Back when I was in high school—in the late 20th century—our superintendent told us that 60% of the jobs that would await our generation in the next twenty years hadn’t even been heard of yet. Back then, we didn’t even have the internet. That came later in college, and mostly we saw it as a curiosity in those early days. I would have to say now that the advice we had gotten grossly underestimated what is out there today. Nobody really mentioned doing what you love on that list.
I didn’t know what I wanted to do back then anyway. I relied on what they told us in school. If you get good grades, go to decent college and graduate (even from a mediocre college), you would be guaranteed a more lucrative career than if you just jumped into the workforce after High School.
By the time I went to college, the inflation of education had already begun to reach its peak. We didn’t know it at the time, but employers wouldn’t be lined up to hand us job interviews as we wandered around the football field looking for our mortarboards. College has been more of a delay—albeit an important one for exposing us to what was available—but a delay nonetheless.
The jobs we were all geeked out about doing were becoming obsolete. I had friends who were journalism majors, philosophy majors, “computer science” majors (which was still attached to mathematics programs and leaned hard into the realm of statistics). Lost souls like myself went for the low-hanging fruit. English Majors, liberal arts. We were told we had the flexibility of knowing how to read, how to process information, and how to adapt that towards critical thinking. Many of my classmates hedged their bets with a teaching license. I knew I had been a rotten smartass in high school, and the last thing I wanted to do was deal with my version 2.0. I doubled-down on writing.
I thought I was good at it. My professors told me I was good at it. Once I overcame that Dunning-Kruger effect, I realized I wasn’t all that good. I felt like my mentors were patronizing me, and by the time I fell on my face enough times to understand that I should have either gone to grad school, or abandoned my BA and gone into some kind of trade school, I would not even be a memory to any of them.
The thing is that I loved writing. It had become a better tool to create with than paints and pencils, clay, or ones and zeroes. I continued to write, and more importantly to read outside of what was on the curriculum for my undergrad. Then I found a steady job and lost my way in that for the next twenty years.
Remember I told you I went to high school in the 1990s. I’ve had a long time to make mistakes. Back in those days, I was surviving. The sole breadwinner for my growing family. I didn’t particularly like my job, but I liked starvation even less. I felt stuck, like some kind of rechargeable battery for my then-wife and three kids.
A divorce, a massive layoff, and a pandemic changed everything. The safe office job of 20 years that would have been familiar to 1990s high school administrators and guidance counselors had become obsolete. They told us there would be jobs we had never heard of, but nobody mentioned that the jobs we knew about at the time might disappear.
Over the last four years, I have had the opportunity to get back to what I wanted to do in the first place: writing. I don’t make a whole lot of money (yet, fingers crossed) but I enjoy doing what I do. I am writing a couple novels. I have a blog (you are reading right now), and as a freelance travel journalist, I write articles for anyone interested in buying them. I’ve had some great luck at that. I also have a podcast and a YouTube channel.
I wonder sometimes what my creative writing professors would think of me now. I’m also working on my travel photography. My interest in that might actually pre-date my desire to get into writing. With affordable equipment and access to tutorials and networking online, I have the resources to improve my work every time I get on YouTube. Whereas college offered one or two classes (and they were expensive back then), I can take dozens of classes for almost nothing. I can make mistakes.
I think the biggest bummer of what I am doing right now is I always feel like I’m a dollar short and a day late. Journalism and travel writing aren’t what they were 20 years ago. Freelancing is getting killed by AI. Nobody really wants to watch a man with a lot of grey in his beard on TikTok or YouTube, and even the affiliate marketing seems to have hit a bubble.
It always seems like I’m just a little bit behind on the trends. I keep treading water, waiting for the right wave to ride in. But sometimes it feels like the shoreline just keeps getting further and further away. A reason for this might also be that the right job, or combination of things, is still one of those careers that hasn’t even been created yet.
I know what I don’t want to do, which is what I did for twenty years. I feel happiest when I am creating. Writing stories, taking photographs, meeting interesting people, visiting new places. I live in a bus full time with my dog. I’m seeing the world that very few of us get to experience anymore. The sticks and bricks life doesn’t really interest me anymore. Unless somebody has a cottage on the Irish coast they would like to trade for a skoolie.
The key is to just keep treading water. Wait for the right wave. Paddle like hell when it comes in. My whole life up until this point has been directed by what I’m “supposed” to be doing. Conformity hasn’t ever really brought me any joy.
Would it have been nice to have ridden that wave of food bloggers in the early 2000s? Or the early days of YouTube? Yes. But I had no idea how to get into any of that, let alone the resources—the most crucial of these being Audacity. The sheer, flat-out audacity to try and risk falling flat on my face. I always placed the safe bets.
That isn’t my life so much anymore. I’m living on the fringe. I used to look at people doing what I do and think they were lowlifes. I had no idea the amount of freedom they had. Even though that seems to be diminishing now. One day, living on the road will probably be viewed as a crime. Right up there with a bad credit score, or using paper money, gasoline engines, and reading paper books.
We live in a weird world, my friends. And the only regret I have is not having gotten weird much, much sooner. At 48 years old, my eyesight is getting worse, my hair fell out, and now I have a bad limp I just woke up with for some reason. I am single, but not lonely. I am no longer green. I don’t see the world in black and white, unless I have my camera set on monochrome. I’m not young and beautiful anymore, but I have also faced my demons. The road is a meditative experience. A pilgrimage.
I have fought depression, anxiety, PTSD. I have overcome self-loathing, doubt, and begrudging others for their fortunes. I have seen some shit. My life is mine, and that includes ownership of the mistakes I have made. As much as my own empowerment belongs to me too. I know what I want, and more importantly what I don’t want. It’s taken me a while to get there, but at least I’m not too late to the show for that.