When Ambition Changes Direction

I have been thinking lately about how our definition of success changes over the course of a career, and I am not sure we talk enough about the fact that it probably should. What motivates us at thirty does not necessarily need to motivate us at fifty-five, and the questions that once pushed us forward may eventually need to be replaced by different ones. That is not a loss of ambition or evidence that we have somehow become less driven. In many ways, I think it is what happens when experience finally gives ambition some perspective.

Early in my own career, the definition of success was fairly straightforward. I wanted to know how far I could go, how much responsibility I could handle, and whether I could succeed at the next challenge, the next command, or the next organization I was entrusted to lead. There was always another level of responsibility somewhere ahead, and I was interested in finding out whether I was capable of carrying it. Looking back, there was nothing particularly unusual about that mindset, especially in the military, where careers are built around progressively greater responsibility and where much of your professional development is designed to prepare you for what might come next.

There is nothing wrong with that kind of ambition. Organizations need people who want to lead, build, compete, solve difficult problems, accept accountability, and produce results. Someone has to step forward when the mission becomes harder, and some people are naturally drawn toward positions where the stakes, complexity, and responsibility continue to increase. I spent much of my career in that space, and I remain grateful for the opportunities I had because they taught me lessons I could never have learned from a classroom, book, or leadership seminar alone.

Over time, though, I have come to think there are roughly three paths many of us follow. Some people spend most of their careers driving organizations forward. They seek increasing levels of responsibility, lead larger teams, take on more complicated problems, and continue doing that work until they eventually decide it is time to step away. For them, leadership is expressed primarily through direct responsibility for mission, people, resources, and outcomes, and there is tremendous value in having leaders who are willing to carry that burden well.

There is another group that seems to understand much earlier that their primary calling is developing other people. They teach, mentor, coach, educate, advise, and spend much of their professional lives helping someone else become more capable. Their influence may not always be as visible as the person sitting at the top of the organizational chart, but over time it can be just as consequential because they shape the people who eventually occupy those positions. Some of the most influential people in my own life belonged to this group, and much of what I carried into command or executive leadership came from people whose greatest contribution was not the organization they personally led, but the leaders they prepared.

Then there is a third path that I have become increasingly interested in because I think it describes where I find myself now. These are people who spend much of their careers in the first group and eventually realize that perhaps the next chapter is not about taking on another organization, another title, or another level of authority. Instead, the experience accumulated through years of carrying responsibility becomes something to invest in people who are still making their way through the challenges we have already encountered.

I find myself increasingly drawn in that direction, and not because I regret the years spent in operational leadership. Quite the opposite. Maybe those years were the cost of admission. Maybe the value of spending decades making decisions, leading through uncertainty, getting things right, getting things wrong, and being accountable for what happened afterward is that eventually you have something worth passing on that cannot be learned entirely through theory.

I have tremendous respect for education, scholarship, and the disciplined study of leadership, and I believe strongly that leaders should read, study, and remain intellectually curious throughout their careers. At the same time, there is something uniquely valuable about teaching a lesson you learned while carrying responsibility for the outcome. It is one thing to understand conflict, organizational culture, ethics, decision-making, or change management conceptually. It is another thing to have lived through the consequences of making the wrong call, recovering from it, and knowing what you would do differently if someone gave you the opportunity to live that moment again.

General Jim Mattis has written about the importance of studying military history because leaders should not force themselves to rediscover lessons that others have already paid for in blood. Human beings have been fighting wars for thousands of years, and there is very little wisdom in ignoring that accumulated experience simply because we want to believe our current problem is entirely new. I have always appreciated that argument because it recognizes experience as something larger than personal memory; once captured and passed forward, it becomes a resource for people who have not yet had the opportunity, or misfortune, to learn the same lesson themselves.

I think leadership works much the same way. Every experienced leader eventually accumulates a library of decisions, successes, failures, mistakes, instincts, relationships, and moments that changed how they see responsibility. Some of those lessons were expensive. They cost time, credibility, opportunities, relationships, sleepless nights, or the uncomfortable realization that something we once believed about leadership was simply wrong. If all of that experience remains only with the person who earned it, then much of its value disappears when that person leaves.

When experience is transferred, however, it becomes something larger. A younger leader may still have to make difficult decisions, and no mentor can remove every hard lesson from another person's path, but we can sometimes help someone recognize a problem sooner, ask a better question, avoid a mistake we already made, or recover more quickly when things go wrong. There is a difference between protecting people from experience and preparing them to make better use of it, and I think that distinction becomes increasingly important as we move into the later chapters of our careers.

Maybe this is also how ambition should evolve. Earlier in life, ambition naturally asks how far we can go, how much responsibility we can handle, and whether we can reach the next level. Those questions push us to grow, and I do not think we should apologize for asking them. Eventually, though, there may come a point where the more meaningful question is no longer how far we can go ourselves, but how far we can help someone else go because of what we have learned along the way.

None of these paths is inherently better than the others. We need leaders who remain deeply engaged in operations and continue driving organizations forward, just as we need people who devote entire careers to teaching, mentoring, and developing others. What interests me is the transition between the two, particularly for people who spent decades in command, executive leadership, clinical operations, government, business, or other environments where they accumulated a kind of practical wisdom that should not simply retire when they do.

There is something powerful about taking decades of authentic experience, including the successes you are proud of, the failures you would rather forget, the scars nobody else can see, and the lessons you paid dearly to learn, and deliberately investing them in someone who does not necessarily have to learn every one of those lessons the hard way. That does not mean turning every conversation into a war story or assuming that what worked twenty years ago should be repeated exactly today. It means giving the next generation context, perspective, judgment, and enough room to make the lesson their own.

Most of my closest friends are now at or nearing the end of what I think of as that first group. We have spent decades leading, building, commanding, operating, and solving problems, but we have also spent those same decades being poured into by people who came before us. Mentors invested time when they did not have to, leaders gave us opportunities before we were completely ready, teachers challenged how we thought, and organizations allowed us to accumulate the experience we now carry. None of us arrived here entirely through our own effort, and I think there is an obligation that comes with recognizing that.

The return on that investment is not another title. It is not another promotion, another command, or one more line on the résumé simply because there is still room to add it. At some point, the return may be measured by whether the people behind us are better prepared because we were willing to share what was given to us.

That is probably where I see the final evolution of ambition. It does not disappear, and it does not become passive. It simply changes direction, moving from the question of what else I can become toward the question of what I can help someone else become with the time, experience, and perspective I have left to give.

For many of us, there will always be another opportunity we could pursue, another organization we could lead, or another role we would probably be capable of doing well. The harder question is whether continuing to accumulate responsibility is still the best use of everything those years of responsibility taught us.

Maybe the next chapter is not about stepping away from leadership at all. Maybe it is about changing where the leadership is directed, from carrying the mission ourselves toward preparing someone else to carry it when we are no longer there.

After years of asking what is next for us, perhaps it is time to start asking a different question: who is next because of us?