Career Change: 4 Stages of the Flying Trapeze

In the Fall of 2015, I made one of the most transformational decisions of my life. I decided to make a career change. It doesn’t sound like a big deal…until I tell you that I was 34 years old. And solely financially responsible for my own survival. And that I left a six-figure income as a Director with a nationally renowned, Pulitzer Prize-winning publication in exchange for a temporary minimum wage position as an intern.

Why? If I were being dramatic, I’d tell you it was the pursuit of passion. But in reality, when I did it, I wasn’t yet sure what my true passion was. I was just wildly unhappy. In this post, I’ll share with you the four stages of career change I experienced and the path I took to catalyze my own new beginning.

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Stage 1 - The Downswing: Questioning Everything

When I was a little girl, I wanted to be a superhero. As I grew up, life happened, and the din of others’ opinions filled my mind. “Go to college.” “Get a stable job.” “Get married.” “Buy a house.” “Have kids.” I’m not exactly sure when I stopped listening to the voice inside me that was filled with wonder about the world I inhabited. It seemed like one day I just woke up with a college degree, a house, a car payment and the haunting question, "Is this all there is?" It’s not that my jobs were terrible. They just didn’t fit me. Each day as I left for work, I folded myself into the shape of the corporate box I was expected to inhabit. I was on autopilot with no idea how to re-engage the controls of my life. At the time, I felt like I was falling. But really, I was holding on to the bar of a trapeze swinging downward and building momentum.

Stage 2 - The Upswing: Building Momentum

So, what could I do? I had a grown-up life with grown-up bills and responsibilities. How could I possibly explore other options and still meet my obligations? I needed to take action, and the first step was to put myself out there and start meeting people. I began talking to everyone I knew. I asked friends, family, and trusted colleagues what they thought my strengths were. I also asked them about my weaknesses.

They were honest.

REALLY honest.

Those friends and family referred me to people in their networks, and I began to learn about new and exciting options I had never entertained. I was soon introduced to a fabulous digital marketing maven. This self-made woman had chased her desires until she uncovered her passions and was very successfully pouring herself into all of them at once. She agreed to meet me for tea one sunny autumn day in Boulder. She shared about her successes and, more importantly, how her failures led her to meaningful work. She said, “In the Startup community we have a saying, ‘Fail Fast.’ It gives us permission to try new things until we arrive at the best possible solution. It’s the ultimate freedom in experimentation, and it’s addictive.” I left that meeting with a notebook full of inspiration and a mind overflowing with ideas.

Months went by and still I continued meeting people, asking questions, and investigating new paths that were opening up. Whenever my natural curiosity tapered off, I would move on and explore the next avenue. Fail fast. At times, I felt discouraged, frustrated, and anxious. Would any of this research ever pay off? What I didn’t realize was that by being proactive, my momentum had shifted, and I was on the upswing of the trapeze, gliding higher.

Stage 3 - Release the Bar: Taking a Leap of Faith

One day, I found myself sitting in my well-appointed office staring at a budget spreadsheet for the upcoming fiscal year. I had spent several weeks revamping our marketing and events strategy and was pleased with the work I’d accomplished. But something was missing. The haunting question, "Is this all there is?", still lingered. How much longer could I stare at spreadsheets designed to be presented to far-away owners I'd never even met? I longed to channel my talents into a calling that would allow me to be both creative AND analytical. I sought an environment where leadership was transparent and accessible. I was ready for a career where I could have a direct and measurable impact on the success of my company. So, I asked the universe for a sign. Moments later, my boss delivered news that another department, one critical to the success of the organization, would be experiencing layoffs. I knew it was time to move on.

The next morning, I gave my resignation. I had no job lined up and no source of income. My modest savings would have to get me through until I could ascertain the next step, but at least I had given myself the gifts of time and mental freedom to fully commit to that process. I had let go of the bar and was soaring through the air, like the superhero I wanted to be as a kid.

Stage 4 - Catch a New Bar: Starting Fresh

The day after I resigned, I received a call from the Maven offering me a digital marketing internship with her startup for two days a week. They could pay me, but only minimum wage, she cautioned. I told her I was interested. As soon as I hung up, I panicked about money, but stuck to my guns. Two days later, I received a call from a friend in my newly spun network. She was looking for someone with my experience to help her company three days a week. This would be just enough for me to squeak by. The seeds I had planted to grow my new career were sprouting.

When I first began my internship, I could barely turn on a MacBook. I had no idea about any of the online tools, software or terminology of the industry. It was like moving to a foreign country where no one speaks your native language. You see the street signs, but you can’t read them. You’re forced to rely on the hospitality of the locals to guide you in the right direction, and help you find your way. That’s exactly what happened to me.

I fell in love with the country that is the Startup community and learned to speak the language of Digital Marketing. Now, I dream about marketing automation. I communicate in gifs. I go to amazing industry events in my free time. I tell my friends about all the fascinating new startups that are forming and getting funded. I practice outbound and inbound marketing methodologies. I craft compelling content and have a whiteboard for ideas in my bedroom. I collaborate with interesting, creative, and talented people who share my passion for digital marketing and technology ALL THE TIME.

I was a part-time intern for the span of three months, and in that time, I evolved more rapidly than I did in 10 years as an executive. During my career changing trapeze act, I was working without a net. At times I felt my belly flip, my palms sweat, my grip loosen and my equilibrium tilt. I tried not to look down, and to trust that each stage of the act was necessary to reach the next one. At the end of this show, I am no longer distracted by the din of the crowd. I hear only voluminous applause, and it’s coming from within.

We all have defining moments in our lives. Turning points where we can choose to invite in the unexpected, the unknown and the uncertain. I’ll leave you readers with this and I challenge you to step off the platform and swing on your own trapeze:

"The only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle." - Steve Jobs

Saylor is an agile marketer, startup evangelist, mentorship advocate, tech aficionado and world traveler based in Denver, Colorado. She is most likely to a) stop and pet that puppy and b) sweet talk you into giving her an upgrade.