A New Job!

Why I’m changing jobs—and how change feels as an adult.

January 24, 2019Filed under blog#adulthood#career#tolkienMarkdown source

Assumed Audience: People interested in my career shifts—whether out of personal interest or technical interest.

Big news: Yesterday was my last day working for Olo, and on Monday I start working on front-end infrastructure for LinkedIn!

This is a huge change for me: I’ve been at Olo for almost exactly three years now1 and it has been the best job of my career. The people I’m leaving behind are fantastic, and I’m going to miss working with them day in and day out. This is the best team, and the best culture, of anywhere I’ve been so far. Granted a small sample size—Olo is only my third full-time job since I graduated college—I’m still comfortable saying that it’s unlikely to be topped in that sense any time soon.

With such a significant change comes a big blog post, in two parts:

I. On Moving From Olo to LinkedIn

So: if Olo’s people are so great and I’ve enjoyed working there so much… why am I moving on? The short version is that the opportunity at LinkedIn is a better fit for my current ambitions. The long version… well:

When I came to Olo, I just wanted to be working in front-end web development and UI/UX full time. I had spent the preceding six and a half years writing C, C++, Fortran, and Python in my full-time roles. As much as I enjoyed many things about that work (and as grateful as I am for what I learned on those projects), I was ready to be working full-time on the kinds of things I actually enjoyed: namely, front-end web development! My goal in late 2015 was simply to get a job doing that. When a good friend said, “Hey, Olo is hiring and you’d be a great fit,” I passed along my résumé and gladly took the job when it was offered—and I have never regretted it. There have been bumps and frustrations along the way, to be sure, some of them large—as there will be with any job—but my overall feelings on Olo remain extremely positive.

For the last three years, I worked full time on one project: Olo’s first Ember application. I deeply enjoyed a lot of that work, for a long time. It was only the third time I had ever worked on a greenfield project in my entire career—and the first time working on something at this scale. Building UI was indeed a lot better than the kind of work I had been doing previously. Over the course of that project, I grew from just working on the code as others decided it to its technical lead—and I enjoyed that, too.

More, over the course of those three years I got over a deeply internalized sense that my job was to shut up and build what I was told. Previous job experience had beaten me down pretty thoroughly in various ways. I had come to expect that my opinion would neither be asked for nor appreciated if offered. Olo expected the opposite of me: to think about a problem hard and to argue strongly for what I thought was the best solution (if also to listen well to what others thought). If something seemed like a bad idea, or it seemed like there was a better way forward, I was not only allowed but expected to offer that input. It took the first half of my tenure at Olo for that to sink in, but it finally did—and I’m profoundly grateful for the change.

Something else happened over those three years as well, though, and this is why I’m moving on now. Within my first few months at Olo, I had started contributing little bits here and there in the Ember open source community. By the end of that first year, I was experimenting with first Flow and then TypeScript, looking for ways to improve our development flow and decrease our bug rates—and found that there was a huge void of leadership in that space. So, a little over a year in, I was leading the effort to make TypeScript good in Ember. By the end of 2017, my friend Ben Makuh and I had built True Myth, a TypeScript-native library for (in our humble opinions!) better handling for null and undefined and errors. And over the course of 2017 and 2018, through the combination of writing, teaching, and collaborating on code, I helped make TypeScript much more mainstream in Ember.

Those efforts, and the small—but real—impact they have had on the broader ecosystem, are far and away the things that have brought me the most satisfaction in my tenure at Olo. And so, over the last three years, my ambitions have slowly but steadily shifted: from write front-end web software to find ways to move the whole industry forward. To be clear: it’s not that ecosystem work is better than the work of product development, and in fact the best ecosystem work is deeply informed by the experience of product development—but they are very different.

The result has been increasing misalignment between what I want to be doing—what I find most energizing and motivating—and what Olo needs at this phase of the business’ life. And not through any fault of Olo’s or mine! Olo is still a relatively small organization; it does not yet have the room to support engineers working at the ecosystem level full time, or the need for that kind of investment. Some work in that direction is welcomed within the organization: certainly no one ever complained about the work I was doing …but mostly Olo needs product built and improved, and yesterday! Over the course of the last many months, I had a frank dialog with my manager and others at Olo: can we find a place where my aims and Olo’s overlap? Ultimately, we concluded that the answer was no.

By contrast, LinkedIn is at the scale where it makes sense to have engineers investing in ecosystem-level work. Going there lets me align my passion for that kind of work with what the business needs. So here I go, and I’m excited to see what I can accomplish with the rest of the folks at LinkedIn! But not without some some melancholy: as I noted at the top, I’m leaving the best job and the best team I’ve ever had. It’s a strange mix.

II. On The Experience of Change as An Adult

That strange mix of emotions is the topic of the second half of this post. Life changes like this are simultaneously momentous and strangely quiet. When I was younger, I expected large shifts in life to have some sense of their importance: a “big bang” feeling to them, and a feeling of finality. It would seem that days like yesterday—as I wrapped up everything that was on my plate and even had a little (all-remote!) hang-out to say goodbye—would lend themselves to just such a sense of import and finality. Instead, it was mostly a day like any other, and at the end of it I was left only with a lingering melancholy.

I recall feeling much the same at every major event in my life since I graduated high school—save three: my wedding, and the birth of each of my first two daughters. Graduating from college with a bachelor’s degree, starting my first job, quitting that job and starting my second job, moving across the country to start seminary, quitting my second job and starting my third (at Olo!), graduating from seminary, moving back across country to live nearer family, and now quitting my third job to start my fourth: each of these seems like a major moment in life. In many ways they were major moments. I can mark important shifts in my own history with them. None of them quite felt like I expected, though.

Much of adulthood is like this, I think: where stories train us to think that life is experienced as stories, with rising action and climax and denouement and clarity about which is which, life as we actually experience it is more self-contiguous than that.

When I was younger, I found the end of The Lord of the Rings rather curious in many ways: Sam’s response made sense to me, and Frodo’s… didn’t, exactly. A truly momentous thing has happened in the world, with his efforts at the center of it. Yet he returns home and finds things not as he expected: the world has changed, and he has changed, and he enjoys his life and goes on living it for quite some time, but with a deep and lasting sense of melancholy. I wonder now, having lived through nothing so momentous as the War of the Ring—or Tolkien’s own experience of the first World War, which was itself an event deserving of the word “momentous”—if part of what Tolkien was painting there was his own sense of life as it simply went on and he found that both he and the world had changed. Though the events we experience do inevitably mark us, they mark us in slower and subtler ways than we imagine as children.

More: the marks they make come not at the moment so much as in all the moments afterward, when many things are just as they were before but so many others are different (and even those, often in ways so small we don’t notice them all that much at first).

I have at times found this actively disorienting. When we moved across the country to be nearer family in late 2017, I kept expecting to feel… something: to have some heightened experience of difference. That wave of emotion never came. My days went on just as they had before, just with a different local time for the meetings courtesy of changing time zones. That there was no obvious half-empty page at the turn to a new chapter left me feeling off: shouldn’t there be?

Yet a year and some months in, my life in North Carolina feels a lifetime away. My friendships are different. My rhythms and routines have all shifted in little ways, pushed on by everything from differences in my family’s schedule to the differences in the weather. I feel the difference the more keenly (if still in that melancholic way) now than I did when I expected to most. It comes out and batters me with grief in surprising ways and at surprising times; and it comes out in little joys at times as well.

I am sure the same will be true of this transition in jobs. These relationships I have built up over the last three years will shift and change. Some of them will fade; others (perhaps surprising ones!) will endure and change but for the stronger. My daily routine will be subtly different, and the particular sources of frustration and joy will shift in kind with the differences in task and the differences in my company culture and all the myriad small things that will be different—and I will not really be able to feel any of those, I think, for quite some time.

This is, I find, much of what it is to be an adult. Life is full not so much of the big moments we expect (and even, to some extent, experience) as children; but rather the slow accumulations of change, the long melancholia, the slow-built joys. Life is sediment, slowly forming something deep. The mighty eruptions that are a marriage or a child’s birth are few; and thankfully so are the earthquakes that are a loved one’s death or other such griefs.


  1. The 18th was my 3-year anniversary, so it’ll be just under three years and one week!↩︎