When the Words “Self-Employed” Get Lost in Translation - Craft Your Content

When the Words “Self-Employed” Get Lost in Translation

Public service announcement: if you tell people you’re going to work for yourself, there’s going to be some confusion. I’ve discovered this over the past few months.

The Backstory

About two and a half years ago, I came roaring out of college with a fierceness. High off the fumes of academia’s self-congratulatory culture, I was going to put on my sensible pumps and get busy climbing the rungs on the corporate ladder at a speed heretofore unseen.

It took only two years in the corporate world for me to realize that wasn’t the life I wanted. What’s more, I would never have the life I wanted if I stood still.

It wasn’t that the job was awful. In fact, many would call me lucky. It paid well, and I felt valued and respected there. But just because I was lucky didn’t mean I was fulfilled. I wasn’t doing the kind of work I felt I was put on the planet to do, and that fact was getting harder to ignore. It ate at me.

I also began to better understand a deep, lifelong discomfort: the restlessness of never feeling like I was home. After some travel, I finally got it. I was never meant to stay in one place. I had to get out and see the world, soak in the different cultures.

But most importantly, I saw how much I didn’t actually want this life I had daydreamed about, the one of a super-important businesswoman leading team meetings, mentoring her reports, and signing autographs for her adoring fans. (I had an active imagination.)

It didn’t take long for my mentality to fully switch over. I was going to build the life and career path I wanted, and the conventional route wasn’t right for me. Once I understood what I needed to do, I felt it wouldn’t be hard for other people to see it, too.

That was a silly assumption.

The Reactions

If you’re looking to transition from nine-to-five employment, here are some of the interpretations of “self-employment” you can look forward to when you tell folks you’re moving on.

1. The Traditionalist

The Traditionalist - When the Words “Self-Employed” Get Lost in Translation by Amanda Muledy on Craft Your Content

Your Traditionalist is likely an older Baby Boomer co-worker. He thinks “self-employment” literally means, “Okay, that whole ‘having a job’ thing was cute, but now it’s time to get down to real business: BABIES.”

You may have sent out an email to your co-workers to let them know that your relationship with the company is changing to one of contractor/client. The Traditionalist will respond to this email by knowingly telling everyone about your intention to “spend more time at home.”

2. The Doomsday Prophet

The Doomsday Prophet - When the Words “Self-Employed” Get Lost in Translation by Amanda Muledy on Craft Your Content

The Doomsday Prophet is differentiated from the Traditionalist only in that she’s heard of this whole “self-employment” thing—and she knows just how badly it’s going to go. You will recognize her barely-concealed look of pity as she imagines the fate of that friend who quit his job in order to focus on promoting his combination radio/waffle maker back in 1967 and went bankrupt.

The long translation of “self-employed,” to the Doomsday Prophet, is “entering a period of life where I write off deodorant and cry into my 9 AM vodka tonic while I contemplate my lack of societal worth and send out cover letters that are thinly-veiled pleas for pity.”

3. The One Percent

The One Percent - When the Words “Self-Employed” Get Lost in Translation by Amanda Muledy on Craft Your Content

Oh, of course. The One Percent, as part of that small group of Americans that control a majority of the country’s wealth, knows exactly what you’re doing. Your partner will take care of obnoxious details like paying the mortgage, and you’ll donate your time to volunteering at your local after-school arts program or organizing benefits for a children’s hospital. Maybe you’ll even start your own charity.

The One Percent is kind, and she means well. She just can’t wrap her head around why you would want to make money. Frankly, that pursuit seems a little vulgar.

4. The Boggled

The Boggled - When the Words “Self-Employed” Get Lost in Translation by Amanda Muledy on Craft Your Content

No matter how many words come out of your mouth, he will not understand what it is you’re planning to do. He thinks you’re probably some kind of hippie. Whether or not you are on drugs, he isn’t sure. Explain yourself all you want; it won’t matter. He cannot comprehend it.

5. The Green Monster

The Green Monster - When the Words “Self-Employed” Get Lost in Translation by Amanda Muledy on Craft Your Content

The Green Monster doesn’t hear much of what you say after “self-employed.” She’s overwhelmed with her own hatred of the job, and she’s exhausted from the endless work it takes to come up with reasons why she can’t take action. She hasn’t the energy to listen to how you’ve been working to build up clients. The bitter voices in her head are too loud for her to hear when you talk about your 14-hour days. All her resources are going toward one thing: figuring out all the ways she’s stuck where she is. Unfortunately, that usually includes imagining that you have some essential privilege she lacks.

6. The Kindred Spirit

The Kindred Spirit - When the Words “Self-Employed” Get Lost in Translation by Amanda Muledy on Craft Your Content

The connection between you and the Kindred Spirit is almost telepathic. She instantly knows what you’re after. Freedom. Maybe she’s already a digital nomad. Maybe she has simply taken you at your word instead of looking for ulterior motives.

Either way, she gets it. When Kindred Spirit asks when you’re planning to leave, she does it with a sincere smile on her face.


If I’ve learned anything these past few months, it’s this: if you’re looking to leave your current gig for the big, scary world of self-employment, expect some side eye.

Some reactions can be baffling—even hurtful. But don’t let it get you down.

For every person who can’t understand what you’re doing, there’s one who can. And for every person who can’t be happy for you, there’s one who will celebrate with you on your last day in the office. These latter types know it’s about taking hold of your career and leading the kind of life you want to live. They know it’s about freedom.

That connection, when made, will warm your heart in a way you never could have expected.

About the Author Amanda Muledy

Amanda Muledy graduated from Lake Forest College with a B.A. in English and a concentration in literature. A longtime lover of letters, Amanda combines her passion for simple, elegant prose with her reader-centered strategies for writing. While most of Amanda's professional life has largely centered around technical and business writing, she has worked with marketing departments to develop promotional materials and web copy, and she is on the board of directors of a literary magazine. Amanda is currently a freelance writer and graphic designer, creating everything from brochures to poetry to magazine articles.

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