When are you getting a real job?

Thanksgiving marks the start of the holiday season and for many solopreneurs, an annual round of “Whack-the-Freelancer.”  This “fun” activity takes many forms, depending on the unique psychological makeup of your relatives, but it’s a yearly reminder that quitting your job doesn’t just affect your paycheck and benefits, it can change relationships. So, suit up in advance for the most popular versions of the game including “Granny’s Benign Befuddlement”, “Jealous BIL’s Unprovoked Snark”, and “Uncle Fred’s Outright Hostility” when the conversation turns to your career. 

Some rounds of this game can sting but some understanding and prep can help you deal with the barb whether they are intentional or not. 

Why do they give a s–t? 

The simplest answer: They hate you cuz they ain’t you. But sometimes it can be more. 

  1. You are messing with what they know. By disrupting the familiar and choosing something new and “risky”, they believe you are invalidating their life choices. This is ALL about them not you.  
  1. Befuddlement: They’re from a generation that had fewer options and more employer loyalty. Back in their day, if you were hired at a major company and worked hard, you were set for life. They are a few decades removed from today’s workforce reality and don’t get that employment security is rare now. They might have missed the era of hostile takeovers, bankruptcies, meager severances, and non-existent pension plans. Security these days rests solely on your ability to perform a useful service that is marketable, and they don’t get that. 
  1. Your passion causes uncomfortable introspection: Why don’t they feel this way about their work or life? If you had an honest conversation, you might learn they hate their job and life and seeing you follow your bliss (real or imagined) is more than they can take. 
  1. Or is it you? Are you overzealous and does it come across as smug superiority? Sometimes too much enthusiasm is a turnoff as it can come across as boastful.   
  1. Your mom just misses you: Has your freelance path taken you further away from them in miles or time together? Often relatives, particularly parents, think they want what’s best for you, but it is really what’s best for them. They want more of you, but you are busy living your best life right now. 

Prepare for the onslaught 

Train for the game 

While you should not have to justify your choices, preparing your 30-second spiel can give you more control over the narrative. Stating simply, “I’m a finance journalist and I write articles for a variety of publications” can often be enough to satisfy their curiosity, whereas saying, “I’m a freelancer” or “I’m a digital nomad” might raise eyebrows or among those who see “paying your dues” or waiting for someone else to decide your fate as a rite of passage. Thirty seconds of curated job details might help. 

 Avoid jargon 

Using conventional language to describe your work can help bridge the divide. Unfamiliar terms can intimidate someone already feeling out-of-touch or unhappy with their own job. While new tech is changing the way we work, many aspects of work remain the same at their core.  Social media is still about selling things and we all still hate meetings, Zoom or no Zoom. Share the familiar. 

Consider your social media presence 

Some of your nay-saying relatives might follow you on social media or grudgingly lurk in the shadows silently hating on your lifestyle posts. How curated is your freelance experience online? While you aren’t responsible for your audience’s reactions, be aware that your posts might fuel the jealousy they bring to the gathering. Be open with your loved ones and your followers on social media by exposing the sweat equity you have invested in your business and the hassles you face. This might earn you respect and minimize spite. 

Ease their troubled minds 

 If the pushback is born of genuine worry for your welfare, a simple way to ease a loved one’s troubled mind is to walk them through what exactly it is that you do, explain how you earn and manage your money, address the common fears of retirement savings and healthcare.   

Share the downside 

Total transparency about your freelance life can earn your critic’s respect if they aren’t too hostile to listen. It is undeniable that the life of a digital nomad or solopreneur can be amazing, but there are responsibilities and worries that go with it – concerns that are foreign to a conventional worker like unpaid invoices, clients who ghost you, and paying for healthcare. Tell them. 

Staying sane is the aim 

Whatever animosity surfaces over the holidays, your mental health should be a priority in your relationships. If a family member lacks the self-awareness to see their own jealousy or spite, you aren’t responsible for this shortcoming and can’t fall victim to their judgement. Most freelancers have busted their butts to earn their lifestyle and need to keep their head in the game to push forward. Success has a way of shutting down the haters. Keep at it if you love it and your results will speak for themselves. 

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