The 10 Regrets Of The First Part Of My Life

It was Socrates who said, “My only regret is that I have no regrets.”

No, it wasn’t really Socrates, it was me who said that.  Why do we have to reference some ancient Greek guy who has been dead for over 2000 years and probably anally raped more young boys than Jerry Sandusky just to give a saying gravitas?

Look, I really don’t like to dwell on the negative, but not unlike in trading, you learn more from the negative events than the positive ones.

So as I reach the middle of my life (I am forty-five and plan to live until at least ninety), I figure it is the right time to take inventory of the ten biggest regrets of my life in order to learn from them, and perhaps prevent others for making the same mistakes.


Anyway, here they are;

1.  Spending too much time in book stores in my youth looking for ANSWERS instead of INSPIRATION.

2.  Shorting $KBH going into the summer of 2005.  I had the right idea, but the wrong timing,

3.  Arguing with my father that there was no way that the cowbell part on “Born on the Bayou” by Creedence Clearwater was done live, and HAD to be an overdubed.  It turned out that I was wrong.  My father died two months later.  I was twenty years old.

4.  Spending so much time in my 20’s and 30’s pretending how much I didn’t care what people thought about me, when I really did.

5.  One of the few things in my life that has come “naturally” to me was parenting. With one exception.  My daughter was having problems getting “calendar marks” on her daily reports in Kindergarten.  Nothing we did could stop her from getting them. One night I decided I would pretend that if she got enough calendar marks she would have to go to a different school.  Here is how the conversation went….

Me:  So if you keep getting calendar marks, they may make you go to another school.

Daughter:  But where would the school be?

(At this point I thought if I “casually” said, “oh, it would probably be a school far away, where mommy and daddy would have to come and visit you” that I would get the reaction of, “oh don’t worry, I will make sure I never get anymore calendar marks.” Unfortunately, that’s not how it went.)

Daughter: But….but…..*sniff* *sniff*….then I would be…..*sniff* *tears* *lip* *sniff* *big tears*…so lonely without you *HUGE lip* *sniff* *tears*…and mommy.

At this point I had a choice.  Stay the course, and drive the point home, or fold like a fuckin’ Pick ‘n Save tent in a hurricane.  Call me Mister tent.

But I still regret making my little daughter ever think that there was a scenario where she would be without her family.

6.  After vacationing for six weeks in Australia, at the tender age of eighteen, my Aunt who lived there said I could stay as long as I wanted.  On the plane ride back I remember looking out the window thinking that I wanted to stay.  I should have stayed. I wanted to stay.  But I was too scared.  Who knows, I could have been Mr. @RogueTraderette if I had.

7.  Wasting the years I had with my grandparents.  There was so much love and knowledge that they wanted to share with  me, but I couldn’t wait to get out of the various Thanksgiving, Christmas, or Birthday celebrations to join my random friends, most of whom I am no longer in touch with anymore, at the bar.

8.  Turning down the “Blake” role, ultimately played by Alec Baldwin in “Glengarry Glen Ross.”  I had the part locked up but thought it would pigeonhole me as a “tough, pretty boy” in Hollywood going forward.

By the way, my reading of the line was, “See this watch? Do you see this watch?  It’s pretty isn’t it? I bet you wish you had one you stupid jerky guy.”

I think that version played better.

9.  Not selling my business ten years earlier than I did.  That company sucked a decade of my youth away from me, stuck doing what I hated, what I loathed, all in the guise of taking the “responsible” and “prudent” route.  Fuck responsible prudent people in the ass!

10.  Paris.  Wine bottle.  Utility knife.  Hot French doctors.  “Le Dork.”  Read about it in “The ‘Second Mistake’ Theory.”

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