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Answering a Craigslist Ad Led Me to the Job of My Lifetime

How a random ad and a bit of kismet transformed my career.

Lisa Gastaldo
Jul 13 · 6 min read

I had spent months perfecting my corporate interview attire: Navy sheath dress. Mid-heel black patent pumps. Black leather tote just the right size to stow spare copies of my resume and sturdy enough to stand upright beside my discreetly crossed feet. My online research had indicated that a slouchy handbag puddled on the floor would project unprofessionalism.

It never occurred to me that sheer desperation would soon prompt me to answer a small ad on Craigslist. I certainly didn’t envision that hitting send would embark me on the path to self-discovery and career fulfillment.

Not your typical job applicant

I was at the end of my rope and at the precipice of drowning in debt. Widowed eight years earlier, working full-time at this stage in my life was not part of my initial life’s plan. But, my sons were now both away at college. I had depleted what reserves I had. I needed a steady income — and a reason to get up each day.

Out of work for quite some time, I was the most unlikely candidate for every position coming across my Indeed feed. I was just recovering from a six-month stint on disability and over 50. My resume was all over the place: Public Relations straight out of college, stay-at-home-mom, part-time elementary school librarian, full- and part-time volunteer positions, and a recent stretch as a content creator. (Turns out, their particular office environment was not a good fit and partially led to my illness.) Instead of presenting a steady rise to success, my CV read like an Emergency Room EKG: Glitchy ups and downs and currently flat-lining.

A kind relative had treated me to a session with a job counselor. Since the traditional format would only highlight gaps in my experience, she suggested I create a skills resume. This style did not have to be linear but focused on my areas of expertise. She also advised treating my volunteer work skills with the same importance as those garnered from paid employment. When all was said and done, I thought my innovative document conveyed I could tackle anything presented to me.

When people would ask what type of job I was looking for, I could never give them more than a vague answer. I could only describe the feeling. “I want to work at a small company where I can make I difference,” I would attempt to explain. “It could be public relations, event planning, insurance, I don’t care. Just somewhere that appreciates my work more than just hours on a timesheet.”

And so, I applied for nearly every position that struck my fancy: Public Relations Manager — I’d carnival pitched with the best of them. Administrative Assistant — Gatekeeping? Making copies? Correspondence? I’m quite adept at multitasking. Non-Profit Volunteer Coordinator — I had just spent four years rallying troupes and raising funds for a large high school football program — I could do that one in my sleep.

I visualized myself being a star employee in any of these positions. The problem was no one was taking a liking to my sparkle.

Take a chance on me

When I realized my unconventional resume wasn’t making it past corporate filtering algorithms, I decided to take a chance on Craigslist. Nestled among the posts for telemarketers and dubious work-from-home opportunities was an ad for a Customer Service/Office Assistant position with a small, family-run company. There was a little subtle wit in the ad that told me these could be my people. The ad ended with a “Must Love Dogs” tagline, so I included a postscript in my cover letter. Written in the voice of my pup, Jenny, I assured them of my dog-friendliness and snuck it a bit of my creative writing in the process.

A boisterous Samoyed greeted me upon arrival. While attempting to avoid him, my heels scraped into the cracks of the shale path that led to the office — a converted detached garage next to the owner’s home. My straight dress was a bit snug causing me to do a little shimmy and then “plop!” into the rolling chair offered to me. Careening across the floor, I quickly regained my bearings and faced the staff of three: Founder (S.A.*), Son (M.A.*), and Assistant #1(Q*). M.A., the main interviewer, was clad in a faded millennial style t-shirt — appeared threadbare, but most likely brand new and purchased on Melrose — and shorts. The others were dressed just as casual. “No need for an office attire budget,” I noted to myself as the white beast of a dog rummaged a Luna bar out of my tote.

The meeting started with brief company history: Just over 30 years earlier, S.A. was a newly sober travel agent. He realized that most vacation spots are rife with alcohol and loads of temptation. Counting on strength in numbers, he reached out to his friends in the twelve-step community to see if they would like to join him. He had over 200 people on that first trip. By the next year, they were buying out entire resorts for a week and the company was born.

Fellowship, self-care, and fun were the hallmarks of the trips — nicknamed “Sober Villages.” The entire premise was you could have just as much joy — if not more — on a vacation without the assistance of alcohol. Their signature trips had grown so popular, they were adding additional events to their roster. Hence, the need for another assistant.

I hesitantly noted that I wasn’t “in the program,” certain it would be an immediate disqualification. They assured me it wasn’t an issue. While S.A. and Q were sober, M.A. was not. I would just be balancing the foursome.

The trio then took turns commenting upon and complimenting nearly my entire resume. It was the first time my volunteer experience was given equal weight. I was flabbergasted. There was no need to pitch how my atypical skillset could best serve their company as I had at countless other interviews. “If someone is bright and willing to learn,” Q explained, “you can teach them anything. What you can’t force is chemistry.” I knew all my random talents and bag o’ tricks could be utilized and appreciated.

Call it providence, serendipity, the universe’s plan — whatever you’d like — but there are times when things inexplicitly progress like a prewritten tale. You feel a little unsettled. You can’t quite control the narrative, but it’s oddly comforting. This was one of these times. I knew within ten minutes I wanted the position. By twenty, I knew I had pretty much nailed it. Before I even arrived home, I received the call asking when I could start.

Alchemy is the art that separates what is useful from what is not by transforming it into its ultimate matter and essence — Philippus Aureolus Paracelsus

To date, I’ve worked on four Sober Villages and several side tours. My job has allowed me to visit Mexico, Turk and Caicos, Jamaica, Italy, Greece, Croatia, France, Spain, Monte Carlo, and Hawaii. An extremely limited traveler before the position, I am now the envy of my at-home friends. “If you should ever need an assistant…” is a common request when I regale tales of my adventures.

I’ve made my mark on the company by creating a Day of Service on each of our big trips. Giving back is a pillar of the twelve-step program. The projects entail identifying a local school in need of assistance, then soliciting our guests and our host resort for donations. We have collected and distributed thousands of dollars in school supplies, water systems, and playground equipment. It all culminates in a single workday where hundreds of man-hours are devoted to repairing and beautifying the school. These days are my proudest career moments.

This position has provided the opportunity to create my personal job title: Director of Client Relations. I have been able to craft something uniquely precious — and entirely my own. I’ve been granted the gift of knowing my talents are valuable. With each trip, I have become more secure in my role and confident that this amalgam of tour operator, travel logistics, party planner, and client care was my true calling. I have discovered my artistry.

COVID Epilogue

Travel bans have placed my career in limbo and I am uncertain whether it can be resurrected. Will I be able to forge a new path? Transform yet again? With a stroke of luck and, perhaps, a bit of help from Craigslist, anything is possible.


*Initials used instead of names in keeping with twelve-step protocol.

Change Becomes You

Life advice that will (actually) change your life.

Lisa Gastaldo

Written by

Writer. Mother. Widow. Survivor. Featured in GEN, Human Parts, & Huffington Post. Looking for life’s perfect fit at SearchingForBigGirlPanties.com

Change Becomes You

Life advice that will (actually) change your life. Curated stories from The Good Men Project.

Lisa Gastaldo

Written by

Writer. Mother. Widow. Survivor. Featured in GEN, Human Parts, & Huffington Post. Looking for life’s perfect fit at SearchingForBigGirlPanties.com

Change Becomes You

Life advice that will (actually) change your life. Curated stories from The Good Men Project.

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