Ditch Your Job – Why I’m Leaving Corporate to Hike the Long Trail

Hey out there! My name is Dana and I’m attempting a NOBO end-to-end hike of The Long Trail in Vermont this summer. In January I quit my design job, started contract work, and decided to make the life I wanted a reality. This is my first of hopefully many long-distance hikes and I’m excited to share my journey with you!

The Green Mountains and The Garden State

Originally hailing from suburban NJ, I have a strong connection to Vermont. Every vacation or long weekend was spent at my grandparents’ house, a stone’s throw from the trail town of Rutland. Summertime meant horseback riding, swimming in ponds, blueberry picking, and – of course – hiking along the southern section of the LT/AT. White Rocks, Little Rock Pond, and Clarendon Gorge were among the places I first became acquainted with the iconic white blazes of the green tunnel.

A Few Years L(AT)er

I first became enamored with long-distance hiking after my freshman year at the University of Alabama. A friend from high school asked if I wanted to give backpacking a try. Starting at Delaware Water Gap, we bumped into a group near a tent site I’d come to find were thru-hikers. They explained they’d come from Georgia and were just over halfway through their nearly 2,200 mi trek to Maine. I thought they were crazy, but I couldn’t stop picturing what that kind of freedom must be like. I was overcome with the urge for my own epic adventure. One day, I was going to hike the Appalachian Trail too.

The ‘If’ in Life

Through college and into my professional career, I couldn’t see a thru-hike coming to fruition for me. Quitting my job and putting my life on hold felt massively irresponsible. On top of that, such a feat comes with a pretty serious price tag, especially with no steady income. Because of that, my hiking experience was limited to day trips and overnights. While quarantine restrictions eased, I began working on the AMC peak bagging lists across the northeast. Friday nights were dedicated to driving 7 hours one way, with the intent of hitting a few mountains and making it back for work on Monday. Still, hiking the AT never truly left my mind.

Two years ago I thought I’d achieved my dream job, but by the end of 2022 things had gone sour. Bankruptcy, mass-layoffs, poor management, workplace abuse, financial uncertainty – I’d made myself sick from that stress, both physically and mentally. I’d had enough, so I quit. My M.O. had always been to escape to the mountains when things went awry, why should this time be any different?

On top of Killington – Sept. 2020

Journey – Begins?

Enter: The Long Trail – a place that amongst the chaos, felt like home. This seemed like a perfect preparation hike for the more lofty goal I’d set 7 years ago. I’ve heard on many counts if one can complete the LT as a first thru-hike, they can do anything. Fortunately (to my mother’s chagrin), I’ve always been one to jump off into the deep end.

I’m not going to sugar coat it; the timing for this kind of sucks. By the time my contract job ends, it’ll be the tail end of mud season and just when the Green Mountain Club green-lights thru hiking. This means I’ll likely be hiking in some of the most unsavory conditions the LT has to offer. However, in addition to completing the 272 mi walk from Massachusetts to Canada, my goal is to get more comfortable with being uncomfortable. To the snow, ice, rain, mud, heat, cold, and black flies – I say bring it. Any day on trail is better than a day in the office.

Above all, I’m looking forward to revisiting the high peaks in the context of a thru-hike. The rugged beauty of the Green Mountains is incomparable and I can not wait to take my first step on America’s oldest ‘footpath through the wilderness’ headed to Canada. 

I think that’s all for now. More updates with gear and prep to come.

✌? ❤️⛰️

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Comments 4

  • Smitty : Mar 15th

    The AT is too long, PCT too dry and long, the Long Trail is just right. Good choice Goldilocks, write us a fun story with lots of sensory detail how beer and burritos taste after hiking 20 miles.

    • Dana Tokarzewski : Mar 17th

      thanks – gotta earn it first!

  • alison : Mar 16th

    Good choice! See you out there–we’re starting NOBO just after Memorial Day.

    • Dana Tokarzewski : Mar 17th

      wahoo! see you on trail


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