Are You an Enterprising Artist or an Entrepreneurial One?

On self-knowledge, sustainability, and designing a creative career from the inside out

For a long time, I thought my problem was focus.

I moved from interior design to interaction design, then into interactive installations. I wrote about sustainability and creative careers while designing physical work that needed fabricators, permits, and budgets. I worked in tech and systems while trying to maintain an art practice. It looked, even to me, like indecision.

What I didn’t realize was that I wasn’t unfocused; I was misunderstanding myself as a creative. (I am still wrapping my head around this)

And that misunderstanding kept showing up in my career decisions.

When “Entrepreneurship” Looks Like the Answer

Prana App - Financial App for Creatives and Immigrants

In 2019, I won the Power Up Business Plan Competition organized by the Brooklyn Public Library. Over 400 businesses applied for the $20,000 seed grant, and we won.

The idea was a financial app for creatives and immigrants, inspired by long-standing community savings systems like the Susu or Tanda. A group of people contribute a set amount regularly, and each month one person takes home a lump sum. People use these systems to pay tuition, put down deposits, fund businesses, or manage uneven cash flow.

I felt strongly about this idea, personally and politically.

There had been many moments in my own creative practice when I needed a lump sum to pay a fabricator, build a prototype, or simply stay afloat, and couldn’t get there. This app felt like it could solve something real.

Then COVID hit.
I had a baby.
And the app struggled to gain traction.

What I hadn’t fully grasped was how burdensome financial regulation is in the U.S., how hard it is to move money between banks, and how dependent these systems are on local, trust-based communities. The app stalled.

At the same time, I had quietly stopped applying for public art commissions. I thought I was “pivoting.” I believed, deep down, that you could either run an art practice or build a software business, and that trying to do both meant you weren’t serious about either.

When the app failed to take off, I was left without work. I eventually returned to freelance design in tech to stabilize things.

That period forced a reckoning.

Not just about risk, but about how I actually work.

The Wrong Question Artists Ask

Artists are constantly told some version of this:

“You need to be more entrepreneurial.”

But that advice skips an essential step.

It assumes that all creatives should want the same things, build the same systems, and get energy from the same kinds of work.

A better question is more challenging:

What kind of creative labor gives me energy and what kind drains it, even when I’m good at it?

That question led me to a distinction I now find far more helpful than “art vs. business.”

Enterprising Artists and Entrepreneurial Artists

Some creatives are entrepreneurial by nature.
They enjoy building systems, running platforms, managing complexity, delegating, pitching, selling. Their creative work and business instincts reinforce each other.

Others, many others, are enterprising.

Enterprising artists create value through:

• Thinking

• Writing

• Research

• Synthesis

• Making meaning legible

• Translating ideas into form

They are not less ambitious.
They are ambitious differently.

The problem is that enterprising artists are often pressured to behave like entrepreneurial ones, applying endlessly, marketing aggressively, forcing themselves into systems that quietly exhaust them.

I’ve done this to myself more times than I can count.

Mapping My Own Work (Honestly)

Recently, I sat down and tracked how I actually spend my time.

What emerged wasn’t flattering, but it was clarifying.

Nearly half my energy was going into public art applications. They drained me. They didn’t feel meaningful. And they rarely resulted in work.

Writing, on the other hand, consistently gave me energy. So did research, synthesizing ideas, hosting events, and developing concepts. Even admin work felt fine when it supported something real.

Physical making was interesting. I loved the outcome, but not the fabrication itself. I worked with fabricators consistently. What mattered to me was directing ideas into the world.

That was the first clue.

What I Learned About Myself

When I looked across my answers, patterns became obvious:

• I am most myself when I am writing

• I lose track of time when I am designing and synthesizing

• I am good at connecting ideas and seeing patterns

• I am bad at sticking to rigid systems, but good at creating temporary frameworks and habits to support them.

• I over-invest in free work and under-invest in income

• I don’t go out of my way to garner visibility even when it would help me

• I tell myself I can’t pull off projects alone, even when evidence suggests otherwise

None of this is a failure.
It’s information.

And once I treated it that way, I could start designing around it.

From Self-Knowledge to Strategy

Out of this reflection came a one-page career strategy.

At its core was a simple decision:
Writing and research are my primary modes. Spatial and functional work are my translation layer.

That meant:

• Moving toward interior installations and functional art

• Moving away from speculative work that never sees the light of day

• Prioritizing libraries, hospitals, civic spaces, and homes

• Letting go of low-level IC design work that fragmented my attention

It also meant redefining success.

Not applications submitted, but:

• Work that exists in the world

• Writing that circulates

• Relationships that compound

• Income that doesn’t erode my energy

Designing a Weekly Operating System

Insight without structure doesn’t last. So I built a weekly operating system to protect what matters.

Each week now revolves around four buckets:

• Writing and synthesis

• Translation into real projects

• Visibility and relationships

• Admin and maintenance

The rule is simple:
If something doesn’t support writing, visibility, or real-world work, it has to justify its existence, or go. Justifying its existence means that it needs to give me happiness or energy.

Every week ends with reflection.
Not productivity metrics, but questions like:

• What actually moved the needle?

• What drained me unnecessarily?

• What should I stop doing next week?

This is how self-knowledge becomes a system.

Why I’m Sharing This (and Why There’s a Paid Tier)

I am providing transparency into my process. This isn’t a course.

Creative careers are usually presented as polished success stories or abstract advice. What’s missing is visibility into how decisions are actually made over time, especially when things don’t work, which may very well happen here. In which case you can learn from me without making your own. That said, I would suggest doing this alongside me for maximum effect.

Let’s fail together and succeed together.

Over the next year or so, I’m taking readers along as I design my creative business in public:

• What I double down on

• What I stop doing

• Where I miscalculate

• What sustains me

• What surprises me

You’re not paying for answers.
You’re supporting a space where thinking, reflection, and iteration are valued.

An Invitation

If you’re looking for a single right way to succeed, this won’t offer it.

But if you’re trying to understand what kind of creative you actually are, what you should stop forcing, how to build a career that fits your temperament, and how to make work that is visible, useful, and sustainable—then I hope this gives you language, and company.

You can download the Creative Direction & Strengths Discovery Worksheet here. It’s the same tool I used to map my own patterns, contradictions, and instincts, not to lock myself into a box, but to see myself more clearly.

For paid subscribers, I’m sharing what comes next. Tomorrow, I’ll be publishing my completed worksheet, my one-page career strategy, and the weekly operating system I’ll use to run my professional life. Over the coming months, I’ll also share ongoing updates as I adjust, fail, refine, and course-correct, out loud and in real time.

This isn’t a reveal of a polished master plan. It’s an invitation to walk alongside me as I design one.

Because the goal isn’t to become more entrepreneurial.

It’s to become more accurately yourself, and design from there.