The year is 1996. I’m sitting in my college’s guidance office in a gauzy babydoll dress, rocking Clinique’s Almost lipstick in Black Honey. I feel like a fancy lady with my glossy brown pout, balancing a portfolio of writing samples on my knee. Clippings from my school’s newspaper, The Montclarion jutt out of a saddle leather folder along with an array of short stories and poems published in our edgy, angst ridden literary magazine. My counselor asks to see my work. I hand her a poem titled Allison, written as a tribute to a free spirited, yet wayward friend who drove too fast and smoked way too much pot. With tortoise shell glasses perched precariously on the bridge of her nose, my counselor carefully reads, nodding randomly, the corners of her crimson mouth curling. With her thick brown hair piled in a messy bun, and a silky scooped neck blouse, I find her very au courant. 

After reading, the counselor puts down my poem, pauses, and then purrs, “You’re going to make Montclair University very proud one day.”

I nod my head enthusiastically in agreement. Yes, that was my plan. I had big dreams of writing gorgeous prose, maybe at a magazine, touching people’s hearts, making them think, or at the very least entertaining them with my wit and candor. I envisioned my name on the masthead of some splashy publication, penning articles ranging from finding the perfect bronzer to body acceptance. I would write a book too, with a passionate protagonist, catchy title, and intriguing plot twist. Following my dream, I’d forge a path to a fabulous future that didn’t involve punching a time clock, or squashing my youthful creativity at a normal job. 

One year later when it was time to chose my internship, I had the opportunity to interview at a respected, long running magazine, one that I adored, located in Chelsea NY. I remember standing in the elevator, wearing a yellow blazer, borrowed from my mother, stacked heels, and a sensible black skirt. Looking a bit like a bumble bee, I waited shrinkingly for the elevator doors to open and my grown-up life to begin. A week later I got the call. I was chosen for the internship and could start that Monday. Foolishly, I declined. 

I’ve regretted it ever since. 

There are moments every middle-aged person looks back on and wishes they could slap some sense into their younger, foolish self. That was my moment. A few days after the interview with that magazine I had one with my college newspaper. It was a safe, paying internship, located on my familiar New Jersey campus. I took that job. 

There were a few reasons why I passed on my dream internship, one stupidly being a man. I was dating someone and desperately wanted to be on a path towards marriage. A job in a city with limitless possibilities, and cosmopolitans after work would surely veer me off the safe, predictable course I craved. I’d wind up having casual sexual encounters with vapid men in Hugo Boss suits who feared commitment and I’d never have babies. But there was another, more prominent reason why I just couldn’t bring myself to accept that job. I was terrified I wasn’t good enough. 

In my English Lit classes I excelled, but this was the real world now. Everyone was talented, skilled, poised, confident and, it seemed to me, way more attractive. There was no way a chunky, nervous girl like me could navigate herself among the cool, elite world of fashion magazines. Yes, I had gotten the job, but in my neurotic mind I was a joke– a lame mess who was terrified of not measuring up. My low self-esteem was crippling, and I convinced myself the editors would find out how little I had to offer and fire me in the first week. 

Eventually I graduated, married that man I was dating and had those babies. I also got divorced, and got that steady, time clock punching job to support myself and children. Through the years I dabbled with writing, trying to keep the embers of my dream stoked amidst the temper tantrums, ear infections, and IEP meetings. I wrote for the local paper and loved it. Seeing my byline on an article I had researched and written gave me a sense of purpose that extended beyond vomit cleaner upper. As my articles were well received, my confidence grew. I began to branch out, writing for a local magazine, as well as online publications. It certainly wasn’t Chelsea, but it was something. Still, my decision to pass on that internship years before haunted me, as I wondered where I would be if I had just been brave enough to believe in myself. 

So when my son came home from school with a form for the PTA scholarship essay contest, I was over the moon excited. I knew he was a good writer, a gene I flattered to think he inherited from me, and since we mothers tend to project ourselves onto our children, I assumed he would throw himself heartily into crafting a well written piece complete with compositional risk and higher level vocabulary. I assumed wrong.

He looked at me incredulously as I filled out the form signing him up for the contest. There were to be two winners, announced at the graduation ceremony in a packed gym filled with tearful mothers, and proud grandparents. Both students would receive two hundred and fifty dollars. 

“This contest is for smart kids.” 

“You are smart.”

 Major eye roll in that dramatic fashion only a teenager can manage.

“No Mom, I mean it’s for the really smart kids, like the Valedictorian is doing it, I don’t have a chance so why bother.”

Apparently along with my writing gene, good hair, and overbite, my son had also inherited my self doubt. Crushed, but hopeful, I decide to tread carefully. Lecturing a teenager about the follies of youth is about as effective as nailing jello to a wall. I take a different approach, pull up my Submittable app on my iPhone, and show my son the long list of declined articles peppered with a few accepted ones highlighted in green. It works. He starts on the essay, begrudgingly so, hunched over his Chromebook, grunting exasperated syllables under his breath. I think he even says the F word. I bite my tongue. Four paragraphs in he dramatically concedes this is stupid. 

“I’ll never win.” 

I almost let it go. It’s June, he’s graduating, no kid feels like writing an essay, but I know how good he is and I fear his doubts will suffocate his spirit and he’ll end up at a menial job, living paycheck to paycheck, eating processed foods and eking out a dismal existence. I’m projecting again. In essence, I’m worried he will end up like me– with a well of regret and a thousand what ifs. Finally, I share with him my story of turning down the internship, my lack of bravery, my sheer stupidity. He seems unmoved, but finishes the essay nonetheless. 

Graduation night. He’s sweaty in his polyester gown. I start crying within the first few chords of Pomp and Circumstance. For all I’ve done wrong in my life, for all the mistakes I’ve made, I did something right with him. I’m teaching him to be brave. If there’s one lesson I can impart on him, one thing I can burn into his soul, it would be to tell that voice that whispers, “I can’t” to be quiet. It’s a lesson I’m still learning. 

He wins the essay contest. 

I joke with him that I’m going to use the prize money for a spa day. He says he’s using it to attend The Walking Dead convention.

That night, after he’s changed out of his stiff slacks and into gym shorts, after he’s devoured a pound of chicken fries and a dish of chocolate ice cream, after all the cards have been opened and congratulations have been said, my man child sidles up next to me as I’m elbow deep in dishes. 

“So I really won.” 

“Yup, and you didn’t even want to try.” 

“You really were that scared to work at that magazine?” 

He’s standing close enough for me to see the faint brown hairs on his upper lip. The once cranky jaundiced baby with a gumdrop nose now towers over me. 

“I really was that scared.” I admit. 

He puts his lanky arms around me. The sink is filling up with suds, my eyes with tears. 

“I’m glad you made me do that essay, Mom.” 

He unhooks his arms and I watch the one thing that I’ve never regretted slink upstairs into the cave of his room. 

After the dishes are washed, I sit down for what feels like the first time in weeks. The floors are sticky, I have wet dishes to dry, and thank you notes to write. Instead, I open up my laptop, its familiar hum and tropical screen saver greeting me, and google magazine internships. 

It’s never too late to start to be brave. 

Claudia Caramiello

Claudia Caramiello is a certified pharmacy technician by day, freelance writer by night, mother of two teen sons both day and night. Hailing from New Jersey, she survives single motherhood on caffeine, humor, and listening to Twenty One Pilots. Her articles have been featured on Scarymommy, Bluntmoms, Sammiches and psych meds, Elephant Journal, and Moms & Stories. You can find her on Facebook at Espresso & Adderall and read more from Claudia on her blog,