Should I Stay or Should I Go?

Jeremy Dizon
10 min readAug 23, 2021


Lego Stormtrooper leaving tracks in the sand.
Photo by Daniel Cheung

In April of 2020, with a year under my belt working at Lyft, a lot of changes started to happen very quickly. Not only were tech companies transitioning to employees working from home in a virtual setting but the combination of layoffs and attrition happening everywhere seemed more devastating to morale in general.

My immediate team said goodbye to 3 amazing and talented individuals during this time, and unfortunately, in the coming months, the farewell emails would steadily come as it seemed like I was saying goodbye to colleagues every week. It was a tough time to say the least and at the start of September, with my manager still on maternity leave, I became the only surviving designer on the Design Systems team as my two senior colleagues exited stage left.

Naturally, I started to question a lot of things as it seemed like the writing was on the wall. I knew things were going to get much more difficult as the crushing weight of being the only design systems designer rested firmly on my shoulders. But this wasn’t the first time I had to make a tough career decision. While the decision never gets easier, here’s how I evaluated whether to stay at a company or choose to leave for another opportunity. I hope it helps, if you’re in one of these sticky situations.

My Framework

When I was a young designer, one of my first bosses shared some wisdom that I’ve kept in mind throughout my career, especially when faced with hard professional decisions.

No one else will look after your career but you.

It’s in this piece of advice that I’ve really thought through my reasons for staying at a company. Not only do my reasons cover my professional goals, it also factors in what point I am in my life and of course, my family situation. Call it being a grown up or adulting or whatever you’d like but including my family and mortgage into the equation is super important to me.

These are the main questions that I ask myself to help determine if I stay at my current role and company:

  • Am I continuing to learn or add to my skill set?
  • Am I making an impact with each project that I work on?
  • Am I supported by my manager (and peers) on my career path?
  • Do I feel valued by my team and the company?

Reasons to Leave

Man in a blue suit carrying a briefcase walking forward.
Photo by Marten Bjork

Most people assume when someone leaves a company it’s for a negative reason: not being paid enough, the schedule is hard to manage with all the other things you manage in your life, etc. But my reasons for leaving were different.

Humor me with a quick visualization exercise. Picture in your mind a new college grad, roughly the tender age of 23.

Young? Yes.
Ruggedly handsome? Maybe.
Naive? You betcha; but filled with a huge desire to learn.

The young, ruggedly handsome and naive “kid” had spent the last 5 years studying to achieve a Bachelors of Science degree in Engineering. But now he was at a crossroads because he had just decided that his career path was to become a designer. Better late than never, right?

At this point, I’d never have thought that I’d work at companies like Apple, Facebook, or Google. Growing up in the Bay Area, I’ve been able to witness firsthand all of these companies evolve into the household names they are today. But being able to call myself an employee of any one of these companies was something I only considered in my wildest of dreams. Well, that dream became a reality in the summer of 2014 where I found myself as a Noogler (new Googler) on the Analytics UX team.

Was it everything I dreamed it would be?

Pretty much, yes!

The perks were overwhelming:

  • Seeing the band Chvrches perform live and discuss the sexism front-woman, Lauren Mayberry, experienced
  • Meeting Brian Lee O’Malley, cartoonist known for the Scott Pilgrim series, and get his autograph
  • Learning from a talented team of product designers, researchers, and engineers
  • Working on impactful projects, like the Material Design toolbar component
  • Enjoying free meals from a number of lunch rooms across the Google campus

So, why did I leave after just 6 months?

There were a number of factors why I left but the main one was based on my employment status. Up until this point, including my first design job at Symantec, I had been hired as a contractor. What enticed me to leave Google ended up being a full-time position from an up-and-coming startup that was growing fast called Airbnb. You might have heard of it.

At Airbnb, I soaked up as much as I could and learned from everyone around me. For the next 4 years, I hustled to not only prove myself but ended up falling in love with design systems. I knew then that I had to set my path to become a design systems designer. And this was when I had to make another hard career decision because a ride sharing company primed for an IPO decided to call.

Lyft called at an interesting time in my professional career because Airbnb was steering me towards a Lead role that planned, strategized, and led projects within my team. I felt like I didn’t have the confidence or experience to do that yet. Plus, I really wanted to continue my education within design systems. Unfortunately, Airbnb couldn’t offer that to me. So I decided to gamble on Lyft and see for myself if I could not only learn a new design system but provide a positive impact on it.

For those keeping score, I left 2 companies within a 5 year span. Each time, it was to take a step forward on my career path:

  • I went from contractor to full-time employee when I left Google for Airbnb
  • I went from being a Production Designer to Design Systems Designer when I left Airbnb for Lyft

Reasons to Stay

Two woman around a single laptop collaborating on a project.
Photo by KOBU Agency

Remember those questions that I asked at the beginning? To provide more context, let’s tackle each one individually.

Am I continuing to learn or add to my skill set?

To cultivate a growth mindset, I’m constantly finding ways to learn something new or hone an existing skill. As a serial contractor at the start of my career, I’m always striving to prove my worth; mostly to myself but the added benefit is gaining that full-time role. And I never turned that switch off, even when I was hired to a full-time position. Talk about #hustle.

If I can say that I’m still learning and growing, then the answer to this question is a resounding yes.

Am I making an impact with each project that I work on?

As a designer, I want to know that the work I do makes an impact. When I worked on Airbnb’s design system, I had found more than just a project but a calling. Being able to not only support my fellow design colleagues but also my engineering partners seemed like a win-win. And since that day, I’d found a way to make a huge impact while continuing to learn about the design systems world.

These days, I’m focused on creating a robust and scalable contribution program while also writing a ton of documentation. All of these aspects of a design system are important and impactful work.

Am I supported by my manager on my career path?

For a good portion of my career, I didn’t have a defined career path. And unfortunately, I’ve only had a handful of amazing and supportive managers that cultivated my potential and growth. A manager’s job is not only to provide air cover to allow you to work without distractions but also to find opportunities for you to make it to the next level of your career. There are far too many instances when people leave because they are not happy or supported by their managers. And though it’s difficult without a manager to advocate for you, it isn’t impossible.

You’re still not off the hook because you should still be thinking about what you want to accomplish in your career, but I’ve found having a supportive manager to partner with has been immensely beneficial to my own career growth.

Am I supported by my peers on my career path?

Similarly, your peers can support your growth as well. I’ve been lucky to work with talented designers who’ve provided constructive criticism and feedback on my career as well as extended opportunities to further my growth by collaborating with them. Talk about learning by doing!

One respected colleague in particular found a way out of Production Design which I’ve modeled my own career path on. This shared journey really helped me stay on course by taking those difficult steps forward through all the struggles and continuous uncertainty. Plus having a sympathetic ear or shoulder to lean on goes a long way to know that people, other than my family and manager, are cheering me on from the sidelines.

Do I feel valued by my team and the company?

This question can be interpreted in many ways but it’s one I consider the most important to me. I define being valued as understanding a person’s unique situation and treating them like more than just an employee. For example, right when I started working at Airbnb, my team fully supported my non-typical work hours from 7:30am to 3:30pm. This worked the best for a commuter like me with a toddler at home. I was able to have quiet, productive time in the mornings and still have enough daylight in the evenings to spend time with him.

The flexibility for my work-life balance was a big reason why I spent 4 years of my professional life at Airbnb. Being a new parent at that time really stressed me out because I had to figure out how to be both a professional and a dad. I’ve come to realize that we should have the space to be our authentic selves, whether your team helps create this environment or your company. It goes a long way in retaining talented individuals in my opinion and if I can be honest, should be provided on day 1.

Choose your own adventure

Photo by Drew Hays

I obviously have been thinking a lot about this and understand that everyone is at a different point in their careers, especially when thinking about their overall path. So to start ya’ll on the right foot, here are some prompts to help you start to see what’s important to you and craft your own questions.
What’s something in your current role at work that you especially enjoy?
Is it the people? The collaborative environment? Or is it just the fact that you’re able to solve complex problems on a daily basis? Whatever it is, latch onto that to help define what actually makes you happy. It might not even be about the work!

What’s something in your current role at work that you don’t enjoy?

Understanding this answer is as important as the things that make you happy. If you don’t particularly like the number of meetings you have to attend, then this is something that can help define your working style and how you stay productive.

What’s the absolute best job that you had?

Why was it the best compared to the others? List out the reasons! Compare them from your other answers and maybe you’ll start to see a pattern start to emerge on what’s important to you.

What’s the worst job that you had?

This one is self-explanatory. We know what we don’t like, so we don’t want to experience that again.

What’s your dream job scenario?

If you had a blank slate to define your dream job, what would you write? Though this is a thought exercise, you can discover a lot about your motivations through these aspirations. So dream big!

What’s something in your life that you want to do more of?

Whether it’s to travel more or spend time connecting with friends or family, this question gets at the idea of balance. If you feel like you’re too focused on your work, then defining your work-life balance is important and something that helped me create my value question.

One of the hardest decisions we’re faced with is those that deal with our professional careers. Are we making the right decision for ourselves? Are we making the right decision for our families? Are we making the right decision for our careers? It’s a stressful choice to make but at the end of the day, you have to listen to yourself.

Find a quiet place.

Take a breath.

Take another.

Listen to your heart.

No, don’t play that song by Roxette. Just be open to your feelings on the matter and then, if you’re like me, break out the pros and cons list and get to work. Or you can have a candid conversation with a friend, trusted colleague, or even your manager. Whatever helps you weigh all the options ahead of you.

As you can tell, I don’t take this decision lightly as evident from my checklist of questions. What do you factor in your decision making process? Any tips on coping with the anxiety and stress of making a decision like this? I’m all ears! Comment below and let’s continue this conversation.

Jeremy is a product designer currently working on the Design Systems team at Lyft. In his spare time, he balances being a Star Wars nerd, a father, and a Star Wars nerdy father.



Jeremy Dizon

Product Design / Design Systems super-monkey 🐵 | @jeremydizon on Twitter 💬