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How to Explain Your Freelance Career to Confused Loved Ones

  • By Ryan Eick
  • November 25, 2020

Today’s modern workforce is more open to freelancing than ever before. While most of the country now welcomes freelancing as part of the modern workplace new normal, some still don’t quite get it. You can explain it any which way but they seem incapable of wrapping their mind around it like we do. Instead of seeing you as an independent, driven, business professional they see it…differently.
You can’t avoid these situations sometimes. So, here’s some freelance advice for you: when you’re faced with these scenarios, embrace the proverbial chaos and show them the bright side of your career.

Your Grandma Who Can’t Stop Worrying

Gam Gam loves to worry.
To make sure that she’s ready to take the life-altering news that you don’t have a traditional job start by getting her comfy. Surround her with the items she loves: her cozy blanket from her childhood, that sweater with a bird on it and her favorite show. We can’t guarantee this will totally change her mind about freelancing, but she loves you and you’re making her comfortable. That alone should allow her to take the news better than the time your brother got that tattoo celebrating the anniversary of Lionel Richie’s classic “Dancing on the Ceiling.”

Your Conservative Grandpa

For a man who had the same office job for 37 years and still thinks Barry Goldwater should be President, explaining an office job might be tough enough for him, much less freelancing. To make it easier on him, offer to come over to watch the game. Which one? Doesn’t matter. He watches them all.  If you’re lacking in the sports banter, Google some facts to make it look like you’ve actually been keeping up with the team. Man, that Tiger Woods sure knows how to dunk a fastball…
Enjoy a 6-pack of Schlitz over the next few hours. During a break in the action, he’ll ask about work. By that point, the hardened exterior of gramps should have whittled down a bit. When he asks about work, keep it vague on specifics while highlighting how “the shop” (Starbucks) is bustling and business is booming.

Your Significant Other’s Dad

An ex-Marine with an iron grip handshake, he has callouses on his callouses. This guy understands grit and hard work. When he asks you what you do, he might not understand what you mean. It’s cool. He may not understand you, but he understands hard work and drive.
Start by making plenty of references to “the office” and “coworkers”. Maybe he won’t ask for specifics, but he will. This guy’s career was built on specifics. That’s why it’s vital that you describe the corporate structure you have in operation. From having your own Chief Operator, legal department and accounting team on your side, Dad won’t be able to find a bad aspect of your career choice. In fact, seeing his child dating a competent, thriving professional is likely to make him remember his baby child as a rapidly-growing, independent adult.
Just don’t mention the tear you notice rolling off his cheek.

Your Significant Other

Your significant supports you but still doesn’t totally get why you tour coworking spaces and can work at your desired location. It sounds great but they remain skeptical.
To drive home your correct career path to them, invite them over under the pretense of catching up on Peaky Blinders. When they get to your apartment, surprise them with a candle-lit dinner of homemade (you ordered on Seamless) gnocchi. Get out that bottle of three-buck chuck and pour them a tall glass and, OOPS, how did that Fiverr Workspace quarterly earnings report wind up on the table??
You go to clean off the table but hesitate just long enough to see their eyes go wide as they see what you’ve earned. It may not completely sway them over, but it should be a real good start.
So, when you find yourself stuck in these precarious circumstances with your loved ones be sure to highlight the awesome aspects of freelancing they might not understand just yet. With you in their lives, they’ll soon understand that you’ve made an awesome decision that millions are joining you in. All the best!

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