Seven Commandments of The Chill Hustler

One of my biggest bottlenecks is my marketing and distribution strategy. I become a limp noodle whenever I think about sharing my work, so I generally don’t strategize about my work. I associate marketing and self-promotion with “hustling”, which I associate with intense pain. I don’t know about you, but I like living my life not feeling like I’m being flayed alive, so that’s why I don’t ever promote my work.

Now, you might be thinking that I seem to be making some false assumptions here. In particular, it doesn’t follow that all marketing and self-promotion has to feel like pulling teeth. I completely agree with you! I just don’t have a conception of marketing that feels aligned to my values.

Enter the chill hustler. The chill hustler is a concept I’ve been playing with over the past few weeks, as I’ve tried to be more intentional about my own marketing strategy. The premise of the chill hustler is that hustling isn’t inherently dirty, and that I can stand to promote my work more, in a way that doesn’t make me want to spontaneously combust into flames.

Basically, I’ve started to more regularly ask myself, how can I relentlessly hustle and relentlessly relax at the same time? Then I implement the results. I’ve gotten a few people who run 20k+ follower Twitter accounts to promise to retweet my next essay so far, and I feel way less weird about asking people to read my work in general.

I’ve found the chill hustler to be a helpful concept in overcoming my own psychological blocks about self-promotion and wanted to share some of my learnings with you. Here are the Seven Commandments (so far!) of being a chill hustler:

don’t be this hustler, she’s a thief

1. Thou shalt not view self-promotion as dirty.

While there are many people who rely on pressure tactics and sleazy tricks to make a sale, self-promotion doesn’t have to be dirty. It can be about sharing something you’ve created with others who might enjoy it. The chill hustler recognizes that authentic self-promotion won’t feel like manipulating people to make a quick buck and will explore how to network and self-promote with integrity.

2. Thou shalt take rejection in stride.

Jason Levin

has a cold DM guide, where he succinctly describes his DM strategy. One of my favorite parts of it goes: “Get ignored? Send more. Get rejected? Send more. There’s millions of people out there to connect to.”

If you’re not getting rejected more than 2/3 of the time, you’re not reaching out to enough people.

The strawman of the plenty of fish in the sea attitude can lead to grinding and treating people as interchangable. While this can be the case, my steelman of the plenty-of-fish-in-the-sea attitude is that rejection becomes a part of the game. If you increase the number of people who are exposed to your work, you increase the number of rejections, but you also also increase the number who resonate with it. Seems like a worthwhile trade to me.

3. Thou shalt not feel like a completely helpless piece of shit for being bad at marketing.

You know what’s not chill? Self-contempt. The budding chill hustler understands that self-loathing for their lack of marketing prowess is not the way to go and adopts a growth mindset instead. Sure, they might suck now, but that doesn’t mean they’ll be horrible forever. After all, there are so many resources to become better at marketing, such as Derek Siver’s Your Music and People.

4. Thou shalt never rush.

Creative life is a marathon and not a sprint. This means that if you’re going to run a marathon and not a sprint, you have to take it at a marathon pace. The chill hustler understands that the best long-term strategy is to relax into their natural stride, rather than become an anxious wreck by trying to artificially speeding the process up.

5. Thou shalt discern when thou art avoiding out of fear.

Is it really unaligned for you to message someone, ask them to read your essay, and then ask them to retweet it if they like it? Or are you avoiding it solely because it’s outside of your comfort zone, and you’re afraid of rejection?

The chill hustler understands the difference between the two states — in the former, you’re not doing something because it’s not aligned with your soul, whereas in the latter, you’re not doing something out of fear — and strives to promote themselves anyways in situations like the latter, even if it’s pretty fucking scary.

Feel like it’s soul-crushing to send the DM? Don’t send it. Feel scared? Laugh a little about the discomfort, and send it anyways.

6. Thou shalt support others in thy community.

Hustlers do not hustle in a vacuum. Marketing isn’t just about promoting yourself; it’s also about supporting others in your community. See an essay by a smaller account that’s piercing and well-written? Retweet the hell out of that shit. Feel grateful that a larger account promoted your work? Pay it forward and leave a thoughtful comment on someone else’s work.

7. Thou shalt not covet.

As Exodus 20:17 states, “You shall not covet your fellow creator’s following; you shall not covet your fellow creator’s salary, nor their relationships with famous creators, nor their poppin’ apartment, nor their invitations to eat nice cheese, nor anything that is your fellow creator’s.”

This is probably the hardest commandment for me to follow, but it’s an important one. I don’t want to be so jealous of the people around me that I can’t feel happy for them or have deep relationships with them. The chill hustler understands that success doesn’t have to be a zero-sum game. Other people succeeding doesn’t mean that they won’t succeed in the future; if anything, it’s another piece of evidence that succeeding as a creator is possible and less far away than one might think.