25 Stories About Work – Experience

I was recently on a plane doodling and thought of some funny / interesting stories from 25+ years of working and traveling. So I decided to write them up as short, random chapters of a non-book with the title of this post. Hope you enjoy them and / or find them interesting. Certainly the value will be at least equal to the marginal cost of the book (zero)…

Chicago, 1990s through today

I just finished reading the book “Disrupted” by Dan Lyons about a journalist from Newsweek who takes a job at a start up which eventually goes public called Hubspot.  Mr. Lyons is out of place from day one as he describes how the company acts without much oversight, firing workers on a whim (they ‘graduate’) and rapidly turning over employees as the company attempts to get to the public markets before the money runs out.  To make this even stranger, the author also writes for the HBO sitcom “Silicon Valley” and Hubspot allegedly goes after him to stop this book from being published, and the board finds out about it and fires / sanctions some (but not all) of the managers that he portrayed in the book.

All that aside, the purpose of this post is to talk about experience, and how it changes you over the decades, and its value and detriments.  Reading that book caused (not “inspired”) me to think about my own views and how they’ve evolved over the years.

It is strange when you go from being the “new kid” to being the grey-ish haired “experienced” one.  Recently I was at 1871, the incubator in Chicago for new start-ups at the Merchandise Mart in River North where I used to live.  As I walked around I noted all the fresh faces, the beer on tap, and the grown men riding around on razor scooters to get from meeting to meeting.  Then I realized – hey I am just an old guy here.  I’m not one of them, although I could probably be a boss of some sort in one of these companies (depending on what they are looking for).


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