Why I Always Paint TWO Pieces for Every Commission

For years, I hated doing commissions so much that  I had to stop entirely. Even though people wanted my work… The moment I started painting, I’d forget about myself and only think about pleasing the client. Then I discovered two counterintuitive strategies that changed everything. First, I offer a 100% money-back guarantee, which sounds like more pressure but actually sets me completely free to make what I love. Second, I always paint two pieces for every commission, one for them, one for me. My goal is to make them so good that the client can’t decide which one they love better. These approaches transformed commissions from miserable obligations into joyful creative experiences.

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When Making Art Stops Feeling Like Yours

I remember being in my studio, brush in hand, working on a commissioned painting. And I literally felt like I wasn’t even the person making the art.

Someone had paid me in advance. Good money. I’d said yes enthusiastically because it seemed like an amazing opportunity.

But then I started painting.

And all I could think about was their comments. The colors they liked. Their couch. The things they wanted to see in the piece. All the specifications they’d given me.

I wanted to please them. I wanted the work to be successful. I wanted them to be thrilled. But in trying to make everyone else happy, I’d completely forgotten about myself.

The Problem with Painting for Others

These commission experiences were some of the most unpleasant moments I’ve had in my studio.

I hated doing them.

And here’s what made it so frustrating. I had people wanting my work. People willing to pay for it. A clear path to making money from my art.

But I couldn’t do it because the process was so miserable.

So I stopped. I turned down commissions entirely.

For a while, that felt like the only solution. If commissions meant losing myself in the work, then commissions weren’t worth it.

Then I Figured Something Out

Eventually, I discovered two strategies that changed everything about how I approach commissioned work.

The first one sounds completely backwards. Like it would add more pressure to an already stressful situation.

The second one? Well, my clients don’t even know I’m doing it.

But together, these two approaches made it possible for me to love doing commissions again.

 

Strategy #1: The 100% Money-Back Guarantee

Here’s what I did first.

I made an agreement with myself that I would give clients all their money back if they weren’t happy with the finished painting.

Eventually, I gained enough confidence to tell them this upfront.

I’d say something like this: “Just so you know, I guarantee the work. I have to make this painting so that I love it. And I’m pretty confident that if I love it, you’ll love it. But if for any reason you don’t? I’ll refund you 100% of what you paid.”

Now, this sounds like it would create more pressure, right?

Like I’m putting myself on the line even more.

But actually, it was massively liberating.

Why the Guarantee Sets You Free

Here’s what happened when I offered that guarantee.

Knowing they could walk away if they didn’t love it meant that all I had to do was please myself.

That was my only job.

I was free to make the work I wanted to make. To follow what brought me alive. To paint from my authentic voice instead of trying to read someone else’s mind.

The guarantee relaxed me completely.

And here’s the beautiful part. They always loved it.

This has never been a problem. Not once has someone returned a painting.

Think about how easy it is for clients to say yes to this arrangement.

I take a 50% deposit upfront. And I’m telling them, “If you don’t love this 100%, you get all your money back. I wouldn’t want you to have a painting you don’t love. But if I can make it so I love it, I’m confident you will too.”

It removes all the risk for them. And it removes all the pressure for me to be someone I’m not.

Strategy #2: Always Paint Two

But I didn’t stop there. I doubled down on my freedom.

Now when I do a commission, I always do two paintings.

The client doesn’t know this. But I’m creating one for them and one for me.

I’m about to start a really large commission right now—a 14-foot-wide piece. And yes, even with a project this size, I’m doing two.

My goal is simple. When I show them both paintings and say, “I got so into this that I made another one,” I know I’ve won when they can’t decide which one they love better.

What This Really Means

Sometimes clients end up buying both pieces.

Sometimes they have a friend who buys the second one.

But either way, I end up with another large painting that I love. Work that came from my authentic voice. Art that represents who I actually am.

Because here’s what matters most.

I’m in the studio by myself, making the art.

Not making it for them. Making it for me.

And that changes everything.

The Transformation

These strategies completely transformed my relationship with commissioned work.

I love doing commissions now.

They’re no longer about abandoning myself to please someone else. They’re about trusting that when I make work I genuinely love, others will love it too.

And they do.

Every single time.

Beyond Commissions

But here’s what I want you to think about.

This story isn’t really about commissions.

It’s about something much bigger.

It’s about what happens when you forget yourself in your art. When other people’s voices get so loud that you lose your own.

Maybe you’re not doing commissions. But maybe you’re making art while thinking about what will sell. Or what your art teacher would say. Or what looks “right” according to some external standard.

Maybe you’re painting while worrying about whether it’s good enough. Professional enough. Marketable enough.

And in all that worry, you’ve forgotten the most important thing.

Your art has to please you first.

Everything else follows from that.

The Question to Ask Yourself

Have you ever felt like you weren’t even the person making your art?

Like someone else’s voice got so loud you lost your own?

If so, I want you to try something.

Make an agreement with yourself that the next piece you create, you’re making it only for you.

Not for Instagram. Not for a show. Not for anyone’s approval.

Just for you.

See what happens when you give yourself that freedom.

See what shows up when you’re the only person you need to please.

Because here’s what I’ve discovered.

When you make work that genuinely moves you, that comes from your authentic voice, that represents what you truly love—that’s when others connect with it most deeply.

Not because you were trying to please them.

But because you weren’t.

Your Turn

I’d love to hear from you in the comments.

Have you ever felt like you lost yourself in your art? What helps you come back to your own voice?

And if you’ve done commissioned work, how do you maintain your authentic expression while creating for others?

Share your thoughts below. Your experience might be exactly what another artist needs to hear today.