Beyond Trial & Error: A Smarter Way to Build a Thriving Art Business

Lessons from the Self-Made Artist Academy with Chelsie Tamms

I’ve been running my art business as a part-time venture for a few years now. Along the way, I’ve discovered countless “no” routes—paths that didn’t quite lead where I hoped. Informative? Absolutely. Discouraging? Many times.

I’ve taken programs, joined classes, participated in groups, sought coaching, attended lectures, and sat through a bazillion webinars. And through it all, I held onto this idea that one day, I’d cross a finish line, finally having it all figured out. But the truth is, as I grow—both as an artist and as a person, everything keeps shifting.

Still, particularly finding clients and pitching into what often felt like a void became exhausting. So, I started looking for a part-time gig. Maybe it was for the best that I lost count of how many applications and cold emails I sent. Once in a blue moon, I’d get a response. So, I also started paying closer attention to where I’d love to work.

That’s when I took a bold step and reached out to Lettering Works, hoping they might need a studio assistant. The founder, Chelsie, responded!
Not with the answer I wanted, but with something really good.
While they weren’t hiring, they have many offers hard to resist. The more I learned about Lettering Works, the more I wanted to build something like it.

Chelsie has an amazing Artist Trade Program, and I wanted to make the most of it. I started by enrolling in her Self-Made Artist Academy. My goal was to be on the same page for our 1:1 time to be as productive as possible. Learning from someone who’s not just teaching but actively doing the work made the experience even more inspiring.

Stay in the Know

Chelsie has a gift for making things simple and doable. The course is structured into six modules with bite-size videos and an immediate call to action.

I’ve taken many courses like this before, so I assumed it would be easy. It wasn’t difficult, but it required commitment from the start.

The first module? Know Your Numbers. A wake-up call. It finally pushed me to transition my bookkeeping software, something I had been putting off for far too long. Quickly, I had a clear picture of my finances before tax time. And with that clarity, my business goals became more intentional.

For the first time, my goals weren’t just things that sounded nice, they had real weight. More reasons why. More meaning.

Chelsie sprinkles gold nuggets of wisdom throughout the course, and what I love most is that she practices what she teaches, so it is all well tested.

I took my time with each section, but even then, the course is designed so you can move through it in less than eight weeks—and you end up with a solid, actionable plan.

A Clearer Picture of My Ideal Clients

One of the most eye-opening exercises was defining my Target Market. I’ve done similar exercises before, but this was different. Instead of just listing age, gender, and the usual demographics, there are questions and other prompts that helped me paint a full picture—a logical, detailed profile that actually informed my business decisions.

Better knowing why someone would like what I am doing, made it feel like I wasn’t just guessing. I could prioritize my long list of projects and offers based on a real understanding of who and how I wanted to serve.

Intentional Offer Creation

Once my finances, goals, and clients were mapped out, reworking and narrowing down my offers became a well-informed process.

Too often, I’ve jumped straight into brainstorming offers. While I love dreaming up ideas, an endless list without anchors causes me to lose my own attention quickly. Chelsie challenged that process. She guided me to create with intention, ensuring that my offers aligned with my clients, my interests, and my talents.

And then she took it one step further, building scalable offers.
Each step lays a solid foundation. Every module connected to the next, with clear action plans that bridged short-and long-term goals.

The course began with Know Your Numbers and ended with Roadmap to $100K – It made it all real.

Completing the course was both enlightening and empowering—I find myself returning to my workbook again and again, each time polishing and clarifying my own answers.

With a solid foundation in place and the new year just beginning, I felt more than ready to dive into a coaching session, eager to make this year truly exceptional.

For the Artist Trade Program, I had the opportunity for 1:1 consulting time with Chelsie. By the time I got to our session, the course had already helped me ask better, more thoughtful questions—and Chelsie answered them with incredible depth. That conversation deserves its own blog post to be honest. It was the cherry on top of a solid plan!

As a bonus, I gained access to the Are You a Brand? training and The Power of Passion Projects mini-course—both of which drew me to Chelsie’s work in the first place. I love meaningful work, and when you can tie it to a greater purpose, it becomes something powerful. What I learned there helped me take inventory and realign the previous work done. Very helpful.

I stepped into this course curious about what more I could learn—and I learned a lot. What I gained was not just knowledge, but clarity, structure, and a path forward that truly aligns with who I am and what I want to build.

If you’re an artist or any creative trying to navigate your business, I highly recommend Chelsie’s Self-Made Artist Academy. It’s more than just learning, it’s about refining and strengthening the unique way you approach your work. To me it is about finding my “yes” routes.

And that, I believe, is truly invaluable.