Real time notes on changing careers

career change pt 1

The other day at work, during our weekly performance review meeting on Monday afternoon, we paused at the beginning to talk about the protests that had erupted around the country over police brutality and the murder of George Floyd. People spoke openly and honestly about police brutality. One or two people wept. It was actually a productive conversation–the kind you don’t often see in corporate America. And then…it was over. We went right back to talking about how performance was 3% off from the forecast that we made six months ago–before impeachment, before the coronavirus, before George Floyd. It was a jarring transition. The world is burning outside and we’re talking about some irrelevant financial forecast? I’d been coming to terms with my career for a while at this point, but this is the last straw. I have to get out.

When I made the decision to change careers and started looking online for advice, I didn’t find anything that useful. There are tons and tons of articles and resources out there, but they all felt like they were written by people who studied a career change from afar, rather than by people who actually changed careers themselves. I use online reviews all the time, and they are incredibly helpful. I thought it was important to actually contribute, instead of just being a lurker, and maybe this can be helpful to someone thinking about or going through the same change.

In this series of posts I’ll do my best to explain how I realized I needed to change careers (that’s this post), how I’m going about learning and getting experience to prepare for the transition (in very practical terms), and how I deal with the day to day challenges. My goal is to generally chronicle my journey along the way.

When I graduated college, I had big plans. I was going to move to San Francisco and take over the…yeah, no. I had no plans. I had no idea what I wanted to do with my life. Some friends of mine with jobs already were moving to San Francisco, so I figured I would, too. The problem was that I spent so much time screwing around in college that I managed to graduate without any real skills. I’d done a summer internship at a tennis tournament once, so working in sports seemed like the path of least resistance. I got one job offer and then abandoned that plan when I realized how little behind-the-scenes people get paid and how much they have to work. I think I calculated that I’d be making $2/hour or something like that. Not exactly enough to live on. My heart was never really in it, anyway. Instead, I took the next offer I got: at a startup as the CEO’s assistant. As the company grew, I switched jobs a few times and eventually moved into product management. If you don’t know, Product Managers work with a team of engineers, designers, and data analysts to basically decide what features to build and how to build them. PMs are also supposed to do a lot of “stakeholder management” which always reminded me of the scene from The Wire where Tony gave advice to Tommy Carcetti. Fast forward a few years and I lost that job. I and a dozen others were laid off when the startup was trying to “cut costs.” (I don’t think the executives took a pay cut, though.)

I was planning to move to New York anyway (to be with my future wife, for the record!), so it wasn’t a huge deal. When I moved, the only job I was qualified for was a PM, and the same was true when I changed companies a few years later. I didn’t grow up wanting to be a PM. No one does. Product management is a job you stumble into and then convince yourself you love. There were two parts of the job that I genuinely liked: talking to customers and using statistics to tell a story. There is just something so energizing about hearing directly from the people you’re building your products for. Then, you can combine those individual anecdotes with data from all of your customers and put together a story on what the future of your product should be and why. That part was fun. Making 6-month financial forecasts, sitting in hours of boring meetings, having dozens of conversations trying to convince people who don’t know anything about user experience design why automatically copying Airbnb’s design is a bad idea–those parts are way less fun. Unfortunately, those parts are also most of my day. A few years ago I started to think that the problem wasn’t the job, it was the company. Maybe if I just moved to a new, well-run company all of my concerns would go away. Wrong.

Momentum is one of the most powerful forces in our lives. We’ve all got a lot going on each day. Dishes, laundry, a long commute on a crowded subway, frustrating projects. Most of the time, it’s just too exhausting to spend hours each night learning new skills or chasing some unlikely dream. So as frustrated as I was feeling at work, and for as long as I had been feeling it, I didn’t exactly see a clear path forward.

Oddly enough, it finally became clear to me during the pandemic. With nowhere to go, I couldn’t stop my mind from racing. I couldn’t stop thinking about the coronavirus, the election, the murder of George Floyd, the protests that were happening, and the systemic injustices that led to it all. I couldn’t stop thinking about how I had been largely silent through it all. I’d been involved with campaigns and activists groups before, but when it comes down to it, I spend the majority of my waking hours in meetings like the jarring one on that Monday: going over meaningless 6-month financial forecasts, writing memos and briefs and emails that no one will ever read, while the city and the entire country burn.

In 2019, during a period with the lowest unemployment rates on record, I lost my job and was unemployed for six months. In 2020, during the height of the pandemic when the unemployment rate reached its highest point since the Great Depression, I’ve kept my job so far (knock on wood). I am so, so grateful to have a job. I know what it’s like to not have one and be on unemployment, to be wracked with anxiety over every little purchase or cup of coffee. I’ve been on that emotional rollercoaster of getting an interview, thinking you’ve done well and have a shot, and then getting that rejection letter. I was having panic attacks almost daily. Before interviews, at home in the morning, in the afternoon, on the subway to interviews, even during the interview once. There were stretches when I was essentially non-functional. Losing my job was a completely paralyzing experience for me, and not one I’m eager to repeat.

But I’ve made the decision to change careers. Of course, I feel conflicted about this decision. I have a good job with a good salary at a good company. We’re in the middle of the biggest economic crisis since the Great Depression. People would love to be where I’m at. But I don’t love it; I feel constrained by it. At times, it makes me angry. At times I feel guilty and shallow. At times I feel contemptuous of my co-workers. I just want to scream at people: “you’re spending all your waking hours making fucking spreadsheets so that some CEO can make $6 million this year!” Maybe a better person would only feel grateful and not conflicted, but I feel both ways.

What I realized, though, is that I can be grateful I have this job and still aspire to do more. I realized that, to really come alive, I need to find a job and career that really aligns with my values. I’ve made my decision but that doesn’t mean I’m ready to just up and quit, though.

So at the same time my frustration with my job is pushing me out, I know I have to have an equally strong positive vision that is pulling me forward. Earlier in the year, I took a data analytics class, just to learn some new skills in my current job, and at some point I realized I was learning skills, like Python, that could be applied to other areas. Of course, that also meant that I was learning, more generally, how to “code.” This was something I’d never really done before. My newfound skills and the resultant confidence opened up a world of possibilities in my mind. I’d already been day dreaming for a while what it would be like to be a data visualization expert, but never seriously considered it because it felt so out of reach. Now, though, anything seems possible.

Well, it’s not actually just data visualization I’m after. Long term, I want to help progressive women and people of color hold elected office and utilize their power to fight for equity and justice. I’m especially interested in and passionate about protecting voting rights for communities of color, reducing gun violence, and fighting climate change. I got interested in data visualization because I thought: “how can I use these new skills to achieve these goals?”

Turns out, some of the best work in these areas have been by data journalists. ProPublica holds election officials accountable, FiveThirtyEight puts a face to gun violence, and the Washington Post shows that climate change is already here. It’s less about what your job is than about what you can achieve and about how many opportunities you have to make an impact.

Movements start with stories and are bolstered by facts. To me, this is the promise of data journalism: using digital tools to break down complex issues and bring the truth to light; using storytelling and writing and reporting to bring a human face to those facts. It’s the opportunity to fight for justice, to fight again, and to keep fighting. Of course, it’s not the only way. But it’s the way that resonates with me the most. Not only because of the power of digital storytelling and the range of issues you can cover, but because of the breadth of where it can make an impact. Obviously, data journalists fit nicely with newspapers, but those same skills can be leveraged across political campaigns at every level and activist groups like Sunrise Movement or Campaign Zero. As I’m writing this (June 2020), we’re seeing the power of those activist groups like Campaign Zero, which I volunteered on in the past. This stuff really matters.

It matters right now, actually. It is urgent. But it will be a years-long process to build up the writing, reporting, storytelling, and technical skills necessary to make a career out of it. I keep asking myself: How am I going to make it through day by day in a job I actively dislike? Well, first, I am probably at the best company around if I want to learn visualization and storytelling and be exposed to politics. I need to make connections, ask for help, and take advantage of my situation. This is the most important thing I can do and, indeed, I’ve already asked for and gotten tremendous help on some personal coding projects. Second, aside from the obvious factor of needing a paycheck, having a good track record and a good reputation will be immensely critical to helping me move positions. Reporting jobs are competitive. If I can get a good recommendation from company leaders I already work with, that will be huge.

There’s also the chance that this will not make me happy or give my life as much meaning as I think it will. I have a tendency to idealize the grass on the other side of the fence. I have always had a tendency–no matter what job I had or what I was working on–to resent the time spent and wish instead I was reading or learning about something else. Might that happen again? I suppose it might. But I wonder if finally aligning my interests and values with my job and career will at least blunt that to some extent. I can only hope.

edit: see part two here:

- 5 toasts