Is it Time for a Career Change? Dream Big in 2022!


“You can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

-Steve Jobs

As an Enneagram 3, I’m someone who is energized by productivity. Because of that, a big part of my life has always felt defined by my work. When I turned 16, I took my first job as a cashier at a local grocery store in my hometown of Middlebury, Indiana. In the years that followed, I became a waitress, then an elementary school teacher, a computer science teacher, and finally a district instructional technology specialist.

For the 15 years I was in education, I was never comfortable with mediocrity or stagnation. I was constantly evolving my practice and reaching for what was next in my career. But in the midst of the Covid crisis, I changed my mind. I realized that the traditional workforce wasn’t working for me or my family, and I walked away. That’s right, I said goodbye to an amazing position that I worked so hard to earn. Goodbye, standard 40-hour workweek. Goodbye, W2 income. Goodbye 401K. Goodbye stability and security. 

If you asked me at the beginning of my teaching career where I hoped and dreamed I would be today, I probably would have said married with kids, living in a bougie single-family home in Lincoln Park, and teaching in downtown Chicago. Or maybe I would have said teaching and living in the suburbs of Chicago, but you get the point. And you know what? That would have been great. If I would have been in Chi-town tonight, I could have eaten Pequod’s for dinner, devoured Sweet Mandy B’s for dessert, and had a nightcap at a gorgeous rooftop bar. Living and teaching in Chicago would have been a really nice life, but it’s not how things panned out after all, and that’s because of the intentional choices I made.

A change in plans

My goals and aspirations evolved with time, and so did my career trajectory. While I absolutely LOVED being a fourth-grade teacher, I learned pretty quickly that it wasn’t something someone with my personality type would be able to sustain with a family. The time demands and emotional commitment were all-consuming, but to be the teacher I wanted to be, there was no such thing as balance.

So the moment I felt an urge to leave the classroom, I set out to make it happen. I worked my tail off to earn a Master’s Degree in Educational Technology and became a Computer Science Teacher, then later an Instructional Technology Specialist for a school district. I LOVED those roles. These positions provided me with tremendous leadership opportunities, flexibility and balance, and they challenged my creativity. Honestly, I had no plans to leave. But when the pandemic hit and my family was faced with tough choices, I really started contemplating my life and what was most important to me. I took a leap of faith and resigned from my 9-5 job in order to better support my family and manage our short and long-term rentals full time.

Was I scared to leave a stable career? You better believe it. Did I have to work even harder to be successful working for myself than a corporate job? Absolutely. Was the flexibility and time with my family worth it? 100% yes. But here’s the thing about me, I’m a little more jaded and a little more willing to take big risks than most people. Caring for two sick parents has made me this way. I watched my sweet parents work tirelessly and save every penny for their retirement, basically for nothing. So my mindset is a bit different. I don’t dream about retirement; I have fears about not being able to enjoy it. And I’m not afraid to take chances; I’m afraid to miss out on opportunities.

If you’re still reading this, it has to be for a reason. I imagine you feel stuck. You don’t like the job you worked so hard to attain. Maybe you feel like it’s too late for you to make a change. Maybe you’re exhausted from chasing each paycheck and counting down the days to retirement. While there’s no “one size fits all” answer for the question, “What’s next for me?” I can tell you this: IF YOU PUT IN THE WORK, YOU CAN DO ANYTHING YOU SET YOUR MIND TO.

That’s the JOY of life. You’re in control! The second you’re no longer fulfilled with where you are or what you’re doing, make a change. Fill each season of your life to the brim with whatever it is that brings you the most joy at that time, and let each season completely run its course. When it’s time to welcome the next season, you’ll know it. Smile, say thank you to the past, and welcome what’s next with open arms.

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Steps you can take to make a change

  • Read. Listen to podcasts. Journal. Hire a career coach. Go back to school. Do whatever soul-searching you need. Follow your heart and mind.
  • Find like-minded friends. In the past year, I’ve met more like-minded people than I knew existed. Many of them don’t have traditional jobs, and yet they’re some of the hardest working and most passionate people I’ve met. It has been really good for my soul to talk with people who are also living unconventional lives and chasing big, wild dreams.
  • Turn your envy into energy. Instead of scrolling through Instagram and feeling jealous of “influencers” or friends’ lives, figure out what it is they have that you want and go get it.
  • Get on the same page as your partner. My husband and I are teammates. We are working toward the same goals, and that’s huge. Grow together, not apart.
  • Imagine your perfect day and dream BIG. In ten years, my husband and I see ourselves living in a beautiful home in Old Village or Sullivan’s Island that is filled with the happy sounds of two or three children giggling together. When we aren’t traveling, we envision slow mornings, with no alarms: coffee on the sunlit porch (decaf for me – I don’t need any extra energy) and watching our kiddos play with our pup in the backyard. We see ourselves taking the golf cart to breakfast, checking in on our properties/businesses as necessary, and investing the great majority of the day in ourselves and our family: kayaking, paddle boarding, yoga at the beach, and scrubbing the catamaran as we prepare to set sail for the summer. 

“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma – which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition.”

Steve Jobs

Dream big, y’all.

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Born and raised in Indiana, Brandy spent a decade as an elementary teacher and instructional technology specialist in Chicago. After marrying her husband, Chad, rescuing their beloved pup, Harper, and having two beautiful children, Emerson and Charlie, they traded in their snow boots for swimsuits and purchased a duplex in downtown Charleston. Brandy loves being outdoors, capturing memories in photographs, exploring new restaurants, blogging, and organizing anything and everything! From being landlords and Airbnb hosts to parents and travel enthusiasts, you can follow her family's adventures at