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A Day in the Life of a Freelance Writer Attempting to Find a “Real” Job


Your day:

5:00 a.m.
Birds chirp. Your eyes shoot open. Remember today is the day of your first job interview as a freelance writer in fourteen years. Wipe sweat beads off your forehead. Quell impending stroke by hyperventilating into your pillow.

5:30 a.m.
Too early. You get up anyway, tripping over six pairs of interview-appropriate black shoes on the way to the shower.

illustration of freelance writer looking for a job

Question 1: “What’s your greatest weakness?”… Illustration by Josh Quick

6:00 am
Iron pants. Wonder why people enjoy ironing when creases persist. You stare at the iron. Give up. Find another pair of black pants. You riffle through the closet for a blouse that doesn’t look like you’re heading to yoga. Text friend for opinion.

Response: “Purple blouse is too monochromatic.”

“I thought that was the point.”

Another ding: “Try blazer.”

“People still wear blazers?”

“Yes. Yes, they do.”

“Holy hell! In summer? When it’s 100 degrees out?”

6:15 a.m.
Torpedo through the closet as fifteen floral dresses avalanche to the floor. You pull out a black blazer with a paint stain. Scrape off the paint; try it on. Too tight. You throw the blazer to the floor and hatch a plan to shop for a new one on the way to the interview.

6:30 a.m.
You dump a vat of costume jewelry on the table and scrounge for a matching pair of earrings. Jam them through your closed ear holes; wipe away excess blood. Comb hair over earrings.

“Creative jobs need a statement piece,” dings friend.

Mental note: You need new friends.

You fasten on a never-before-worn necklace found in a dusty box in the basement the previous night while wondering which dead ancestor it belongs to.

7:00 a.m.
Put on makeup, comb eyelashes—as if anyone is noticing your eyelashes. Find a bottle of essential oils labeled “Calm.” Violently rub applicator over your head, neck, and face. You’re still not calm.

7:30 a.m.
Consume a bowl of oatmeal the size of your head because you have never gone six whole hours without eating as a freelance writer and fear you will die of starvation.

8:00 a.m.
Catch a bus to New York City, but try not to lean back because it will mess up your already too frizzy-in-this-humidity hair. Bus driver makes announcement: “No alcoholic beverages.” You wonder if that includes whiskey. Mental note: Applying for a “real” job means no more day drinking.

10:15 a.m.
You arrive too early. You’re concerned your stomach will growl during the interview, so you browse four potential cafes, but fear smudging makeup or dribbling on your outfit. You don’t order food; instead, sneak into each café’s bathroom to “freshen up.” Despite the best of efforts, your hair continues to expand.

10:30 a.m.
You run into H&M and accost the most fashionable sales associate you can find, dragging him to the blazer section. Ask him to pick out a blazer. There are only two options; this shouldn’t be difficult. It is. You try them on and take them off seven consecutive times until the sales associate decides for you. You ask the cashier for a second opinion. She cracks her gum and stares past you to the next customer.

10:55 a.m.
You look for evidence of other blazer-wearing New Yorkers as you rush through the streets. There are none. The temperature reaches “scorching” and you’re convinced you’ve descended into Dante’s ninth circle of hell. Hair has frizzed to three feet wide.

11:00 a.m.
Approach the building. You observe the automatic security turnstile, side-eyeing employees to determine how it works. You’ll need to swipe your pass. Practice swipe technique in your head. Arrive at appointment just in time for your regularly scheduled nap. Try not to doze off in waiting area while going over potential questions in your head.

Question 1: “What’s your greatest weakness?”

Your Answer: “Ask my husband; he keeps a list.”

Question 2: “Any other weaknesses?”

Your Answer: “My bladder. Definitely my bladder.”

11:15 a.m.
Practice relaxing your face into a warm and open smile. It physically hurts.

11:20 a.m.
Begin interview. There are no windows in the office. It’s dim. Beige cubicles surround you. You envision recycled germs floating through the air and remember why you became a freelance writer. You consider asking HR if you can do this job from home if you promise to wear extra fancy yoga clothes.

12:00 p.m.
You’re introduced to the president of the company. It’s going well. You’re having a pleasant conversation. You’re rocking it. You can do this. Mental note: Don’t let on that you’re riddled with anxiety, that you barely leave the house. And for God’s sake, don’t think about your bladder.

1:00 p.m.
You meet more people, shake hands, nod a lot, and then say goodbye. You rip off your blazer in the elevator, have lunch with a friend, and book it back to the bus. Feet scream, ears bleed.

4:30 p.m.
You find a seat and briefly wonder if whiskey is banned on the outbound before slipping into a coma.

7:00 p.m.
Home. You strip. Step over hurricane remnants of jewelry, shoes, and clothing strewn across the floor. Put on your yoga clothes; nurse anxiety hangover. Vow to write eight articles about the experience. From bed. Under the covers. Tomorrow.

If you’re a freelance writer looking for a “real job,” you might also be interested in 11 soul-sucking truths of rebooting a midlife writing career.

author photo
Aileen Weintraub (Guest Blogger)

Aileen Weintraub writes about women’s issues for publications such as Glamour, Scary Mommy, and Kveller, among others. She is also the author of over fifty children’s books, including the award-winning Never Too Young: 50 Unstoppable Kids Who Made a Difference. She moved up to the country from Brooklyn and now spends the majority of her time obsessing over what may or may not be watching her from the woods that surround her home. Her comedic memoir about the whole debacle is currently out on submission. Follow her musings on Twitter @AileenWeintraub.