If Not Now, When?

“If not now, when?” I’ve always loved this quote by Eckhart Tolle. It’s a great reminder that tomorrow may never come.

Why I decided to leave a 27+ year career with a Fortune 500 company to try something completely new.

So often in life, we’re waiting for the right moment to happen or the right time to come so that we can pursue that life goal or stop doing that thing that’s been a bad habit for way too long. We keep waiting for the perfect moment to pursue the dream because when everything’s perfect, it won’t be that scary. But, we all know that there is no perfect moment and, even if there were, it will probably still be at least a little bit scary.

I have been and probably always will be described as “pragmatic” and a “planner”. The thrill of taking on a big problem to solve or making sense out of chaos energizes me. I look at all angles with practicality, breaking it down and creating order so that someone can do something with it. I know I’ve been this way my whole life as I can still hear my Aunt’s voice when I was a kid telling me how efficient and organized I was. I was always the one corralling the cousins, planning the group activity, assigning roles and then directing everyone accordingly. 

My planning nature carried over into adulthood and this made me well suited for life in a corporate work environment. I excelled at creating documents and project timelines no matter what my job was – sales, human resources, operations or training. Having a plan on paper calms me and the feeling of checking a box brings a sense of euphoria when I complete a task or milestone.

When it came to my career plan, it was, of course, written down so others could see what I was aiming for and so I could track my own progress. I identified mentors to support and provide me guidance, put myself in new and challenging situations and made sure I was an above average performer in whatever my role was at the time. My career plan worked and I eventually rose to the level of Vice President. Along the way, there were a lot of different types of moves: lateral, scope building, line to staff, staff to line as well as moves where I managed technical functions even though I am not a particularly technical person. All of this experience gave me a tremendous amount of functional breadth and leadership depth and positioned me well for senior leadership positions in any organization. So, when I recently made a major career change, a lot of people asked with polite curiosity (and maybe a little skepticism) why I would give up all of that for a small, unknown company in the healthcare industry. My response was, “If not now, when?”

When we’re early in our careers, the goal is to build our resumes and become responsible self-sufficient adults. There’s an oft-held expectation that you go to college right after high school, you get a job and eventually become a homeowner. Maybe you settle down with a life partner and/or start a family while continuing to work your way up the proverbial corporate ladder. If things go according to plan, fifteen years later, you’ve got a decent salary, maybe have upgraded your housing, have some money in savings and possibly more disposable income for hobbies and charitable giving. As you get into your 40s and 50s, you start thinking about retirement and how much longer you need to work, what you will need financially to retire and how you envision spending your soon-to-be newly available time. Making a big career change during this phase is not usually on the plan because disrupting your retirement vision at this point seems way too risky.  

But that's when I felt a spark inside me that something was missing and I wasn't having as much fun in my work as I used to. I decided to hire a career coach to help me identify my skills, strengths and passions. I interviewed a half dozen leaders I had worked with to get their perceptions on my unique abilities and when they saw me at my best. I took four different personality tests and spent hours in interviews with my coach as she unpacked my experiences and the emotions that came with them. After four months of working together, the end result was what I ended up calling my “midlife clarity project”. After all of these years, I could easily describe the three elements of a perfect role for me: direct impact/helping others, "field marshal" (rallying the troops and resources to achieve a particular goal) and developer of talent.

I took my newly empowered self on a roadshow within my company. For the first time in a long time, I could confidently articulate what my strengths were, what job criteria needed to be in place for me to have the highest level of success and what type of work I was most interested in. I put myself out there for roles I never would have considered previously and declined opportunities that didn’t fit, even if there was a hard sell pitch by a top executive. However, after a few months of shopping myself around, I had no takers and that’s when I started having a hard time time seeing my future there.

Buoyed by my sharpened focus, I didn’t let this deter me and I decided to take my roadshow outside the company. I chose to make my initial connections with people in the health/wellness/outdoors/recreation/fitness industry, as I was personally interested in being around a community where health and helping others was the mission. Doors flung open left and right and I quickly realized how much value I could bring to a variety of organizations. The feeling of being valued and in a role that fit my interests and strengths was something that could not be underestimated. It’s something everyone deserves.

Along the way, I met a CEO of an amazing company with an award-winning culture and big dreams to impact more lives. I had been a patient there in the past and was inspired by the incredible customer service and high energy environment that delivered results (I personally improved my half marathon time by 25 minutes and did so without pain). While he didn't have an open position at the time, he recognized that he needed someone like me by his side to help him bring his vision to life and my skills and experience were a perfect complement to his. After much consideration and a little bit of fear about the perceived risk of such a move, I had to follow my heart. If I didn’t give it shot now, when would I? 

In my short time there, I’ve been able to drive value added work without bureaucracy and tiring complexity. I’ve been able to impact the business and team with new ideas. I’ve helped team members grow and stretch themselves into new spaces. I've built my industry network too and have met some amazing CEOs of small businesses looking to change the world. It’s been a boon for my life outside of work too. I have better work life balance and flexibility with my schedule (heck, my office is only four miles from my house) and the fact that I’m happier at work makes everyone at home happier. To this day, I have absolutely no regrets.

So, what are you waiting for? Because, if not now, when?