Your Career, Your Marathon. Don’t Peak Too Soon!

As we come to the end of another action-packed year, and I am also finishing an epic career chapter, I have been taking much-needed time out to “re-fire” and decide what I am going to do next. This period of reflection led me to dig up some of the notes I had written to myself early in my career, based on advice from mentors and friends.

I'm struck by a pivotal conversation I had with an executive recruiter back in my 20s. At the time, I was hungry, ambitious, and eager to climb the corporate ladder as quickly as possible. I didn’t yet have a family, so I didn’t have a grasp of how much more complicated my life was going to become. Quite frankly, I was all about me—my hustle, my achievements, my compensation, my bragging rights. I also had absolutely no idea that the winds of my career would continue to change many times over—from wonderful tailwinds to gale-force, sidelining headwinds. When I look around my peer group now that we are all reaching our 50s, I realize that the vast majority of us have had this exact experience.

I realize now that my recruiter friend was spot on when he looked at me and urged me to sloooow my roll. As he reminded me, career management is a marathon, not a sprint. It's about playing the long game, understanding that your professional life will have constant highs and lows. What matters is the strength of the foundation you build along the way, both in terms of your skills and your sense of resiliency to get better at rolling with the punches. It's easy, in the early stages of your career, to compare yourself to others who are crushing it with their posts on LinkedIn and feel like you’re falling behind. But fear not—like the tortoise and the hare, you have a long way to go.

Here’s an overview of the advice I received in my 20s about the milestones and challenges that can come with each decade of your career, along with some thoughts and observations from my own journey. Ready, set, go!

Your 20s: The Foundation of Functional Expertise

In your 20s, the goal isn't to become an overnight sensation or to land that dream executive role immediately. Instead, this decade is about deep learning and developing serious functional expertise. Think of it like training for an athletic competition—you’re building muscle, understanding technique, and mastering the fundamentals.

For me, this meant diving headfirst into marketing roles, understanding every nuance of brand strategy, consumer behavior, and digital communication. I wasn’t just doing a job; I was becoming an expert in my field. And as I learned later in my 30s, having deep expertise in one functional area is critical for your confidence and the value you add to a team when you first start leading broader teams.

So if you’re in your 20s, try not to get distracted by titles or immediate compensation. Focus on gaining skills that will become your professional superpower. Ask for challenging assignments, seek mentors who can provide honest feedback, and be willing to take lateral moves that expand your skill set.

Your 30s: Leadership and Broad Perspective

As you transition into your 30s, the game changes. This is where you start to overlay leadership skills onto your functional expertise. It's no longer just about being great at your specific job—it’s about understanding how different parts of an organization work together. For many people, this is SUUUCH a tough transition. Suddenly, what you can do as an individual is NOT what the game is about; instead, it’s how you can inspire others to get the work done.

I distinctly remember a huge shift I had to get my head around: spending less of my time “doing” and more of my time building relationships and coaching. It’s so easy to get buried in our to-do lists, but you have to be intentional about carving out time for the management stuff, which is going to be so critical as you work further up the ladder.

General Management (GM) experience is ideal during this phase. Seek out roles that give you cross-functional exposure, as it will give you more options as you make your way toward the C-suite. I can’t tell you how many people I have mentored who wanted to be a CEO one day but didn’t take the chance to broaden early enough in their journey. For me, I knew I wanted to be a CEO, so I deliberately chose assignments that allowed me to work across marketing, sales, finance, operations, and strategy—even though at least a couple of the roles I took were “side steps” as opposed to promotions.

This broader perspective is what separates good professionals from truly exceptional leaders. Even if your dream is to be the chief of your function, the broader perspective will enable you to reach that kind of level.

So don’t be afraid to step out of your comfort zone and step backward in money or title if it helps you get the hands-on experience you need. Take on projects that seem slightly beyond your current capabilities. Volunteer for broader assignments that will stretch you. Build relationships across different departments and learn to communicate effectively with diverse teams.

Your 40s: The Power Decade

If your 30s were about building your leadership foundation, your 40s are about leveraging your accumulated expertise and really hitting your stride. This is when you play to your absolute strengths. You've developed a deep understanding of your industry, built a robust network, and refined your leadership style.

For many professionals, this is also the decade of maximum earning potential. You’re no longer proving yourself—you’re delivering exceptional value. Your reputation, your track record, and your ability to drive significant organizational change become your most valuable assets.

But remember—you don’t get to harvest the winnings of the power decade if you haven’t done the hard work in the decades prior. I can count so many young executives who might have had their startup success or made the Forbes 30 under 30 list in their 20s but quickly flamed out because they had received all the accolades without building the required foundation. What’s more, it’s hard to imagine in your 20s how much value comes out of having deep relationships and a strong reputation, but it is going to become the single most important “asset” you have. Like I said at the start—there WILL be headwinds in every decade, and the strength of your foundation will directly correlate with your ability to withstand them.

Your 50s: Freedom and Fun

This is the piece I remember so clearly from that conversation 20 years ago when he said to me, if you’ve played the game right, your 50s can be about pure enjoyment and impact. By this point, you’ve likely achieved financial stability, so you have the freedom to be more selective about the opportunities you pursue. THIS decade is the summit of the mountain—which is why even in your 20s, it’s worth looking up to see where that summit is to ensure you’re charting your path to get there.

This phase can include exploring board directorships, mentoring the next generation of leaders, and choosing projects that genuinely excite you. Hell, it might be the moment you go back to college and change it up for the sake of doing something new. It’s ALL open to you when you’ve accumulated enough wisdom and financial cushion to say "no" to things that don’t align with your values or goals.

Final Thoughts

Managing your career is an art form that requires patience, strategy, and self-awareness. At the end of the day, every piece of it comes down to the quality of the relationships you have built along the way. So if there’s one thing I would add to the advice I heard in my 20s, it’s pretty simple: “Don’t be a dick!”

I reflect on the numerous conversations I’ve had with friends in the moments when their careers faced headwinds—and they found that people they thought were friends were suddenly not returning their calls because they no longer wielded the influence of a big business card. And then, literally one cycle later, the person who didn’t return the calls is down and out, frustrated and surprised when nobody is there to support them in their time of need. It’s a LONG road—and you’re never as great as your big wins lead you to think you are, or as bad as your epic fails make you feel. So BE the person that returns the calls. Care about others when they are facing headwinds—you never know when it’s going to happen to you.

That conversation in my 20s wasn’t just advice—it was a blueprint for a fulfilling professional life. Success and financial freedom are important, but when I reflect on my journey, the most rewarding part has been the friendships I've built along the way—I wouldn't trade those for anything.