Six Ways to Dodge THOSE Pesky Questions During the Holidays

For those who do not work traditional 9-5 jobs, the holidays can be a particularly trying time. Whether it’s a bombardment of prying questions or just an inability to comprehend certain career paths, family gatherings are rife with pesky scrutiny.

Freelancers are (unfortunately) used to hearing questions from family and friends who don’t quite understand what they do or how it all works.

Yes, we get that working as an independent contractor can be challenging to wrap your head around. If someone has been a corporate desk jockey their whole career, they may need help to fully grasp the freelance thing. Questions naturally abound—How do you make money? How do you handle multiple clients? Do you ever get out of your PJs?

Younger folks’ career paths may seem relatively “unconventional” to older generations—but freelancing is fast becoming more the norm than the exception. According to research published by Fast Company, 48% of Gen Z workers are freelancers, with about half of working millennials also working as independent consultants in some capacity. By 2027, 86.5 million Americans will be freelancing—about half of the U.S. workforce.

While we understand some generational confusion, that doesn’t mean that the questions don’t get (sometimes very) annoying. While it may fall on us to educate about the freelance world, we can still have fun doing it.

Here are some top questions pesky family and friends will likely ask about your freelance career this holiday season—and how to respond.

1. “Do you actually make money as a freelancer?”

Cue the *eye-roll* — this one gets us every time. I mean, it’s not often you ask full-time professionals detailed questions about their salary. But believe it (or not), this is often one of the first questions lobbed when family discovers you’ve gone to the freelance side. At the risk of delving into a doctoral discourse on your financial history, you can nip this one by being concise and to the point.

How you might respond:  Yes, I’m making money—in fact, freelancers typically make more (often far more) as independent consultants than in traditional full-time jobs. Boom.


2. “When are you going to get a real job?”

Oof—this one rankles. Doing work consistently for several clients and getting paid for it is essentially the definition of j-o-b. While being a freelancer is not the prototypical norm, we are often better paid for our skills and experience.

How you might respond:  When this one is lobbed my way, I explain that while I don’t report to an office or work a classic 9-to-5 schedule, I am working all the time, often longer than those in more traditional careers.


3. “Aren’t you worried about your future?”

Ah, the future, the lovely “certain” future. Freelancers and standard FTEs alike are all susceptible to job insecurities. Layoffs are a thing—ask the high-paid folks from Twitter, Meta, and other tech behemoths who recently got pink-slipped. Most freelancers are acutely aware of the pitfalls of not having enough work to cover a slow month (or, gulp, year), which is why we cover our bases and plan for rainy days.

How you might respond:  Yes, I’m worried about my future, but guess what—you should be too, which is why you need a solid financial plan.


4. “So, what’s it like to not have a boss?”

Questions about freelancing can swing wildly from irritating to starry-eyed. For those frustrated by their own work leadership, imagining freelancers frolicking happily, with no upper management to contend with, is the stuff of fascination station. But it’s important to (maybe after having a weensy bit of fun with it) remind family and friends that being your own “boss” is not quite as glam as it sounds.

I share that I’m responsible for things I’d rather toss up the ladder, like accounting, insurance, payroll, and more. And the truth is everyone answers to someone. Yes, there’s no direct supervisor—but freelancers function at the mercy of their different clients. They are accountable to the people who write them checks, so it often feels like there are multiple bosses at once. Ouch. It’s not the pretty rose-colored Vaseline on the lens view that most people picture.

How you might respond:  Share that while you love being in charge of your workday and career trajectory, going it solo also comes with challenges.


5. “I bet you take vacations all the time, right?”

People often assume that freelancing is synonymous with jet-set trips to exotic locales. And while the ability to work anywhere is great, an actual “vacation” is one where you can actually unplug and disconnect from the digital grid—and typically requires quite a bit of advance planning.

I remind folks that there’s no PTO in the land of the freelancer. Shutting things down for a week or more involves planning ahead and oodles of communication with clients. It’s more complex than picking a cool destination, packing, and setting an out-of-office response.

How you might respond: ”While I do have the option to work from wherever, it can (somewhat ironically) be more complex to get away. True vacations require a lot of prep and planning, which means they don’t happen as often as they do in my fantasies.”


6. “What’s your five-year plan?”

Five years? Freelancers often don’t have the next five minutes planned. Sometimes there’s an idea of what one would like to accomplish in the next five years, while other times, it’s more about planning for next month. If you don’t have a five-year plan mapped out and color-coded, that’s perfectly fine. And even if you do but prefer not to go into detail about it, this genius response keeps the mystique.


How you might respond: ”While I could tell you, it would ruin the surprise.”




Bottom Line

The best overarching advice for annoying questions about your freelance career? Get curious about their curiosity. Why are they asking—are they just curious? Concerned? Jealous? Both? It will help guide how much fun or seriousness you inject into your responses. So, when Uncle Larry asks when you’re going to get serious and go to law school, you can let him know that you’d love to chat about this but must check on the roast and then lament how you’ll be sitting on opposite sides of the table. Or, get a little cheeky and tell him you’ll get right on that as soon as you get his tuition check.


About the author.

An award-winning creator and digital health, wellness, and lifestyle content strategist—Karina writes, produces, and edits compelling content across multiple platforms—including articles, video, interactive tools, and documentary film. Her work has been featured on MSN Lifestyle, Apartment Therapy, Goop, Psycom, Yahoo News, Pregnancy & Newborn, Eat This Not That, thirdAGE, and Remedy Health Media digital properties and has spanned insight pieces on psychedelic toad medicine to forecasting the future of work to why sustainability needs to become more sustainable.