I had the pleasure of catching up with my neighbor and friend, Kim Masiello, about her incredible career journey one sunny afternoon in my home office, surrounded by plants and, of course, my pup Dwight by my side.
When we're not working remotely, Kim and I often take breaks to stroll around the neighborhood, catching up on everything from local news to travel adventures and our latest exercise routines. Recently, Kim introduced me to my first cold plunge—a new experience that I ended up loving!
Having good neighbors like Kim is a blessing—they keep an eye on your home, water your plants, hold your packages, and are always up for a chat about life. So, you can imagine how excited I was to dive into her career path together!
From Art History to Education
Kim started her career journey in New York City, studying art history and interning at prestigious museums. She was set on becoming a museum curator until a dinner conversation with a friend sparked an interest in teaching. This led her to Columbia University’s teacher education program and eventually to teaching middle school English in New York City.
Career Shift: From Teacher to School Director
After moving to San Diego, Kim took on the role of directing a school in Southeast San Diego. This challenging role exposed her to the harsh realities some students face, which took a toll on her emotionally. Kim shared, "I cried almost every day. It was sad, it was long, it was frustrating." Despite the difficulties, this experience helped her grow and eventually led her to seek a different path.
Finding Flexibility and Freedom
Kim transitioned to a homeschool charter where she discovered the benefits of hybrid and remote work. She also started two small businesses—a web design and development firm and an ESL school. However, she realized she didn’t have the entrepreneurial drive, especially for the administrative and sales aspects. Kim mentioned, "I crave the ability to work remotely but hate looking for clients and doing payroll."
The Power of Persistence
Applying for hundreds of remote teaching positions, Kim landed five different roles as an independent contractor. She juggled all five until she narrowed it down to one that fit her needs perfectly—a private school based in Oregon that allowed her to work remotely and travel. Kim’s perseverance paid off, and she now enjoys the stability and freedom she craved.
Actionable Takeaways
Be Open to Change: Kim's career path shifted several times, and she embraced each change with an open mind.
Perseverance Pays Off: Kim applied for hundreds of jobs before finding the right fit. Don’t give up!
Listen and Adapt: Listening and adapting to new opportunities can lead to unexpected and fulfilling career paths.
Define Your Stability: Stability isn’t just about a steady paycheck. It’s about finding a balance that works for you.
I love how Kim took her own personal values and used them to build her own career path that supported her needs of stability, growth and working remote.
Thanks for reading this story on The Career Flipper Podcast!
Every week, I, Jenny Dempsey, chat with folks from all over the globe about their amazing career flips. I dive into stories from every industry imaginable—big flips, small flips, and everything in between, whether they were by choice or circumstance. Sharing these journeys makes me feel less alone in my own career flip from customer service manager to furniture flipper and podcast host, and I really hope it does the same for you.
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