Getting Coffee With Younger Me
A Short Story #5
It has been 5 years since I moved to New York City. When I think about that guy who took the leap from Tennessee, it’s hard to believe we are the same person.
I wonder what it would be like to get coffee with him. I wonder in what areas he’d be relieved and which disappointed. I wonder what he’d resent me for and what would surpass his wildest dreams.
He’d probably ask what our biggest changes are, expecting to hear how much money we made or places we traveled, but neither would cross my mind. Assuming it wouldn’t change the past, these are the changes I’d tell him he can look forward to:
You Develop a Reverence for Makers
You haven’t yet learned how hard it is to make things. All you know is competing for existing jobs at existing companies managed by people who took your same path. You are playing house in the home a maker built.
Luckily, you get to meet some great makers along the way, but even then, you won’t understand what it takes until you try it for yourself.
Inspired by your maker friends, you will create products and projects of your own. Most will fail, but through failure you develop the eyes to see. Every entrepreneur, regardless of size and success, will earn your respect because they are the ones building the world around you.
You Put The Goal Above the System
I know you love habits, it is true that you they were instrumental in changing you from an undisciplined shirk to someone with focus, but you will take it too far.
Your journal will fill entire pages with all the current health and productivity trends you wish to do daily. Things like: cold showers, gratefulness, affirmations, stretching, and supplements.
These pages contain things that are ‘good’ for you but it irks you when you miss a day and really upsets you when you miss two. You will look at your system and wonder, what is this all for?
Eventually, you admit defeat and accept you can’t do everything. You declare habit bankruptcy and now only keep a few that help support your health and writing.
We Want to Write
One day, you will be at the museum with a few friends, and you will be sooo bored. You will look around and see creations of great skill and dedication, but lament that it’s just not your thing.
The thing you will take away is how your friend Aurora floated around the museum in a state of bliss. She found intricacies in every painting we looked at and you could tell she loved every moment. “How do I get like her?” you will wonder for years.
In your own life you will read books and and excitedly tell people about them. You will see them mentally check out of the conversation. You will bore people with quotes and concepts. But you will realize, good books are your museum.
After this realization, you decide there is no effort as worthy as trying to be a writer yourself, and that being a not-great, broke writer is better than a rich anything else.
Younger Dylan might resist the Maker and System points, certain he knows better than his future self. But when I tell him about becoming a writer, I think he would smile. I have always carried journals and used writing to find clarity, it just felt impractical to treat it as anything more than a private habit. But, luckily for me, becoming a Maker meant not letting practicality determine what I do.
Thank you to Slobo, Eve Marsh, and Angelica Ndayiragije for help with this piece.


Relate heavily on this - never thought I’d consider myself an artist 😁