Part 3 of a 3-part series on The Career Path Less Traveled
Warning: The following, if taken as career advice, could be hazardous to your income. It’s my individual career path story, shared in hopes it will help you think differently about how to shape your own.
It’s revealing to look back on a career spanning more than three decades and to see, from the perspective of hindsight, the steps and decisions that led from there to here. Unlike some people whose upward trajectory is steady and true, mine was always more like the ‘80s video game Frogger: I hopped on a log and rode it until another good option came along, or until circumstances forced or encouraged me to jump for the next, usually more advanced, opportunity.
While some of those leaps were lateral moves or even the occasional step down, my general career path was onward and upward. Without even thinking about it, I was on a management track, and (in the early days) couldn’t get there fast enough. I measured success not just by my paycheck, but in the number of people reporting to me and the degree of influence I had on my organization. Fortunately, that rookie attitude gave way to some hard-earned wisdom over the years, and I like to think I grew into the mantle of leadership and recognized the privilege it afforded me to actually do some good for my organizations and the people in them.
As described in Part 2 of this series, a year ago I pressed “pause” on that career path so I could dig deep to discover what I really wanted out of my (likely) final decade of paid work. I knew a few things innately: I needed to get back to my community-based, not-for-profit roots with an organization I could be proud to serve, and I wanted to be surrounded by smart, talented, committed people. I knew I’d probably take a pay cut no matter where I landed, and I carefully built a “must-have” baseline budget to guide me.
Armed with these non-negotiables, I began to think about what I could do that would check all the boxes. Despite all the intentionality, I was still operating from what soon revealed itself to be a faulty assumption: that I’d pursue another leadership role.
But as I reflected back over my career and the times I’d felt the most satisfied in my work, my thoughts kept returning again and again to the role that launched me on my eventual career path. While it carried a different title, it was essentially an executive assistant role working with the CEO and board of an established organization that was well-respected in our community. It drew on all my strengths, offered me autonomy and influence, but didn’t require me to give my life over 24/7 to the organization.
The more I contemplated it, the more I knew it was exactly the kind of role I needed and wanted for my next step. But…with recent titles of VP and Director on my resume, surely no one would take me seriously. In fact, I knew that if I were a hiring manager for a role like this and saw someone with those titles applying, I’d never trust they really wanted “just” an assistant role. And what would people who “knew me when” think when they heard I’d stepped off that leadership path?
Time for more soul searching. I acknowledged my heart wasn’t in the higher level roles any more. My recent experience had made it crystal clear that some titles and paychecks simply aren’t worth it. I’d been saying all along that I wanted balance, and realized taking a less demanding role was one way to get it. A role I could turn off at 5 pm every day offered the prospect of more “life” in my off hours – from writing, to spending time with loved ones, to taking care of myself. And as for “what will people think,” I decided (belatedly) that this had no place in my life or career. I also reflected on the many brilliant and talented people I know who have made exactly this kind of role their profession, and knew I’d be in great company if I moved in that direction.
Knowing I’d face skepticism, I began working my connections. Even among people I knew wanted the best for me, I heard the doubt. They listened to me with kindness, but I could tell they were thinking, “She says this now, but she won’t want this for long.”
What happened next was nothing short of a miracle – actually, a series of them. I found a role description that so perfectly matched what I was looking for that I wept when I read it. I convinced the recruiter to get me an interview.
When I met the hiring manager, I spoke my truth. I acknowledged that if I were in her seat, I’d be highly suspicious of someone with my background wanting a role like this. I told her exactly why I wanted it, and what I could bring to it that would set me apart from her other candidates. And in a true moment of what can only be grace, she heard me. She got it. She shared with me the story of her friend who’s on a similar path. And she had the courage to offer me the job.
The role hits all the marks: It’s with a highly respected organization with deep roots in the community. I continue to learn new skills, while drawing on my years of experience. I’m surrounded by smart young people every day.
There are other intangibles. This move has taken my ego out of the equation; it’s intrinsically rewarding to have skills to contribute, but without the pressure to climb or be on an upward trajectory. As a more seasoned worker, it’s less about me and more about giving a boost to the next generation. Rather than compete with them, we complement each other, and it is a huge joy for me to see them learn and grow and succeed.
Lest this be another “sunshine and roses” story, let’s talk about the financial implications. They are substantial. I acknowledge that it was a luxury, one not everyone has, for me to even be able to consider such a move. My husband and I joke that we are the poster-children for downward mobility (hence that warning at the beginning of this piece). We have less disposable income than we once had, but my less demanding job leaves me time left over for freelance work, and we’ve further diversified our income by creating a little short-term rental apartment in our now empty-nest home.
On to the moral of this little fable: For hiring managers reading this, I encourage you to keep an open mind when you see someone looking for just this kind of bell-shaped career path. Having been in your seat, I know it’s often so hard to know what an applicant really wants. Trust your instincts; remember my story. There just might be a treasure there.
And for those seekers out there, please hear this: You’re the architect of your own path. You get to decide the trajectory. If upward and top of the heap is what you want, I’ll be cheering for you every step of the way. But don’t let habit, or others’ expectations, keep you heading in a direction you no longer want to go. Chart your own course, and keep an eye out for the wonders awaiting off the beaten path. Wishing you traveling mercies.