A Letter to the Me of January 19th, 2026

My Future Past, My Present Self, and Art of Conscripting a Dream

Dear Matthew,

ChatGPT suggested I write this letter to you. I’ve been looking for a way back into writing, so I gave it this prompt:

I want a single writing prompt that will inspire me to create my first Substack post (in ages) that helps to begin my new journey of writing and creating. It needs to be something that sparks creativity, but also authenticity. Nothing gimmicky. Nothing fake. Something that opens up a channel for my own creativity, and that allows me to start writing about what's happening in my personal life again. It's been ages since I felt like I knew how to do that.

The behemoth responded:

Write a letter to your future self, dated exactly one year from today. Begin by describing where you are right now—physically, emotionally, creatively—and what has brought you to this moment. Then, let your imagination unfold as you paint a picture of the life you hope to be living a year from now. What dreams have you embraced? What fears have you left behind? How has your creativity shaped the path ahead? Allow the letter to be both an honest reflection and a bold declaration of your hopes and intentions, inviting your authentic voice to lead the way.

Let this letter be your bridge back to writing—personal, vulnerable, and unapologetically yours.

I feel compelled to begin this letter by revealing its origin, being that the goal is transparency and authenticity. The rest of these words are mine alone. They’ve come from the me you once were, and perhaps – I hope – the me you’ve come to see as courageous, bold, innovative and insightful. The me who made your new life possible.

I hope you read this letter with a sense of gratitude for the life you’ve built from these choices I’ve made, because I’ve made some big choices lately.

I chose to leave my salaried, benefitted job at Iliff School of Theology, our alma mater. I gave them a month’s notice, and I could paint my motivations as purely noble, but that would be a lie. I wanted one more month’s pay and insurance through February, and that would only be possible if I stayed through the start of next month.

As I write these words to you, I’m aware of how money – the uncertainty about making it, the fear of not having any, the motivation to try and keep it - played into my decision to work at Iliff in the first place, and, more importantly, my decision to stay long past the feeling that it was the right job for me. I could have quit last spring, to be honest. But I liked knowing that the money would come. That seemed like the most adult way of approaching my life.

Now, I feel like I made more adult-like decisions, decisions that were more in line with creating the kind of life I want to live, when I was much younger. Now, it doesn’t feel like it was wisdom keeping me at Iliff, but fear.

So I said fuck you to fear during the winter break and decided that everything needed to change. I knew I couldn’t plan every little step. That’s never been my approach to living. But making the decision to leave shifted something. I made room for the possibility of something better. I made space for curiosity about what a different life could look like.

This feels novel, but this process of breaking apart my life and reconstituting it in an unexpected way has happened multiple times over the last several years. In fact, it’s been a through-line throughout my life. That doesn’t make it any easier to write about though.

For me, and I imagine for many people whose nascent identities were shaped within the world of entertainment, branding, and performance (and isn’t that all kids these days?), there is a pervasive pressure to explain life as though it is a series of perfectly ordered events, each sensibly following the last and leading to the next. My story should be an easy read, even if was anything but an easy journey.

Of course, this is bullshit.

A good brand has a good bio, but a good life defies writing conventions.

I hate bios. Truly. I hate writing them. Anymore, I pass them off to robots. I feel confined by bios. I feel like the logic of the bio runs contrary to the scattershot nature of my own history. Yet it feels like I need a story that makes sense.

When the Mickey Mouse Club wrapped in 1994, and 15 year old me was jaded and a little wounded from a year of intense stress, a forced coming out paired with an immediate closeting, a near miss from a seriously predatory crew member, and a heartbreak, I took a different path from my colleagues. I opted not to pursue a record deal, or a tv show, or some other frivolity that I was perfectly poised to achieve. I trashed the expectations and the trajectory and chose to do something different; something ordinary and meaningful.

When I tried to figure out how to put those experiences into a safe, digestible bio, I had to omit some of the things that were most poignant during that period. Creating a public narrative is always an act of omission, and so is all writing for that matter. It’s never about the things that a public figure tells you. It’s always about their careful selection of what to withhold.

But OpenAI’s baby told me to write you a letter and to be vulnerable. It also encouraged me to tell you what I hope for.

I hope that this new job at The Lamb Shoppe continues to feel as joyful and filled with beauty and possibility as it does today. It didn’t feel so much like I found this job, but rather that I created it – or co-created it with some unseen force of serendipity and kismet. I hope that between when I write this and when you read it, the job is serving (or has served) its purpose. I hope that this joy I feel every time I talk to someone about making beautiful things, or every time I encourage them in their creative endeavors, is a joy that has grown and maybe even given birth to something new and unexpected.

Maybe you have your own yarn store now. Or maybe something happens that’s unimaginably better.

I hope you’re free from worry about money. I’m taking a huge cut in pay by leaving Iliff, and this part-time, minimum-wage, insurance-free job was clearly not a job I took for financial reasons. It was a job that promised joy, and it’s delivering tenfold. But things do cost money, and I hope that you’ve found some way to afford your life.

More than that, I hope you feel a sense of flourishing, and I hope that feeling plays out not only in your work and social relationships but also your finances. I hope you’re reading this and feeling super flush. I hope you feel like you have enough money to travel again, or to live somewhere big enough that you can take your piano and your guitars out of storage. I hope you don’t even have to have a storage unit anymore, and that all of those Tupperwares full of old Disney photos and newspaper clippings from 2010, all those Sharpie-marked boxes of unsold CD’s and vinyl, don’t weight you down anymore.

I hope you look back at this post and the community you’ve built around your writing and feel proud. There are just under 2000 people who follow this Substack as I’m writing this, and I hope that number increases by a zero or two.

I hope that you’ve found your voice again – in prose and in song.

Tomorrow, January 20th, 2025 is a day that will usher in changes of a magnitude that is hard to imagine, and I hope that when you’re reading this you’ve managed to weather the storm and find a path through. I hope you, your lovers and friends, your family and your colleagues, have all survived the year with as few bruises and breaks as possible. I hope you’re stronger for what you’ve been through.

As this letter comes to a close, I recognize that I haven’t painted as clear a vision of the future as ChatGPT may have suggested I do. But I think that’s ok. I think it’s ok just to place a marker here to remind you of how far you’ve come. You’ll have a better sense of where I’m at when you’re reading this than I do now.

And I hope you can look back at me with gentleness. I haven’t always afforded that to earlier versions of myself.

Please try to do that for me.

Yours in every way,

Matthew

P.S. This is what your happiness looks like.