Sixteen years into my career, I’ve learned enough to know how much I still don’t know. That may be one of the first lessons experience teaches us.
When I entered the workforce, I naturally thought about a career largely in terms of destinations: find the right opportunity, become good at what you do, earn more responsibility, advance and build something. There’s nothing inherently wrong with any of those ambitions. I still have plenty of them. But 16 years have given me a different appreciation for the journey.
I’ve succeeded and failed. I’ve led people and been led by others. I’ve been promoted, changed directions, started over and watched some professional ambitions turn out differently than I imagined. Through all of it, I’ve also learned that reflection is most useful when I keep my own hands on the plow. It would be easy to write about what someone else should have done differently along the way. There are lessons there, certainly, but these are lessons I am responsible for practicing myself.
Looking back, six stand out.
1. Your Career Will Make More Sense in Retrospect
We put tremendous pressure on ourselves to make every career move look like progress. Upward is good. Sideways is questionable. Backward must mean something went wrong. Real careers are rarely that tidy.
Sometimes a position gives you experience you won’t understand the value of until years later. Sometimes the job you thought was preparing you for one destination is actually preparing you for something completely different. My own career has moved through accounting, management, customer-facing work, compliance, administration and other responsibilities that don’t always form an obvious straight line on paper. In practice, those experiences overlap constantly.
I’ve learned to stop demanding that every season explain itself while I’m still living it. Learn what you can, develop transferable skills and pay attention to what a particular season is producing in you. Today’s detour may become tomorrow’s preparation.
2. Understand the Work—Don’t Just Complete It
Early in a career, completing the assigned task feels like competence. Eventually, I learned to ask more questions: Why are we doing this? What happens before it reaches me? Where does it go afterward? Who depends on it? What happens if it’s wrong?
There’s a significant difference between knowing a process and understanding a system. The person who understands the system can troubleshoot when the normal process breaks, recognize connections that aren’t immediately obvious and understand how seemingly small decisions affect people farther downstream.
That distinction will probably become even more important as artificial intelligence and automation handle more mechanical tasks. Knowing which button to push may become less valuable; understanding why the button exists will become more valuable. Don’t become indispensable because you’re the only person who knows how to perform a task. Become valuable because you understand what the organization is trying to accomplish and how your work contributes to it.
3. Become Really Good at Learning
I’ve spent portions of my career walking into situations where I didn’t know nearly as much as I wanted to know. That can be uncomfortable, particularly as you progress professionally and begin feeling as though your experience should mean you already have the answers.
But I’ve learned there is a massive difference between inexperience and incuriosity. You don’t have to enter every room knowing everything. You do need enough humility to ask questions and enough confidence to say, “I don’t understand this yet.” Investigate discrepancies instead of working around them. Receive correction without allowing embarrassment to stop the learning process. Be willing to discover that the way you’ve always done something may not be the best way to do it now.
Some of my greatest professional growth has happened when I stopped worrying about whether I should already know something and simply started learning it. You don’t have to know everything. Become someone who knows how to learn.
4. Don’t Ask Your Career to Tell You Who You Are
This one has taken me longer to learn. There’s nothing wrong with ambition. Work can be meaningful, accomplishment can be satisfying, and promotions and professional milestones are worth celebrating. I believe we should take our work seriously and pursue excellence in whatever has been entrusted to us.
But a career makes a terrible identity.
Jobs change. Companies change. Leaders change. Priorities change. Doors we expect to open sometimes don’t, while doors we thought would remain open sometimes close. And sometimes the professional future we imagined simply doesn’t happen.
If our identity is anchored to our career, those experiences become more than disappointments. They can begin to feel like verdicts about our worth. I want to care deeply about what I do without requiring my work to tell me who I am. I want to remain ambitious without making achievement responsible for answering questions it was never capable of answering.
Build an identity sturdy enough to survive professional disappointment.
5. If You Lead People, Know Them
I’ve become increasingly convinced that getting to know the people you lead isn’t an optional component of leadership. It’s part of the job.
Metrics matter. Performance matters. Professional development matters. Accountability matters. But none of those things completely describes a human being. Good leadership also notices behavior, confidence, collaboration, well-being and maturation. What motivates this person? What discourages them? How have they grown? How do they respond under pressure? What environment allows them to do their best work? Are you evaluating only what they produce, or are you paying attention to the person they are becoming?
Knowing people doesn’t eliminate accountability; it gives accountability context. There are still expectations to meet and difficult conversations to have. But the more a leader understands the person behind the performance, the better equipped that leader is to distinguish between a pattern that needs correction, a person who needs development and a human being who may simply be navigating a difficult season.
And responsibility runs both ways. If I’m being led, I have some responsibility to allow myself to be known—to communicate, receive feedback, explain how I work and not expect someone else to decipher me entirely on their own. Healthy organizations don’t merely develop better employees. They develop people.
6. How You Work With People Will Outlast Much of the Work
Sixteen years have introduced me to plenty of projects that once felt incredibly important. Deadlines felt enormous. Problems demanded immediate attention. There were assignments that consumed hours of thought and projects that seemed, at the time, as though they would define an entire season of my career.
Many of them barely cross my mind anymore. But I remember people.
I remember those who taught me something, encouraged me, showed patience and made room for me to grow. I also remember moments when I should have listened better, communicated better, extended more grace or handled something differently. Time has a way of shrinking the urgency of yesterday’s project while clarifying the significance of how we treated the people who worked on it with us.
Someday, the spreadsheet will be replaced. The project will end. The organizational chart will change. Someone else will sit in your chair. The work matters, but so does the effect we have on the people sharing that stretch of road with us.
Sixteen years in, perhaps that’s what has changed most about how I define a successful career. I still want to build something worthwhile. I want to become excellent at my craft, stay curious and keep growing. I hope I’m still doing all of those things 16 years from now.
But don’t become so focused on building a career that you forget you’re also building a life. And don’t become so good at the work that you forget the people doing it beside you.
Graphic creds: ChatGPT
