What I Thought Quitting Law Would Feel Like

Versus what it actually feels like

When I left the legal profession, I pictured something different. Not just a gentle pivot, but wildly different. Like, "who even am I anymore" different. Like, "this life is held together with sawdust, trail mix, and ambition" different.

In my previous life, I spent one hour commuting each way to my office. Every Monday morning started at the courthouse - sometimes inspiring, sometimes soul-crushing, depending entirely on which judges I had that day. After my Monday morning court outing, I spent the rest of the week parked in a chair, back aching from the lack of real movement, facing two monitors and an endless stream of client problems, court deadlines, and unread emails I swore I’d get to “later.”

Then, a million hours later, I’d leave the office, sit in traffic again, make dinner, clean something (or feel guilty about not cleaning something), tie up loose ends from work, and then maybe - maybe - get 30 minutes of quiet before bed. And then I had to do it all again.

Every day felt exactly the same. Life was happening without me. I was living the lyrics to Cat’s in the Cradle.

So when the chance came to do something else, entirely else, I couldn’t look away. I couldn’t stop thinking about it. The idea of working for myself, making things with my hands, writing, creating? It lodged itself in my brain like a catchy song (♪ ♩ ♫ Pink Pony Club, I’m gonna keep on dancing ♪ ♩ ♫) and would not let go.

I had a vision of this new fantasy life: I’d wake up naturally (no alarm clock), sip my coffee while writing something meaningful, spend my afternoons in the woods, and my evenings packing a handful of Etsy orders that rolled in while I was off hiking through some misty forest like a feral poet.

I would be free. Creative. Grounded. Glowing.

And in some ways, I am all those things. Some days feel exactly like that, and I cannot begin to express the gratitude I have for that.

But mostly? I’m tired. Fulfilled, yes, but also sweaty, scattered, and still answering emails at all hours of the night.

Let’s rewind for a second.

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What I Thought It Would Be Like

Quitting law was a big move. I’d practiced for over 20 years. I was a partner in a boutique firm, wore the professional outfits, drove a car that the firm paid for. And one day, I said: enough.

I wanted a different life. One with more art. More nature. More time with my son. Less burnout. Less stress. Less sitting in a chair for hours on end.

Photo: A visit to the Grand Canyon

I thought it would feel like:

• Flow state.

• Long walks.

• Creative freedom.

• A manageable inbox.

• Maybe even passive income?? (Ha.)

• Peace. Space. Possibly a faint scent of pine.

I thought I’d become the kind of person who wears linen and doesn’t scream internally when their Wi-Fi cuts out.

But as it turns out...

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What It Actually Feels Like

Some days, yes, I do get the walk in the woods. The freedom. The quiet joy of making something with my hands. And those days are golden.

But more often, it feels like:

• Standing in my workshop counting tiny wooden pine trees for the zillionth time

• Spending half my life in Canva and the other half at the post office

• Appeasing customers who are upset at something out of my control (it’s the post office…it’s always the post office)

• Packing orders at midnight and forgetting to eat lunch (but somehow eating four snacks)

• Watching my various sales platform dashboards, willing a sale to happen

• Gluing, sanding, painting, troubleshooting, emailing, updating, scheduling, copywriting, fixing things I broke while trying to fix other things, and why isn’t this damn laser cutting right?

• Juggling parenting, small business chaos, trail running, and oh yeah, trying to write thoughtful things to send into the internet void

It’s a lot. I went from a world with defined wins and clearly marked success metrics to a world where I make my own rules and also make my own messes. And the whole while, I get to wonder whether I’m doing the right thing and whether tomorrow is the day I just completely fail.

I don’t miss the law. But I do sometimes miss knowing what the heck I was doing. Also, a regular paycheck was kind of nice.

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But Also: I Wouldn’t Go Back

Here’s the truth I come back to:

I don’t have client audits anymore. I have time to pick my son up from school.

I don’t have to take a vacation day when I need to do something basic like go to an eye appointment.
I don’t have a big office. My car is old. I still struggle to create a coherent answer when people ask what I do for a living.
I don’t have stability. Hoo boy, no. That’s not a thing. But I do have agency.

It’s not glamorous. But it’s mine.

I’m so glad I didn’t wait.

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If You’re New Here…

Hi. I’m Jenn. I used to be a lawyer. Now I write, make trail-themed things, and for fun I run at an entirely unremarkable pace.

This newsletter is about reinvention. And running. And crafting. And what happens when you blow up your career to chase a version of yourself that’s been waiting in the wings for years.

I don’t have it all figured out. But I’m figuring out how to love the figuring.

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The Real Win

I didn’t quit law to become a brand. I quit law to become more myself. And that’s a weird, squiggly path lined with pine needles, packing tape, occasional bursts of confidence and deep valleys of self-doubt.

It’s not what the brochure said it would be. It’s a little messier. Definitely harder. But I am definitely in the right place.

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See You On The Trail is always free, but if I wrote something that resonates with you, I am happy to accept a cup of coffee. Thank you for reading.