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On Leaving Jobs

I did some reflections on my past jobs. What was going on in my mind and in my life when I left? Here's what I learned.

There’s a phrase I’ve read a lot lately:​ people join a ​vision and ​leave a boss. I’m sure like many cliches, it becomes a cliche through frequent use. And it’s been used frequently because it rings true for many people. You can imagine hearing a friend say it “I was so excited for the work we’re doing, but now my boss sucks.” Maybe you’ve said it yourself.​ And yes, I can imagine it. I've been frustrated with a manager at many points in my career. In fact, I can't think of a manager I wasn't frustrated with at one point or another. I’ve left 6 or 7 jobs in my career, depending on how you count them. I don’t think I’ve left because of a boss…or definitely never only because of a boss.

“Join a vision. Leave a boss.”
The cliché never felt true for me.

Why all this thinking about leaving a job? I became part of “the great resignation” when I left my role as the Head of Design at Grab, a superapp in Southeast Asia. As the broader narrative around global workforce trends shaped up, some of it resonated with me personally. A lot did not.

Seeing these various messages about why people leave jobs, and not feeling like they represented me much, I felt it worthwhile to articulate why I left my job in hopes that it might be instructive or at least illuminating for others - it has been for me. It made me reflect on why I’ve left each of the jobs I’ve had.
What follows is a list of all of the jobs I’ve had and why I left them. I’m lucky that these were all by choice.

Bookkeeping & technical support – When I was in high-school, I had two jobs. One doing bookkeeping for a retirement community and another doing telephone technical support for an internet service provider. For the bookkeeping job, I can’t even remember who was managing the operation nor what I thought of them. Things went according to plan each month and quarter. It made sense. I didn’t question it. I was in my late teens. At the tech support job, I remember my manager’s name. I thought he was nice. Other than that, not much recollection. High school was ending soon, I needed to focus full-time on my school and tests. I was moving to a different city for college shortly thereafter. I didn’t leave my manager. I left because the job didn’t fit my life anymore.

Designing at a boutique design studio – I was the only employee at first as we regrew an awesome little studio through some ups and downs. I left this small studio out of ego. I felt that I had a vision of how a small studio could work, and I wanted to have my own go at it. It definitely wasn’t my manager’s own management of me nor the other people in the studio. We remain friends to this day, and I’ve got a huge amount of respect for what they all did then and are doing now. It was like a dream team, but one I felt I needed to break away from to explore my own specific points of view about the work to be done and how to do it.

Being a studio owner, creative director, blah blah blah – I was the boss here, so if I was leaving because of anyone it was me! Seriously though, this was more of a slow ramp down as my other professional endeavors took over. I took on only smaller clients, then no new clients at all, then only operated the studio for self-initiated projects. Either I never quit or it was a slow Homer Simpson-regression into the bushes of history.

Multihat-wearing co-founder at a start-up – I committed to this project because of our shared vision, the business opportunity, and learning potential. Over time, those didn’t line up with where I wanted them to go. It’s important to highlight that the vision, opportunity, and learning potential were still there…I simply saw more potential elsewhere and had a different view from my co-founder partner. Neither view was right or wrong, just different. I choose to leave. It had nothing to do with the people, their character, how they ran the business, or how I was “managed,” if there is management in a partnership.

Leading design at a fast-growing tech company – I was at this job longer than I’ve been at any other job. I chose to leave after 8 years, for a few reasons. First, similar problems recurred – while the job changed dramatically over the years, and that contributed to a ton of growth and learning,  the overall problem space and customer needs were within range of one another.

Because of that, I was less motivated to push. I didn’t feel like me. I wasn’t stretching myself and no one was stretching me. As an executive at a company of that scale, it isn’t a realistic expectation that others would explicitly stretch you, but if you’re going to be the driver of your own progression, feeling motivated to do so is essential. When I wasn’t feeling that, I took it as a sign.

Finally, there was a great team in place that I had confidence would not only continue to lead, but would transform things in their own way. I was excited to see that happen.

Design leader at a mid-sized start-up – I left this job when I felt that I had made the change I could make. Further change required a change of context. That might sound like it’s a polite way of saying the company wasn’t good, but that wasn’t true at all. The company was great! I was brought in by the founder, and at the time I believe the fundamental unlock in the next stage of the business, the product, and the brand was going to require a larger change in the perspective of the co-founders than there was appetite for. I was also happy to see that a team member who had joined was easily capable of doing my job, and I was pleased to leave and have them do so. I left because I wanted to feel like I was spending my time effectively driving change, and not waiting longer for the conditions to be right.

Design leader at a large and quickly growing start-up – Why leave “a rocketship” as they say? I’d gotten conviction on what my next steps in life would look like. Not completely clear, but clear enough… After nearly two years of lockdowns and restrictions, being “one flight away” (even if it is the longest flight in the world) from most family and friends, no longer seemed  close. My wife and I wanted to be more accessible to family and friends. This role, at this company, in Southeast Asia wasn’t the best fit for that. Even when the company  offered to make it work, it didn’t feel right to have a leader not fully embedded in the region. Also, important to me: I felt there was a team in place that could weather the transition. And thirdly, I started to have a sense that the way I wanted to spend my days – the kind of work I would do – might be more satisfying if it took some kind of substantial shift.


Looking back, I’m so grateful for all of these experiences. I’ve learned so much along the way. I’ve grown as a designer, a manager, a business person, a leader, a friend, and a partner. That never would have happened if there hadn’t been changes along the way…changes unlocked by having new challenges, new contexts, new partners in new jobs.

I didn’t leave jobs because of managers. I left because life!

Several years ago I read On the Shortness of Life by Stoic philosopher Seneca, and this passage ends with one of his most famous quotes:

It is not that we have a short time to live, but that we waste a lot of it. Life is long enough, and a sufficiently generous amount has been given to us for the highest achievements if it were all well invested. But when it is wasted in heedless luxury and spent on no good activity, we are forced at last by death’s final constraint to realize that it has passed away before we knew it was passing. So it is: we are not given a short life but we make it short, and we are not ill-supplied but wasteful of it… Life is long if you know how to use it.

I left jobs to have new things in my hands, coming into my eyeballs and ears, running through my mind and beating in my heart. I left jobs to do different things with my time, which is to say to live life differently.

What’s next for me professionally is a job, but what’s next for me is more life – creative exploration, time spent applying the parts of myself I’m most proud of, and time developing other parts of myself for me and other people in my life. Oh, and fun. There’s something I’ve been saying for years to teams, and that I need to remind myself, “Do serious work. Don’t take yourself too seriously.”

Was leaving my last job pandemic-related? I think it was. The pandemic, both my own direct experience and observing that of others, made me realize more than ever just how limited time can seem when things change outside of my control. Knowing that. I may as well change it up and make it as enjoyable as I can.

Posted on

February 22, 2022

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