Coaching practices for I'm an Artist and I'm Terrified of Failure How Do I Get Over it and Make Money From My Art

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Does this sound like the set of challenges you might be facing?

• When something I make doesn’t land, it doesn’t feel like the idea missed
• Every single thing I try feels like a referendum on whether I’m any good, so I cling to the first passable version rather than risk a worse one
• My whole approach is to wait until I’m in the mood to do the work, and the mood comes maybe one day in ten, so weeks go by with almost nothing made
• I keep waiting to feel like a creative person before I’ll let myself actually make anything
• Some part of me treats this failure as final

Practices that may help

1. Reframe failure as information, not verdict
   Build a personal rule: "I got data" replaces "I failed" after every attempt that didn’t land.
   Creative Confidence, Made Practical
2. Experiment without attachment to outcome
   Make many small experiments and treat each result as information — not as success or failure.
   The Creative Act: Rick Rubin’s Approach to Making
3. Turn pro: do the work on a schedule, not a mood
   Commit to showing up for your creative work at the same time every day, regardless of how you feel.
   The War of Art, Made Practical
4. Accumulate small creative wins to rebuild confidence
   Do deliberately small creative acts every day until the identity "I am creative" begins to feel true.
   Creative Confidence, Made Practical
5. Plan how to repair each worst case
   If the worst case happened anyway, write how you’d get back to where you are now.
   Fear-Setting, Made Practical
6. Keep side projects and play
   Protect a low-stakes project with no goal — the “waste” is where the real ideas surface.
   Steal Like an Artist, in Practice
7. Deliberately generate bad ideas first
   Start with the worst ideas you can think of — bad ideas are faster to generate and reveal hidden assumptions.
   Quantity Over Quality: How More Drafts Produce Better Work
8. Creative Confidence, Made Practical
   Creative confidence, as defined by Tom and David Kelley of IDEO, is the belief that you can generate good ideas and act on them — and research on self-efficacy shows it is learnable, not fixed. The core method is accumulating small creative wins through guided practice, which rebuilds confidence that was typically damaged by early criticism or comparison.
9. Work the affirmations and blurts
   Surface the negative beliefs about your creativity ("blurts"), then counter them deliberately.
   The Artist’s Way, Made Practical
10. First-draft permission: produce something deliberately bad on purpose
    Commit to writing, sketching, or making the worst version you can imagine — terrible on purpose removes the evaluative stake.
    The Beginner’s Mind in Creative Practice

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