Dear Designer

Dear Designer: All Jobs Must Come to an End

How to know when it’s time to move on to another opportunity

Mike Monteiro
Published in
7 min readNov 14, 2019
Illustration: Eugenia Mello

Dear Mike,

How do you know when it’s time to leave a job?

Dear Designer,

You’ll have a number of jobs during your career. Some will be good. Some will be bad. Most will oscillate wildly between those two poles. But the one thing all those jobs will have in common is that, at some point, you will leave. Sometimes it’ll be your call; sometimes it won’t. Sometimes it’ll be a happy occasion; sometimes it won’t. But rest assured, every job has an endpoint.

The fact that a job ends shouldn’t be a surprise, although the manner in which it ends might be. So, let’s talk about some of the reasons people leave jobs and see what we can do to mitigate the negative impact. Because jobs equal income and all that.

But first, let me start with a story. I’ve been running my own shop (along with my partner, Erika Hall, who has a new book out about design research) for 18 years. In those 18 years, we’ve hired somewhere in the neighborhood of 50 people. The first time one of my employees left, I was devastated. I thought it was my fault. I started thinking our little studio sucked, because why else would someone want to leave? I took it personally. It wasn’t a good look. I asked them why they were leaving.

“It’s just time for something new.”

As a former employee myself, that made total sense to me. But in my still very newish role as an employer, I’d thrown sense out the window. Here I thought I’d built this great little studio where everyone enjoyed coming to work every morning, which had always been my dream, and someone was leaving. I called up a few colleagues who ran their own small studios. They all told me the same thing:

“Everybody leaves. Get used to it.”

As time moved on, and as more people left and others were hired on, I did indeed get used to it. I also came up with a little thing I’d tell new employees on their first day. It went something like this:

“I’m glad you’re here. I hope your stay here is long and fruitful and that we both get a lot out of it…



Mike Monteiro
Writer for

English is my second language. You were my first.