The defining decade

It’s a strange feeling to be turning twenty nine. It signifies the end of what many write up to be the decade the shapes the rest of your life and who you are as a person. It’s the decade where you typically graduate from college, start working full-time, figure out what you enjoy doing, maybe fall in love, and start settling down. Many feel the pressure to do all of these things before they turn thirty, and a lot of them constantly feel like they’re “behind” on some arbitrarily defined list of things society deems you should’ve accomplished by now.

A lot of folks also have regrets about things they did or didn’t do in their twenties. It’s an easy time to be lulled into activities that you never see yourself doing but want to try anyway because you never know when you might get another shot at it. Alcohol and substance abuse is an easy destructive trap to fall into here for many. Mistakes made with loved ones and people who are close to you can also be common and sting deeply when they stir in your memory. So many people wish they could relive their twenties with the knowledge they have in their thirties, knowledge about themselves, their behaviors, habits, attitudes, and approaches towards things. It’s a clear indication that the decade has a lot to teach people about who they are and what they need to do in order to succeed.

I feel lucky enough that I have little to no regrets about how I spent my time in my twenties. I enjoyed everything I did and very consciously chose how to take the next leap forward. I tried a whole bunch of things to see what I do and don’t like. I experimented with lifestyles, meals, workouts, relationships, people, work, friends, and careers. I’m ending the decade with a much stronger understanding of who I am and what I do well in. I also have a much clearer picture in my head of what I don’t want to do and where I don’t want to go, which is arguably more important.

If there’s one thing that stands out above the rest in terms of the biggest change in my personal mindset that I’ve acquired in my twenties, it’s self-confidence. I had none of it when I was nineteen. I was a college freshman who was being forced into studying something he didn’t really enjoy and had major self-esteem issues. I had a hard time fitting in, it was difficult to explain to others that I enjoyed spending time by myself, and I had no vision of what I really wanted to be doing with my time. But over the course of my twenties, this slowly started to change.

I ended up graduating college with a degree in engineering, but midway through it, learned that I could be getting paid to do design. I had always dabbled in graphic design and web design as freelance or part-time gigs on the side throughout high school and college, but never truly considered it could turn into a full-time career. It didn’t help that the career-oriented “role models” around me didn’t know the first thing about it. No-one knew any designers and didn’t think it was a real job.

But as I got more and more specialized in my major, I learned that Human Factors and Cognitive Ergonomics was a field of psychology and design that I was really interested in. Having the self-taught design background and the technical foundation in engineering set me up to start applying to loads of places for a design job. Almost none of them worked out. I ended up taking an engineering job at a company to see if I’d enjoy it. I didn’t. A few weeks into working there, I knew it wasn’t the place for me. Everyone seemed to have grown up in or around the area (which was in the middle of nowhere), had no real career aspirations or goals, and seemed like they were content to just have a job that paid the bills. No passion, no excitement, and no creativity. Just monotonous boring work. Not exactly the place you want to start your career off.

So I got working on the side. I started more seriously building my design portfolio to apply to places, cold-called tons of people working as designers to see if they had any advice, and incessantly emailed lots of industry veterans to ask about whether they had any job openings. Yeah, I was that guy. Honestly, hating my first engineering job so much lit a real spark in me to get out of there as quickly as possible. My older co-workers talked about how they could get the next promotion or get a slightly bigger raise so that they could afford a down-payment on a slightly nicer car that would make their commute slightly more exciting. Yeah, that’s a huge red flag about the kind of lifestyle you don’t want to end up having, so it was a nice natural catalyst to get me hustling and applying anywhere I could.

And I did snag a pretty good apprenticeship at a company in Cambridge. I ended up joining full-time as a designer and worked there for a couple of years. It was a stark contrast from the other company. People were actually passionate about what they were doing, enjoyed the work, and generally enjoyed each others’ company. Heck, they were all friends and loved to hang out with each other outside of work too. I’m making it sound like a cult, but this was tech in 2015 and literally every startup was like this. After a couple more stints at some tech startups in Boston, I’m now about to ship off to San Francisco to work as a designer at a larger tech company.

Career-wise, I’d say my twenties have been really good to me. I learned my lesson at my first job right off the bat. I realized instantly about the kind of place I didn’t want to be at and the kind of work I didn’t want to do. This is incredibly important to know early on and this is why I encourage people to still take jobs that they’re uncertain about if it’s the only option they have. Sure, they’ll hate it but it’s only temporary and they’ll learn loads about themselves. Some of the best career advice I was given was to experiment in my twenties with my career. Work in small companies and big companies. Work at corporate cultures and startup cultures. Work on B2B and consumer products. Work at agencies and product companies. Maximize the types of places you can work in and try to figure out what you like best. Look for patterns about what excites you and frustrates you. Figure out what types of people you work well with as a manager and a co-worker (and what types you don’t work well with). Learn as much as you can at one place and take it to the next. Then rinse and repeat.

When I turn thirty, I would have worked at five companies in about seven years of being a full-time worker. That seems like a lot, but this is actually the average for a tech worker job-hopping from place to place in this era. My dad has worked for three companies in his entire life, and here I am working at five different places in less than a fourth of the time he’s been working full-time. This just goes to show the massive difference in how generations are approaching and changing work culture. Nevertheless, my self-confidence has only surged every time I’ve gone from one company to another. I know this because my imposter syndrome has almost disappeared after having worked at so many places now and I feel more and more confident about my skills and abilities than I did at my first company. The twenties have been very good for my career.

Outside of work, my self-confidence has primarily come through travel. Yeah, believe it or not, it’s true. I’ve written at length about solo traveling before, and I truly believe that my perspective and worldview significantly changes every time I take a solo trip. It’s honestly stunning how much self-confidence you build through the mere act of surviving a trek through a foreign country with nothing but your wits and senses. If you haven’t done it, I implore you to try it. Book a trip to a foreign country where you don’t speak the language. Spend at least two weeks there. Do things by yourself, visit attractions by yourself, eat meals by yourself, and go on walks by yourself. It’s incredibly liberating and freeing to do whatever you want, whenever you want, and however you want. You’ll run into scenarios that seem dire and disastrous but will be impressed at your own ability to solve the issue and move on from it. Your only worry is the immediate next thing, you don’t have time to obsess over the long-term plan or the end-goal. It’s a daily survival game and it is a true triumph to make it back in one piece.

I’ve had the privilege and good fortune of visiting a lot of places in my mid-twenties, and I definitely made sure to take advantage of it. When friends weren’t available or couldn’t afford to go on extended vacations, I went solo. And when I enjoyed the solo trips more and more, I started doing them even more frequently. These trips have very clearly defined who I am and how I fit into this world. The biggest thing I’ve learned is that people everywhere are just doing the same old routine, but in different ways. Everyone just wants the same things, a meaningful career, someone to love, and a fulfilling life. They’re just going about it in slightly different ways that are attuned to specific micro-cultures as a result of where they live.

Traveling, observing, and surviving in all these places has greatly made me appreciate my role in the world. It has given me perspective that I would’ve otherwise never had if I had just stuck to the corner of the world where my immediate network happened to be. Being able to just live in a foreign place every day as a local and actually making it back has boosted my self-confidence in this defining decade more than anything else. And the twenties are certainly the best time to do it, because it’s the only time in your life where time, money, and energy are somewhat in equilibrium. They only get more out of balance as time goes on.

Finally, gaming has consistently been a big hobby of mine throughout this decade. I used to primarily only play multiplayer shooters on PC ten years ago, but that slowly evolved in experimenting with single-player narratives, and then eventually gravitating towards a certain type of genre: immersive sims. I then briefly dabbled into entering the video game industry as a UI designer and tackled a couple of small indie projects on the side to see if I’d enjoy it. This necessitated that I familiarize myself with all kinds of games from all kinds of genres, which I did and learned that the medium is full of incredible, enriching, and enlightening content that I can never fully consume or devour no matter how hard I tried.

When I was nineteen, I used to be shy about my gaming habits. I’d make up excuses about being sick when my roommates asked if I wanted to hit the bars. In reality, I just wanted to stay in my room at play Team Fortress 2 or battle people online on pokémon. At twenty-nine, I’ve grown far, far more comfortable in straight up telling people that I prefer playing games to going out. It’s taken a while to come to terms with this, but it’s true. I don’t see it as my responsibility to explain to people why gaming is an incredible medium, or why I’d get more out of an hour of Fallout New Vegas than sitting in a noisy crowded bar talking about nothing in particular while sipping an Old Fashioned. I personally believe that gaming is the highest form of entertainment, but I don’t see it as my job to convince others of it. I can happily game away for days in a room while the world goes about its business without a care in the world.

The truth is, my experiences with games have fostered a greater sense of awe, empathy, kindness, and wonder in me than anything else from any other medium has. You literally get to step into the shoes of a character from a different place or time and roleplay as them. You get to make meaningful decisions, important choices, and decide their fates. Combat focused games have you improving your reaction times and motor control skills in the blink of an eye. Narratively driven experiences have you completely immersed in fictional worlds where you get to move chess pieces around to choreograph the story and characters. It’s all just so fantastic and all the different parts build off of each other beautifully.

I’ve gained a great sense in my own ability to listen, empathize, and understand as a result of playing video games. Yeah, it’s true. With books and movies, you’re nothing but a passive observer sitting back and taking in the action as it’s told to you or as it happens. With games, you get to interact in the experience and shape the outcome. It’s difficult for someone who’s not a gamer to understand this because they associate “gaming” with shooting, violence, and guns. In reality, games like Animal Crossing, Total War, Civilization, Breath of the Wild, Assassin’s Creed, and Super Mario Maker have more history, creativity, and engagement built into them than many other mediums combined. Again, there’s huge misconceptions and stereotypes floating around about these things, but I really don’t see it as my responsibility to address or clear any of them up. Any time spent on that is time that could be spent actually playing games, so I don’t really bother chiming in on the discourse.

So yeah, that’s my twenties. Lots of career learnings from jobs, a ton of confidence boosts from traveling solo, and a lot of life lessons by playing through some truly incredible video games. People frequently ask me the question about what I would’ve done differently if I could go back in time, but I don’t think there’s a single thing I would’ve changed about my twenties. I truly believe I don’t have any regrets about how I’ve spent my time and how I’ve grown into the person I am. I was very conscious about every choice I made and how I got to where I am now. If anything, I’m actually more excited for my thirties because I seem to have a better understanding of who I am and what I like to do. So I’m excited to see where the next decade takes me into shaping me as a human being.