The Ambitious Artist's

Planning Workshop

Dream, Plan, Achieve

Start the year with a plan you can actually follow.

Create a 2-Year Plan + 90-Day Action Map

Being ambitious isn’t the problem

Planning in your head is

Stop trying to carry your entire art career alone

Leave with a complete, functional roadmap for your next two years—built live with guided prompts and real-time support.

And let Jennifer’s custom artists’ planning GPT do the heavy lifting.

Turn your top 3 goals into a detailed 2-Year Plan and start the year with confidence and clarity.

January 17–18, 2026

11:00 AM–2:00 PM Mountain Time

Live on Zoom*

$97

Registration closes January 16, 2026 (midnight MT)

*Replay access for 2 weeks

It’s early January.

You’re in your studio with your journal open, trying to do the “right” thing—plan.
But the longer you sit there, the heavier everything feels.

Because you’re not just planning a week.

You’re trying to hold:

• the work you need AND want to make
• the opportunities you don’t want to miss
• the deadlines you can’t ignore
• the admin that keeps multiplying
• the part of you that needs rest, too

And it’s not because you’re not disciplined.

It’s because the plan you keep trying to make is quietly based on the most heroic sprint you’ve ever pulled off.

That version of you can’t be the foundation for the next two years.

You don’t need a new planner.
You need a system that helps you get clear on what matters now—so you can build a realistic, professional plan around it.

A plan that protects your studio time instead of stealing it.
A plan with margins.
A plan you can follow.

If you keep trying to fit an art career into a one-year plan, no wonder it keeps collapsing.

DREAM

A vision you can actually stand inside.

Before the spreadsheets.
Before the deadlines.
Before the “I should.”

We start with the part that most artists skip because it feels indulgent—or too big to name.

But this is the truth…

If you don’t start with your dream, you’ll accidentally build a plan for someone else’s life.

In the workshop, you’ll clarify what you want in this next chapter of your work and career—without over-explaining it, defending it, or shrinking it.

You’ll use:

• guided prompts to name what you’re moving toward
• an artist-centered filter for what matters now (and what doesn’t)
• a simple way to translate desire into direction

And then we do something that changes everything.

We cap your focus at three goals.

One is allowed. Two is powerful. Three is the maximum.
Because ambition isn’t the problem—diffusion is.

PLAN

Turn your dream into structure.

Most planning workshops help you think.
Then you go home and spend hours organizing.

This one is built for completion.

You’ll build your plan live, with support, and you’ll use Jennifer’s custom artists’ planning GPT to help organize the moving parts—sequencing your actions and shaping your ideas into a roadmap you can use.

You’ll still be the artist making the choices.
The GPT helps you move from clarity to structure faster, with less mental load.

You’ll leave with:

• a complete 2-year plan with month-by-month benchmarks
• a detailed first 90-day action map (your real launch ramp)
• an optional week-by-week rhythm for month one (so you can start immediately)
• a built-in buffer strategy so deadlines don’t require panic
• a “next right step” checklist that tells you what to do first

Two years is long enough to be realistic and short enough to stay actionable.

Create a living plan that protects your creativity while ensuring you reach your goals.

What you’ll experience over the weekend

This is live, interactive, and built for completion.

Expect:

• guided prompts and clear steps
• dedicated work time both days (so your plan gets built in the room)
• live Q&A both days (so you can get unstuck fast and move forward)

You won’t be sent home with an outline and a “good luck.”
You’ll leave with a plan that answers the question, “What do I do next, right now to move me forward?”

Who this is for

This workshop is for artists who:

• have a consistent studio practice and want to move forward with focus
• are preparing for exhibitions, applications, grants, residencies, fairs, or major bodies of work
• have teaching and/or other obligations and need a realistic plan with buffers
• feel pulled in too many directions and want a clear “yes / no / not now” filter
• want to use AI as an ally, but want guidance so it supports your voice and your decisions

This workshop is not for people looking for a quick fix or an overnight transformation.
It’s for artists who are ready to make clear choices—and follow through.

What you need

You’ll receive an email after registration with everything you need to access the workshop and prepare.

At minimum, you’ll need:

• Zoom access
• a free ChatGPT account

FAQs

Is this live or pre-recorded?

Live on Zoom.

Will there be a replay?

Yes. You’ll have replay access for two weeks.

I’m not “good at AI.” Can I still do this?

Yes. This is guided. You’ll receive a workbook that shows you exactly how to use the planning GPT during the workshop. You don’t need to write “perfect prompts.” The GPT will ask you clear questions, and you can simply answer—like you’re talking it through with a smart, supportive friend. If you want, you can use voice dictation and speak your answers out loud instead of typing.

AI isn’t my thing. Is this workshop still for me?

AI isn’t for everyone, I get it. Many people have strong opinions about using it. I believe in the judicious use of these tools. I have worked with experienced artists for over 25 years. At some point, your art career requires more from you than you can consistently deliver. You can either try to do it all yourself or hire help. AI helps bridge that gap between solopreneur and hiring help. AI can help you consistently do the administrative tasks that inevitably fall through the cracks. And it can be a sounding board and studio assistant, corralling your ideas, notes about your work, and so much more. Planning is one of the areas where AI excels. I want you to spend less time figuring out “how” to map your plan, more time deciding what is most important, and where you want to be in 2 years, so you can spend more time in your studio. So if you aren’t interested in at least trying to use a custom AI to help you make your plan, this isn’t for you.

Do I have to speak or share in the group?

No. You can participate via chat, listening, or sharing out loud if you want to. There will be live Q&A both days.

What exactly will I finish by the end of the workshop?

You’ll leave with a complete two-year plan (month-by-month benchmarks) and a detailed first 90-day action map. You’ll also have an optional week-by-week month one rhythm if you want it.

What kinds of goals can this support?

Studio goals (body of work), professional goals (exhibitions, grants, residencies, outreach), and life support goals (schedule, travel, health, margins). We’ll cap it at three so the plan stays workable.

What if my goals shift during the two years?

That’s expected. You’ll build a living plan with a clear structure so you can adjust without losing direction.

What time zone is this in?

Mountain Time (America/Denver): 11:00 AM–2:00 PM.

Why do you need my email?

So you receive the Zoom access details, prep instructions, workbook, and replay information.

How long will I have access to the customGPT?

The custom planning GPT will be available for 1-2 weeks after the workshop.

If you’re ready to start the year with a dream you can name…

A plan you can follow…

And a path to achievement that doesn’t require burnout…

Come build it with us.

P.S. You don’t need a perfect plan. You need a functional one—the kind that tells you what matters this month, helps you follow through, and protects the studio time your work deserves.