I’m approaching one of those dreaded milestones. Just around the corner is year 60. Sixty. Six-Zero. How did that happen? When did that happen?  Thanks to modern medicine I’m half way to 120. How’s that for glass half full thinking?

As I complete my sixth decade I find myself occasionally wandering into reflective mode. Family. Relationships. Career. Travels. Education. Try as I may, it’s hard not to spend some time on regrets. Many say “what’s past is past, no need to revisit it” but we can learn from our mistakes, right? Certainly we want to avoid repeating our mistakes. I’ve had plenty of them.

For example, take my job. Please.

One of my big regrets is all the time, energy, and youth I spent climbing some version of the corporate ladder. I tried to improve my family life by trying to advance my job. I tried to build up my self-image by trying to advance my job. I tried to travel the world by trying to advance my job. Everything I wanted in life seemed to point towards getting to the next job level.

Early in my career it worked like a champ. Advancements came quickly and along with them more interesting work, more money, more learning, and overall more satisfaction. But then things started to change. I am not sure if they changed because I was getting older or if the corporate world changed as the economy tightened. Maybe I just gained insight into what was really going on in the companies where I worked. I began to feel like a small pawn on the corporate chessboard. Even when my job was a significant leadership position, I felt used.  Certainly I felt misled by the promises my bosses made to me. I saw corporate leaders demand more and more from their jobholders yet consistently returning less and less to them.

And then there is the poor personal behavior, leaders that are unapologetically self-focused and greedy. Corporate leadership teams began to focus more on personal gain than corporate purpose. They focused on the right things to say more than the right things to do. Jobholders became something you easily replace, not a place to invest. It looks a lot like a pyramid scheme in many companies today.

What’s my takeaway? If only I knew there were options to start my own business while working under the perceived safety net of my J.O.B. I am sure I was even exposed to such business opportunities, but I was too focused on climbing the ladder! I never considered looking off the path I was running.

Good thing I have the next sixty years to course correct and get it right. Damn straight.