Midlife Career Exploration

Over the years Ada and I have both enjoyed being informal career mentors to countless of our friends and colleagues. We were recently reflecting on how dramatically those career conversations have changed as our friends and colleagues have aged from early in their career to mid-career.

In many ways, early career conversations were actually far simpler in nature. Like a video game, most individuals were focused on leveling up as quickly as possible and wanted to know how to acquire the hard and soft skills they needed to climb the career ladder laid out in front of them by their current employer. Or they were exploring a new role or company that might meaningfully accelerate their timeline for leveling up. When asked about their dream job, they often aspired to one of just three roles: a VP in their discipline, a CEO, or ultimately a startup founder.

In stark contrast, the midlife career conversations we've been having look entirely different. While to some it may initially feel a bit like a midlife crisis, the reality is that through the course of their careers many friends and colleagues have developed unique insights and a deeper self-awareness that enable them to now re-orient their career towards truer fulfillment.

I wanted to share some of the most common insights friends and colleagues have at this stage in their career that lead them to be more thoughtful about their next career move.

It most often starts with the realization that time is actually life's most precious asset. Part of it is certainly the understanding that we no longer have the gift of youth. With likely a decade of our career already under our belt, we realize that our career arch no longer feels infinite. But more important than that is the realization that building skills, expertise, judgment, and intuition are not things we can quickly rush through as we may have naively thought early in our career. Building mastery in any competency takes time, deliberate practice, and a real dedication to our craft. With this understanding comes the need to make hard trade-offs and focus on building the few specific skills that truly matter to us.

At this point, we also often transition away from the explore phase of our careers, where we sought out new opportunities to build our breadth of experiences and to learn more about what we were good at and enjoyed. We instead move on to the exploit phase, where we leverage the deeper understanding we've garnered of our strengths and passions to narrowly focus in on opportunities where we are likely to thrive. Similarly, while we might have spent a lot of our early career shoring up weaknesses, at this point it makes sense for us to spend more of our energy finding opportunities that specifically play to our greatest strengths.

Another realization that we often have is of the gap between the roles and responsibilities that we excel at and those that we actually love doing. Justin Kan describes this as the difference between our zone of excellence and our zone of genius. It's so easy to spend our careers simply focusing on what we excel at because that's what we are most often rewarded for. But Justin rightfully encourages us to find ways to transition our roles more to operating within our zone of genius because it'll allow us to operate from a source of constant energy and ultimately be happier for it.

On a deeper level, I've seen many folks transition from an external scorecard to an internal scorecard. So many of us spend so much of our youth being measured by the same external scorecard as everyone else: things like our grades, what college we got into, and our major. It's no wonder then that we continue that practice with our early career, with company, title, and compensation as the measures we most often hold ourselves up against. We also so often become used to trying to please everyone around us and in doing so, seeking their approval, whether it's family, friends, or coworkers. But the gift of age often gives us a deeper understanding of what truly matters to us. We start to define our own inner scorecard. And realize that keeping up with the Joneses is rarely on that list. And that the only approval we truly need comes from within. It is so powerful when we achieve this understanding as it allows us to pursue a path that will truly be personally fulfilling regardless of how it makes us look to others.

And finally, so many come to the obvious-in-hindsight realization that there is so much more to life than just their work. Some finally take the opportunity to realize their life-long dream of traveling the world. Others realize their true passions lie outside of the workplace and seek to find ways to spend more of their time pursuing those hobbies, whether it's art, fitness, cooking, or something else entirely. Personal lives also often grow in importance, with some wanting to devote more of their time to finding a spouse or ultimately having kids. All of these are incredibly important and worthwhile pursuits that demand that precious resource of time that we may have historically found hard to find when our life was far more one dimensional in nature. For others, it dawns on them that having it all was always a pipe dream and even the most fortunate of us still need to make the hard trade-offs of what is ultimately most important to us.

So often these insights make us realize that the career path we have been pursuing may no longer be the straightest path to our ultimate career fulfillment. This is the true mark of the midlife career exploration. And it's up to each of us to embrace it as doing so can enable us to achieve previously unattainable heights in our own career satisfaction.
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