A Millennial Career Ramble for 2021
In the past five years I’ve had three career changes, one of which involved a nine month, full-time educational program. It sounds like a lot, and maybe it is, but at the age of 35, I’ve finally realized that this is the new normal. Not only is it normal, but switching companies (and careers) leads to unexpected opportunities.
I’m currently having a “full circle” moment. In the mid 2000s I attended college, as you do (I’m very happy to see younger generations re-thinking traditional education and putting off going to college, or not going at all — I probably should have taken a gap year in hindsight to figure my sh*t out). In the mid 2000s I knew I loved writing, but the thing is, you don’t really need a college degree to write books, which is what I wanted to do. While I took fiction and non-fiction writing classes, I also took classes like marketing, technical writing, and journalism. I liked marketing a lot and thought, hey, while I’m writing my books, it would be cool to work in the advertising industry — like copywriting!
I graduated college in 2008, so yay me. My cousin happened to work at a well-known advertising agency in Boston, and told me it was not the time to get involved. Companies weren’t spending money on advertising, so advertising companies were laying people off as they tried to navigate the recession. I ended up getting a job at Apple. In 2008, Apple was well known to me, as I grew up in an Apple household, but surprisingly, it wasn’t the super store it is now (though it wasn’t long before that changed). In 2008, the genius bar was mostly empty all day, and while iPhones had made their debut, they were unaffordable for a lot of people.
I stayed at Apple for about seven years. Apple customers span the entire spectrum, from the coolest people you’ll meet, to literal demons. Being Boston adjacent in Cambridge, we also had the “but I work at Harvard so I’m a special snowflake” type, to which I always wanted to respond literally the whole town works at Harvard you f*ckwit, you’re not special. But I digress.
Eventually, toward the end of my career at Apple, I was working as a scheduling administrator. We had a large team, and their schedules needed to be created, managed (in 15 minute intervals), and maintained. I really enjoyed this. I weirdly enjoyed this. Who knew that I might be happiest in an office administrative role? The problem is when I started looking for this type of job around Boston, they all paid less than Apple. I knew I needed a different plan, because I couldn’t afford to live in Boston and take a pay cut (I was mostly living paycheck to paycheck during these years). Then in 2015, Boston had a Terrible, Horrible, No Good, Very Bad D̶a̶y̶ Winter. I reached a breaking point, quit my job, and moved to Denver (300 sunny days a year)!
While it was kind of a quick decision to move, Denver wasn’t random. I had been going to Denver for three years to visit friends, and from the very first trip I made, I knew Colorado was special. There’s just something about Colorado. People who live there hate when other people figure out how amazing it is. And I don’t disagree. I was part of the transplant problem. Though arguably, the Californian transplants are the worst (jokes, jokes, jokes…but not really). I found a job at a small law firm as an admin pretty quickly (career change one). Turns out it was not as fun as I thought. Though this was also due to the fact this law firm was trying to get away with having someone act as a legal assistant without actually being a legal assistant. I did get to become a certified notary though, which was cool.
Then I realized I was repeating a problem. While being an admin seemed like the thing I wanted to do, there wasn’t much room for growth that I could see. I’d likely get stuck in a certain salary range, and never leave. Denver is cheaper than Boston, but not so much that I didn’t still feel stressed about money (and in 2020, maybe it’s as expensive — Denver’s growth has been huge the past few years). So I made another dramatic decision, and I took out a loan to attend a full-time software engineering program. I studied frontend development for nine months at the Turning School of Software & Design in Denver (highly recommend if you’re looking for a much cheaper web dev/CS college alternative, or are interested in making a career change to development). While it kind of seems like another quick decision, it also wasn’t random. I had always been interested in development. Back in the day, I would do that weird hacky thing in LiveJournal where you could change the code. I loved playing with iWeb when that was a thing. Not to mention my college roommate, who I moved to Boston with, studied web development at our college, and immediately got a high paying job in 2008 — I paid attention.
While I didn’t intend to leave Colorado, after my program ended, I got the opportunity to move to Amsterdam for work through a referral. I became a frontend developer at a SaaS company in The Netherlands (career change two). This company was in a growth phase, and was hiring a lot. I was hired around employee 80(ish), and within two years they had grown to 250(ish) employees. This was my first experience with start-up culture, and it had all the trademarks. Lavish holiday parties, and annual company off-sites in neighboring countries. A lot of benefits that were meant to be a shiny distraction from some core problems.
I stayed at this company for just over three years. As a woman in tech, I can say it was a great company to work for. Yes, there were a lot of micro-aggressions, and there was not any female representation at the C-level, or on The Board, but overall, being a female developer at this company did not come with any of the major problems I’ve heard other female developers talk about. However, after about a year and a half, I was starting to become disillusioned. Since it was my first time in the start-up environment, I didn’t know if this was a me problem, or if this was just the natural cycle. I’ve heard a lot of tech start-ups sort of build their culture around the expectation that employees don’t stay more than a few years.
Having worked at Apple for seven years, it felt weird to want to leave a new job after just a year and a half. I went on a few job interviews at other tech companies in Amsterdam, some of which were really cool, and I would have liked to work there (but I didn’t get the job), and some of which I could have gotten a job at, but I didn’t like the vibes. I know it’s a privilege to make a decision to stop an interview process because there’s something I don’t like, but until a robot can do my job (which honestly might be soon), I’ve learned that it’s okay to be picky about where I work, and how a company can work for me, as much as I can work for them.
Fast forward six months later, right after I had gotten back to Amsterdam from the US for winter holidays — I made the decision that I would try and move back to the US in the spring of 2020. While I loved living in Europe, and I loved the friends I made, I felt ready to buy a house, and was contemplating only applying for fully remote jobs so I could live where I want (foreshadowing in the worst possible way). Why not buy a place in Amsterdam? Honestly, I never fell in love with the city. When I left Boston, I kind of knew I never wanted to live in a huge city again, and not only is Amsterdam super crowded, like, all of the time, there were a lot of little things about living there that gnawed at me.
Of course, 2020 did not go as planned for anyone, so right after I started my job search in February, I stopped. I stayed put and just anger-coded my way through most of the year. My company obviously went “work from home” (and I use that phrase instead of “fully remote” for a reason). The people in charge of my team had always argued that we simply couldn’t work from home because it just wouldn’t work. Turns out they were wrong, like we all knew they were. For the most part, I think we were more productive working from home.
When September rolled around, and the company hadn’t announced any plans to be fully remote — everyone would still be required to go back to the office when it reopened — I knew for sure that I wanted my next job to be a fully remote one. By that time the working world had gotten a chance to figure out how to move forward, and I found a lot of companies had started hiring again, especially for remote workers. I casually applied and interviewed at various companies, both in other European cities and in the US. With everyone’s emotional and mental health taking a turn in 2020, I decided to treat this job search as a if it’s meant to be kind of thing, and didn’t burn myself out on the hunt.
And now here I am, my third career change in five years. Through a network I happen to be a part of, I found out about a fully remote company that needed to hire a technical writing team. This is the “full-circle” moment I mentioned at the beginning. I had three years as a working developer, and nine months as a development student (which honestly at times was much harder than an actual development job). I also had a degree in writing and communication which I had never used. My job in Amsterdam kind of burnt me out on development, so I thought it would be interesting to utilize those skills in a completely new way. Switching to tech writing felt like the right fit for this time in my life.
So far, I love it. My experience as a developer at a SaaS company came in handy day-one at my new job. I have first hand experience in a lot of things I’m writing about. I’m also really excited to learn about things I’ve only passively had a role in as a developer, like SEO best practices. Software development salaries are high, another thing I know is a privilege (along with hard work). I was able to become debt free thanks to breaking into the development world. While my new job pays well, it doesn’t pay developer salaries (though there is definitely room for good salary growth at my company, which was a huge consideration on accepting the offer). But the fact that I was debt free meant I could make a career decision to take a small salary hit to do something I thought would be a really great fit.
The generations that have defined the Internet will have the final say in how companies grow their workforce and culture.
I think Millennials and Gen Z are in a good position to redefine work culture, especially after 2020. I knew I wanted my new job to be fully remote (I did move back to the US), with a well defined growth structure for employees. Those were the two things I was looking for, and even better, I got fully remote, a well defined growth structure, and a company with transparent salaries (this could be a whole other post). As more companies move online, or recognize that online revenue/growth is likely the future, the generations that have defined the Internet will have the final say in how companies grow their workforce and culture.
If you’ve read my entire ramble, thank you. I wanted to start writing again for myself, and thought this would be a good topic to start on. I realize I’m writing this from a place of privilege, but I’ve also seen people from all walks of life break into the tech industry and succeed, or make dramatic career decisions like starting their own companies, and succeed. Young people have started questioning the educational status quo. Millennials and older Gen Zers are looking for new jobs — and interviewing the company as much as the company is interviewing them. It’s time to start making jobs work for us, fit our lifestyles, and allow us to live a life not defined by work, but by our individuality.
