I Have an Unconventional Career and I’m Tired of Hearing These Things

I love the alternative nature of my career as a freelance writer. I love being able to take a vacation day without clearing it with anyone. I love working in comfy clothes with a blanket draped over my lap. I love the creativity, independence, and sense of ownership my off-the-beaten-path career affords me.

But, I don’t love the constant comments and questions I receive when I tell people what I do. And if you have an unconventional career path, you probably know exactly what I mean.

It’s 2018, and we’re living in the age of digital influencers, gig economy-embracers, and people who are more inspired than ever to create their dream jobs. Despite this, many 9-to-5 workers just don’t get it – and they don’t always say the right things to those of with non-traditional work setups. That needs to change: Entrepreneurs, freelancers, and creatives deserve to be taken seriously. And we definitely don’t deserve to hear any of the following.


1. “So what do you really want to do?”

It’s never okay when you ask anyone this question, whether it’s your waitress, your bartender, your friend with an unconventional career. Why? Because it implies that whatever he or she is doing at the moment isn’t worth wanting. I constantly have people asking me what kind of job I’d like to get, and they don’t seem to believe me when I tell them I’m totally happy with my freelance career.


2. “Are you working these days?”

I get this question SO OFTEN even though I’ve worked consistently since I finished graduate school five-and-a-half years ago. Maybe people don’t mean to suggest I wasn’t working the last time I told them about my freelance career, but that’s definitely the vibe I get.



3. “Wow, I would never get anything done if I worked from home.”

Um, you don’t really have a choice? I heard this one so often when I held a work-from-home staff position. My answer to this? “Well, my boss wouldn’t exactly be cool with it if I missed a deadline because I got distracted by the TV, so that helps.”


4. “You’re so lucky you don’t have to go to work.”

You’re right, I am lucky. I’m lucky to have a talent, a solid work ethic, and a willingness to chart my own path. I’m lucky to have a husband who supports my creative career and offers a safety net in case the very unstable industry I work in throws me a curveball. I’m lucky I work in a field where being your own boss is a viable option. But make no mistake: This is hard work, despite the fact that I can make my own schedule and work from my couch.


5.  “Oh, so you’re between jobs.”

Do some people pick up hustles or entrepreneurial pursuits while job hunting? Sure. But it’s rude to assume we’re all waiting for 9-to-5 opportunities to come along. I’ve turned down a lot of job offers in favor of the freelance life. Because guess what? It is a full-time job.


Source: @alexasuter


6. “What are you working on these days?”

A fairly innocuous question, but a really tough one to answer. It would probably be easier for someone with an unconventional career to explain what he or she isn’t working on; multitasking is a major part of what we do. As a freelance writer, I’m constantly juggling projects, pitching editors, invoicing clients, accounting for my earnings, managing an editorial calendar, and so much more. Explaining what I’ve been working on is exhausting and, frankly, probably not that interesting for the person who asked.


7.  “So how’s housewife life?”

There is NOTHING wrong with being a housewife, and so many people who do it full-time are rock stars. But here’s the thing: Calling me a housewife diminishes the career I’ve worked really hard to build. And I have to wonder if anyone would ever ask a man with an unconventional work-from-home career what being a “house husband” is like.


8.  “Wait…so who exactly do you work for then?”

I work for myself! Freelancing is, above all else, entrepreneurial. Technically, my work is evaluated and used by my clients, so they have a lot of say in how I do my job. But at the end of the day, I’m my own boss. And that feels pretty awesome.



9.  “So you’re surviving but not thriving.”

Yes, someone actually said this to me once. Those of us with unconventional careers don’t necessarily have the usual benchmarks of success (like certain salaries, bonuses, or promotions), but that doesn’t mean we aren’t doing well. And of course, there’s the classic. Let’s all say it together now…


10. “How do you make money?”

If your work takes you off the beaten path, chances are you’ve heard this question. A lot. I mean, if I had a dollar for every time someone asked me this…well, that would be how I make money. Instead, I do it the way everyone else does: By working hard. And if you have a friend who is rocking a nontraditional career path, that’s how he or she is making it work as well. We may not have super early mornings, long commutes, bosses watching over our shoulders, dress codes or uncomfortable desk chairs – but we have hustle. And that ought to be respected.


Do YOU work an unconventional career path? Tell us your own experience in the comments!

  • I wish I had an unconventional job, trust me. I’ve spent the past nearly fifteen years working in a traditional 9-to-5 office environment and I can’t tell you how much I hate it. It literally sucks the life out of me every single day. I work part time as a freelance writer as well, but the work is never constant so that’s the reason why I’ve stuck with my full-time job all this time.

    • Emilia

      Oh my, I can relate to that. I hope you find a way out of the soul-sucking environment sooner rather than later!

  • Cailin Riley

    Teach me your ways! haha I’m a blogger on the side but I still balance that with a 9-5 job. I’d give anything to do blogging full-time so I’m slowly working toward that.

  • I have such respect for freelancers and entrepreneurial types because I’m just not cut out for that kind of work and discipline. I enjoy my 9-to-5 because of how structured it is and my responsibility is limited to what I’m willing and able to take on, so again, mad respect to those who run their own businesses and do their own thing – whether that’s happening in their kitchen or the coffee shop down the street.

    As a blogger (who does it only for fun and NOT to make money) I get tired of people bugging me about quitting my 9-to-5 to be a freelancer and make this my career. I don’t think there’s anything wrong with having a blogging platform as a hobby. I don’t need to “Be my own Brand” or whatever the rhetoric is these days. I think we should all just do what feels right to us career-wise and not judge others for how they live.

    On The Cusp | https://on-th3-cusp.blogspot.com/

  • It’s interesting that you call Freelance work “unconvential”…I wouldn’t considering it unconvential at all. Especially not by today’s standards. More and more people are working from home or blog as their career. I’m wondering if it’s just the older generations who are asking these questions because these weren’t common careers/ways of making money in their day.

    • That’s what I was thinking! Living in Los Angeles having a 9-5 working for the “man” is so uncool. I freelance on the side and am always tempted to lead with that when talking about work at parties.

  • Kate

    I’ve been a (freelance) musician for over 20 years now, with even a bit of “success”(whatever that means!), and I still hear all of these things all of the time. The important thing that I try to keep in mind is that they are nice people who are trying to engage with me and ask about my life in order to be supportive––even if they use the wrong words and ask the wrong questions in order to do so. Also, I think they are a little big fascinated by our lifestyles, so they ask more detailed questions. When i ask my 9-5er friends about their jobs, it’s usually just a generic “so, how’s work?”. Somehow, they often don’t get that the same would work for us as well.

  • Kara

    I love love love this posting. Thank you for it!

  • This piece gave me life! Obviously people ask these questions because they are confused how you can support yourself and not have to sell yourself to a 9-5 lifestyle. Honestly, I think what you are doing in enviable. I would love to see a piece on how you began freelancing, market yourself to prospective clients and manage your administrative stuff as well!

  • Mary Shaughney

    I worked as a horse farm manager for several years and got similar comments that drove me crazy. The worst one was, oh so you get to play with horses for money, that’s not a job! Yes, it was incredible to get paid to work with horses, but I worked 60 hours a week, often all 7 days in all weather regardless of if I was sick. I was always on call, never had health insurance or other work benefits and my salary barely scraped $20,000 before taxes. Now that I’m in a 9-to-5 I always respect unconventional positions because after busting your butt all day the last thing you want to hear is someone telling you that your job isn’t hard work!

  • Omg yes to all of this. I run a blog and do some freelance work and people keep asking me, “So when you get sick of it, what are you really going to do?” or “Isn’t being a mom your “real job”?” (air quotes actually put there by the person! )

  • Allex

    Thanks for sharing! I enjoyed reading this article, especially since our culture in general defines success as climbing the corporate ladder or having that full time 9-5 job. Not that there is anything wrong with those, but it’s refreshing to hear that having an unconventional job is just as challenging, rewarding, and normal. I appreciate your story that doesn’t pressure me into feeling like I have to do what everyone else is doing.

  • Thank you posting this! In this day and age there are soooo many paths to take all with pros and cons! I’ve been a freelancer in many ways since I graduated from college and everyone is always so concerned with what I’m doing for work. Now I have some good answers to these ridiculous questions!

  • Yep, frustrating questions when you get them 7 days a week. But I can’t see any reason getting frustrated when people ask what you are currently working on. When you’re a freelancer you work on diffrent projects. Most people know this so instead of wanting to know about you making invoices and other everyday stuff they might actually be genuinely interested in what you’re working on. Maybe it’s a culture and education thing but I don’t find this problem in Scandinavian countries. Well, older generations are of course sometimes confused but mostly people are very open towards different career paths 🙂

  • I’m not asked most of these questions. As an author, I get the noob questions like, “Where do you get your ideas?” and “Do you publish your own books?” (I buy them on eBay and No), and the Stump-The-Chump questions like, “Oh, you’re a writer, are you published?” said with an air of superiority, and the surprised, and still skeptical, “Really? By a publisher I’ve heard of?” (Yup and “I don’t know, have you heard of HarperCollins?”).

    Though as a mother of six, I DO get the question almost daily, “How do you find the time?!?” I still don’t have an answer to that one.

  • Emilia

    Hi Zara, what a great piece! I’d be curious to know more about the editorial calendar you mentioned. Is it for your own social content and/or blogging?

  • Jennifer C.

    This article is just what I needed to read. I have an unconventional job and I love it, and make more than I probably would if I had an office job. But sometimes my friends with 9-5 jobs and my parents make me feel like there’s something wrong with my job choice. It was reassuring to hear that there are others with the same concerns. It’s hard, but I have to keep reminding myself that I’m happy and doing well, so there’s no need to change what I’m doing just because other people don’t understand it.