Over the course of 30 years, a career can teach you a lot about yourself and the kind of person you are. You will likely develop some opinions about the type of businessperson you are as well. I have had the chance to try many different things with many levels of success and failure. I have no regrets.

I Quit:

I walked out of a small software company. Why? The guy who ran sales was one of those jump-on-the-desk-and-tell-you-you’re-stupid kinds of leaders. He would threaten to fire you daily. I refused to go through the abuse.

  • The Pros – It was over, and I could focus on something new. I felt good being away from all the negative energy and I clearly wasn’t going to learn anything I wanted to emulate. I learned many things “not” to do at this company.
  • The Cons – Loss of income, especially as my wife was pregnant. I selfishly created stress for those around me. Some feared I might be labeled a “quitter” though that never really bothered me. Labels suck.

I Was Fired:

A large brokerage firm fired me. Why? I refused to sell proprietary products to my clients, so my production fell, and they showed me the door.

  • The Pros – Few people who get fired are surprised, so there is some element of relief that comes with the experience being over. I could sleep again. I had checked off one more thing I wanted to try; it didn’t work, so I was one step closer to my career ambition.
  • The Cons – Loss of income, as my wife was pregnant again. Being on the 72nd floor of the former World Trade Center was –  bar none –  the most dynamic environment in which I have ever worked. A couple of hundred brokers and traders who were smart, witty and equally adept, whether male or female, at telling the best jokes on the planet. I still miss them, 25 years later.

Then I Retired … Well, Almost:

After we (the executive team I was part of) had negotiated the sale of the software company we managed, I walked away from a large retention bonus and took a shot at retirement. Why? I worked every day for eight years and missed every significant milestone important to my kids and our family.

  • The Pros – Time, free time to do whatever I wanted. I got to spend time with my beautiful and wonderful sister before she died. I learned how to go to the supermarket, and I enjoyed it. I cooked a lot.
  • The Cons – I had too much free time. I had no plan, no bucket list. I had all this time and nothing to do. I don’t play golf and am not a boater. I stayed up late, slept even later and developed every vice a middle-aged man with a few bucks in his pocket can have.

In my quest to experience everything in my career I think I have just about closed the book, but there is a lesson learned here.  With all I have experienced, I still have a thirst to learn and try new things.  That’s why I went back to the business world after retiring. I think  I am improving my business skills and still have career-related goals that I would like to achieve.

So I have quit, been fired and retired and just don’t recommend any of them… at least not for me. There are still many mountains to climb.

My best, Chris
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