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From Corporate Creative Director to Painter: Living the Dream

I think we are all pretty much our own worst enemies. Fueled by some version of fear and limiting beliefs, we’re the ones who get in our own way. It’s why writers have editors, athletes have coaches and CEOs have a Board of Directors or an Executive Team.

We all need help getting out of our own way.

Today I want to share another true story of one of my clients. In just two months, he created his dream life. I want to share it so that you know what’s possible for you, too.

His dreams aren’t unique. Like many of us, he wants to make a positive contribution to the world, do work that is fulfilling, and have time to enjoy his family. And, also like many people I work with, he was burned out from the corporate grind. Tired of slaving away on projects that make money, but don’t make a difference.

Fortunately, his company laid him off.

With time on his hands and a severance package, he was contemplating a big life question: How can I do what I want and still pay the bills?

He knew what he wanted—to paint and to work on freelance projects that were interesting to him—but the responsibility as sole provider for his family was paralyzing. In the past when he had been a freelance designer, all of his time and energy had gone to the work. There wasn’t anything left over for painting.

And yet, there we were, drinking coffee and talking about painting.

“So what stops you right now, given that you have the time?” And he launched into the explanations that I hear from nearly every client I talk to:

You can’t make any money at it. It’s not realistic.

I have BILLS to pay, lady.

There are some decent, interesting corporate jobs out there I should apply for. They might not be that bad.

I have to clean the garage so I have a place to paint.

What if I’m no good?

“Clean the garage, huh?” I pressed. “How long will that take?”

“Three hours, probably.”

“Ok, so what stops you from doing that today? It’s like 9am. You have all day.”

He looked sheepish, his shoulders drooped, and he glanced away. “I have some full-time jobs I need to apply to.”

“So let me get this straight: You’re going to spend all day applying to jobs you don’t want instead of getting your garage ready to do something you do want.”

Excuses = Fear (but fear won’t kill you)

We all do this. We make up a million reasons and excuses for why we don’t take risks. Because we are really afraid of finding out we aren’t any good at whatever we want to do. We think we will die of disappointment.

But all of that stuff we tell ourselves? It’s just fear squawking to keep you safe and complacent.

We tell ourselves we have to do the things we don’t like. We have to do the thing that’s “realistic.” We have to have a corporate job in order to pay the bills. We have to do the soul-sucking work because it’s the only work that pays.

It’s not necessarily true. We just live as if is, and make it true. We create a reality that supports our viewpoint.

What is true is that we are afraid and our brains dream up excuses to keep us safe.

Have you ever heard the saying: “Our perception is our reality”? Once we believe something, we only see the evidence that supports that belief. It’s how our brains filter things.

This is why I introduce my client to this concept:

Thoughts —> Feelings—> Actions —> Results

What we think determines what we feel; emotions drive our actions, and from our actions, we get our results.

So if we don’t like our results, we need to look at our thoughts.

Most of us usually just try to change our actions, but we really need to examine our thoughts.

You can change your thoughts IF you are aware of what you’re thinking.

Build Awareness

So that’s what my client did: He became aware of what he was thinking.

What he noticed was that his process always followed a path, albeit a path that included emotional peaks and valleys, but one that also produced a painting. Once he became aware that his process followed a general path, it was easier for him to accept that it was part of the creative process. Allowing himself to paint and experience the fear and discomfort of this process also allowed him to learn some things.

“There’s always a time when it’s terrible, and I’m not sure how I’m going to fix it or how it’s going to work out. And then I figure it out. Now, the valleys aren’t as low.”

This is vastly different from what he learned when he spent his time applying for full-time jobs he didn’t want, getting bored, turning to Facebook, wandering down that rabbit hole and then reading the news, which created all-out demoralization and a distinct desire for happy hour.

The path that told him he had to find a full-time job actually led to happy hour.

The riskier path, painting, led to several paid commissions.


In short, here’s what he learned.

Setbacks are gifts.

Getting laid off was a gift.

Taking on a crappy, disorganized freelance project because he was anxious about money—and then the client pulled the plug on the project—was a gift because it was a project that would’ve turned into a huge time suck.

Experiment. Withhold criticism.

Now, the whole valley part of the peaks-and-valleys process wasn’t necessarily pleasant, but the key is that he was wiling to tolerate it and trust that he’d figure it out. What happens to most of us is that when things get uncomfortable, we assume we’re on the wrong path and bail out.

He learned that being uncomfortable IS part of the process. And he didn’t judge himself for trying something new. He experimented.

Perhaps the most important thing is he didn’t criticize himself or spend too long swimming in self-doubt. Instead, he’d go into the garden and literally plant some seeds.

Manage your time.

It sounds so mundane and boring, but it helps. He put “Painting” in his calendar just like an appointment or business meeting. This was much harder than he thought it would be. He kept getting distracted by running errands and picking up kids, walking the dog, making dinner, etc.

The problem wasn’t the kids or the errands or the dog—it was his thinking.

He wasn’t taking himself seriously.

“It’s a prison. You feel like you can’t risk doing this other stuff [gardening, painting] until the work is done. Then one day, you test the cell door and realize it’s been open this whole time. That door is always unlocked, there’s never a chance that it’s locked. You realize you never were in a prison.”

To shift this, he found ways of holding himself accountable, e.g., doing a portrait of his daughter for her birthday, trading me for services, etc. (Yes, that is my dog he painted that I used as the image for this post.) With a deadline and desire, he made it happen. And proved to himself that he could work (freelance) and paint.

One day a week, he puts painting first. In the daytime. During normal working hours. Even when he has freelance work that would pay him money.

He learned he could get it all done. He knew he’d get the freelance work done. He never missed deadlines. Allowing himself to take breaks from it to paint actually helped the quality of the freelance work. The work feeds the art, and the art feeds the work.

“I gotta give it a shot.”

When you’re 80, what do you want to be able to say when you look back on your life? He realized that for himself and his kids, he wants to be able to say he gave it a shot. So, he’s giving himself a year to experiment.

Down the road, he may get a full-time job, but even if he does, he knows and trusts himself to make time for painting.

“If I had gotten a job right away, I wouldn’t be painting now. But now I know, even if I get a job, I don’t have to leave any of this. What defines success for me now, is that I do it. I paint.”


It used to take him a year to complete a painting. Now he can do one in a day.

He never cleaned out the garage.

If you want to check out his work, shoot me an email and I’ll send you his website address. He’s taking commissions, by the way. ;)

If you want to learn how to get out of your own way, email me for a free mini-session by phone.

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