Funniest Quotes From Friends and Relatives About Freelancing

Funniest quotes about freelancing

Freelancing raises many questions with people you’re close with. Since the majority of the world is sprinting to the train at 7:00 AM in nice clothes and sitting in a cubicle, the very thought of working from home and managing your own business is silly. Over my freelancing years I’ve heard some interesting statements and questions about freelancing, so I figured I’d put together a list of the funniest quotes about freelancing that came from friends and family.

After you read over my zingers, let me know what gems you’ve heard in the past.

Well, the economy is tough for everyone right now.

This is my all time favorite comment, which actually came from a former employer. I chatted with her through GChat and she asked where I was working. When I mentioned I was a freelance writer, this was her response. The funniest thing about this instance was that I went into detail a little bit, explaining that I focus on technology and that I’ve built a client list. Even after all of that she still just figured I was struggling.

So do you just wake up and work in your boxers all day?

This comment came from a good family friend, and he was genuinely interested in my daily rituals. His eyes widened at the thought, so I could tell that he always dreamed of working in his boxers.

You’re really talented. You’d be able to get a job at lots of companies.

This comment is one of the more annoying ones, since it comes from family members. I don’t want to work for other companies. It’s kind of the reason I’m doing the whole freelance thing. I already tried working for those companies who would be “lucky to have me.” I hated it.

This guy’s a deadbeat.

When I’m out with one of my good friends from high school and college he introduces me and then explains my career with this gem. It’s a beautiful joke and conversation starter wrapped into one. You can’t get mad with buddies for teasing you about your freelancing career. Why? Because it’s funny, and no matter how much you explain your situation, they will never completely understand.

Just come visit, you don’t have to check with a boss or anything.

This refers to some friends who have wanted me to come visit or take a vacation, since I don’t need to ask a boss for time off or worry about how many vacation days I have left. There’s no way this could ever annoy me because it’s true, but it’s freaking tempting. Whenever a group of friends is going on a ski trip to Windsor or a road trip out West I really want to drop everything for a bit and go. Unfortunately, when they take vacations they get paid for it. Not so much here.

I hate you.

Most responses I receive from friends is what I like to call envy humor. They know that I have it easy, but at the same time they are not saying they really want to be me. They joke around just like with everything else, since they probably enjoy their job and see plenty of benefits with it as well. And I assume they know that it’s actually quite difficult to freelance.

Share the funniest quotes about freelancing you’ve heard from your friends or family members.

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About Joe Warnimont

I am a writer, marketing expert and adventure seeker. I help people write, market their writing, live truthfully and embrace their lives through creativity. You can find me riding my bike around the streets of Chicago. Follow me on Facebook, Twitter and Google Plus.


  1. Terry Weber says:

    Joe, the one i get a lot is “It’s not like you have a REAL job…” I get the “I hate you” one a lot too, but only from my closest friends. 🙂 Love your site, keep up the good work!

  2. I’m with Terry – before I moved my work out of the house (I have a “real office” now) people would just drop by. If I told them I was busy they’d say, “Doing what? Oh, that writing thing?”

    The only thing that cut me deeper than that was when my next-door neighbor asked, “How is the journaling going?” After years of waving to her out my home-office window and chats about writing novels & freelancing, she still just thought I was a very avid diary addict. Gah!!