Why did the gamer take a ladder to school?
They wanted to get to the next level.
Hey, I’m Caleb. Welcome—or welcome back—to my monthly column, Breaking Trail, where we kick things off with a dad joke. Just like this, just because.
Last week, I reached for comfort.
I picked up my XBOX controller and started a replay of Knights of the Old Republic, a Star Wars RPG I’ve been playing since it first came out in 2003. For me, this is the same thing as rewatching one of my favorite comfort shows. I can beat the entire game in roughly 13 hrs and have gone through nearly every dialogue option. I now “change it up” by creating and guiding characters through choices that mirror popular characters from books I’ve read. Since childhood, I’ve been enthralled by the idea of “leveling up” in video games—or leveraging your experience to gain new skills. Especially, as I got into open-world games, where that meant wandering into new places you may not be quite ready for. Almost certainly, you’ll fail no matter how hard you try. Then, you have to go back to build the skills needed to be successful.
Leveling up in life.
10,000 hours; that’s the benchmark that has entered the cultural zeitgeist from Malcom Gladwell’s seminal work, Outliers. Hell, it even made it into a Macklemore song literally called Ten Thousand Hours. Yet, we all are shown “experts” constantly in a myriad of forms — from professional career coaches to influencers with TikTok crafting tips. Are these people actually experts? Why am I never watching people in progress? What is the message we’re sending here, that everyone is an expert? Even though everyone has their own method of doing things, or a style that’s uniquely theirs…? I love leveling up, or building enough skill, over time so that I can use it in my work. For me, that spans travel and stories, people and places, experiences and skill development. I used to joke that I was a jack-of-all-trades, master-of-none; however, I think I have mastered a few (but I’m still just a jack in a lot of other areas).
In addition to games, I often think of my life in chapters, as I think many of us do. It’s an easy analogy to apply. Plot and narrative development occur as we age, gather experiences, and find our pursuits.
What is the kicker, though, in this line of thinking is that many of us apply the extra step in this analogy of closing chapters. This is where I go back to the XBOX rationale, where once the chapter or quest is done, it’s on to the next with the skills learned. I don’t like the idea of “closing chapters” necessarily, as it often implies unnecessary finality with what continues.
Jack-of-all-trades, master-of-some.
“You signed up, you’re going to see the season through.”
I was seven years old, playing football in central Alabama and it’d been a particularly hard practice:
The temperature was 102º outside
When going down into a three-point stance, I placed my hand directly into a fire-ant bed.
I got yelled at by my coach for jumping-the-gun on the play (he hadn’t realized what happened).
For a child, this made for a bad day. So when both of my parents spoke about sticking to my commitments, I was a little sheepish… but reluctantly agreed to keep playing football. I’m glad I did. I learned a lot of lessons over the years, and it is one of the experiences that, among other things, led to playing rugby in college.
I don’t play football anymore. I’d explored that path and found that, while fun, it wasn’t for me. But, I still know the game and can throw a hell of a spiral.
Jack.
The following summer, I attended a summer camp that had a huge theater component. While I had always been a fan of “performing,” this camp opened my eyes to the entire world of theater through stagecraft, lighting, costumes, sets, and how they all contribute to bringing a final performance to life. The dedication of rehearsal and practice. The wonder of improv, when someone forgets a line, but doesn’t panic.
I do still perform, whether on podcasts or in business pitches, and I still apply the lessons I learned in theater consistently in my life. They’re things I’ve continued to pursue since childhood, in various applications.
Master.
My childhood taught me valuable lessons in teamwork, the importance of being part of something larger, and how working together can accomplish great things. Football and theater were both significant. But one was much more for me. I’ve acquired a myriad of “jack” skills, things I know just enough to be dangerous about. Things where I could chat with a new friend or teach a kid just enough to maybe spark their passion in something. But, I’ve also mastered a handful of skills that I have picked up, fallen in love with, and nurtured for years across hours of intentional and subconscious practice. Each has their place. Honestly, the jacks are what make it easier to meet new people and share stories. I think there is a lot of beauty in the “jack” approach of not looking at everything you no longer pursue as a closed chapter, but as a skill or a story acquired to carry with you. It’s an exercise in framing, not a failure, that you don’t play the saxophone anymore… you’d still have a head-start if you wanted to try it again. Life is long and you can always choose to go from “jack” to “master” if something sparks joy.
Performative masterhood.
If you aren’t doing 15 side-plank-burpees per hour, you’re never going to achieve your maximum fitness potential…
We’ve all seen these asinine types of fitness or self-help ads on social. Or, even more nefarious, the “one hack to fix all of your revenue generation” type of ads on LinkedIn from the “guru” who cracked the code, rather than from the person who will willingly admit their far more humble approach of, “hey this worked for me, so you might want to try it - but your situation is probably different.” As a marketer by profession I have developed a vehement hatred for the “gurus” and peddlers of performative masterhood. It’s modern snake-oil elixir “cure-all” sales. We exist in a world where everyone is showing their “brand” online and trying to generate “trust” and a “vested interest” in following them. How can you do that if you don’t have something to share that is worthwhile? Rarely (sometimes, but rarely) do these people show the muck and mire of process and practice — the humanizing elements.
For the Swifties out there, this is why the “Behind the Scenes Eras Tour” on Disney is so popular. It offers a glimpse into all of the work and dedication required to execute something at a high level. This narrative needs to increase. Sure, some people have lucky breaks, or may have more natural talent than others… BUT to be at the top, you also need to work hard. You need to work at something where you truly want to become a master.
Progress, not perfection.
What online masterhood doesn’t account for, though, is “style.” Everyone’s peddling a narrative of “this is the only way” or “this is the best way” – which, ok fine, is how you sell stuff. What we really need more of, though, is “this is my way” or “this is my style”.
I think everyone has something about themselves that they are uniquely good at. I have travelled and experienced enough —moved enough—to find that everyone has a story. And, more often than not, they have both a story and a skill that are uniquely their own. They just may not think it’s what everyone wants to see or hear about from them; God forbid, they think they aren’t good enough to share that stuff because other people are better at it than they are. But leveling up, in life and in video games, is about leveraging your experience to gain new skills.
Working on skills and collecting stories you can carry with you is, after all, how you squeeze all the experience points out of life.
It’s how you find another level to explore.
Cheers,
Caleb
P.S. In addition to opening this column each month with a dad joke, I’ll be closing them with a musical coda—songs and lyrics I feel touch on the theme of the essay.
Musical CODA:
Levels by Avicii
Key, relevant lyrics:
“Oh, sometimes I get a good feeling, yeah. Get a feeling that I never, never, never, never had before, no, no. I get a good feeling, yeah.” Performed by Etta James