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
Nov 14, 2019 · 7 min read
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. However, someday you’ll want to leave. My most important job is to prepare you for that day so you can walk out of here well prepared for the next job. While you’re here, I’ll do my best to teach you everything I know, and the minute you’re ready to go, let me know. You’ll have my full support on figuring out where you should go next, if you want it. I’ll make calls. I’ll write references. Leaving is a totally normal part of a job, so let’s deal with it like we deal with everything else. We’ll plan. We’ll research. We’ll celebrate. And the sooner you tell me you’re thinking of leaving, the sooner we can start all that. It’ll also give me adequate time to find your replacement.”

A few people took me up on that offer, and I kept my word. Together, we researched companies that might be good for them. I made some calls on their behalf. I did what I could to get their name out. I even helped a few employees negotiate a better offer from their new workplaces. At the same time, I was interviewing their replacements.

A few employees didn’t take me up on the offer, and I understand why they didn’t. I imagine every employee has a story about a shitty boss who freaked out when they told them they were leaving. Because I was that boss once. But this is how I believe leaving should be handled: out in the open, with honesty, and as a normal part of work. Sadly, not all bosses understand this, so I get why employees don’t want to trust them. If you’re in this situation, let me give you a tip: You are not the first person to come up with masking interviews as dental appointments. When you start lining up three dental appointments a week, your boss knows what you’re doing. Be more clever.

Now that we’ve established that leaving is an expected and normal part of the job cycle, let’s take a look at the reasons people leave.

You’re just done

Chapters have beginnings, middles, and ends. You can be in a job you totally love, solving problems you’re good at and enjoy solving, working with people you enjoy working with, and one day, you just come in and decide you’re done. It happens. This job has run its course, and it’s time to move on to the next thing. If this happens to you, the best thing to do is take stock of where you are professionally and personally.

If you’re doing project-based work, where in the project cycle are you? If you’re close to the end, you should see if you can stick it out. Finish strong. Wrapping up a project is a natural point for closure, and you won’t leave your co-workers in a bad spot. If you’re between projects, it’s a great time to leave. If you’re in the middle of a project, things get a little trickier. Can you make it to the end? Can you stay focused enough to finish the project with the level of quality people expect from you? If not, be honest with yourself and your team as soon as possible.

A better opportunity came up

Even if you like your current job, you might’ve been offered something that excites you more. Put in some due diligence. Make sure this isn’t a grass-is-always-greener situation. Maybe this is the job you’ve always wanted at the place you’ve always dreamed of working. You only make this trip through space once. Take it. Just finish strong with the current boss. Nothing ever freaked me out like offering someone a job, asking when they could start, and them replying, “I can start right now!” when I knew they already had a job. If someone’s willing to ditch their current job without giving notice, they’re willing to do it to you.

You’ve grown beyond the job

Sometimes you grow beyond the job you were hired to do. Say, for example, that you were hired to knock out prototypes in Sketch, but you’ve been learning a ton about design research and are looking to try your hand at that. If your company doesn’t offer opportunities in the new skills you want to practice, you need to convince them to expand. If they’re not open to that, you need to find a new place.

You’re in the wrong place

There are big-company people and small-company people. There are self-motivated people, and there are people who need oversight. Some people like to build things from scratch; some people like to work on mature products. Some people thrive in chaotic environments; some people need a ton of structure. None of these are right, and none of these are wrong. And sometimes you don’t know which type of person you are until you find yourself in the wrong environment. The good news is that workplaces of all varieties, sizes, and structures exist. And if you’re in the wrong place, you might be making the people around you as miserable as you’re making yourself.

Your workplace turned out to be a Hellmouth

I think it’s safe to say we’re all hopeful when we start a job. We’re happy for the opportunity. We’re happy to contribute our skills and our labor to society. And obviously, we’re happy to be able to earn a living. But sometimes what you thought was going to be a decent place to work turns out to be less than ideal. And look, all workplaces have problems. I’m not talking about the kind of place where someone would reheat fish in the microwave or ask you to empty your own trash. I’m talking about the kind of place that exploits your labor. The kind of place that would cut your pay right before it had to report quarterly earnings. The kind of place that would use your labor to rise to success, only to abandon you as your efforts were about to come to fruition. The kind of place where management benefits from your labor, but you don’t. The kind of place where workers stand up for themselves to improve their situation and get punished further. That’s a horrible place.

Every worker deserves a safe workplace. Free from harassment. Free from abuse. Free from exploitation. Labor is an exchange. And when it’s respected, everyone benefits. The company does well, the workers do well, and the people who use the products or services that company makes do well. And finally, the ecosystem in which all of that exists does well. But a company that exploits its workers, its customers, or the ecosystem in which it operates doesn’t deserve to exist. And it certainly doesn’t deserve workers’ labor or customers’ hard-earned money. Eventually, everybody will leave.

Companies don’t have an inherent right to thrive. People do.

If you have a question, email me, and I’ll be happy to answer it. Maybe. If it’s a good question and answering it could help a lot of people, I’ll be more likely to answer it. “Should I quit my job because my boss is a dick?” is not a good question (and you already know the answer anyway).


Helping designers thrive.

Mike Monteiro

Written by

English is my second language. You were my first.


Helping designers thrive. A Medium publication about UX/UI design.

Mike Monteiro

Written by

English is my second language. You were my first.


Helping designers thrive. A Medium publication about UX/UI design.

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