Explore the balance between work and creativity, why passions don’t need to pay the bills, and how imagination thrives outside the nine-to-five.

Hey Friends! This week’s newsletter is about career advice, imagination, standardized testing, creativity (duh), and rock ‘n’ roll. Let’s get into it!
Work and Play
In a recent interview, entrepreneur, investor, and modern-day philosopher Naval Ravikant (at 44:53) offered the following career advice:
No one is going to beat you at being you… Find what feels like play to you, but looks like work to others… Productize yourself.
You’ve probably heard similar advice along these lines at some point, something like “Chase your passions,” or “Do what you love, and you’ll never work a day in your life.” If you’re one of the lucky ones who pulled this off, congratulations.
For the rest of us mere mortals, especially those of us decades into our not-perfectly-aligned careers, relax. There’s absolutely nothing wrong with working a nine-to-five to support your five-to-nine. There are plenty of careers that offer reasonable pay and a healthy work-life balance that provide you the ability to play… after work.
Many would be better suited following this route than trying to carve out a career doing what you love most. Not to mention, making your passion your full-time job runs the risk that you’ll eventually resent the very thing you once loved. If the market doesn’t value the thing that you consider play, it’s going to be a tough go turning that into a career.
Granted, today the internet makes it more possible than ever to productize yourself, but there’s a big difference between setting up a Shopify site and finding product market fit.
Takeaway: I’m not at all anti-capitalist, but I think it’s totally fine to pursue activities solely for the sake of the feeling you get when you participate in them. Sometimes play should remain just that.
Imagination and Consequences
James Clear recently shared a quote from toymaker, inventor, and author Roger von Oech on wide-open thinking:
The amount a person uses their imagination is inversely proportional to the amount of punishment they will receive for using it.
I’ve previously written about how high school students in my digital graphic design class frequently struggle with open-ended creative assignments. Most are used to meeting the criteria of detailed rubrics: checking boxes, dotting i’s, crossing t’s, and so on. Creatively iterating over a concept to meet a design objective is often much harder for them.
This month, high school students at my school, and across the country, will take the ACT or SAT—a high-stakes standardized test that will influence their ability to get into college and contribute to the ranking of their school as a whole. Lower grade level students will similarly take multiple days off from regular instruction to complete their own state mandated testing.
Some schools have been preparing for these exams with test prep for weeks.
The contrast couldn’t be starker when compared to the demands of creative work where there is no single right answer—and certainly not one that is predefined.
Considering the impact these tests have on instruction, and the emphasis we place on getting the right answer, it should come as no surprise that students struggle with creativity. Standardized testing doesn’t just undervalue creativity, it unintentionally discourages it. This isn’t to say we should abandon standardized tests altogether. They certainly serve a function, but we must recognize that when we hold test performance up on a pedestal, we send a message to students that selecting the one right choice is superior to coming up with a completely new solution.
Takeaway: You may not be in a position to shift educational policy, but you can reward imagination instead of punishing it—and that’s a start.
The Creative Circle of Life
I found this great post from last week. It’s a circular flow chart titled The (Creative) Circle of Life and features four nodes that say, “Read something encouraging > Be inspired > Write something encouraging > Inspire others.” See the original below:
I love this.
It offers a great framework for considering creative work. Creativity doesn’t exist in a vacuum. Creativity is a team sport, even when you’re working alone. The work of others serves as fuel for your creative fire and influences your creative decisions—sometimes overtly, sometimes only subconsciously. Blending those influences into something new serves as fuel for someone else and starts the circle over again.
Takeaway: If you’re in a creative rut and finding it hard to be productive, pause and consume creatively to stoke your flame. Then share your work to do for others what they’ve done for you.
The Most Famous Chord in Rock History
Rick Beato is a musician, educator, and YouTube personality known for his in-depth analyses of music across a variety of genres. In the video below, he interviews Pink Floyd guitarist David Gilmore.
They examine what Beato describes as the most famous chord in rock history. It’s first played at 3:40 in the song Shine On You Crazy Diamond (Parts I-V). Gilmore explains that he and his band were in a rehearsal room “trying all sorts of little things,” as he describes it when Gilmore happened upon an arpeggio that captured the room’s attention. He describes it as an awakening moment. After playing the notes several times, he states:
“There’s something to that… There’s a possibility here.”
He later explains that the whole of Shine On grew out of that one moment. Watch the interview below.
What this illustrates about creativity is the exploratory nature of it all. Rarely is a creative act entirely conceived of in one’s mind and then manifested in whole cloth. Rather, it’s more often an act of discovery—the end result revealing itself only once you’ve begun.
My brother paints abstracts in acrylic on canvas. My favorite texts from him include photos of his work followed by the question, “Is this done?” Like Gilmore finding a tune, his creative expression has no grand plan. It’s a search. What he finds is his art.
Shared without permission below, is his latest piece that I find reminiscent of Michelangelo’s The Creation of Adam (obviously in a completely different style and context, but beautiful nonetheless).

Takeaway: If you’re waiting for inspiration to start, you’re doing it wrong. You must first start to find inspiration.
The Dangers of the “Dream Adjacent”
In an interview with Quentin Tarantino (at about 38 minutes), he discusses a period in his life where he worked in a movie rental store (remember those?). This was before he’d made a name for himself as a film director. He explains that during this phase, he wasn’t exactly living his dream, but he was working in a field that was dream adjacent.
He didn’t get to make movies, but he did get to watch and talk about movies all day which was close to what he wanted to do, but not exactly. For several years, he “fell asleep,” as he describes it working in a field within spitting distance of what he really wanted to do.
An awakening of sorts, spurred by an older colleague complaining of wasting his youth in that very store, shook him out of his sleep and urged him to move west to pursue his actual dream.
Listen to the original telling of this story below:
In contrast to my take on Ravikant’s advice, the other side of the pursuing your passion coin is that if you don’t, you may live a life of regret. Imagine a world with no Pulp Fiction or Reservoir Dogs. That’s not a world I’d want to live in.
At the end of the day, chasing your passions or living the dream adjacent is a decision that only you can make. My advice to young people, considering such a decision, is to go for it while youth is on your side. Every job, car loan, mortgage, spouse, and child, makes it that much more difficult to risk it all.
Takeaway: If you’ve been living the “dream adjacent,” perhaps this is your wakeup call to do what you’ve always dreamt of.
One More Thing
Good things are better when shared. If you liked this, it would mean the world to me if you sent it to someone who might like it too.
I’ll see you in your inbox again next week.
Until then,
-Mike