When It Doesn't Look Like Success

A few days ago, I came across a picture I hadn't seen in a while. It was from what my wife and some of our closest friends jokingly called my "retirement party."

Four years ago, they gathered together to celebrate me leaving my full-time job and taking the leap to pursue my creative business JW Creates full time. At the time, it felt like the beginning of a brand-new chapter. Looking back at that picture today, I realized something. 

I don't think they were celebrating that I quit my job.

I think they were celebrating that I finally had the courage to try.

That picture made me stop and reflect on everything that's happened over the last four years. If I'm being honest, it's been nothing like I imagined.

The Dream

JW Creates officially became a full-time business in July 2022, but the story started years before that.

Looking back, I can trace it all the way to 2015 or 2016. Back then I was creating simple logos for hobby projects and designing cover art for my own music that I was uploading to SoundCloud. I didn't think of it as a business, I just loved making things.

1ST JW Creates logo designed in 2016

By late 2019 and early 2020, with a little push from my wife, I found myself asking a bigger question: What do I actually want to do with my career? I knew I wanted to create, but I hadn't figured out what that looked like professionally.

Then I had my lightbulb moment. I decided I wanted to design cover art.

I also realized that if I wanted to build a real business, I couldn't wait around for cover art projects alone. So I started saying yes to just about every creative opportunity that came my way. A logo for a friend's business, cover art for a local musician, podcast artwork, branding projects, and eventually websites. If it gave me the chance to learn and create, I was all in.

Slowly, project by project, my evenings and weekends began to fill up. I'd wake up before work to squeeze in a few hours of design, head to my day job, then come home and work on client projects late into the night. Little by little, what started as a creative outlet began turning into something much bigger.

It was exhausting. But it was also exciting. For the first time, I could see that maybe this wasn't just a hobby anymore. 

Then something happened that changed everything. My employer knew I had been doing freelance creative work on the side and approached me about redesigning their website. At the time, it wasn't just the biggest creative project I'd ever been offered, it was the first time I thought…Maybe I can actually do this.

More importantly, it started an idea in my mind and heart. If I was already this busy outside of work, what could happen if I actually gave this dream my full attention…? After a lot of conversations, a lot of prayer, and the support of some incredible people around me, I decided to take the leap.

What I Thought Success Would Look Like

Like most entrepreneurs, I had a picture in my head. I figured that after about a year, I'd have enough steady work to hopefully pay the bills, continue growing the business, and keep building relationships with amazing clients. Looking back, I realize success was never just about money.

It was about freedom. I wanted flexibility with my schedule. I wanted time to invest in friendships and community. I wanted to support my wife, our dog, and the life we were building together. I wanted to wake up excited about the projects sitting on my desk, especially album cover projects. Those are still my favorite!

I imagined a steady stream of meaningful creative work and the freedom to keep chasing it.

Instead...Life got complicated.

When the Story Changes

There wasn't one dramatic moment where everything fell apart. There wasn't one terrible client. Not one terrible month. One catastrophic decision. It was slower than that.

The projects became less consistent.

The income became less predictable.

The stress became harder to ignore.

My wife was incredibly supportive of the dream, but like any responsible spouse, she also cared about things like paying bills and planning for the future. We had already agreed before I left that we'd set benchmarks along the way. If the business wasn't reaching certain goals after a specific amount of time, we'd reevaluate. Six months later, that's exactly what we did.

I made the decision to go back to work part-time. Thankfully I was able to return to my previous employer in a completely different role, one focused on the creative work I love doing, while still giving me the flexibility to continue building JW Creates.

From the outside, that probably doesn't look like success. In fact, for a long time, I was afraid to even tell people. I worried they'd think...

"Well...I guess that didn't work out."

I'll admit it. I felt embarrassed. I wondered if people thought I had failed. I wondered if I'd disappointed the people who believed in me. I wondered if I had made the wrong decision.

But here's what I've realized.

Sometimes we judge a story before it's finished.

Looking Back Instead of Looking Around

That picture from my "retirement party" forced me to stop comparing my story to someone else's and simply look at my own. When I did, I realized something surprising.

I wasn't thinking about money, I was thinking about people.

I thought about the incredible clients I've gotten to work with.

The musicians who trusted me with the cover art for their songs.

The podcasters who trusted me with their branding vision.

The entrepreneurs who trusted me to help tell the story of their businesses.

The nonprofits trying to make a difference in their communities.

I thought about launching Judged by the Cover, a podcast that gave me an excuse to geek out over album artwork with my friend Phil. I thought about joining Podnooga and eventually having the opportunity to help lead this community that's encouraging podcasters and creators throughout Chattanooga. I thought about speaking at a creative conference about podcasting. Speaking at a Rotary Club meeting about my love for album cover art. Even getting invited onto a local television station to talk about the podcast.

None of those things were on my original business plan. None of them.

And perhaps more importantly, I thought about having the flexibility to be present for my wife's family during her dad's cancer journey & passing. That's not something you put on a vision board. But it's something I'll always be grateful for.

If I had never taken that leap four years ago, I honestly don't know how many of those opportunities would have happened.

Success Looks Different Now

Somewhere along the way, my definition of success quietly changed. Four years ago, success looked like owning my own business full time.

Today…? Not so much.

Today, success looks like having meaningful work. Working with clients who’s projects genuinely excite me. Creating cover art that tells someone's story. Designing logos that help launch a dream. Building websites that help businesses grow.

Having time for my wife. Having time for friends. Being part of a creative community. Having enough stability that I don't have to say yes to every project simply because it pays.

Ironically, returning to my previous job didn't kill my creativity. It protected it. Because I'm not relying on every single project to pay next month's bills, I can be more intentional about the work I accept.

I can spend more time on projects that truly matter.

I can politely say no when something isn't the right fit.

I can keep building the business I actually want instead of the business I feel forced to build.

That's a freedom I never expected.

What I Actually Learned

Owning a business has taught me plenty. I'm more confident than I used to be. I'm a better designer. I communicate with clients more effectively. And I've become much more comfortable putting my work into the world without obsessing over every little detail.

I've also learned that time management is still something I have to work on. Procrastination still has a way of convincing me that deadlines are farther away than they really are. Some lessons never stop teaching us.

But maybe the biggest lesson has nothing to do with business. I used to think successful entrepreneurs were simply more disciplined.

More gifted.

More driven.

Now I think something else matters just as much. The people around you. Looking back at that retirement party picture, I'm reminded that I didn't make this journey alone. My wife supported me, even through the uncertainty. Our friends encouraged us. People believed in me long before I felt like I had earned it.

That's a gift I'll never take for granted.

When It Doesn't Look Like Success

If someone only looked at my career from a distance, they might see someone who left a full-time job only to eventually return to the same one. That's one way to tell the story.

But it isn't the whole story.

The whole story includes friendships. It includes clients who trusted me with their ideas. It includes podcasts, speaking opportunities, creative growth, confidence, a community I love, and a business that's more focused today than it's ever been. Most importantly, it includes a life I genuinely enjoy living.

Looking at that picture now, I don't see someone who took a risk that didn't work. I see someone who had the courage to take the first step toward a life that ended up looking different, and better, than he expected. 

Maybe success was never about being fully self-employed. Maybe it was always about building a life where I get to use the gifts God has given me, serve people well, create work I'm proud of, love my family, invest in my community, and keep chasing the projects that make me come alive.

If that's what success looks like...

Then I think I'm doing just fine.

And if you're reading this wondering whether your own journey looks "successful" enough, maybe stop comparing it to someone else's highlight reel. Instead, ask yourself a different question.

Are you becoming the person you hoped you'd become?

Because sometimes success doesn't look like success at all.

Sometimes it just looks like growth.