Entrepreneurship, a.k.a. quitting our perfectly stable traditional jobs with a steady paycheck and benefits to be our own boss, is rampant in the millennial generation. There’s even a new word for us: millennipreneurs.

Those who aren’t full-time freelancers are tormented by Snapchat stories and Instagram feeds full of friends taking yoga classes midday, hopping on planes for trips whenever they please, curled up on the couch for a midday siesta and extolling the virtues of being a “digital nomad.”

A 2014 study conducted by the Freelancers Union and Elance found 38% of millennials are freelancing.  And I get why – it appealed to me too. That’s why I took my own leap of faith two months ago and left my steady, but already pretty stereotypical millennial job of working as employee-number-one at a startup to try my hand at freelancing full-time.

The motivation came after signing a book deal (even though everyone tells rookie authors not to quit their day jobs). This decision didn’t come lightly nor without putting my savings into turbo boost and laying a strong foundation for a business. I’d already been freelancing for three years and had built a steady stable of clients and opportunities as a personal finance writer and speaker. The increase in demand coupled with the book encouraged me to take the risk and invest in myself. Plus, if it all blew up in my face I figured I could always crawl back to the workforce with my theoretical tail between my legs.

Being your own boss doesn’t just impact your wallet – it affects your relationships

It’s only been two months since I decided to be my own boss and,boy, do my social media feeds make it seem as if my life is suddenly all jet-setting and power lunches. I’ve been to Seattle, Los Angeles, San Diego, Abilene, TX, Waitsfield, VT, and Rochester, NY (twice), in the last eight weeks. Mostly, these were already planned excursions for weddings and a conference – but the sudden blitz in travel coupled with the seemingly glamorous photos on my Instagram and Snapchat left my friends and family wondering: “No, but really – what do you do?”

It’s the question that makes every millennial working outside the construct of a 9-to-5 job bristle.

Whether you’re a freelancer/contractor/ solopreneur/entrepreneur/blogger/writer/designer or whatever other trendy term is about to pop up, it all results in people thinking you just sit around in your sweatpants all day binge watching Netflix and somehow magically get paid to do so.

Okay, we may still lounge in our sweatpants, but there is actual work involved.

Brace yourself for snarky comments

It’s likely everyone from well-meaning friends, to jealous former co-workers to even a loving partner will eventually make a snarky comment about your job (probably by using air quotes around the word job when talking about your career).

Sooner or later you’re going to get a “Well, we can’t all just sit at home all day in our sweatpants” or “You don’t have a real job – why can’t you handle the grocery shopping?” or “I wish I didn’t have to go to work like you.”

Depending on your relationship to the person, it may be some time for a little education about what it is you do. But, you should also be empathetic to the fact that it’s a bummer to wake up to an alarm, get dressed in business clothes, and head off to work when your partner gets to keep sleeping and may or may not actually need to shower that day.

Why you should expect a freak out from loved ones

It makes sense why parents, aunts, uncles, grandparents and even your traditionally employed friends would balk when you decide to forgo a “real job” in the pursuit of setting your own schedule. Our parents and loved ones truly want what’s best for us and currently, they’re hardwired to believe what’s best comes in the form of a job with a medium-to-large sized company that offers a 401(k) employer match and subsidizes the staggeringly high cost of health insurance. After all, this route would make your life easiest and parents certainly don’t wish a struggle upon their children.

When I announced my freelance career plans to my parents, they maintained composure better than I expected. There were certainly lots of questions about my plans, goals, and some slight concern about whether or not I’d be able to support myself in the manner to which I’d become accustomed.

These questions encouraged me to open up about my business plan in order to receive feedback and to show my parents the career shift was in my best interest.

Explaining what you do

A simple way to ease a loved one’s troubled mind is to take the time to sit down and walk him through what exactly it is that you do, show how you earn money and prove you’re not neglecting the future because you’re still saving for retirement and paying for health insurance. It also doesn’t hurt to show a business plan outlining how you plan to grow and, of course, earn more money.

Then you need to come up with your defensive mechanism for cocktail parties, chatting with strangers on planes, and the fact we as humans seem to default into asking, “What do you do?” as a conversation starter.

Saying, “I’m a freelancer” or “I’m a solopreneur” may get derisive looks, especially from (and apologies for the stereotyping) Baby Boomers. Despite the fact that a recent study found 20 – 30% of the workforce in the U.S. and the EU-15 is self-employed or contractors, it’s still looked upon as millennials experiencing Peter Pan syndrome and refusing to become fully-functioning members of society.

A quick way to inoculate yourself against potential ridicule or snarky quips is to have a specific job title you use. I default into saying, “I’m a personal finance writer.” Sometimes people ask more questions, but usually they just redirect conversation back to themselves and what they do.

Don’t just show people the social-media curated version of life

Finally, the best way to earn respect and explain what you do is to be transparent about freelance life. Yes, being a digital nomad is a delight, but what about when you quite literally have tens-of-thousands of dollars owed to you but bills are due today so you have to clear out your emergency savings fund to make ends meet while pending payments come in? Or how about the time you sunk hours into project, turned it in and the client completely ghosted you (and your bank account)? Or the sheer nightmare of trying to get and pay for health insurance. Or maybe it’s your realization that you just don’t enjoy having to be your own boss and want to opt-back into the traditional workforce.

Be forthright with your loved ones and your followers on social media by showing some of the grit behind building your business. The honesty will earn you respect and pacify the jealous feelings the traditionally employed may be experiencing.


It should be noted, my parents were very accepting of my freelance move. I just found the title snarky!