Ben Horowitz starts a lot of his posts with a song quote.  When I started thinking through this one, I couldn’t stop singing this song in my head even though it’s not really relevant.

Regrets, I’ve had a few; But then again, too few to mention. I did what I had to do And saw it through without exemption.        -Frank Sinatra  “My Way”

The other day marked one quarter (the 27th) of the year and half way to my goals deliverable which I targeted for my birthday.  I was thinking of my progress to date and my new motto “Self-Control and Focus.”   That lead to thoughts of how I have made a lot of choices to sit on the couch on many nights instead of getting things done, which finally leads to regrets that I have.  At some point, I will get this question in an interview.  So let’s get some prep work done.  This has been a good exercise just writing it down, I would recommend it for everyone.   “Mr. Rutstein, what is your biggest regret?”

There are two kinds of regrets.  Some are just choices you make in life, we evaluate these on how they affect our decision making process in the future.  Hopefully, we learn from them.  I wanted to cite a few examples:

  • I should have done homework in high school, I was smarter than my grades reflect as college showed.  I also should have kept my mouth shut more – special apologies to Miss Moynahan, Mrs. Peal and Mr. Fitzpatrick
  • I should have played football in HS, I would have been a great corner
  • Sucking up debt to live at college would have been worth it.
  • I screwed up so many interviews at Bentley, I won’t even mention those
  • Megan and I should have dated more people so we could have had the perspective to appreciate each other more
  • I should have taken the $5000 offer for the Alfa
  • After quitting IBT in 1995, I should have really started a business, not that half-hearted crap.  Home theatre then, was a great opportunity
  • I should have focused on my career instead of working on the house at 30 Windsor, probably the same here in Salem
  • I should have stuck with programming on my Commodore 64 and kept with it now
  • Respect your parents more than I did

These are all lessons I have learned, and I think about them when similar choices come now or when the results of those choices become poignant.  But they aren’t the second kind of regret.  The life altering kind.  This is something that changes your path in life and affects the core of who you are.  If someone asks “what is your biggest regret” you should know it right away, because it hits you every moment of every day.

“I should have served my country in the Armed Forces.”  If you know me and how I approach politics and civil discourse, it probably makes sense that I regret this one.  I will walk it through.

My dad served in the Navy and my grandfather served in the Army in WWI.  I have two uncles that served as well.  Growing up, dad talked about his service, but more in the context of stories that he remembered;  Dragging the MG with a troop transport to free a ceized engine, his friends, fixing a radar with a meter that somehow would only work when attached, mess hall serving better food than my grandmother (that is a whole separate thread that I will deal with at another time, but it’s a funny string of stories that my grandmother would love).  Dad’s service is important to him and I used to like to wear his coat (which wasn’t his, another funny story) but he never displayed his military career in any sort of overt way.

I had always thought of joining the military.  I wanted to join the Navy like he did and fly.  In the 80s after Top Gun, who didn’t?  I remember dad took a trip to Mirimar for work and I wanted to go and just walk around.  It wasn’t until I met Tom (father in law) that I really started to think through the specifics.  Tom’s career was much different and he displays his medals and citations around the house.  Each has a story, only some of which I have been privy.  He recommended that with my 18 year old mouth (yeah that is a pervasive theme) and inability to take orders, that I should only consider service after college and try to become an officer.  That actually worked with my flying plans.  Despite the first Gulf War while I was in college, I always thought this is the way I would go.

College changed this, but before I detail why, let me be 100% clear.  I don’t blame anyone for my decisions, these are all on me.  And while I regret this decision, I am not sure that given other choices I made that I would have made this one differently.  A whole series of events would have needed to be different.  So while I regret the way things unfolded, it is the result of life and not because I was pushed somewhere.

As with any story, it begins with a girl.  Megan was always supportive of me joining the military, we talked about it during college a good bit.  Being a military brat, she knew exactly what it was like (even though she can’t spell Huachuca:) ).  As our relationship evolved, I saw more and more how military life effected her.  She was quiet, shy, in a way that was always the source of jokes with friends.  “Was Megan ok last night?  She hardly spoke”…”Yeah she’s just quiet.”

I attributed this character trait to growing up and moving around.  By college, she had only lived 3-4 years outside of the military construct.  We were getting closer and she was opening up and developing close relationships, the kind you only grow by being around people for a sustained period of time and having stability.  Could I really ask her to go back to a life of moving around following me?  Her success in college definitely pointed at a career that could not sustain picking up and moving every few years.  Would that lead to resentment?

Despite the crappy job market in 1993, the 4 months I spent landscaping, and the HORRIBLE first job I eventually landed, I decided against enlisting.  1993 was a strange time politically.  The country was in the midst of being convinced that a smaller and nimbler military was all that was needed to win wars.  I believe that was about the time that the 2MRC strategy went into effect.  Also, I had been following the procurement of the F22 and JSF programs and knew that better planes than the F14 were on the way.  I would have to truly be “the best of the best” to fly fighter jets.  No one inspired me to take risks in life back then, I just didn’t have that sort of circle, and I never read anything inspirational.  So I took the other route and went back to being inspired by another movie of the 80’s “Wall Street” (yeah I know, but back then I didn’t understand it as the social commentary Stone meant).

Over the years I have had thoughts of going back and enlisting in the National Guard.  The age maximum is 35 and as I watched that creep up, something always got in the way.

After 9/11 my brother-in-law enlisted in the Army and he has developed a career that amazes me.  I miss skiing with him, but every day I think about the fact that he gets to make a difference in the world.  As of yet, I have contributed exactly nothing.  I remember talking to him just before a deployment a few years ago.  “Take care of yourself and be safe.”  I will never forget his response, and this was right around the time that his daughter was a newborn,

“Fuck that.  We’re the US Army, we lead from the front.”

If you know a soldier who has a family, you know the toll that it takes on what is normally a pretty boring home life.  Their devotion to their unit and country is beyond question.  It’s something I wish I could experience firsthand, something that I wish I had in me, something I wish that was part of me.  It has changed the course of my life and effected who I am.  I am turning 40, I am in the best shape of my life and while I read every Navy SEAL workout program I can find and train as hard as I can, I will never be that guy.  No one will ever think of me the way I think of Ian, Tom, Dad, and the millions of others that can say something that I can’t:  I love this country so much, that I was willing to risk (or give) my life for it.  I follow the news and I write my little blog and someday I hope to run for office, but that is all just my way of making up for the gaping hole in my resume that will never be filled.  Imagine having military service as the cornerstone of every decision you make;  Should I cut corners in production, should we offshore these jobs, if we use chemicals it will preserve this food longer, how can we squeeze more profit.

How can anything be more regrettable than that?

About Josh Rutstein

I am an aspiring entrepreneur and hopeful political candidate. Father of 2 very special girls, husband to an amazing woman, and passionate American. I snowboard whenever possible and follow a 20x mentality for exercise. I also play golf and ultimate frisbee and am a die hard New England Patriots fan and season ticket holder. Everyday I wake up wanting to make this country a better place, someday I hope to actually succeed.
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