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How to Explain Your Freelancing Career to Your Dad

By Joshua Danton Boyd June 25th, 2014

My dad is convinced he knows what’s best for me. He’s been mapping out my life since the day I was born, and even though he’s supportive, it can seem like he tries his hardest to encourage me to take on his path rather than my own.

That might explain why your dad is going to be skeptical when you tell him you don’t have a proper boss and you work for yourself doing something called freelancing. In my case, trying to explain why I spent my Christmas break writing hundreds of toy descriptions proved to be difficult. But struggling to talk to pops got me thinking about how we can get passed these differences.

Here’s a short guide for getting dad on your side.

1. Frame your work the right way.

The idea of freelancing conjures up some negative stereotypes about work ethic and wearing pajamas all day—even in the minds of people in their twenties and thirties. To an older person only used to full-time employment, the concept of contract work must seem like something from another planet.

First, I had to rebuild how my dad saw my work. We don’t live in the same place, but whenever we spoke on the phone, he’d start every conversation with “Have you got a job yet?”

When you’ve just finished one of the most difficult and important projects of your life, those five words make you want to rip out your hair and chuck your phone out the window. Of course, this is still my dad, so I initially gave the same forced politeness to him as a poor peasant does to his dictator.

A few casual references to getting up early to meet clients, mentioning you skipped going out with your mates to get some work done, and going over how much time it took to finish your last project will at least get your father to re-evaluate what he thinks you do.

2. Use marketing buzzwords to confuse him.

Of course, the way you talk about your job is important, too. I had one job that involved writing an article per week for a company’s blog and then trying to build a few SEO links for them elsewhere. The work was simple and didn’t take too much time. With a clever tongue, I made this seem better than it actually was by telling my dad I controlled the company’s message and helped them increase their brand awareness.

You might sound like a used-car salesman, but buzzwords can also work. Your dad could still think you’re an idiot, but at least you’d be an idiot who is accomplishing something. Leveraging the content marketing cloud? Sure, why not? Optimizing a pivoting scale? Throw it against the wall and see if it sticks.

Always keep in mind that many dads never like to show they don’t know something. With convincing gibberish, he’ll nod along and talk about how back in his day, they used to do that all the time.

3. Reassure him about your taxes.

If there’s one thing nearly all dads are sure of, it’s that their sons would be destitute and living in gutters without their experienced financial advice. So when they hear you’re dealing with your own taxes, don’t be surprised if they break into fevers as they envisage you being hauled away to a government prison.

The best solution is to jargon your way out of it, like this:

“It’s fine, I’ve filled out my P11D form, and stored my triplicates. My Self Assessment is currently under review, while my Q132 paperwork is safely in my G-R12 folder. The deadline for my RTI submission isn’t till the seventh Tuesday of next quarter, so I’ve still got plenty of time to finish off my LOL-Catcheck.”

Three of those terms actually exist if you live in the U.K.

And if that plan fails, just keep saying you can write everything off until your father hangs up or falls asleep.

4. Create a fake plan that might accidentally become real.

Even when I was off the dole with a decent income and the ability to buy Christmas presents for the first time in a year, my dad would go on and on about my plan. I was only 22 at the time, so my plan was to get drunk a lot and not starve to death. A solid plan for most kids.

Obviously, that isn’t a plan to please a father. You need to sound mature and responsible so he’ll leave you alone long enough to go and pass out in a pub. A great way to achieve this is to invent an intelligent plan you have no interest in completing. My alleged strategy was to gain experience as a freelancer until I found a permanent job.

That seemed to appease Pops for awhile, but every so often I’d have to give him an update. What soon dawned on me was that the plan I’d invented was starting to sound quite attractive.

See, there is something to gain from lying to your dad. And when you stop optimizing a pivoting scale, maybe he’ll be more inclined to let you borrow some money.

Image by Tony Fischer
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