(Part 1) Buck the System & Create a Remote Work-Life

A woman I admire (hey Beth!) emailed recently asking how I went from a “normal” job to working remotely. Here’s the full message to fill you in:

Hey! I’m loving your open book posting on IG! Question for you (if you don’t mind), how did you get started working remotely?

I’d love to get your take on choosing that remote life. Like, actually making the conscious effort to buck the system and forge your own path?

This 8-5 thing is a black hole that you just slide into, not always intentionally, which can be kind of depressing. I would love any advice you can offer up! 🙂

First of all, GO, YOU for even considering this amazingly scary yet fulfilling idea of going out on your own.

The fact that you admitted it to yourself and typed it on a page is the first step.


So if you really want to know the moment I stuck it to the man, I’ve got a story for you.

Though it isn’t directly connected with my current remote, freelance writing career, I feel the need to share this story first because it was the defining moment I said PEACE OUT to a conventional life, which eventually let me to working remotely.

Here were go.

Foraging My Own Path: A True Story

My decision to “buck the system” started my Junior year of college.

Wearing a top I made out of vintage t-shirts (this was 2002), the owner of a local boutique loved the style and encouraged me to make more and sell them in her shop. (The boutique is, M. Public thank you to the owner, Emily, for giving me a chance!)

I couldn’t believe she wanted to sell my clothes. And I was even more surprised when the tops sold out in a week.

I made more and sold more. I sought more boutiques around South Carolina and Georgia to carry my line, and they did.

I was hooked on the fact that I could make money off of a craft I loved. Little did I know that entrepreneurship wouldn’t continue this way – it would take me almost ten years to figure that out. But still.

Part 2

After graduation, I was offered an assistant managing position at a local boutique I worked for at the time. The only catch? I needed to work at that job for a full year, which meant my plans to move to California or NYC in six months would not happen.

The offer was right there, on a silver platter, ready to give me a safe and simple life in Columbia, South Carolina. But in my heart, I knew I had to leave. There was more out there, and I was ready.

So, when my boss offered me the position, I graciously turned it down. It wasn’t about the money, I said. I wanted to move to a big city and learn more about the fashion industry, first-hand.

I remember sitting there in the living room of her big ass mansion, proud that I handled the conversation so well. It turns out she did not appreciate my answer one bit.

My boss looked up from her notebook, stared straight into my eyes, and said, “Well, Megan, I think you need to consider what options you actually have.”

I was stunned, and it took everything for me not to scream, “BITCH, I HAVE OPTIONS!”

My hands were trembling as I left the meeting.

Part 3

My aunt had a designer friend in the industry that was visiting Atlanta for a trunk show in the coming weeks. I was so pumped to meet a *real-life* fashion designer and I wanted, no, NEEDED, to soak up as much information as I could.

The only thing? I had to ask off work to go, but since my co-worker had already offered to pick up my shift, I figured it’d be fine. No big deal.

I was wrong.

After a week of getting the cold shoulder from my boss (avoiding my emails, phone calls, the works), I called one last time to get permission: The event was in two days. My shift is covered. Could I please have off?

She answered on the second ring and proceeded to blast me in a way I’ve never experienced in my life again. She was cruel and rude, and didn’t give me a chance to speak.

I could barely catch my breath when I hung up the phone.

I burst into tears, wondering what to do next. I checked my bank account. Luckily, I had the foresight to save enough money to cover rent till the end of my lease.

That was the moment I decided to buck the system.

I decided I’d rather struggle and build my own career than feel I’m missing out on my true calling at a job that no longer served me. So, with the help of my father, I wrote a bomb-ass resignation letter to quit that fucking job.

The next day I dropped off the letter, along with the key to the shop, jumped in my car, and drove to Atlanta with the windows down, music blasting with a big smile on my face, never to look back again.

I realize this may not be your current situation, but looking back, I needed this dramatic moment to jerk me off the path I was currently on.


Although I’ve worked in other boutiques (and a grocery store) since then, those jobs have just been means to pay rent. The side-hustle (whether it was fashion or, later, a children’s book I co-authored) was always number one.

Writing came almost a decade later.

And with writing came that sweet remote life.

The best part? You don’t have to be a writer to create one for yourself.

And you’re already on your way.

Stay tuned for next week when I reveal 6 steps to creating a remote work-life!

Do you have questions about remote work-life, writing life, or just want to chat? Please let me know; I’d love to hear from you! Comment below or email me directly at meganwaldrep@icloud.com. xo

Catch up on the Freelance Writing series, Money Talk:


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6 Steps to Working Remotely & “The Fashion Story”

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  1. Ooooh the cliffhanger is real! I feel like ”we” just quit that effin job! Thanks for sharing the drama on this road to remote redemption.

    • That’s the best compliment ever! THANK YOU! The Part 2 (out tomorrow 😉 ) is turning out to be more intense than I thought. Reliving stuff from your past can be exhausting, but worth it because it’s like a big-ass cleanse. Not an “ass cleanse,” per se…but maybe that, too. Basically, it feels great! Ha ha! Ok, I’ll stop…(I have a hard time turning down the opportunity to make a pun). Seriously, thank you for reading and for taking the time to share your thoughts! I truly appreciate you!! xoxo