"Don't Ever Work For Someone You Don't Want to Become"
On Poisonous People and Anti Role Models
“Don’t ever work for someone you don’t want to become.” - Kevin Kelly
I never realized this until I met a guy who drove a Lamborghini and a G-Wagon.
Last year after dropping out of college, I applied for eight different jobs. One of them was car sales. Although I’d heard about the greasy stereotypes, there was no limit on my income. I love leverage like that. So even as an introvert, I had to at least try it out. [1]
Let’s rewind to February 2023.
An older guy gets up from his desk to introduce himself. He has a white buzz cut and a scruffy white beard. He wears a wrinkled white dress shirt, tucked in, sleeves rolled up. He invites me over to sit down. I meet my interviewer—Robert Roberts.
But before I sit down, I see something shining: his Louis Vuitton belt.
Right away, I judged him, thinking he was trying to show off. The contrast of his belt and cheap clothes made me think that he was a regular at a Las Vegas casino. But maybe he just liked belts.
Then naturally, he asks me what my dream car was. After telling him about my V12 Prius, he blurts out something without hesitation: he tells me that he has a Lambo and G-Wagon.
At first, I thought he was trying to show off, just like with his belt. He really didn’t impress me. I’m pretty immune to big-dick behavior, but for an interview it threw me off.
Then out of nowhere, he tells me about his dream to retire to Mexico and to live in a beach house with his wife. At this point, I’m thinking to myself, dude, you can retire right now if you just sold your fucking cars. Of course I didn’t say that. But selling those two exotic autos would have him set in Mexico, where the cost of living is peso low.
Manager > Job
Now, maybe I got a false impression of Robert Roberts. I had a limited sample size of his character. Maybe I built an artificial mental construct based on the one hour I spent with him. Sometimes I’m too judgmental.
Even though he fit the stereotype, I know that there’s some car sales guys out there who aren’t like him. But the lesson makes more sense now: don’t work for someone you don’t want to become. [2]
Why? I didn’t want to spend another second around Robert. He disgusted me. I sensed greed and hollowness in him. I didn’t admire him, I didn’t respect him, and I definitely didn’t want to be like him.
I didn’t want to be someone who traded his time for money in his 60s. I didn’t want to be stuck in a self-created prison cell, playing status games and giving up my dream life for the absurd approval of people I didn’t even know.
In his book, Career Advice for Uniquely Ambitious People, Eric Jorgenson wrote that the “single most important factor in the quality of your job is your boss.”
“You can have a dream job in your ideal industry for the best company, and if your boss is a gigantic asshole who hates you, the whole thing will be a miserable mess.”
So even if you’re working in an unsexy job like car sales, your boss matters. Why? Because they’ll mentor you. Teach you. Protect you. Help you. And you’ll spend time with them.
But on a deeper level, why does it matter? I’m still searching for that answer, but one thing I found is this—miserable people will make you miserable. Excellent people will make you excellent.
Working with mediocre moms in a retail store made me feel like a gossip guy. I felt old and feminine. I found myself complaining more. I always escaped at lunch break to read a book and regenerate some lost neurons.
For most of my past jobs, I didn’t last more than a few months. I got bored and quit because I stopped learning. But these past work experiences were vital: they helped me figure out how I don’t like to work and who I don’t like to be around.
Now as I write this, I’m looking for jobs with more growth opportunities. I want to be around elite people. Those who push me, teach me, and hold me accountable. It might take time to find that strong signal. But for now, I’d rather sacrifice my savings than sacrifice myself to poisonous people.
Notes
[1] Remember when you were young and found out that you could shoot peas across the room with just a spoon? That’s what leverage is. It’s the difference between what you put in and what you get out, like working less and getting paid more. This article from Eric Jorgenson has some sweet, actionable examples.
[2] I have a friend who worked in car sales and had a great boss. I’m also not saying that wanting a Lambo makes you evil. The idea is more about self-awareness and figuring out what you really want regardless of external approval. My favorite question to help with this is from Tim Ferriss: would I do this if I couldn’t tell anyone about it?
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This was great Baxter. Once I return home from travels in late Feb I’m going to start looking for work again and this kind of mentality has reinforced what I want to find in that future job.
I’ve seen so many of my business graduate peers take on jobs for just the money. While there’s nothing wrong in making good money, making it the only criterion for which you select a job is sure to lead to that hollowness you describe.
Anytime I want to do something - take on a job, for instance - I simply look at the people deemed successful in the thing under consideration. If I wouldn't be happy becoming them, I say no with ease.
For example, I can't work in banking, because the best one can become - a CEO, maybe - wouldn't make me happy. But I can spend years becoming a better writer, because having 1000 people read my emails every week is success to me.
It's all a question of what we want to become; it's all one of what and who we define as success.