I’m taking a side trail from my usual nature and outdoors content today. See you back at the trailhead in a few days for a piece about an incredibly inspirational trailblazer. Until then, there’s this:
There’s this moment I keep thinking about. Not a big one, just a regular Tuesday morning sometime last fall. I was standing in my workshop, wearing sweatpants, coffee in one hand, paint can in the other, when it hit me:
I am no longer a lawyer.
I am now...a wood-dust-covered, podcast-listening, self-employed artist (that word scares me because it feels so fancy…crafter? artisan? maker?) who sells things online and hopes enough people click "add to cart" so I can pay for groceries.
And my first thought wasn’t relief or joy or “look how far I’ve come.”
It was: What the hell am I doing?
I don’t regret leaving law behind. Not for a second. After more than two decades of legal practice, I knew it was time. The stress, the clients, the grind—it was a life that never quite fit. There were parts I loved: arguing in court (arguing for sport is still one of my favorite things), solving puzzles, writing briefs sharp enough to slice through nonsense - delightful! And I was really good at what I did. But at the end of the day, I always felt like I was playing a version of myself that wore heels and said “per our last communication” way more often than was natural. I wasn’t “me.”
Now, my version of “professional dress” is usually jeans with wood stain and a little paint on them. I spend my days making things with my hands. I design trail maps and tracker boards, I personalize awards and make snarky coasters. I take long afternoon walks outdoors because it is essential to my creativity (or so I tell myself - I think maybe I just like walking during the hours I used to be confined to my office). I write essays about camaraderie on the trails and quiet places and weird little state parks with names like Bong. And on a good day, someone buys something I made and tells me it made them laugh, or cry, or want to get outside. And that, to me, feels like success.
But…and here’s the part that no one really prepares you for…freedom is kind of terrifying.
I used to get a paycheck every two weeks. I used to have a job title that people recognized and said “oh, wow” to. I used to know how to answer the question “What do you do?” without launching into a ten-minute explanation that includes Etsy, eBay, art shows, Substack, WhatNot,and the phrase “well, it’s kind of a weird business model.”
Photo: my old office. It feels like 100 years ago.
Now, I make art and run a business. Which means I also do marketing, accounting, logistics, customer service, packing, shipping, sourcing materials, photographing products, troubleshooting website issues, brainstorming social media posts, and occasionally lying awake at night wondering what happens if nobody ever buys another wooden map again.
It’s exhilarating and empowering and deeply absurd, all at the same time.
I traded a steady paycheck for a pile of dreams, predictable work for creative chaos, client expectations for “please let someone like this design enough to pay $35 for it.”
And I would do it again in a heartbeat.
There’s something electric about making your own thing. Something sacred, even, about creating something that didn’t exist yesterday and watching it go out into the world. But holy hell, the vulnerability. Every time I release a new product or write a new post or send out a newsletter, it feels a little like opening my ribcage and asking, “Would anyone like to buy this small piece of my soul? Handmade, sustainably sourced, ships in 3–5 business days?” It’s not for the faint of heart. (Especially not in this economy!)
But I think the secret is: most worthwhile things aren’t.
There’s no roadmap for this, and definitely no guarantees. But there’s a weird kind of comfort in knowing I’m not alone. I’ve met so many other artists, makers, writers, and creative business owners (a weird number of whom are former lawyers - why is that?) who are also walking this tightrope, balancing between freedom and fear, trying to build something meaningful in a world that doesn’t always value slowness, sincerity, or hand-painted mementos.
We cheer each other on. We swap tips about shipping providers and commiserate about algorithm changes. We laugh about the ridiculousness of trying to write heartfelt copy for a coaster that says, “Please use a F***ing Coaster.” (Guilty.)
And sometimes we cry a little, too, because we’ve staked so much of ourselves on this path. It matters in a way that can’t be measured in quarterly revenue.
It matters because it’s real in a way that client audits and local court rules never did.
So yes, I’m scared sometimes. Of slow months. Of creative ruts. Of the million tiny uncertainties that come with being self-employed in a field that most people still think of as a hobby.
But I’m also so happy. Happy that I chose this. Happy that I bet on myself.
Even more than that, I’m grateful.
Grateful for everyone who’s bought something, shared something, read something, or told a friend, “Hey, check these out.” Grateful for the support, the community, and the quiet encouragement that keeps me moving forward even when I’m unsure of the trail.
So if you're also doing something that feels absurd, if you're chasing a dream, building a business, or trying to make your life feel more like yours, this is your reminder that it’s okay to be scared. That fear isn’t a sign you’re doing something wrong. It’s just a sign you’re doing something real.
And real is more than enough.
***
If you are so inclined, the coffee keeps me writing:
Jean, I wanted to encourage you in your new adventure as an artisan! I've been through a similar experience (not as a former attorney), but as a multi-line sales rep who decided to strike out on my own. Trust me, it will work out! I had a very rewarding career selling jewelry, women's accessories, etc. to gift shops and decided to start creating & selling my own jewelry designs. I'm 74, and still have a display of earrings locally. My most successful effort involved a women's retreat; conducting jewelry-making classes and selling hand-crafted jewelry to hundreds of women from many different cities on the East Coast. (I recommend thinking outside the box.) Also, Etsy was not a good fit for me due to the fact that jewelry was a hot item, therefore it was overloaded with talented artisans. My success was within one hour of our community...but I know many artisans find Etsy works out great for them. I just happened to land on the Women's Retreat, which happened multiple times per year, and provided custom orders through referrals.
Here's wishing you all the best!! Having your own business is very rewarding, I can attest to that.
I needed to hear this today. Thank you for sharing!