can face.

First understand why you’re unhappy. Frame the problem before coming up with solutions.

At Strava, I was pressured to adjust my design process to deliver on company wide goals. This shifted my expectations for the role — and I didn’t know how to react at first. But after hearing similar concerns from various colleagues, I knew I needed to dig deeper.

The first step is exploring your thoughts with people you trust. They’ll help you think through some of your concerns. Perhaps they’ll even have an alternate viewpoint that could help broaden your…