I imagine jumping out of an airplane (with a parachute, of course) is an uncomfortable and counterintuitive act for most sane people; it certainly was for me. But just because it's scary and intuitively feels like a bad idea, doesn't necessarily mean it is. Pushing oneself to skydive is a lesson in courage, trust, and perseverance. Once the fear subsides, it can also be an incredibly exhilarating experience. Compelling ourselves into situations that help us become comfortable making uncomfortable decisions may be one of the most essential aspects to becoming stronger humans; it is also vital to building a successful career. The truth is, sometimes even scary choices empower us; they force us to leave the security of the familiar in favor of the spirit of learning, adventure, and new challenges.
Like diving out of an airplane, leaving a great job at a great company can be an incredibly difficult decision. It can also be hard on your ego. Take me, for example; I had a fantastic executive job at Equinox where I led a significant portion of the overall business, i.e., Personal Training, Spa, Pilates, Retail, Food & Beverage, and Kid's club, among other things. Three years into the job, when the company had grown to about 80 clubs, I decided to leave in pursuit of a CEO and Board role with Oath Pizza, a Venture Capital-backed early-stage premium fast-casual business, which at the time had 4 locations.
As you may imagine, the reaction from many when I told them of my decision was a combination of confusion and surprise; why would someone leave a great job at a prestigious and successful company to run a small pizza business? To wit, why would anyone voluntarily jump out of a perfectly functioning airplane?
The answer is simple and is a principle that has guided me throughout my life: To continue learning, growing, challenging myself, and finding unique opportunities to contribute. To explore unfamiliar territory and ceaselessly push the boundaries of my leadership skills.
In the case of Oath, there were a few things I knew would be difficult for me to experience in a larger more established business: 1) Raising capital; 2) managing a board; 3) building something from very small to large with few resources. Only by jumping out of my comfort zone and taking a risk would I be exposed to these opportunities for growth.
I left a great job at a prominent company because my approach is to evaluate the opportunity cost of staying in a job. Opportunity cost refers to what you have to give up to get what you want concerning something else. If I had stayed at Equinox I would have given up the chance to learn all that moving to Oath had to offer, in essence, I would have lost out not only on what the experience of jumping out of a plane had to teach me but the exhilaration and sense of achievement that came with it.
So in situations where I've had to make a decision to leave a great job, I consider the following: 1) Where will I learn the most; 2) will I be able to contribute in unique and new ways; 3) if it turns out to be the wrong decision, what is the downside; 4) will either outcome bring me closer to my long-term goal(s)?
I wanted to experience running an early-stage business, raising capital, and managing a board, so for me, the answer was simple. I also determined that gaining these new skills would give me an advantage that I could either apply to larger companies, another startup, or early-stage businesses at some point in the future.
We have a finite amount of time to learn as much as possible and apply it in unique ways and new contexts. To my mind, for individuals who aspire to lead companies one day, developing a discipline that includes a proactive instinct to leave great jobs in favor of new learnings is a core value that can’t be overstated. Admittedly it can be very hard emotionally, but breaking down this hard decision into its most straightforward questions "where will I learn the most, and can I contribute meaningfully" may make it easier to answer. And in my experience, once you get comfortable with being a little uncomfortable, you can conquer anything, be it a challenging new position or jumping out of a plane.