- My first paying job was scooping Ice Cream down at The Polar Bear in my hometown. I learned how to make change the hard way and hated cleaning the walk-in freezer. We got to take 1 free scoop of ice cream home a night. I never forgot to.
- I graduated from The Polar Bear to The Golden Guernsey in high school and developed a really big right forearm. I loved gossiping behind the snow cone machine about customers. Mom and Dad were my best tippers.
- Before freshman year of college began, I signed up for a week long retreat called “FYSOP” (First Year Student Outreach Program) to help the homeless around Boston. I called my Mom every night begging her to come pick me up. She almost caved when I told her we were only allowed 1 PB&J to truly experience how it felt to go hungry. She didn’t.
- My sophomore year of college I drove a van that carried college students to underprivileged areas, helping kids learn how to read. My favorite student was a shy little boy named Reade, coincidentally. He only wanted me to help him with his homework and wait patiently until I showed up after school. I was glad my Mother never did pick me up that year before.
- My junior year of college I signed up as a temp agent through the Student Service office. My favorite job was cocktail waitressing at a fancy Beacon Hill apartment for a lovely couple hosting a dinner party. They kept asking me what I wanted to do when I grew up. I just smiled and said “to be in business.” I had no idea.
- That same temp agency led me to a gig answering phones for the offices of the Big Dig’s central command station. My voice went over a loud speaker to 1,000’s of construction workers who kept stopping by the make-shift desk to see who was behind the microphone. Apparently the woman I replaced had a voice that no one could stand. They begged me to stay. I didn’t.
- That summer I worked as a temporary secretary in an Advertising, Design, and PR office. There was a photography studio next door that needed a last minute hand model to hold a weight for a Gold’s Gym shoot. I made $50 holding that weight and got a free french manicure out of it. My Mom still brags about this today.
- Two of the people that worked at that firm left and started their own design firm and I went with them. They taught me to be independent and take risks. They let me write and publish press releases and encouraged me to figure things out on my own. Things like “how to get new business over the phone” and “how to turn on a coffee pot.”
- I was a waitress at The “World Famous” Cask N’ Flagon outside of Fenway Park in the evenings. I used to walk from the Cask at 3am across a vacant parking lot to get home carrying $500 cash in my pocket. I’m not proud of this fact.
- I moved to NYC right after the planes hit the towers and started working for Martha Stewart Omnimedia. I was making 30K a year as an Administrative Assistant for the Creative Director who was 1 step below Martha herself. Every time her name showed up on my office phone I had a mini panic attack, picked it up and blurted “Jonathan Chernes Office.” MS: “Where is he?” If he wasn’t in the vicinity I’d run around the Starrett Lehigh building like a chicken with it’s head cut off until someone helped me find him. When we finally did he would roll his eyes and slowly walk back to his office to take the call. I still love this man.
- I got promoted to Product Coordinator within the year and part of my job was to coordinate photoshoots for the retail division. Once I was out in the Hamptons shooting towels for the Kmart line. We had no idea where to put our trash bags from the shoot so I found a dumpster behind a Pizza shop and placed 2 large bags in there. The next morning I received a message on my office line that he had caught me on camera illegally using his dumpster. He accused everyone that worked for Martha Stewart as being careless and greedy NYC snobs. He threatened to sue and demanded a call back. I decided to use the method referred to as “kill ’em with kindness…” he expected an arrogant employee on the other end of the line- he got a sweet girl that apologized profusely, instead. We never heard from him again.
- Martha Stewart threw the best holiday parties. I attended one at her home in Westport, CT. and got to take a picture with her . I have no idea where that picture is today. Related: Can you still access stuff uploaded to Friendster in 2002?
- Martha approved everything we made from a 5 piece bedding set to the tiniest of ornaments. We developed product development timelines that gave us 2 weeks for a Martha approval. The approval or denial would take no more than 5 minutes.
- I remember standing in a boardroom watching the news with my fellow employees when they announced she was going to jail. I didn’t feel angry, I felt sad. Regardless of what seems to be popular opinion, I thought then (and still do) that she was a remarkable woman that carved out an incredible, powerful position for herself. I’ll never forget the amount of talent I was surrounded with at that office.
- My next job involved product managing for a company that made baby products and ride-on vehicles for kids. I learned all about terms I had never heard before like “Quality Assurance” and “Operations Management.” If I thought 2 weeks was a long time to wait for an approval, I had another thing coming with carseats.
- In 2005 I took a risk and moved to Chicago without a job. After 1 week of searching I found one and traveled all over the country convincing corporate buyers from places like Starbucks, Caribou Coffee, Peet’s Coffee, Macys, and Bed Bath and Beyond why they shouldn’t buy direct from China and instead invest in coffee mugs that offered innovation and an American-based design staff that would cater to their needs. I learned how it felt to be successful and a failure almost every day.
- After 2 years in Chicago I moved back to NYC and lived there for a summer working for the same company but from home. We lived on a loud and lively street you may have heard of between Thompson and Sullivan called Bleecker. The kitchen was too small to cook in.
- In 2007 we had married and moved back to Boston. Still working from home for the Chicago-based company, I moonlighted in Sales for other companies and probably shouldn’t have. I decided to take my first yoga class during a lunch break. I went back every day and eventually got certified. I bought that same studio in 2011.
- When I went back to work for the same baby products company I started out as part-time but couldn’t resist the pull. I landed a Senior Product Manager position and gave more presentations in front of critical eyes than I care to remember. I traveled the country to trade shows. I visited factories in China. I loved my team. I put together cribs. I crunched numbers and stayed late and had interesting discussions with co-workers in the sample room. I was frustrated and exhilarated, challenged and bored. I wondered what it would be like to go out on my own.
- Now it’s 2016 and I work for myself. I scramble and I hustle. I make moves to get ahead. I fall behind a lot. I feel exhilarated and challenged, overworked and scattered. I am hungry for more. I crave less. I am a living oxy moron.
Now I sit and write on the computer after changing diapers, singing songs, making meals, and coordinating drop-offs. Some days I feel like I can conquer the world. Other days I feel as small as the ant currently eating leftover crumbs from breakfast under my feet. Most days I try to take a deep breath, put my fingers back on the keys, and crush that ant.