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).


When I started in auditing and consulting I inadvertently joined a hard life-style.  There were certainly some audit groups that had relatively cushy in-town clients, but I was in the utilities group, so I traveled 100% of the time to lousy cities and then worked in the offices on weekends.  As a consultant I also traveled 100% of the time and worked far into the hours of the night almost every evening.

Since most consulting type operations use a “pyramid” system, there are a lot of lower level staff and fewer managers and partners.  The managers were older and still cutting it, although getting long in the tooth, and the partners that managed to survive all those years had set patterns and other methods to cope with the harsh lifestyle.  They often disassociated their private life from their work; some had never been to a grocery store – and their families lived essentially separate lives from them, only intersecting on weekends in an almost choreographed manner.

One firm that I worked with for several years had a different model than the “pyramid” competitors – we actually had older staff that understood the industry and fielded a balanced team, that knew what we were doing, at higher rates.  This differentiated us from the other firms since our team members could instantly show up at the job site and contribute, while the other firms dealt with growing pains as their “school bus” of new hires had to learn the business over and over again, peppering the staff of the client with inane questions that they had answered for years on end.  On the other hand, our older staff had idiosyncratic behaviors that might not be tolerated by the pyramid firms – you couldn’t just order people around, and they could alienate staff at the client by dismissing their ideas and plans out of hand as ineffective or stupid based on their prior experience (usually they were right and the client was wrong, but it caused waves…).

There are jobs that you retire from because they are physically demanding – imagine standing on your feet all day and moving inventory for instance when you are old – but now there are jobs where you just get burned out by the frenetic pace and need to have some sort of lifestyle (where you can exercise, have a family, and perhaps even interact with them).  Then finally, you have jobs where to keep them, you must constantly heed your place on the political ladder, continually learn to keep up with the newest ideas (or fads), network all the time to find your backup plan, and just hope for some luck in terms of the company having success or your boss rising in the hierarchy.

What does experience buy you?  It buys you some perspective, in terms of seeing the “long game” – the new employees may never have been through a company that lays people off, but you’ve seen it many times, and know the types of behaviors that (usually) tip off that they are coming.  You also have some balance and tolerance of actions and attitudes and different ways to approach getting the work done.

On the other hand, you lose a bit of energy and the “fearlessness” of youth, in that they believe that they can change the world.  It is important to try to capture some of that energy in your work because no one wants to work with the grumpy old person who’s “seen it all” and “knows that this won’t turn out any different”.

There is no “one” story about experience – everyone makes their own journey – but you can look around you and try to take the best from each.  You can try to avoid jumping to conclusions and extrapolating just a couple data points (from your early work experience) into infinity.  On the other hand, you should keep an open mind to change and realize that this time it really could end up different, either for better or for worse.

Cross posted at LITGM