Feeling rundown and stuck from an unfulfilling career? Cali O’Connor helps professionals break free of burnout by creating intentional career breaks filled with adventure and purpose.
She is a former chemical and biomolecular engineer who left the hustle and grind of the oil & gas industry for her own 2.5 year career break spent traveling around the world. She successfully transitioned back into the corporate world, landing numerous interviews and 3 job offers, ultimately changing industries completely. Later she embarked on a second career break which culminated in the birth of her business.
Today we get the details on Cali’s work hiatus, travels, and how she coaches others to take career breaks too.
What was the tipping point that led to you taking your first career break?
The catalyst for my first career break was two-fold. First was the stress and burnout. I had been working as an engineer in the oilfield for nearly four years at this point. My job was demanding. I was always on-call, often receiving dozens of phone calls throughout the night. When I visualized my future at this company, I realized there wasn’t a single role I could see myself in because I didn’t want to be available all the time for my job.
The second driving force was a trip that showed me that a career break was possible. Prior to my vacation to Australia in early 2015, I had NO idea that people just quit their jobs to travel the world. On this trip, I was enrolled in a SCUBA certification course which had about 20 students. Everyone in this course was on some sort of long-term trip. Whether they were on a gap year between high school and college or they just quit their jobs. I was stunned. After I realized that a break from the workforce was possible for all of these people, I couldn’t help but believe it was possible for me too!
Was your break planned or spontaneous? If planned, how long did you plan for?
After my trip to Australia, I couldn’t get the idea of quitting my job to travel the world out of my head. I spent about two months reading blogs by solo female travelers and researching all of the places I would love to visit. At that point, I still hadn’t fully committed to this idea. I wanted it, but it was still scary. From the time I finally made the decision to the time I spoke with my employer, was maybe 2 months. In this time I continued my excessive research, invited my sister to meet me in Rio De Janeiro for Carnival, scheduled all my doctors appointments, sold my stock options, started selling my belongings, booked a non-refundable overland trip through Eastern and Southern Africa, and started letting my parents know of my plan.
How did you feel when you resigned?
Leading up to my resignation, I was all nerves. In fact, I’d find excuses each day to not have the conversation with my boss. I wanted to ensure I provided an appropriate notice, so I finally reached the day that I had no choice but to have the conversation. He was so open, supportive, and accepting and I felt incredibly relieved. However, I still had work to do before I left.
When I hopped on my flight en route to Nairobi, Kenya, is a moment I’ll never forget. I describe it as euphoria. As an adult, I had never experienced the feeling of knowing I was doing exactly what I was supposed to be doing and this was it.
What did you discover about yourself during your time away?
My first career break was all about lessons I didn’t know I needed to learn. These are all things I was able to recognize after the fact. I also love to share my mistakes and learnings with my clients to create awareness around possible pitfalls.
When I first started traveling on my career break, I was going really fast. I wanted to see as much as possible and this was coming from a place of scarcity. I believed this was my only opportunity to travel the world so I need to make the most out of it. Subconsciously, I cared very deeply about how I was being perceived by my friends, family, and former colleagues back home. I wanted to prove to them that I had made the right decision.
The lessons in this? I started feeling burnt out on my travels. This was a rude awakening as I was traveling to recover from burnout from work. Upon reflection I was able to start to see that I was the common denominator in the burnout. Sure, I had a demanding job, but the excessive stress came from the pressure I put on myself to succeed and achieve. This translated into how I traveled. Unknowingly, I associated more countries with greater achievement so I moved quickly and that wasn’t sustainable.
Also, by caring what others thought about my travels forced me out of a place of authenticity. I was so used to people-pleasing in my career that I didn’t realize I did that in every facet of my life. It was important to rediscover who I was, what I liked, and what I didn’t like. I forgot all of these things as my identity was so closely tied to who I was at work.
What was the most restorative place you traveled to and why?
For me, Colombia was the most restorative place I traveled and the destination has nothing to do with it! Colombia was the destination that I finally made a conscious decision to slow down. I rented an apartment for two months and enrolled in Spanish classes. I had roommates and made tons of friends and had a bustling social life and routine. This sense of normalcy was something I was missing when I was packing up every two days or so. Colombia is what made me fall in love with slow travel.
Did you go back into a traditional work setting post travel? What does your life look like now? How did your travels influence your career?
After my career break I did go back to a traditional work setting, but I knew I did not want to go back to engineering, so I conducted my job search very strategically. I ended up landing a number of interviews and ultimately 3 job offers. I accepted a position at an education travel company in an operations role which was the perfect fit for me and I know that my career break had a lot to do with getting me that job!
After about 1.5 years I made a short-sighted decision to go back to the world of engineering (I still identified as an engineer…funny how your identity affects your decision-making) and ultimately left 5 weeks later leading to career break number 2. I needed time and space to reset before I made any more big decisions.
Since then, I have traveled extensively (with the exception of the early pandemic time), taken on some contract roles (both in-person and remotely), and began my business helping burned-out professionals leave jobs that aren’t serving them in favor of an intentional career break to travel, rest, and gain clarity on what’s next.
What is the biggest obstacle you help your clients to overcome?
Oftentimes people believe that the planning and the logistical elements of the career break is the hard part. I have found when people start using logistics as excuses and reasons as to why they can’t make something happen, they are coming from a place of fear. That is why I focus very deeply on the mindset piece with my clients. We focus on why they want this in the first place in addition to addressing the common limiting beliefs that come along with stepping outside of your comfort zone and going against what society says you should do.
What is the next destination on your bucket list?
I prefer less typical destinations. Currently, I spend a ton of time in Mexico and I adore this country. I prefer exploring destinations outside of the typical Cabo and Cancun and it’s been incredible. I look forward to exploring more of Mexico. A dream destination for me has always been Madagascar. I can’t imagine visiting a place with species of trees and animals that don’t exist anywhere else. To me, Madagascar feels magical and I look forward to traveling there in the near future.