Last July, I retired from the Metropolitan Transportation Authority after 24 years working at MTA HQ and New York City Transit, the agency that operates subways and buses. In my final role there, I was the agency’s first Senior Creative Director, leading a recently unified in-house team of nearly thirty designers, videographers, copywriters, mapmakers, and project managers. We were responsible for the MTA’s visual communications and branding, creating marketing campaigns, videos, maps, social media assets, and digital wayfinding, to name some (but not all) of the work that came our way.

My departure was bittersweet. I loved my job — most days, anyway — and there was still so much more I wanted to do there. But two dozen years was a lot of time to spend in just one place, even a place as big as the MTA. Summer 2022 was the right time for me to move on.

As I mark seven months since retirement, I’m sharing this reflection of my time at MTA and the path that got me there. As Steve Jobs famously advised, “you can’t connect the dots looking forward; you can only connect them looking backwards.” Herewith is my dot drawing.

Oh the Places You’ll Go (After a Thousand Hours of SimCity)

My path to the MTA and my tenure there were like nothing I could have ever planned, although in retrospect it looked quite logical — maybe even obvious — because it integrated so many things I’d always loved. From a young age, I was drawn to movies, cities, transportation, sci-fi, design, technology, journalism, and storytelling. Decades later, my day and night jobs would encompass all of these things, but getting there was anything but straightforward.

My mother and stepfather were restaurant workers, working twelve hours a day, six days a week to keep us (barely) afloat in our suburban New Jersey town. In our working-class immigrant household, money was always a concern and financial disasters were not rare. But my parents were determined to give my brother and I as much of a middle-class life as they could afford, allowing us to pursue any interests that caught our fancy and attend any college we could get into.

The freedom to do whatever I wanted meant that I did a lot of exploring, without much focus or structure but always with an eye towards avoiding financial ruin. I seriously pursued journalism in high school and college (Rutgers-Newark, then NYU) until an externship at a paper in New Jersey doused my enthusiasm for the profession. The paper had just laid off a third of its staff and the vibe in the newsroom was poor, to say the least.

The lesson was clear: doing what you love isn’t worth the risk of being laid off.

After that experience, “pre-law” looked like a safer economic proposition that also seemed interesting and reputable. Then by chance I met a lawyer at a well-known Midtown firm who was gleefully quitting to pursue a Ph.D in history. When I asked him about the career change, he eagerly told me that many of his colleagues went into law because they were too scared to pursue the thing that they really wanted to do. Law presented them with a safe way to be adjacent to their real interests without incurring the risks of actually Doing The Thing. Would-be actors became entertainment attorneys, would-be athletes became sports attorneys, etc. He was adamant that he wasn’t going to make the same mistake, so he was getting out before he got in too deep.

This was another lesson: doing what you don’t love for money and security isn’t worth it.

In our family, a “career” was whatever paid the bills, with no expectation that it also needed to be something that you actually enjoyed. I wasn’t ready to give up finding a job I loved, but until I did I’d have to earn some money. Post-college, I worked at a real estate company, followed by a few years at NYU as a junior administrator. These were not dream jobs, but they helped pay the rent and I was fortunate to work with some wonderful people that I learned a lot from. But I suspected that I should keep trying to dream a little bigger.

Partly inspired by playing too much SimCity on the Amiga during college and fired up after reading The Power Broker a few years later, I enrolled in the NYU Wagner urban planning master’s program in summer 1996. I didn’t have any particular career goal in mind. I just knew that urban planning had an enormous impact on people’s lives and that the classes at Wagner looked so interesting and fun that I wouldn’t regret taking them even if they never led to any job prospects. Working at NYU also earned me a steep tuition discount, which helped my finances greatly.

I loved my time at Wagner. The classes were stimulating and my professors and classmates were a diverse and fun group of nerdy do-gooders. We got excited discussing topics like ULURP and CEQR, single-payer and federal funding formulas. We were eager to serve the public and change the world. I wanted to do my part by working in transportation.

1998-2000: Early Years

After graduating from Wagner in spring of 1998, I landed a job that summer with Transit’s Office of Management and Budget (OMB) as an Associate Staff Analyst. The job paid $48,000 per year, far more than I had ever made and an amount that I was sure would fund a comfortable life in NYC (spoiler alert: it didn’t). By this time, my career aspiration had become more clear: to eventually be the “Robert Moses of Transit” (my own actual words, sadly). Excited and more than a little naive about what was to come, I threw myself into the work.

At OMB my job included wrangling the biggest Excel spreadsheet I’d ever seen: the daily tally of subway and bus revenue and ridership. This was a single Excel tab for an entire year’s worth of subway and bus rides, categorized by station, bus route, and fare type. The file took several minutes to load on my Compaq tower running Windows NT and it only got slower as the year went on and more cells were added. To this day, I still get anxious thinking about this monstrous XLS file.

After nearly a year in OMB, I realized that I really liked working at Transit but was no longer motivated to continue crunching revenue and ridership data. I started looking at the internal job postings and got a position with Transit’s Marketing Research team. There, I was involved in a number of customer-focused projects including focus groups on subway floor tiles, prototyping safety signage for construction barricades, and investigating improvements to the system of colors used for station entrance globes. I loved doing customer-facing work, especially involving design. But the team wasn’t particularly influential within the organization, so little of our work resulted in anything tangible. I left the group after a year to join Transit’s Operations Planning division.

Today’s MTA is much more receptive to customer feedback than it was twenty years ago, but much of that has to do with the rise of social media more than the formal customer research functions. For better or worse, I suspect this is also the case at many other government organizations and private sector companies. Nobody likes getting shamed in public, especially virally.

2001: September 11

Like most people who were in New York on September 11, 2001, I remember how beautiful the weather was that morning. The biggest event in the city that Tuesday was the mayoral primary election.

The rest of the day was a blur. I arrived at my desk at 130 Livingston Street in Downtown Brooklyn to find my colleagues gathered around the TVs in the break room and in the division head’s office. There was very little talk. The Twin Towers were on fire.

As part of my job, I occasionally staffed the city’s Office of Emergency Management (OEM) command center as part of an MTA contingent, usually during weather emergencies. Soon after I got in that morning, I was asked to make my way to NYPD Headquarters at 1 Police Plaza in Lower Manhattan where a temporary emergency operations center (EOC) had been established. In the past, the EOC was hosted at OEM’s offices at 7 World Trade Center, but that building was now on fire due to debris from the collapse of 2 WTC.

Getting to Manhattan wasn’t easy. The trains were not running and the Brooklyn Bridge was packed with people fleeing Manhattan. So I sprinted to the Manhattan Bridge, which I thought be would be less crowded. On the Brooklyn side, I flagged down an MTA bus that was heading in but the bus operator wouldn’t let me on. Resigned, I walked over the bridge against the flow of thousands of people leaving Manhattan. Somehow, I made it to Canal Street in Chinatown and then walked a few blocks south to 1PP. After clearing security, I took a seat alongside other MTA colleagues in the NYPD command center.

At some point during my shift, Mayor Giuliani came in to address the room. Everyone stood at attention when he arrived. I don’t recall the speech exactly but it wasn’t very long. The only part I remember is that he said that the people who attacked us were jealous of our freedoms.

Later in the day, OEM set up another temporary EOC in P.S. 89, a primary school across the street from the World Trade Center site. Its cafeteria had been turned into a makeshift situation room and now hosted many of the non-law enforcement staff that had been at 1PP earlier in the day. It was surreal to see all of us there doing our work sitting in kid-sized chairs with children’s artwork on the walls.

I made it back to Prospect Lefferts Gardens around 8 or 9 that evening. Too exhausted to cook, I stopped in a Chinese take-out to pick up some dinner. While waiting for my food, an African American guy in his forties came in and placed an order. He noticed the white dust on my shoes and pants and I noticed that he had it too. We hugged and went our separate ways after we got our food.

For weeks, the plume emanating from the WTC site was a ghost over New York. The Twin Towers had been a familiar and reassuring landmark outside the windows of our Q train when it crossed over the Manhattan Bridge. Now it was a sad reminder of what had been — and a foreboding sign of what was to come. For weeks, we would stare silently though the glass when the Q emerged from the Manhattan tunnel. Inevitably, you’d hear someone quietly sobbing. Sometimes it was me.

2009: Day Job Meets Night Job

At the start of 2009, I was working at MTA headquarters as a strategic initiatives manager in the policy and media department. By the end of the year, I was a videographer on the media side of the team. Armed with a Sony EX-1, a Mac, and Final Cut Pro, my job had transformed from managing sustainability projects to starting up MTA’s first YouTube channel and making videos for it. It was the beginning of an entirely different career trajectory, one that would take me to places I’d never have imagined, both literally and professionally.

How did this happen? I try to avoid cliches, but this really was an example of “luck” being the result of preparation meeting opportunity. Five years earlier, I had started teaching myself filmmaking in my spare time. It was something I’d wanted to do since I was a child but until the advent of digital video and desktop editing in the early 2000s, filmmaking was expensive, complicated, and totally out of my reach. But by 2004, even a newbie like me could make watchable short films that looked good on a big screen with just a Mac and a camcorder.

I couldn’t afford film school, so I learned filmmaking the old fashioned way: by making films. I’d gather actor friends that I’d met in the Asian American theatre scene and we’d make little movies on the weekends. The cheapest one I made cost $94, the most expensive one was $5,500. I would show these movies at festivals around the country, meeting other filmmakers who became collaborators and friends. It’s an amazing feeling to see a movie you made play on a giant screen for a theater full of strangers, especially when they like it! Once you’ve made something that connects with an audience, you just want to keep making more.

As many of you know, however, launching a side gig when you already have a main gig is a heavy lift. My night job of filmmaking was physically exhausting and a significant sacrifice of my time and money for many years. All my extra cash and vacation time went towards film, be it for shoots or for festival travel. I rarely had a “vacation” that wasn’t film-related and I couldn’t splurge on anything other than a nice meal every now and then.

By 2009, small-time moviemaking had become my main focus, but I couldn’t see how film would ever pay for itself, let alone pay my rent. Moreover, I still cared very much about public service and was proud to work at MTA even though I knew I was underutilized there. Together, these activities made for a very fulfilling life but I often felt like I had a spilt personality.

So I built a yin-yang life that integrated both: a day job that would fund my night job, and a night job that would give me skills in moviemaking and storytelling that I could use at the MTA. I pitched my boss at MTA HQ on the idea of a YouTube channel where we could showcase the agency in a way that hadn’t done before. I convinced him that we could do this cheaply: just $8K for an EX-1 and a borrowed Mac from my previous job at Transit.

To my delight, he took a chance on the idea (thanks again, Jeremy!) and we were off to the races. We launched the YouTube channel in early 2010 with an archival upload of my favorite MTA commercial and followed it with a regular stream of new videos about agency initiatives. The early reaction from both the public and our employees was very positive, so HQ management directed us to keep going. At my night job, I received my first commissioned project (finally, someone else was paying for craft services!) and began working with rising stars, some of whom would become household names.

For the first few years, I was the one-man-band video team at MTA HQ. It was hard work but I loved it. Over time, as the demand for video grew so did my team. We got to see parts of MTA and New York City that few people knew existed and share them with the world. There were tiny train fleets and big ones, TBMs and CBTC, police dogs and peregrine falcons, controlled demolitions and hidden artworks, marathons and abandoned trolley terminals, birthday greetings and snow plans, welcoming a new Transit president and sadly saying goodbye to him.

It was especially interesting covering a topic as it evolved, like with Superstorm Sandy in 2012: first there was the disaster, then the repairs, then more repairs, then the really big repair (take one, anyway). We even got to cover how we had covered it.

The MTA is one of New York’s best-known and most highly-scrutinized public agencies. It’s not a stretch to say that there’s worldwide interest with our subway, which for better (and worse) is unlike any other metro system. As a 24/7 operation, the MTA was literally a place where the action never stopped, which meant that there were an endless number of fascinating stories to tell. I felt incredibly lucky to be part of the team that told them.

2018: Just Tap and Go Make Cool Things

With video, I’m proud that we not only brought the MTA into a new medium, but also a new kind of messaging: a voice that was less formal and more authentic, more focused on showing our work instead of selling our organization. I got to help drive this change in a much bigger way when I left HQ in 2018 to become Senior Director for Digital Content at Transit. It was beyond thrilling to be joining Andy Byford‘s team and working for his Customer Service SVP Sarah Meyer. (Pro tip: great bosses help make your great work possible, so choose them wisely. I am grateful to have had several at MTA.)

These MTA superstars empowered me to pursue a simple goal: make cool things that help Transit customers. Over the next few years, we did just that: creating campaigns introducing OMNY and Fast Forward, bringing back the Vignelli-style diagram and rethinking our print maps, and launching a transformative real-time strip map for subway stations, to name just a few. (Sarah and I discussed how we approached this work during our keynote at TransitCon 2022.)

By 2021, I was back at HQ as the newly-appointed Senior Creative Director, leading a newly-integrated all-MTA creative services team. Our portfolio of work was vast, incorporating branding, marketing, and visual communications for the entire MTA. The job was a big one for me, but it paled in comparison to the challenge that our agency faced in midst of the pandemic: winning back riders that left us during COVID-19. The role of public transit in urban life was now in question as it had never been before, an existential predicament that the MTA and other agencies are still grappling with.

2020: The COVID-19 Pandemic and Safe Travels

It wasn’t obvious at the time, but looking back it seems clear to me now that the evolution of MTA messaging culminated at a time when it was needed most: the COVID-19 pandemic. In response to COVID’s arrival in New York in March 2020, we created MTA Safe Travels, a campaign that encouraged mask-wearing on public transit and reassured our riders that the system was safe to use.

Safe Travels utilized the now-iconic black-and-yellow illustrations and punchy copy in every medium available to us at MTA: digital signage; signs and decals in stations, buses, and trains; social media; and even merchandise. If you were riding MTA during 2020-2022 you couldn’t miss these messages, which was precisely the point.

From the start, we decided that our campaign would be most effective if we talked to New Yorkers like a New Yorker: honest, tough, smart, compassionate, and even a bit playful. The pandemic was scary but we knew our campaign didn’t have to be. I like to think that Safe Travels helped embody the spirit of those essential workers who showed up every day on our system, whether they were literally running the MTA or using us to get to their jobs keeping New York going during an incredibly bleak time.

I’m especially proud that the campaign helped encourage a very high mask-compliance rate among our riders — often over 90%. When have 90% of New Yorkers agreed on anything?!?

A Workplace that Never Stops in a City that Never Sleeps

I departed MTA with an overflowing affection for the place where I spent over two decades and for the people who were my colleagues, mentors, and friends. From them I learned so much about transit, New York, public service, leadership, and — most importantly — how to be a better version of myself. Having spent a large part of my adult life at MTA, I feel like I grew up there.

I say this with very clear eyes about what the MTA actually is: one of New York’s great public institutions but also probably one of its most challenging and frustrating places to work. A place where the potential to do great things is as large as the possibility that bureaucratic sclerosis and office politics will kill any initiative. A place where the resources are vast and yet often squandered in so many ways, large and small. A place where your days could be filled with never-ending firefighting or spirit-crushing stasis waiting for someone higher up to make a decision. A place where you’ll work with some of the most dedicated public servants you’ll ever meet and sometimes a few of the least motivated ones.

On a macro level, the outlook for MTA is discouraging: chronic fiscal instability, cumbersome state-city power sharing and co-dependencies, and byzantine formal (and informal) political alliances. All are impediments to success in a tough industry where you’re only as good as your last rush hour, where nobody notices when you do your job well but everybody notices when you screw up their commute. It’s difficult to understand why public transportation in one of the world’s great cities is allowed to exist like this.

Sound hopeless? Not at all. The best of my MTA colleagues were well-aware of the agency’s many weaknesses, but they performed their jobs to the fullest nonetheless. We knew the game was often rigged against us, but we played anyway. Because if we didn’t, we knew our riders might suffer as a result. We couldn’t let that happen on our watch, so we kept going, doing the best we could given what we had to work with.

There’s a real esprit de corps at the MTA that is often invisible to the public but that will always be part of my fondest memories there. In a workforce as diverse as New York, the quiet dedication I saw among so many of the MTA’s 65,000+ employees made me so proud to work alongside them. I did my best to shine a public light on them whenever I could through our videos and campaigns.

I’m grateful for my time at MTA and I hope I was able to give back at least as much as I got. If you ever have a chance to work there, I hope you have a ride as good as the one I had.

Note: I also met my wife at MTA, but that’s a story for another blog post.