How to Get to the Top

How do you get to the top of a career? Here's my insights in making in a creative career.

Jul 07, 2025

I’m well aware that several of my recent posts have been kind of a bummer. When this whole good fight thing began, almost everything I generated was a bummer. That’s not to say that I want to cycle and regurgitate challenge after challenge and loss after loss over and over again. I am concerned, however, that I telegraph a sense that all I’ve accumulated is loss and defeat. I absolutely don’t want to do that, especially when there have been victories. But what do we do when it feels like there are no victories?

Working independently makes everything about money. It’s unfortunate, necessary, and distracting. Everywhere I go, I encounter people who equate, “making it,” with having comfortable or massive wealth. Creative folks want to be a professional, and have strange goal posts for what qualifies that. Sometimes, I even receive sentiments of envy for my position in the creative field.

If we consider creativity, and, “making it,” (whatever that means) as a mountain we’re climbing — which I know most of us do — we think there’s some peak we’ll reach where we get confirmation we’re a success. Maybe we’ll meet a hero who thinks we’re noteworthy? Maybe we’ll get some massive payday? Or maybe a t-shirt saying, “you did it!” will arrive in the mail? Something, anything, to say that we got to the good spot.

If I’ve been climbing this proverbial mountain for over a decade there’s only two things I can conclude at this altitude:

I’m so bad at this that I’m still at the bottom, or,
There is no top and we’re all fooling ourselves

There is No Top

Let’s start with number two. It’s less of a bummer and more true, I think.

After Champions issue 1 debuted, I slouched into a powerful depression. I put twenty-eight days of body-destroying effort into the first issue followed by thirty days of restless promoting of a Kickstarter. I was on the news, I negotiated with our local comic shop, and I spent every second worrying about the book. It felt like something huge was going to happen. But, the book came out, the launch was a challenging success, and life went back to normal. I was slowly working on issue two. I was tired, I was worn out, and I didn’t know why life felt the same.

Several weeks later, while on an artist residency, my colleague and friend, Altman, mentioned that life goes on. “Credits didn’t roll and that’s hard to deal with,” he told me as we drove across state lines. I was shocked because he knew something I didn’t. Putting out a single comic was a goal I had set for my mid-30’s, and here I was, at twenty-eight with that goal behind me. Everywhere I went, I still encountered myself. My life hadn’t changed. So what did anything mean? I sank deeper, unable to comprehend that being on that artist residency was a big deal. My second artist residency ever, and this Altman guy helped me negotiate it into two weeks at full-pay. I had just begun to live as an artist, and yet I felt like nothing meant anything.

Champions 1 - 6, This is my Private Life, Violet 9

Flash forward to now, at thirty-seven, and I have about forty weeks of residencies under my belt. I have six comics out, two webcomics you can still read, a coloring book out, and more on the way. But I’m still me. Sure, I have a growing community, and I make guest appearances at shows now. But I don’t feel like I made it. I’m coming off of dud show after dud show and sinking sales. It’s incredibly challenging not to be consumed by thoughts that I’ve done something wrong.

When I step back and think about it, who I was in my twenties would never believe that I have made the strides I have. Two events in West Virginia in one summer? No way! Guest spots at comic conventions? Impossible. Negotiations with stores to wholesale something I drew? Inconceivable!

A gif from The Princess Bride – INCONCEIVABLE! | Smart ...

Why do things feel like I’ve made no progress, then? Because I’m still looking up at the next handhold, and the next plateau. Everytime I get there, I look around and there’s more up to go. And, when I look closer, I see other people around me who seem to be further up than me. They must be at the top! Or at least close, right? I’m not so convinced. Dealing with health issues, career stresses, and family goals has made me even more convinced there’s never a satisfying ending spot. I think the people who make goals like these look easy and professional are those around us who have the resilience to keep looking up, and the confidence to look down and remember how far they’ve come.

I’m Stuck at the Bottom

Now, for that pernicious thought that I’m all washed up, that I’m no good. Like I mentioned last week, that voice is no more capable of knowing the future than I am. It’s not genuine, kind, or accurate. There’s no value in treating ourselves that way. We all deserve grace and patience. I’ve seen several people drop out of creative careers because challenges build up, lack of income builds up, until they cave to pressures from thoughts like these. It’s painful to see, and never fun to recall.

I don’t hold grudges against those who jumped off… climbed down? (The mountain metaphor only stretches so thin.) While I will never support letting our inner self-defeat win, I am not unable to see how difficult creative fields are, especially in the United States. We have to cover insurance somehow. We have bills beating us down with rising housing costs, and food costs. Gigs like mine require travel, which can strain our health and relationships. It’s not for everyone, and that’s okay. I think there’s dignity in changing gears, or learning something is not for you. If we ever decide to get off this endless climb, we should do it on our own terms and for our own well-being.

This life isn’t easy. Sometimes it beats the hell out of me. I am looking at a tough end of my summer and start of fall. But I am positioning myself to be ready and I’ve got my sights on prospective victories I can’t wait to share.