Shifting Careers

When we were in high school, Pat and I would chat about how much fun it would be to run a business together (a retail shop? or maybe wedding planning…), but these conversations were lighthearted and casual - never accompanied by any real or concrete plans. Instead, we went to college, received our degrees, and pursued our respective professions - hers in law and mine in teaching. When our 15- and 16-year-old selves envisioned potentially working together, we had no idea that we’d both make major career shifts before landing side by side in our future business.

I was a year into my teaching career when the opportunity to hop on board Our Heiday quite literally fell into my lap. My husband and I happened to be living in New York at the same time Our Heiday exhibited at the National Stationery Show for the first time. I held a long-term substitute position at a school on Long Island and while there were parts of teaching that I genuinely loved (and still miss), much of the day-to-day left me drained. Classroom management felt so contrary to my nature and the pressure to be “on”  in front of an audience all day left me running on empty.

That May, I (very) gladly welcomed an opportunity to take a couple days off to help Pat set up and run Our Heiday’s first tradeshow booth...and I loved it. I’m not sure if it was the creative energy that I missed from being a humanities teacher, connecting with people from all around the country with similar interests, or the rush of unexpectedly receiving so many sales, but I fell hard for the stationery + gift industry and could feel my mind start to wander.

Long story short, I decided that weekend to take on a part-time position with Our Heiday and handled Accounts & Operations remotely from my New York apartment. Part-time quickly turned into full-time, and full-time eventually led to becoming Pat’s business partner and one-half of Our Heiday. Life is wild, isn’t it? Never in a million years would I have thought I’d be the CEO of a creative business. I still want to laugh out loud when I have to list “CEO” as my job title on my taxes or medical forms because it’s not at all what I imagined for myself, but I’m so grateful to have a career that I’m passionate about, that utilizes my natural proclivities, and that pushes me to learn new skills at every turn.

It’s an emotional decision to leave any career behind, especially one as personally fulfilling as teaching. There’s something so special about pouring into students when they’re at such an impressionable age and letting go of that platform & privilege was a mental battle for me for a long while. It’s not easy to walk away from something familiar and secure to take a plunge into the unknown, but I do think when the opportunity is right, you'll know :)

xx,
donna