Choose Your Own Adventure 🧙
We dropped our first video essay of Season 1! Plus, how we can figure out our desires through structured chaos — and a note on Rittenhouse
Happy Wednesday! You can expect these letters every Thursday at 7 p.m. CDT over the next month, but with the holiday tomorrow, I decided to put this out today.
In September 2020, I drove through Antioch, Illinois.
Like most of Illinois outside of Chicagoland, it was a pretty sleepy, rural town, with a population just a shade under 15,000. There might’ve been one or two yard signs sporting the message “PRITZKER SUCKS!” in big lettering — referring to the state’s Democratic governor, J.B. Pritzker — but other than that, there wasn’t anything particularly memorable.
Of course, just a month earlier, a then-17-year-old Kyle Rittenhouse traveled 20 miles from his hometown of Antioch across state lines to Kenosha, Wisconsin, where protests had erupted in the wake of the shooting of a black man, Jacob Blake, by a white police officer. The next day, brandishing a semi-automatic rifle belonging to his friend, Rittenhouse shot three people, killing two.
I won’t go into much more detail here, but I wanted to take the time to acknowledge the pain many are feeling after Rittenhouse was acquitted of all charges last Friday. As the trial unfolded, it became pretty clear how it would turn out, but that doesn’t make the result any easier to sit with.
Regardless of the legal arguments that were made, I think everyone can agree that it’s a dark day when someone in our country can enter a community they don’t belong to with a lethal weapon that’s not theirs, kill two people, and get off scot free (Author’s Note: Check out the origins of the phrase “scot free” for some history of selective punishment in America).
After so many people of color have had their lives taken too early at the hands of police, it’s frightening to see how researches are already noting how this verdict can act as a “permission slip,” emboldening extremists across the country. Plus, Rittenhouse is already getting the hero treatment from the right, with sitting members of congress openly offering him internships — Trump even revealed today that the teen paid a visit to Mar-a-Lago.
I think I — and a lot of my peers — see news like this and tend to feel a little overwhelmed by the world that we’re inheriting. But I’ll expand on that next week.
For now, I am excited to announce that our first video essay of Season 1, “How Andrew Callaghan Rebranded Journalism,” is out on our YouTube channel!
We’ll be rolling out new video essays every Sunday night at 7 p.m. CDT leading up to the release of our first creator economy magazine, which drops 12/19. To be the first to get all of our content, product, and event drops — including an exclusive teaser trailer for Essay 2 — sign up (for free) here!
Also, I wanted to wish everyone a Happy Thanksgiving! Though the pandemic still rages on, I know a lot of us are seeing family we haven’t seen in a year or two now (myself included). It’s given the holiday way more meaning to me, so I’m looking forward to digging into some delectable grub tomorrow and spending time with the people I love.
Now, on to this week’s letter, which tackles how we can figure out our desires through structured chaos.
I started doing an exercise this year after receiving advice from a former-professor-turned-mentor. About two-to-three times a week, I open up a new page in my Notion workspace with a simple title: “What I Want.”
The reason my mentor recommended this exercise is because oftentimes, we have so many thoughts running around in our heads that it gets impossible to track the changes. At first, when I started committing to the practice — usually coming in intermittent spurts of energy — I scoffed at the thought that I would figure out much about myself and my desires. I’ve known what I want to do and how I want to spend the next several years of my life for a while now, I told myself.
It turns out, this exercise confirmed the exact opposite: I have no idea what I want. And that’s okay.
I’ve taken a lot of personality tests over the last couple of years, and I’ve always felt pride in knowing that I often score high in “implementation,” meaning I’m someone who knows how to pitch an idea and subsequently follows through to get it done. Nonetheless, there’s also been something else present that I’ve never fully acknowledged: my simultaneously-high quick-start gene, meaning I have the propensity to constantly generate new ideas and iterate on the fly.
Nowhere has this been more present than in my “What I Want” journal entries. Here’s a quick glimpse on the vastly different things I’ve written, mainly on a whim:
Entry 1 (February 23) — Work in an environment where I’m constantly pushing myself to learn, employ a sprinter’s mindset, and become a fixture in the world of media, streetwear, and startups.
Entry 4 (March 2) — Create a bomb-ass newsletter, translate my essays into Twitter posts and focus on building a LinkedIn following, make big bets on myself that lead to six figures in revenue by the end of 2021 through YouTube, a premium subscription of some sort, and hella collabs.
Entry 8 (March 15) — Keep an orderly room, get in peak shape to close out my ultimate career (R.I.P.), go all-in on a nutrition plan (full Vegan?), travel, and take a job with a nearby startup while continuing to develop passion projects on the side.
Entry 10 (March 25) — Invest my time and energy into a “world-building” agency, which would theoretically work with creators to “release merchandise, design special websites, tell stories through audiovisual means, drop new products, get PR, and create popup events” in an effort to better welcome in their fans by assembling a world around their brand.
One week in the spring, I even spent several days contemplating a career pivot to go all in on UI/UX due to a fear that there was no demand for my current skillset in the current workforce (more on that at a later date).
If you asked 18-year-old me what I wanted, it’d probably be along the lines of I want to write and podcast and film and screen-print t-shirts and toss frisbees and collect sneakers and bowl a 300 and watch movies with friends. For some, it may read as a lot, but for any modern creator, you know that it oftentimes feels impossible to label ourselves and limit our endeavors to just one thing.
Things have gotten a little bit more complex over the years: relationships, mental and physical health, graduating college, this pandemic. By doing this exercise, I’ve been able to chart how those complexities have altered my state of mind while acknowledging that I’m okay living in a constant state of growing and learning.
More so, it’s about piecing the thread that connects all of our wants, needs, and desires together in order to figure out what the best opportunities are for us moving forward.
My mentor gave me another piece of advice on this topic: treat life like a constant choose-your-own-adventure. You can take time to do nothing but sprint-sprint-sprint; you can also transition into a new role over the course of a year or two, or maybe even take a sabbatical. He said that when you approach things with this mindset — while ensuring you’re keeping the lights on — you’re able to live fulfilled, stay patient, and build some pretty special things.
Of course, bumps in the road will pop up, and you’ll have to adjust — he pointed out that he left the entrepreneurship world in his 30s and took a teaching job because his wife was sick and they needed a solid healthcare plan. Additionally, not every person has the same structural advantages; I’m incredibly fortunate that I was able to graduate college with a degree and no student debt, something I absolutely don’t take for granted as I don’t share this financial burden that influences many people’s life and career decisions.
Nevertheless, as I work on growing Powder Blue, I’m welcoming in new relationships and opportunities with open arms, focused on collaborating with the right people in the creator economy space with a bias towards the long haul.
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