Personalized insight
6 Essential Questions Every Artist Must Ask to Thrive
Every artist I know is on some version of the Hero’s Journey.
Scholar Joseph Campbell described the Hero’s Journey as separation, initiation, return.
For artists, it looks like this:
- You feel the call to create (separation).
- You step into the unknown and face your monsters – especially the one called “Not Enough” (initiation).
- You come back with something to offer the world: your art, your perspective, your hard-won truth (return).
Most artists get stuck in the initiation phase. Not because they’re not talented, but because they’re asking the wrong questions.
“Who am I to do this?”
“Is my work good enough?”
“Why haven’t I figured it out by now?”
Those are the questions that feed the monster I call “Not Enough.”
I know, because I lived there for a long time.
My own life didn’t begin to change until one professor looked me in the eye and said two simple words no one had ever offered me before: “You can.”
That tiny shift in language gave me a new question:
Not “What’s wrong with me?” but “What might be possible if I actually followed this?”
If you want to actually set your course as a working artist, start asking better questions.
Here are the ones I suggest you begin with:
1. What do I want to accomplish next as an artist?
Not “someday,” not “in my dream life.”
Next.
Is it finishing a body of work? Landing your first show? Raising your prices?
Choosing one clear priority focuses your energy and stops the endless spinning.
2. Why does this matter to me?
Why this work? Why these subjects? Why now?
Your why is your internal compass. When things get hard (and they will), it’s the reason you keep going instead of quitting.
3. What do I already have?
Skills, experience, relationships, time, money, space, tools, curiosity, resilience…
Artists love to obsess over what we don’t have.
A more powerful move is to inventory what you do have and build from there.
4. How do I want my success to feel?
When you close your eyes and imagine true success, what’s the feeling?
Freedom? Groundedness? Visibility? Contribution? Power? Peace?
That feeling is the gold. It will tell you which opportunities align with your real vision and which are just distractions dressed up as “shoulds.”
5. What am I willing to spend my energy on?
Everything is currency: money, time, attention, emotion.
Are you spending yours on stuff, drama, and comparison…
or on learning, making work, building relationships, and taking tiny brave steps?
Travel light, artist. The less you drag along, the further you can go.
6. Who and what will support me on this journey?
This is where the Hero’s Journey becomes real.
Who are your mentors? Your peers? Your community?
How do you feed your Muse – with learning, beauty, rest, and real inspiration – or are you starving Her and then demanding miracles?
No artist does this alone, Crista. Not the ones who last.
These are the questions I’ve asked myself over and over again – escaping homelessness and drug addiction, building a big career in the art world, and eventually selling millions of dollars of art, and today, helping other artists find their own wings.
These are also the questions I ask inside The Working Artist Academy, (details here) where we turn vague longing into an actual course of action, one small, brave decision at a time.
If you’re willing to sit with these questions honestly, you’ll start to see your course appear. Not all at once, not with trumpets and neon arrows… but as a series of small, clear “follow this” moments.
That’s how we grow our feathers into wings.
That’s how we move from potential to achievement.
That’s how we turn the artist’s journey into a Hero’s Journey.
And yes Crista, you are enough to walk it.
