When Discomfort Is the Strategy

On growth, fear, and building a career without permission

During a recent long weekend, I attended two art experiences at opposite ends of the spectrum.

The first was Nicole Cherubini’s exhibition Hotel Roma, her debut solo show with Friedman Benda Gallery. Known for monumental ceramic works, Cherubini’s recent pieces incorporate complex figurative elements embedded within larger sculptural forms, drawing on baroque and surrealist traditions. At the opening, she spoke about her influences, her ideology, and how her work situates itself within the broader arts-and-crafts and ceramics canon. Her work is collected by major institutions. This is, by most definitions, institutional success.

The second experience couldn’t have looked more different.

I attended a 90-minute calligraphy class with friends, led by a stay-at-home mom who had taught herself calligraphy and now offers classes through Sip and Script. The format was simple: the platform organized the event, participants paid a fixed fee, and the instructor received a set payment for teaching.

Both artists created real artistic value. Both were skilled. Both were presenting their work publicly.

But they were operating in entirely different markets.

Same Creativity, Different Economic Logic

A working paper by Marco Thom, “Arts Entrepreneur or What Type of Fine Artist Am I?”¹, proposes that artists can be understood not just by medium or quality, but by commercial motivation and professional orientation.

Through that lens, the calligraphy instructor is producing work that meets an existing, predictable demand. She operates effectively as an artisan, translating creativity into commissioned experiences and teaching a popular style that audiences already want. If she maintains productivity and visibility, this model can generate a steady income.

However, because the work is replicable and style-bound, it commands lower prices than singular, non-replicable works driven by innovation. Thom categorizes artists working this way as contract artists.

If this very talented calligrapher were to pursue gallery representation, she would likely struggle, not because of skill, but because her artistic strategy doesn’t align with the gallery system’s incentives. And this mismatch helps explain a sobering statistic: roughly 80% of artists are unable to sustain themselves through art alone.

On the other end of the spectrum is Cherubini.

Although she works in ceramics, a medium easily positioned within decorative or functional art, her strategy deliberately resists that classification. Instead of selling ceramic objects as design products, she situates her work within an institutional and conceptual framework. She has the academic pedigree, the innovation, and the critical positioning that galleries reward. Her market is gallery-driven, not demand-driven.

Most Artists Live in Between

And yet, most artists don’t live cleanly in either category.

A major study titled Crossover: How Artists Build Careers Across Commercial, Nonprofit, and Community Work², conducted by the Arts Economy Initiative at the University of Minnesota and based on interviews with 2,000 working artists, makes this clear: the modern artistic career is hybrid by necessity.

Artists routinely move between commercial, institutional, teaching, community projects, and consulting, not because they lack focus, but because no single market reliably supports artistic labor on its own.

This is where my own practice sits and where the story gets more complicated.

As a public artist, I have spent years operating in what researchers call the Organised Market Segment, a world governed by commissions, juries, and institutional timelines. The work is meaningful and visible, and it carries cultural weight. But it is also a winner-takes-all economy, defined by long application cycles, opaque decision-making, and low liquidity. I am often rich in prestige and poor in cash flow, waiting, sometimes for years, for permission to work.

For a long time, I experienced this instability as a personal failure: a lack of consistency, a lack of focus, a sense that I hadn’t quite “figured it out.” What the research made clear is that this volatility is not incidental. It is a structural feature of the market itself.

Once I understood that, the question shifted. Not why is this so hard? but what would it mean to stop organizing my life around permission?

To survive the inefficiencies of the high-end art world, I’ve begun pivoting toward what Marco Thom describes as an arts entrepreneur model. Not by abandoning public art, but by building around it.

My large-scale public installations now function as the underlying work, the conceptual and reputational core, from which I am developing small-scale, collectible pieces. These works are not studies or leftovers; they are deliberate translations of the same ideas into a format that can move, circulate, and be owned.

This shift allows me to step into the Self-Managed Market, where I can build direct relationships with buyers rather than waiting for institutional validation. It introduces risk, yes, but it also introduces agency.

At the same time, I’ve stopped pretending that a single income stream is either realistic or desirable. Teaching and design research consulting are no longer framed as compromises or detours. They are structural supports. They provide an income floor that stabilizes the entrepreneurial risk of making and selling art. As the Crossover research shows, this is not a failure of commitment; it is a portfolio strategy, one where commercial stability subsidizes artistic experimentation.

What’s changed most is not just how I make money, but how I understand my role.

I’m no longer trying to fit neatly into one category: public artist, commercial artist, educator, consultant. I’m learning to operate as an integrated professional, someone managing a connected ecosystem of creative labor, where each part serves a distinct function.

But naming the model is the easy part.

Last week was hard.

I want to pause here and say something more personal, because theory can make transitions sound far cleaner than they feel.

If you’ve noticed, I haven’t written for over a week. Not because I didn’t want to, but because I hit a familiar fork in my professional life. One of those moments where I could feel myself slipping back toward what I know how to do: accommodating more paid work, more applications, more visible productivity.

Last week was hard.

I spent most of it with cold feet, hiding behind my computer, afraid to take the next step, actually beginning a new series of small-scale work. I did some initial research on Tuesday. After that, the rest of the week was defined less by uncertainty than by fear.

What’s difficult to admit is that I’m very good at the old pattern. I’m comfortable writing and applying for commissions. I know how to wait. What terrifies me right now is taking control and trying something new. The last time I did that, it didn’t go well, and that memory still lingers.

So even as I told myself I was pivoting, I kept looking at opportunities. I kept applying. I could have written, but I didn’t want to write about feeling like I was back at the beginning again, despite having done the work. Despite going through the Available Means Map, the cost analysis, the permission-versus-control exercises. Every one of them pointed in the same direction: make the small work.

And still, the fear of failing again sent me searching for safer terrain, more commissions, more startup ideas, more things I could pursue from the protective distance of my screen.

At one point, I sent a difficult text to a group of close friends, trying to articulate the impossible feeling of needing to prioritize everything at once: writing, applying for teaching and consulting work, and making new art for an upcoming showing. I’ll share a screenshot of that message here, not because it’s tidy or resolved, but because it’s honest.

I’m including this because I don’t think this hesitation means anything is wrong.

I think it means I’m standing at the edge of a different way of working, and edges are where fear tends to gather.

What I didn’t have last week wasn’t clarity. It was a way to move forward without defaulting to old habits. Knowing why the system doesn’t work is one thing; learning how to reconfigure your own practice, day by day, decision by decision, is something else entirely. That work doesn’t show up in artist talks or case studies. It lives in small, uncomfortable choices: what I make first, what I postpone, what I refuse, and what I allow to be imperfect.

That’s the part I want to talk about next.

What Was Actually Happening Last Week

The first thing I had to accept was that there was no clean starting point, only a decision to stop postponing the work I kept circling back to. And that decision triggered exactly what learning theorists call Cognitive Disequilibrium.