Family gatherings and large groups of friends who don’t freelance congregate around us at the end of the year. Most people are maybe a little clueless, but not necessarily harmful in what they say or do. But there is a (rather vocal) wedge of people who really don’t understand freelancing. And these folks (bless ‘em) have some fairly strong opinions.

Here’s your guide on what to say to the lumbering oaf and the anti-freelance family member in your life

How’s that…thing…you do going?

Never underestimate the wrecking ball wrought by someone not understanding what you do to the point of transforming it into the conversational version of a grey, amorphous blob. It can frustrate when people really don’t understand how and what you do for a living. And people who really enjoy their dizzy self-appointed heights of being (insert the air quotes here) better than you can weaponise it.

It can also trigger that desire to list off all your achievements like a packet of ingredients, together with the nuts and cherries of awards, kudos and financial information.

But you don’t have to be the “approve of me” sundae to the nutty thing they’ve got going.

 All you need to say is, “My career? Yeah, it’s going super well. I’m really enjoying the challenge. How about you?”

And leave them right there, starved of any information to help them continue to dine on your success.

Pro tip:

·        If you don’t want to pack the salties into the day, a great way to bridge the gap is talk about what they do and relate over common experiences. Never forget, a tough boss isn’t far from a hard to wrangle client. Sometimes, we all want somebody to listen.

And don’t forget, struggling to understand freelancing doesn’t mean someone doesn’t care about you. They may want to be polite but lack the vocabulary to talk about it well.

When are you getting a proper job?

Ah, ye olde proper job. The bane of any freelance existence, it’s especially popular when you work in anything related to the arts or you do something immediately identifiable as creative like make music, write, illustrate or design for a living.

Again, it’s not up to you to supply the information. The question has already supplied enough to fill the air for two whole festive seasons.

People who are fond of the real job mentality fall into the following categories:

1.      Stuffed to the gills with capitalist rhetoric and outward demonstrations of success

2.      So miserable in their job, they can’t stand it when they see someone with <gasp> choices

3.      Wedded to the subliminal message that work is to toil and toil is to receive virtue (thanks a lot, Protestant Work Ethic!)

No matter your story, they are unlikely to hear your entreaties and protests until succumbing to some redefining life moment (or their death bed). Mainly because they’ve decided that to work is to suffer on some deeply ingrained and heartbreakingly sad level.

The best response? Play into the narrative.

“I’m really hating making money from something I adore doing.”

“Having this much creativity as part of my day is an enormous struggle. But it appears to be paying dividends.”

And my personal favourite:

“I know, right? You’ll just have to keep on with all that misery without me.”

Pro tip:

Remember the Matrix and the central message about who is and isn’t awake and the burden that brings? No more is this reflected than in our relationship with work. For many, work is a financial means to an end. One where they put their family, hobbies and having a roof over their head over autonomy, freedom and self-expression. That experience is hard. And it’s one that can lead to feeling a little out of sorts with people and opportunities that have a different perspective. It can help to exercise compassion in these circumstances. And it can also help to dwell on the similarities of your experience and remove the barriers of depersonalisation in the process.

It must be so nice to hang out at home all day

Don’t get me wrong, this one used to burn the freelancer to cinders inside of me. The implication is that we’re all watching Passions re-runs on YouTube, waiting for the money to roll in.

This one though, is more of a mindset clue. You’ve likely got someone in front of you who simply wouldn’t work if they didn’t have to. And this is when educating them about the fact that life isn’t all Tim Tams and Tik Toks comes in real handy.

“It’s one of the few real benefits in among all the big arse responsibilities I shoulder, that’s for sure!”

“Few people get to spend forty hours a week in their PJs and make as much as me, granted. But it’s really difficult to stay the heck away from the email and client demands come quitting time, trust me!”  

Pro tip:

·        Be open about the isolation, the not having the watercooler and what that can do to a person

·        Recognise that the judgement is usually not about you and more about the other person. Maybe asking them about their job (and hearing their pain) can create empathy for you and your situation in the long run.

People pay you money for that!?

Explaining AI chat prompt engineering, crowdfunding, or life as a social media manager to Grandma isn’t the easiest of tasks. Heck, it took me an entire day once to convince my incredibly suspicious parent that Google weren’t going to send her any surprise bills just for searching.

Nevertheless, when you’re hit with that conversation moment where someone’s eyebrows shoot off into the stratosphere powered only by their own incredulity, it can be an eensy weensy bit hurtful.

We are in an age of people willingly laying it all on the digital line and somehow making beans. The best way to explain it is to make that freelance lifestyle of yours sound like a masterclass in innovation.

“There’s no such thing as passive income. You’d be surprised at how much I’ve had to learn this year alone to do the things I do. If you ever want to try it, let me know. I am happy to show you.”

“The rapid nature of technological change is overwhelming, I know. But there is a market for it – and it’s enjoyable. Would you like me to show you want I do sometime?”

Pro tip:

If you can find a benefit, they find relatable, it can help. For example, with crowdfunding, talk about how people can support the work to make it sustainable while talking about the hours involved in what you are creating. Or equating the digital skills you’ve learned with community management and how they translate into offline settings to build safer neighbourhoods. Or how great videos can help people talk about end-of-life, what it’s like to have cancer, or help people leave addiction or violence behind.   

You’re speaking to someone who’s taught at the same school for twenty-three years

This was an actual statement said to me by someone when I announced I was starting my freelance business. To them, leaving a workplace seemed bad enough. Let alone changing career and heading out on my lonesome. Talk about risk! And that’s what our family member is telling us – they really hate taking risks. This is the sort of person who eats one of two well known (very Aussified) Chinese dishes at the Thai restaurant because they can’t quite figure what it all means.

Pro tips:

Most of the time, it’s a moment to let that baby have it’s bottle and be done with it. They are unlikely to change because they have a fraught relationship with it.

Or you can lean into the opposite of risk, reward.

“My freelancing allows me to see my kids grow up I couldn’t do if I stayed where I was.”

“I make more money/more interesting work/am more productive these days because I only have to worry about one person at work – me!”

“Freelancing gives me the flexibility to create an online career – which allows us to pursue your child’s goals in the military easier as we move from town to town without having to apply for work or re-establish myself every few years.”  

It’s nice that you can add some pocket money to your partner’s earnings

The assumption, of course, that you don’t get paid when freelancing is not new. Nor is the emphasis placed on it if you are in a creative field and/or a woman or primary carer for children. Try as we might, we still devalue the arts and women in equal measure. And let’s not even talk about the complexity that occurs if you cross cultural lines and/or have a disability.

It can be difficult not to get rattled by the implication you’re a gold digger. Or by some weird anti-feminist Meer Kat that has appeared where your mother-in-law used to be. However, sifting between the layers of patriarchal crap, projection, jealousy, and assumption can be helpful. Especially if you’re trying to work out if it’s default thoughts, unconscious bias or they are just a whackadoo with some weird feelings.

Humour may be the salve that helps with the “naw, look at the cute widdle freelancer and their money box” burning feeling.

“Who’d have thought one little odd job jar could pay for an entire Subaru and three kids at private school?”

“At this rate, I might afford a laptop by next year!” <insert over-exaggerated hand gestures here>.

“Those little gold shovels for the nose candy won’t pay for themselves, Mildred. Prawn cocktail?”

Pro tip:

·        Jokes aside, tone is important. Some people may not understand the pressures of modern living or what it’s like to buck a trend. Especially if they got their mortgage in the 1980s. Education about the cost of living can help

·        Challenging rigid gender lens’ is hard. The financial side of that conversation is well and truly on the advanced level rung. You may need to challenge other forms of assumption and hetero-normative rot before you can tackle this. But it doesn’t mean you won’t get there!

Need to find your allies in the family assumption trenches? Join the Freelance Jungle today.

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