Pros & Cons of the Freelance Lifestyle

Rather than return to the grind of a full-time gig, I've been doing a lot of freelance work instead. (What with being laid off in 2014 and 2017, that's one roller coaster I wasn't up for boarding again so soon.)

While initially I was delighted by the work-from-home, make-your-own-hours freedom of this career choice, as I'm approaching a year of it, it's definitely a mixed bag – one that's filled with its share of benefits and shortcomings.

Topping my list of lesser-known perks is the opportunity to sing along to the most depressing Aimee Mann tunes without colleagues suggesting I get myself some Abilify®.

Downsides you may not imagine include me stalking the mail carrier and muttering my daily mantra, "Where's my check?"

(Yes, many publications roll old school and shun PayPal and direct deposit much to the dismay of my beleaguered postal worker.)

Some facets of the freelance lifestyle actually fall into both categories. Exhibit A: I can spend most of the day working in flannel pajamas and a bathrobe, while enjoying lengthy, one-sided conversations with my cat. But it's putting a strain on our relationship, and lately I can tell he's thinking "Please, woman, get dressed and leave the house – for both our sakes."

He's right.

Many of the advantages -- grazing on Easter candy while a Real Housewives marathon plays in the background -- and disadvantages -- no paid healthcare, sick days, or vacation time -- are so obvious, that, as my dear aunt was so fond of saying "A rhesus monkey could've figured that out!" With this in mind, I'd like to share some of the more obscure pros and cons of freelancing. Being a perennial optimist, I'll start with the positives:


  • I have periods of remarkable self-discovery during which I realize I've lost the ability to do simple addition and subtraction. For example, when I need to call someone outside the Eastern time zone, I require nothing short of a high precision calculator to discern a mutually-agreeable interview time. It's freeing to admit that, for me, math has gone the way of high heels. I just can't any more and won't even pretend.
  • I'm always learning new things like why tax changes make 2018 the year to get divorced (if you're so inclined and live in NJ) and meeting interesting people, who inspire me to toss the 5,000 Bed Bath & Beyond coupons that spring out of every drawer of my home like goddamned jacks-in-the-box.
  • Sometimes I get cool offers. Just last week a PR rep volunteered to send me Husqvarna's Alexa-compatible Automower – if I could find somewhere to place the story. This is good timing as our mower was just swallowed up by our bulk garbage truck after much of its hardware blew off during one of my husband's more violent grass cutting episodes. Then, today, I received a package from Zatarain's, filled with rice mixes, Creole seasoning, and the promise of fresh shrimp arriving next week. (Plus, now we know when National Shrimp Day is – you heard it here first!)


OK, now for the negatives:
  • When I am able to finally keep the time zones straight and schedule a phone interview, it often falls apart in any number of ways:
  1. The interviewee feigns shock, professing no memory of our scheduled call. (This is only slightly less irritating than when the person who's supposed to interview you for a job forgets all about it after you've fought Lincoln tunnel and Midtown Manhattan traffic to be there.) 
  2. The person takes the call on a cell phone from what sounds like either a helicopter (Me: "If you're skydiving, I'm happy to arrange another time..." or the bottom of a well ("Is Lassie getting help, or should I call") and I catch every seventh word while they insist the connection is crystal clear.
  3. Though the interviewee knows I'm calling to help promote his or her business or craft a professional bio, he or she offer one-word answers, making me feel like I need to go full-tilt Barbara Walters to avoid turning in a three-sentence piece of drivel. ("Tell me why you really became a Realtor or I'll be forced to make you cry.")
  • I create my own problems by taking on assignments without realizing I have four others due that day – mainly because I'm a sucker for sentences that go like this: "Thanks so much for taking this on – I should probably mention that something fell through the cracks and well, it kinda needed it yesterday."
  • While waiting for a lone check to arrive, I've spent the same meager amount three times over, as just knowing it's on its way somehow allows me to justify buying anything from an orchid to a gazebo.
  • Every few months I'm asked to interview an obscure singer-songwriter who'd like to be treated like the second coming of Elvis.
  • Rather than simply send me photos that I request to accompany an article, some people like to describe what they're looking at on their computers and then ask me which would work best: "Oh, this is a shot of Ray at that thing holding a whatchamacallit. You think something this might work? Hold on while I ask Carol. Carol?"
  • When the whole family is home, as it seems they have been every day since it now snows continuously, I'll ask my husband, "Do you want me to take this call upstairs or in the basement?" He insists I don't have to leave the room. "No, no, stay, you're good. We'll be quiet!" he says. Then, while I'm mid-introduction, he proceeds to blow his nose just over my shoulder emitting a sound that suggests we're strangling a gaggle of geese over here.
  • It can get isolating. (See the bit above about conversations with my cat)

OK, I guess seeing the ratio of cons to pros makes me realize perhaps I'm losing that once-optimistic attitude – see, again, more self-discovery! But are these drawbacks enough to force me to find a new interview dress and venture back out into the work force again? Time will tell!

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