How to Build a Successful Creative Business in 3 Easy Steps

100% Foolproof

Jun 20, 2025

I’ve been scouring the internet and using Ai1 for some easy tips on making it big as a creative entrepreneur and what I’ve come up with is 100% foolproof. It also is easily digestible as a 3 point listicle. The wisdom of the internets says this too is foolproof.2

1. Be Good at Making Art

Obviously if you’re in the creative fields you have to be a master of making. A bonafide creative genius. A fully formed, art-making savant devoid of blemish. Artwork must grow organically and fully-formed from your head like a Greek God. This is step one and is non-negotiable. You got this.

2. Be Good at Business

Now this combination of being good at making art and good at business naturally is rare, but don’t let that slow you down! You should be able to seamlessly turn your art into profit, much like a real-life King Midas.3 I think it’s best if you can handle the accounting books while creating books and making bank. Emailing with one hand while drawing with the other. Use your whole giant cranium at once like a fully-functional Death Star of Art Making Business™. Not too hard, IMO.

3. Be Good at Everything Else

Ok, you knew I’d go there. The modern creative business isn’t about the art, really. It’s about all the side hustles that you also must have fully mastered. Classics like algorithm 8-ball reading, the newsletter dark-arts, and being a ~~Instagram~~ ~~YouTube~~ ~~Tik Tok~~ video star. This is paramount in the age of Ai. Anyone can type into the magic prompt machine, but not everyone can paint live in front of 16 cameras and your bewildered dog while taking questions from the bots on the internet! Mastering these other 18 jobs should be a cinch.

That’s it my friends. A complete list. See you next week! Wave to me from your jet!

Shhh. The real top-secret newsletter™ is below and is born of my own experiences. I don’t know how to build a successful creative business in 3 steps. Here are three principles that have helped me along on my way:

1. Just Get Better

I have churned out some truly awful artwork, writing, ideas in my time. I mean just awful stuff. I didn’t give up. The desire to make something from nothing is what makes me happy so I didn’t really have a choice. I still don’t. Wake up and make stuff. Learn, grow, play, fail, repeat until something shows up that wows me and feels successful. Share. Repeat.

2. Make Sure Business is 2nd

There are times I’ve felt like I’ve made creative life decisions based on business considerations and the river doesn’t flow that way for me. I can’t and won’t abandon seeing some part of what I do as a business because being successful at making a living means I get to make more art. The art comes first and informs the business. This is the proper flow, edifying and self-propelled.

3. Add Only the Stuff that Helps

I sometimes find myself dreaming about all of the supplemental things that work for other people in the creative industry. Things like being good at video, teaching classes, social media on a schedule, podcasting, self-publishing, etc. and on into infinity. There’s nothing wrong with any of this on its own. The danger for me is in thinking that a) you have to do it all and b) that it can feed my soul like the main thing does.

I’ve found that if I authentically add things that I enjoy, that feed into the main thing (for me picture books) and not distract from it — that is the sweet spot. Drawing a Blank is very much in this mold.4 Getting really into making videos is not. This works for me. I’ve given myself permission to not be good at it all. You should too.

Love you all and I’ll see you next week.

Best,

Jacob

I refuse to use Ai, because I like writing and art-making and see it central to my time on this planet… AND I respect you too much.

I’m completely disgusted with this paragraph and the title here. Even in devising this obvious snark, I didn’t imagine the self-hate it takes to say those things. Forgive me.

Look him up, kids. Just don’t touch.

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