This month has been incredibly productive for me, both in terms of the painting I’ve been doing in the studio and in the amount of writing I’ve been doing. I’ve got multiple paintings in the works and I’ve started sketching out the framework for an entirely new body of work, which, if I can pull it off, will be different than anything I’ve done before. I feel like I’m still riding the wave of momentum that started building over the last couple months of 2022, after coming to some pretty terrific—and in some cases pretty profound—realizations around my work and where I see myself going over the next year. Looking forward is not something I’ve historically been very good at. Looking back, on the other hand, is something I do really well—often to pick at the scabs of some imagined shortcomings where I think I’ve failed myself or others. I just can’t think about 3 or 5 or 10 years out like some people do, especially since I’ve spent so much of my life not being able to see a 10 day plan, let alone 10 years.
At the beginning of last year, I had a bunch of really honest talks with Adrianne about how I was feeling about the work I was doing—or wasn’t doing—and what I thought I could or should be doing. And I have to say that Adrianne is in my corner no matter what. She’s one of the most encouraging and supportive people I’ve ever met and part of her joy comes from seeing me finding and expressing my own joy, which is most often when I’m making. It could be painting, it could be writing, or it could be just getting out in the world and being curious and being interested and engaging with other people. But I wasn’t allowing myself to feel that kind of joy—not very often, anyway. Instead, I started feeling trapped by my own expectations about who or what I thought I should be or what my overall body of work should look like.
One of the places I landed on the back of all of these discussions was that if I didn’t see movement or feel like I had some sort of direction by the end of the year, I would hang it all up—the painting, the podcasting, even the writing—and just go do something else. I’ve been a freelance creative since 2002 and while I’ve had some fantastic opportunities to do a lot of really interesting work, both solo and with teams, overall I wouldn’t say that my professional freelance life has been fun, per se. There have definitely been high points, but for the better part of twenty years, I’ve begrudgingly tried to shoehorn myself into the role of creative entrepreneur, handling everything from concept and design to marketing and billing. As much as I love being a jack of all trades, there’s a limit that I finally reached and was able to acknowledge last year. I made the realization that doing the actual work—whatever that work happens to be—is the only part that I really enjoy, and it’s what I’m best at. In the immortal words of Bill Blazejowski, “I’m an idea man, Chuck.”
Last year I also turned 55 and around the time of my birthday, or maybe a little before, I remembered a terrific episode of Jerry Seinfeld’s show, Comedians in Cars Getting Coffee. Actually, I think Sean may have recommended it, or maybe we just ended up talking about it on an episode of Deep Natter that happened to be around my birthday. Anyway, his guest was Alec Baldwin and at one point they were sitting in this little coffee shop in New York and Alec says to Jerry, “I’m going to be 54 years old in about three weeks and I literally wake up every day and say to myself, what do I want to do with the time I have left?” In some ways, it was a lightbulb moment, or maybe just the reinforcement of many similar lightbulb moments that had come before it. My mom used to say, “you’re not ready to hear it until you’re ready to hear it.” I think when I turned 55, I was finally ready to hear it. I have more time behind me than I have ahead of me, so what is it that I want to do? I mean really want to do. I am in the remarkably fortunate position to be able to do pretty much whatever I want, so what does that look like without the paralyzing self-doubt, without the fear of what I do not landing or finding an audience? What does the freedom to chase joy, not money, or likes, or subs, or anything external really look like?
The short answer is that I don’t know. Not exactly. But I’m starting to move some pieces around the board, beginning with my paintings. I started painting again in 2007 and with very few exceptions, everything I’ve painted since then is either hanging or in storage somewhere in our house. I’ve sold a few and given away a few more, but most of it I still have. And one of the big reasons for that is that I am terrible at valuing and marketing my own work. I always have been, whether we’re talking about my design work or podcasting or really anything I’ve done as a freelancer—I always charge too little relative to the amount of time I put in because it’s not just a job—it’s me. As corny or cliche as it sounds, I love what I do, and by and large, I do what I love. So because I see it as personal and I love doing it, I have historically had a hard time making the business side of creativity work. My friend Maarten Rots coined the term “entreprenervous” that I think describes my approach perfectly.
One of the responses to my “entreprenervousness” is that I’m going to take myself out of the business side of the equation by trying to get gallery representation for my paintings, which solves two issues. Number one, the work isn’t personal to a gallery in the same way it is to me. They are a business and the goal of that business is to sell work. Since marketing and selling work is what they do every day, they will be much better at it that I ever could be, especially with my relatively small social media footprint. Plus, a gallery will have a much more accurate idea of what my work is worth in the world, and as I said before, it’s not personal, it’s business. I need that distinction, especially since we’re running out of storage space in the basement. Number two, by letting go of the business side, which is where I often get stuck, I’m able to focus more on the making. Hopefully that will translate into not just more work, but better work.
The podcasting side of things is going to take a little more noodling. The landscape has changed a lot since I started releasing shows in 2009. I love recording conversations and I have a few new show ideas but I think they need a little more tweaking before they’re ready for prime time.
As I said in the last Iteration, this is tough stuff. It’s personal and in many cases it means trying to stop playing old tapes and change limiting patterns, beliefs, and even ways of doing things that have been in place for years. But the alternative is to stay locked in a cycle of analysis/paralysis, unable to get out of my own way in order to move forward and grow and that type of thinking is no longer on my to-do list.
Questions:
Are you stuck playing old tapes that might be holding you back? If so, what’s keeping you from changing your own narrative?
I follow a terrific graphic designer named Oliver Brooks who recently shared a project he did with Roland to “celebrate 50 years of Roland.” The project is called Studio50 and it’s an online musical interface that allows users to compose and record original music using some of Roland’s most iconic machines, including the TR-707 and TR-808 drum machines, the SH-101 synth, and even the SP-404 sampler, all beautifully designed. You can even download or share what you make on social media.
As usual, what you write resonates with me and hits me where I am. Or where I'm at, to use the parlance of our times. I journal about these questions myself most days and am starting to get comfortable putting these journal pages out into the world. It's taken me a while. One of the things that's helping me is Rob Hardy's Manifesto. Maybe you've seen it. If not, it's here: https://ungated.media/manifesto/
Another inspiration for me is Craig Mod. I'm a member of his SpecialProjects paid membership, which he gave me for free when I told him I couldn't afford it. I think you'd enjoy his creative output and his business model is definitely worth a look. https://craigmod.com/
I Will toss myself in with the rest here and say this resonates as I am going through many of these same things. It is reassuring to see others working through the same issues and making progress gives me hopes as I flit about.