Let Go Lightly
It's often a matter of purpose.
Forgive me Substack, for I have sinned. It’s been over two months since my last newsletter. I know consistency is the mantra of the many on social media, but sometimes taking a step back and temporarily removing oneself from the hamster wheel of write, post, repeat is the healthier play. I know it has been for me. And before I get too deep down this rabbit hole of self-reflection, let me reiterate something that I’ve said many times before: I am not what you would call “prolific” in any aspect of my life, creative or otherwise. For the record, I haven’t painted anything substantial in months — even though I have dozens of sketches for new work — and the last podcast interview I released was with Joe McNally three years ago. In fact, up until about three months ago, the thing I did most consistently (at least on social media) was write. And to be clear, I haven’t stopped writing, I’ve just stopped sharing it. I still write nearly every day, but what I’m writing has taken a bit of a left turn and it’s not for public consumption…at least not yet and definitely not without some additional editorial context.
About 18 months ago, I started seeing a therapist. I had gotten to a place that I’ve only really been once before and Adrianne encouraged me — actually, she implored me — to talk with a therapist. She once said to me, “Every day, I’m terrified that I’m either going to come home and not find you, or worse, that I will.” I’m not going to lie, that hit pretty hard. I knew I was in a dark place, but we often think that we are the only ones who know just how bad it really is — that we are somehow hiding it from the rest of the world. It’s not true, of course, but that was me in that moment, and to hear the person I love the most in the world say that to me…let’s just say that it shone a light on the dark that I felt surrounded by. So for the past year and a half, I’ve been having the sessions and doing the deep work of unlearning what I had learned and letting go of some of the limiting beliefs and behaviors that have seemed so hell bent on keeping me out of the light. Some of those beliefs came from my father, some from my mother, and others were byproducts of where and when I grew up. So part of my deep work has been taking a break from the things that I normally do — and I’m talking mainly about creative things — painting, writing, podcasting, other kinds of making — in order to focus my attention and efforts internally. I’ve gotten back to reading, both for pleasure and for purpose, and with the help of Anne Lamott, Alan Watts, and Sam Harris, among others, I’ve started to revisit a conversation with the divine — and, if not divine, at least something greater than me.
I’ve come to believe that for decades I’ve been living my life backwards in a sense. What do I mean by that? For as long as I can remember, I have been focused on the what, as in “What do I want to be?” or, “What do I want to do?” My focus on the doing (and, by that I mean the achieving), meant that I wasn’t focused on the being, which there’s nothing inherently wrong with. But for me , “Who do I want to be?” has become a much more interesting question than “What do I want to be?”, and in working towards answering the first question, finding an answer to the second becomes far easier to figure out. For example, one of the big things I’ve come around to is that I want to spend the rest of my life being of service — to my family, to my friends, to a community, and to myself. Effort has long been one of my love languages and realizing how much joy I get from making effort for others (which is itself a form of being of service) has helped me to set an intention of who I want to be and how I want to show up. In recognizing and acknowledging my purpose, the means by which I may live that purpose is becoming clearer.
How does that play out in practice? Well, for the past couple of months or so, I’ve been working on building a new website for myself, and this version of the site will be more of a hub — an archive of sorts. In addition to mirroring all of the writing I’m doing on Substack, it will have sections for podcasting, paintings, and projects, which will include new projects as well as anything that I still have assets that I’m able to share. For the things I no longer have access to either because they no longer exist online or because I was crap about keeping my source files (for example, all of the work I did as an Art Director at Universal Studios), I’ll share anecdotes around the work, which will hopefully provide some additional context about what I was doing at the time.
As I’ve been building the site, I’ve realized that there were tools or features that I wanted to include that didn’t exist, such as the ability to get my Substack content into WordPress and keep it synced as I release more newsletters. So, with the help of AI, I built a plugin to handle the import and the ongoing sync. Once I had it working, it occurred to me that it might also be nice to give site visitors a way to sort through the imported posts or any posts, really. So I built another plugin that does just that — it filters and sorts based on user-selected categories and tags. I also built a plugin that serves up random quotes and another that is sort of a visual blogroll where I can highlight or signal boost things that I find interesting that maybe don’t warrant an entire post or newsletter. At this point, you may be asking yourself, “What do WordPress plugins have to do with self-reflection or any of this?” On their own, nothing. The better, and hopefully more interesting, answer is purpose.
I wanted to build these tools for a couple of reasons — the main one, not surprisingly, is because I wanted the functionality that they’ll provide and I wasn’t able to find existing plugins (especially the Substack importer) that did what I wanted — at least not in the way that I wanted it done. The other reason — and this came on the back of realizing who and how I want to be — is that making them available for free, rather than looking at them simply as a potential source of monetization, allows me to be of service. Bingo. Build things that I want to see and use, and make them available to others for free. Now, paintings, zines, and any number of other things that have some sort of “physical” component or real material costs are different. Those types of things are ways that I can monetize some of the creative work I do. But making the more ephemeral or digital work available for free (like these plugins and my writing) are ways I can take the constant and often debilitating barrier of money out of the equation and just be of service.
In his 1969 book The Job, Willam S. Burroughs wrote:
“And what does the money machine eat? It eats youth, spontaneity, life, beauty, and above all, it eats creativity. It eats quality and shits out quantity.”
And this was before social media, before the dot com explosion, before 24 hour news, and before the excesses of the 80s — basically before everything that most of us now know about late stage capitalism.
The last year or so has been a massively reflective season for me. Coming around to taking money out of the motivation question — out of my why, if you will — and replacing it at least in part with figuring out how I can be of service has made an enormous difference in how I move through the world. To a larger extent, it’s changing how I’m able to show up — not just for family and friends but also for me and in why and what I make. I’m excited by the idea of figuring out how to offer at least some of the things I make for free. This feels like the shift I’ve needed for a long time, but haven’t quite been able to make until recently.
I’ll be releasing all four of my WordPress plugins alongside the re-launch of my new website sometime in January, so if you’re not subscribed to iterations, now is a great time.
I really do wish you the best for the coming year. Thanks for reading.




This is amazing Jeffery, it’s inspiring to see you go through this journey and making progress as you go. Your sharing is another service that is more helpful than you might ever
realize. Thank you.
Nice to hear from you. I've picked up the pen (so to speak) again here recently, and can echo much of what you said - Writing, making, quietly in the background. It is a good play.