An Origin Story: How I Quit My Job, Saw America, and Became My Own Role Model

by Anne Dorko

Every badass character has an interesting backstory. I started this blog to fulfill my lifelong dream of becoming a superhero, pirate, ninja, international spy, etc… so, here’s where it all began.

“We should just get out of here, you know?” I said, half jokingly. “Run away. Go on an adventure.” The steering wheel seemed to tingle beneath my fingers as I said it.

My girlfriend Rachel gazed wistfully out of the windshield in the darkness. She sighed in agreement. She was back at Subway after graduating college, I was working under poor management in an office job. I was under-appreciated and overworked. It always felt like management was suspicious of me – what of, I’m not sure.

It was no way to live, really.

But the seed was planted. The idea that I could live free from the shackles of a normal job an average life tugged at me. I hated normal. Normal really sucked these days.

I followed so many people online who talked about uprooting and taking off. No real plan, just trusting that things will work out. Unfortunately, the fear that everything could crash to the ground keeps most of us in the same place. But the urge to leave kept growing in the back of my mind.

I wanted to become like my role models. Did I have what it takes?

Courage to take a road trip

Stare at the car keys all you want, it’s up to you to let them take you somewhere.

Several Days Later

A favorite coworker of mine began talking about his upcoming vacation. He and his wife were planning a trip to the East Coast, taking a trip from the Everglades to Savannah.

“You have to go to Savannah, someday,” he twirled his chair to face me. “It’s gorgeous.”

The conversation followed me to my car over lunch. During my break, I furiously searched for interesting places in America I wanted to see. It turned into a Wish List of cities on Google Map, which I immediately shared with Rachel.

It was too late. I was a woman obsessed.

My day was filled with dreams and ideas of how I could see and visit all these cities. I felt as if a world of new and wonderful things were suddenly thrust into my line of vision. I had only to figure out how to reach them.

The Fruit of the Seed

My obsession only multiplied. Throughout the following weeks and months, the seed continued to grow.

Map of places to visit in America

Rachel started teaming up with me on our city wish list. We talked about which ones we could logistically plan to see if we actually went on a road trip.

“I’d like to see Chicago,” she said. “And Portland, that’s high on my list too. And New York!”

“What about Austin? And New Orleans?” I added. “Those are some of the big players.”

We soured through travel blogs to find small and quirky places around the country. No stone was left unturned. The list was growing to a massive size.

“How are we going to pick out cities from these for an actual trip?” Rachel wondered out loud during one of our increasingly frequent brainstorming sessions.

I was struck by sudden clarity. “We won’t have to. We’ll just have to see all of them.” There was a moment as we both absorbed the implications of my answer. “In fact, if we’re going to all that trouble, why not just make this a tour of the 48 contiguous United States?”

It was the moment that the simple idea for a road trip blossomed into a project that would change the course of my life.

A Bump in the Road

Things at work were becoming more awkward.

The company was a sinking ship. Employees received numerous emails encouraging us to contribute everything we could to the company. I came forward with several ideas to help employees be more productive and improve communication, but I was shut down on every level. No constructive discussion about my ideas, only flat out rejection.

I started absorbing myself in books like Rework. I wanted to learn everything there was to know about running a tech business in today’s world. I let my manager borrow one of my favorite books for a week. It talked a lot about how to bring up morale, and bootstrapping when funds are tight. Later, she returned it while I was away and started chatting with my neighboring coworker. “Yeah, I never read it,” she chuckled. She didn’t realize I was on my way back to my desk and within earshot. “Great book!” she mentioned to me later.

Despite this, I still wasn’t ready to leave because I sincerely wanted to help my company come back from the brink.

Employees all took substantial pay-cuts. Another email asking for ideas. I requested that we try a plan that would allow us to experiment working from home one day of the week. If no productivity was lost, it would effectively subsidize the pay-cuts by reducing commute expenses.

My manager had to schedule our meeting to discuss it on a Friday, because she worked from home Monday through Thursdays. “You see, the problem is that we don’t make exceptions for anyone to work at home,” she somehow said with a straight face. “It would take away from our office culture.”

(I promise you, our office culture was nothing particularly special. Most of us used the online chat to communicate, anyways.)

The work itself was fine, my coworkers were lovely, and the salary was okay. It was hard to quit over this, but it was around this time I started to feel like I wasn’t taken seriously by the management. Meanwhile, I still needed to save up if I was going to ever go on that road trip.

One way or another, I knew I would eventually make it happen. January was a few months away, and I began to fantasize about leaving to start off the new year. Even so, I still valued my job… I only wished they would allow me to offer up ideas without mocking me.

Then an email showed up in my inbox.

“Please come see me in my office when you get the chance,” my manager messaged me.

A weird feeling sank in as I walked to her office. Part of me felt like I was about to be set free, and that made me happy. The other part was anxiety over change, of letting my company down. I tried to settle these conflicting emotions dancing in my stomach as I entered her office.

I sat in the chair across from her desk.

“Are you happy here?” my manager asked. There was a long pause as I met her gaze. This was a baited question, and that enraged me. My heart pounded in my ears. This was the moment I didn’t know I was waiting for. I’d wasted so many hours ranting in the car, crafting speeches packed with well researched points as to why this company would fail if they weren’t willing to make changes. Why, if they weren’t going to listen to their employees and take advantage of that creative energy or the unique strengths we had to offer, this could never be an amazing company to work for.

I didn’t want to give her the satisfaction of intimidating me, so I looked her dead in the face and held eye contact as I answered. “I like the work. I like my coworkers. I don’t know whether I like the environment created by the management. Let me get back to you.”

There wasn’t time for her to answer; I simply stood and walked back to my desk, blood boiling.

I chose to finish out the week. On Friday, I stalked back into her office and handed in my resignation. I wrote each of my coworkers an email to explain I was leaving, and sent it out before going home. I am sure there was some bureaucratic reasoning behind the way they pressured me to quit, but I was beyond caring.

It was only a few years into my career and I was fed up with that entire game. I was disgusted.

What I found out shortly after: A few months later the company was forced to drastically downsize operation due to poor management and overhead decisions. They ended up using most of my suggestions and the entire staff was working from home before long. By the end of the year half the management left to start a new company, and the rest had to restructure.

Dreams Can Become Reality

As you may have suspected, I did make it on that trip. (And you can bet I made it to Savannah, Georgia.)

Savannah Georgia bridge at sunset

Savannah, Georgia 2012

Rachel and I embarked on January 21, 2012 and it was the best adventure of our lives to date. It took seven months, but we hit all 48 contiguous states, made amazing new friends, and visited family in the most unexpected places.

We ran a small blog about our stories while we went, and one day I hope to turn that project into a book.

One thing is certain: The trip changed my life.

I was never able to return to normal. I would go on to move alone several times, take a month-long solo bicycle tour, learn new languages, and explore all over the world. And the adventure is still happening, right now.

The Birth of Without Boxes

The blog we tried to keep during the road trip inspired me to start a project that transcended any one adventure.

I wanted a venue to relate my stories to people who need the inspiration. A project where I could build and offer tools to change a person’s life. A way to use myself as a living experiment, so I can teach others how to achieve similar goals with less risk. All those role models I mentioned at the beginning? After tasting freedom, I wanted to be that for others.

Without Boxes was born out of that inspiration.

The theme of Without Boxes has a lot to do with silly things, like pirates and ninjas. That’s because I’m still a kid at heart. My goals and dreams are things like learning martial arts, swordplay, parkour, blacksmithing, woodworking, and general international adventure.

What encapsulates all these things? That’s right: Your childhood make-believe stories!

Pirates and ninjas are the cliché of childhood fantasy, if you ask me. It’s perfect. Because who doesn’t want to be a pirate or a ninja?

My life is without boxes, and I am the captain of my own crew here.

I’m here for the long haul, and where we’re going – well, I can’t say. The future is uncertain and plans are just guesses. But I’m excited to learn how to roll with the punches and set sail.

Welcome aboard, matey. We’re in for a wild ride.

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First published October 29, 2012

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