Could Have, Should Have, Would Have….

Some days you wake up and wonder ‘What If..?”  For whatever reason today was that day.  I woke up thinking about what would be different if I did this, or made that decision instead.  I pledged a long time ago to myself never to day “Should’ve, Could’ve, Would’ve”, but as the years go by it’s hard not to wonder.  Some people know I started my IT career back in 1998 when I started working at PC Connection taking catalog orders on the graveyard shift for the holidays.  Fast forward to 2004 I got into the IT department building ESX 2.5 for production on IBM Blade Servers.  I was self taught, motivated, and full of questions.  Eventually I made it to VMware where I spent almost 10 years, the longest single stay at a company in my career.

I decided to depress myself and do a little math from my VMware days when I had Stock Options, RSU’s, and Employe Stock Purchases.  I actually went back and looked up all the grants I had…and I say had because they are long gone.  Most of them cashed out through out the years, but this is the “what if” scenario.  All told the would have added up to about 12,233 shares combined, give or take for taxes, etc.  As of closing bell yesterday had I held on to all those they would have been worth about $2,137,105.10.  Imagine my surprise, the things I could have done with that money.  I could have paid off my house, cars, maybe even retired.  Granted some of that did go into building our new house, and helped buy a car at the time.

So why am I thinking about this today?  Honestly I am not sure.  Occasionally I wonder what’s left as I get older when it comes to work and life, and what is it all for.  Most of us don’t leave a “Legacy”.  I’ve never written books, I have no patents, I’ll never be a CEO.  Much of this I have basically accepted so where is my life going?  What’s the next “thing” and fucking hell, was I stupid all those years ago not thinking all that stock would have been worth something.  Funny thing is people ask me all the time why I left VMware.  To be perfectly honest, I didn’t know where else to go there.  I had also been pretty well left out of new equity by my boss at the time for about my last 3 years there.  The thing is once equity grants stop coming there is no overlap on them and eventually you are back to ground zero with nothing vesting.  So in some cases I figured, what’s the point.  If I am going to start over why not start over somewhere else?

What’s the point to this short post?  None really, other than in the last two or three years I’ve been trying to figure out how to get my family to a point where the monthly household expenses are manageable.  Moving to Tennessee cost us a lot.  Even though the living expenses are less expensive, the build of the house, the things we wanted in it, etc were way over budget.  I kept saying “Go Big or Go Home!” except now as I wonder when the sun will set on my career how will those bills get paid.  Some days you just have to wake up and shake your head and say ‘What the fuck was I thinking?”.  We can’t change the past, all we can do is learn from it and move forward.  That does not mean I will make better decisions, but the future is much shorter than it was 20 years ago when I really started my career.  You think you make the best decisions at the time, and in most cases they probably are.  It’s when you look back and wonder, “what if?”.

One comment

  1. Well said, Chris. I hear ya! I think it’s a common problem, but this is a great forum to air it and bring it to the surface for more people to begin to recognize! 🙂

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