Moving Forward From Double-Edged Life Events

Posted on June 10, 2021 by James Harold Webb
Managing Double-Edged Life Events - James Webb

We all experience significant, life-changing decisions that change the course of your life – it’s inevitable.  Sometimes, those decisions are firmly negative or positive. Oftentimes, however, these significant moments result in a complicated mixture of blessing and regret.  I can recall one such moment in my career, one where I realized things blowing up and things burning down can look an awful lot alike and can happen all at the same time.

There are personal relationships that can suffer when one forges paths that deviate from those around them.  I have experienced this. In those situations, while heartbreaking, it was always important for me to recognize and understand where I needed different things in life as I navigated career and personal goals. This is not uncommon as people seek to transform themselves personally or professionally.

There was a time in my life where that transformation, both personally and professionally, converged – leading to significant changes in direction. I found myself at a publicly traded company with a tyrant of a CEO. The culture was toxic and any future with this leader was unstable.  Surprisingly, this dynamic didn’t affect me like it did others. I knew this position was a mere steppingstone for something different in the future. A new career opportunity would arise while at this position, and the consideration and ultimate acceptance of it would lead to simultaneously one of my proudest and most regretful moments.

When I submitted my resignation, I was summoned to the CEO’s office where he proceeded to offer me my current boss’s position in order for me to stay.  He gave me 30 seconds to reply.  I spoke without hesitation or remorse and said, “I don’t need thirty seconds to decide. You can go fuck yourself.” I stood up and walked out of the room. His lawyer, a man I liked, chased me down the hall and stopped to tell me that this “exit” was one of the most amazing things he had ever seen and that no one had ever done that to this CEO. He wasn’t wrong. Quitting that job the way I did was one of my proudest moments. When I look back on that moment, it still brings a smile to my face.

I have the opposite feeling when I think about some of the personal relationships that were impacted by this new direction I was taking. I tried hard to do the right thing, even if pride and history made it feel wrong. I knew these changes were the right thing for me to do, but that doesn’t mean they didn’t negatively affect those around me.

To this day, I think back on these events and the mistakes that came of those choices as essential learning and maturing opportunities. It’s important to recognize the value in moving forward; looking for the lessons baked into every situation, while also leaving behind broken things, mistakes, and highs and lows. Mistakes, failure, and regrets are an inevitable part of success – embrace them.