How to Hustle Gracefully in a Creative Career

Friends, Romans, countrymen, today we're going to talk about something crucially important if you want to make a living from your art: your hustle. Hustle! I love that word. It's getting something you want through forceful action. It's a con or a swindle -- getting people to give you money when they might not be so inclined on their own. Hustle is working hard to find or make opportunities, and then riding them for all they're worth.

Obscurity is the second-biggest obstacle to having a great creative career. (The biggest one is knowing your craft well enough to do solid work when the clock is ticking.) I'm addressing two separate audiences here -- freelancers and independent creators. The same general rules apply to each group, believe it or not. The only real difference is one of scale. In one case, your money comes from a relatively small group of people, your clients (or investors, I suppose.) In the other, you're dealing with a wider audience -- your readership or viewership, your fans, one might even say.

In both cases, you're trying to get people to give you money for stuff you make. How do you do this thing? Dale Carnegie told you lo these 77 years gone by. Win friends and influence people.

In Social Situations, Don't 'Network.' Just Make Friends. You know how they say it's not what you know, it's who you know? That's only part of the equation. Forging good relationships with lots of people is the secret key to successful self-promotion. Be friendly, but don't be a shark. If you approach someone with the sole intent of using your contact with them as a stepping-stone to get things that you want, you're not going to make a very good impression. People can tell when you want something from them and you aren't really interested in them as people. And you know what? Nobody likes feeling that way.

On the other hand, friends are sometimes favorably disposed to make introductions, put in a good word... and even buy your stuff. If you're faced with a choice between buying a book by someone you think is a great person and someone you think is terrible, all else being equal, odds are you're going with the one you like. Make people like you by being a friend to them, not a huckster with nothing but a quick sale on the brain. Good self-promotion is a long game.

Give to Your Community. So how do you make friends? You act like a good friend to someone (or, ideally, to everyone). As Chuck Wendig might say, be a fountain, not a drain. In your interactions with people, don't focus exclusively on what you can get out of the deal. Hell, don't focus on it at all. Instead think about what you can do to give more to your audience, your industry, your colleagues. Share what you know. Pass on referrals and introduce people who you think would love to work together. Make freebies for your fans out of love. Volunteer for the stuff you think someone should be doing. Give give give.

This is where you start a blog and share your secrets or your expriences. This is where you volunteer to speak at conferences, or submit to festivals, or whatever the equivalent is in your community. Do so to genuinely share, and not to gain a platform for your case studies and thinly-veiled marketing materials.

This spirit of generosity makes your community a better place to be. And on a more cunning and calculating level, it makes people notice you and what you have going on. Making the world a better place for other artists and freelancers is a great way to build social capital. There's no downside to having people subtly feel like they owe you one, you know? 

On Social Media, Be a Person, Not A Brand. Marketing-speak has alas infiltrated a lot of our cultural discourse, and even influences how we behave toward other people online. Successful self-promotion in the internet age isn't about intentional branding or marketing, though. It's about being human.  

If you're checking out someone's Twitter account and all they ever do is post links to industry-relevant lists of top five tips, or buy links to their own books, or subscribe links for their email newsletter... that might be a pretty solid 'brand,' but so what? That person is not making human connections. That person is not interested in a two-way give-and-take relationship over social media. That person is being a brand and not a person. It's self-promotion run amuck, and ultimately won't get you very far; nobody likes a relentless sales pitch.

Absolutely curate and filter the stuff you put out on the internets! But don't filter out you. The stuff about your work and your hustle and your business should be only a small fraction of what you do online. Be vulnerable and funny and admit mistakes and when other people talk to you, listen to them. Even if they aren't someone you think can help your career! You know how you can tell who's a jerk by how they treat waitstaff? Yeah, you can tell who's a jerk on social media by how they treat people who don't have as many followers. And yeah, people notice.

When You're Actively Selling, Don't Ever Put Anyone on the Spot. Never, ever put anyone in a position where they have to tell you no directly to your face. There is a world of difference between sending an email to a potential client saying, "Do you have any work for me right now?" and "By the way, I'm looking for projects, mind passing on my name if you hear of anything?" Likewise, there is a world of difference between an open tweet "My book is out today! Buy it at LINK!" and "@hey_specific_buddy My book is out today! Buy it at LINK!"

Again, this is all about making sure nobody feels like you're using them. Nobody likes to feel like all they are to you is an income stream. It's not even that hard to avoid.

Don't Be Shy! Just Be Aware of Context. So sure, if people are going to hire you or buy your stuff, at some point they need to know you're on the market, and the only way they'll know is if you tell it to them. This is the actual hustling part that you have to work at. To be a successful self-promoter, you should send out the odd email to potential clients saying you're on the market. You should send out the tweet with a buy link on launch day. If you're having drinks at a bar, probably a point will come up in conversation where you share what you do, and you absolutely can say "I'm an $ARTIST, hey, it would be awesome to work with you sometime/I have a book out/I'm going on tour."

And then as a follow-up... just leave it alone. Maybe the person you've met will ask a few follow-up questions, but it's absolutely not up to you to extend that part of the conversation.

Look. If you're talking to a hiring agent, a record exec, an acquiring editor, a potential fan, they already know what you want from them. You really don't need to spell it out. 

There is a time for the hard sell. That's in a context specifically designated for it. If you're in a pitch meeting, yeah, talk about how awesome you are. If you're sending out a newsletter that people have signed up for on purpose, hells yes load it up with buy links and your best sales pitch. If you've snagged a great business card, go ahead and follow that up with a shiny email about how glad you are to have met and how you'd love to get something together sometime. Just don't be douchey about it. Don't leave someone under the impression that your sole interest in them is what they can do to fatten up your wallet.

But Don't Be Scared, Either. Self-promotion is scary and hard. A lot of people hate to do it. Hell, I hate to do it. It's kind of a necessary evil. Nobody can buy your stuff or hire you if they don't know you exist, which means getting out there, making friends, engaging in a community, making sure people know you have something to offer.

But as long as you don't go crazy with it, as long as you show restraint and respect, as long as you're not entering a weird transactional twilight zone where people are only as good to you as their potential to get you revenue, then a little bit of promotion goes a long, long way. 


Get the Serial Box App for iOS | Android Coming Soon

Subscribe to the Season ebook & audio ($21.99 for 15 episodes)

Or Buy Single Episodes for Kindle | iBooks | Kobo | Nook ($1.99)