Painting Outside the Lines

Making Art Commissions Less Stressful

Painting Outside the Lines

Show Notes

Artists Rebecca and Valerie talk through the rewards and challenges of commissioned work, drawing on Rebecca’s years of experience and Valerie’s first commission. They share practical ways to set expectations, protect your time and creative process, and build lasting relationships with collectors. Key topics

Valerie describes having creative freedom on her first commission, while Rebecca explains how commissions helped turn her art from a hobby into a business. Rebecca shares how she created six coordinated paintings for a doctor’s practice, balancing different moods and needs while keeping the collection cohesive. They discuss progress updates: share enough to keep collectors involved, but avoid sending images during stages when the work may look unfinished. Rebecca finds video calls especially helpful for showing texture and discussing changes. Rebecca recommends clarifying that clients are commissioning your style, not an exact copy of a Pinterest image or an earlier painting. A questionnaire or conversation can establish the brief: size, orientation, colors, location, atmosphere, timeline, and which of your existing works they like. Set the price early, confirm any changes in size or scope before proceeding, and collect 50% upfront. Rebecca collects the balance when the work is shipped or picked up. Mock-ups can help clients picture the finished work in their space. Rebecca uses them to check scale and placement before final approval. Staying in touch after a sale can lead to repeat business and referrals. Rebecca also shares how commissions have helped her develop as an artist. They compare sales channels, including Instagram, Facebook, and galleries, and discuss why a gallery’s reputation or location does not always translate into sales. Timestamps (00:00) Why commissions can be a rewarding way to sell art (02:02) How commissions helped Rebecca build her business (04:11) Creating six paintings for a doctor’s practice (06:18) Sharing progress without alarming the client (08:21) Why the artist’s own style needs to lead (10:09) Questions that clarify a commission brief (12:39) When a questionnaire works better than a long conversation (14:40) Pricing commissioned work and managing revisions (16:23) Using mock-ups to confirm the finished piece (18:34) What can go wrong when changes come too late (20:01) Why Rebecca takes a 50% deposit (22:25) Artwork shipping: a topic for another conversation (24:00) Confirming costs before a project grows (26:18) Reducing anxiety with clear expectations (28:03) Email newsletters and staying in touch with collectors (30:14) Building trust through follow-up and client photos (32:07) Helping a client repair a damaged canvas (34:08) Commissions as revenue and creative development (36:12) Where commission inquiries and original sales come from (38:34) Why Facebook may need a different approach from Instagram (40:15) Making commission details easy to find (42:06) Weighing gallery fees against actual sales (44:18) The value of choosing a gallery you can work with locally (46:39) Setting boundaries around style, timing, and scope (48:32) How unclear expectations can make a commission overwhelming (50:31) Checking measurements and orientation before painting (52:29) When a project is not the right fit for the artist

More from Painting Outside the Lines

Oct 11, 2026

Faith, life-changing pivots and gold leaf… otherwise known as the devil’s dust. 😂✨ In Episode 9 of Painting Outside the Lines, we’re joined by artist Jennifer Dunlap for a conversation about how her son’s diabetes became the catalyst for the biggest pivot of her life. We talk about faith, finding a new direction and the role creativity has played along the way. And, because it’s us, we also get into the joys—and absolute bloody chaos—of working with gold leaf. An honest conversation with plenty of heart, humour and a little sparkle. Subscribe for more conversations about art and the life happening around it, and tell us in the comments: what’s been the catalyst for YOUR biggest pivot? #ExpectMiracles #JenniferDunlap #PaintingOutsideTheLines #ArtistPodcast #ArtAndFaith

Sep 25, 2026

In Episode 8, we continue our deep dive into the very real relationship between mental health and making art. This time, we’re talking imposter syndrome, fear of failure, the pressure to keep producing and why rest is actually part of the creative process — not something we need to feel guilty about. We chat about those inevitable moments of “Who am I to be doing this?”, what failure really looks like as an artist, and why sometimes stepping away from the studio is exactly what your creativity needs. As always, it’s an honest, unfiltered conversation about the bits of being an artist that don’t always make it onto Instagram. If you’ve ever doubted yourself, felt guilty for resting or wondered whether you’re actually good enough to call yourself an artist… this one’s for you. 🎨❤️

Sep 23, 2026

In the second episode of our deeper dive into mental health & art, we’re tackling two things that so many creatives know far too well: perfectionism and burnout. When does wanting to do your best become a need for everything to be perfect? And when does the pressure to keep creating, posting, selling and showing up start sucking the joy out of the thing you love? We chat about our own experiences with perfectionism, the pressure we put on ourselves, creative burnout, comparison, guilt around taking a break — and why sometimes good enough really is good enough. An open, honest (and inevitably slightly chaotic 😂) conversation about protecting your creativity AND your mental health while still wanting to grow.

Sep 14, 2026

Instagram. Love it, hate it, delete it, reinstall it… repeat. 😂

See all episodes →