top of page
  • Writer's pictureRandall Fisher

Chicago Cubs, the World Series and Annoying Bosses: Making Sense of It All

Have you ever had a boss that you could never make happy? So now you are the boss and have employees that annoy you. They came with qualifications, but they just don’t seem to be working out. I know you would never be the annoying one. But in this age of millenial trophies for just showing up, we should probably talk about it.

Years ago I had a boss like that. I was working as a reporter for a small town in Central Texas. In that scenario you cover both regular news and sports. I worked for two bosses — the managing editor for hard news and the sports editor for sports news. I regularly wrote hard news for the managing editor and never had a bit of trouble or criticism. It wasn’t that way with the sports editor.

The town was a hot bed of high school sports. First round draft picks in both football and baseball regularly came out of this town of 10,000 people. The players who “only” made All-America teams would look like a who’s who from the College Football Hall of Fame. But my problem satisfying him wasn’t football.

I never played it at any level other than sandlot pickup and have knee surgery to show for that. So in covering it, I always made sure I double checked facts, wrote about players’ emotions in the moment and had coaches school me on background about how plays were designed and why they were called.  My problem was baseball.

What’s hard about baseball? You throw the ball, you hit the ball, you run the bases, you tag the runner. Right? Wrong!

My boss was a wisp of a fellow; he looked like he couldn’t throw a baseball through a paper bag or hit one through it, either. But he knew pitching (“if you have top stuff, you have to show them your second and third pitch; if you have garbage, you have to show them all the garbage so they can’t tee off on any of it.”) He knew hitting (“Bad hitters hit change-ups and hate heat; good hitters hit fastballs and hate junk.”) And he knew strategy (“Everyone leaks oil under pressure; the great ones accept it, deal with it and overcome it”).

Professionalism Under Pressure

When I wrote for him, if I didn’t have all the angles covered, it was a personal insult. He sent me back and back and back to get it right, regardless of the deadline. And if I missed the deadline, I caught it from the publisher.

What I came to realize over time was his level of required professionalism drug me forward as a writer. He wasn’t going to accept anything but the best in his section. He also taught me that perfection was a virtue and perfection under fire was true talent.

I am not sitting here trying to tell you I had true talent. In reality, the closest I ever got to a compliment was when I wrote a piece during a state championship game. After I turned it in, he edited it without a comment. Others in the office came marching through telling him what a great job I had done. His only remark once was to look at me, grin and say, “Well, it wasn’t bad once I fixed it.” I could not take the success. I took the rest of the day off.

It was only later I realized he had taught me the game of baseball.

I started to notice it watching the Baltimore Orioles. At one time, they had a relief pitcher named Greg Olsen, who had a good fastball and a vicious knee bending curve. I would start calling the pitch, just like my former boss watching those many high school games.

I also found myself fascinated by the strategy the Cubs and the Cleveland Indians were talking through in the rain delay at the end of the seventh game of the World Series. I found myself trying to guess pitches again in the bottom of the 10th, enjoying it when I was right and curious when I was wrong.

What the World Series teaches.

What it also taught me is to be more like Tony Dungy than him. Tony is known for teaching, even when people are messing up. Demand perfection, but teach through the imperfections. You don’t have to yell to scare the children. Calm, quiet disappointment can be a lot more disturbing to them if you learn how to use it.

So if you are evaluating staff (either current or future), think about their roles. Think about what they know coming in. Think about how far they can go working for you, and think about what you are going to do when and if they decide to move on. I had credentials when I went to that paper years ago. They had roles that they wanted me to play. I had other goals. When other opportunities came along, I moved on.

It wasn’t the best of exits; in part I admit because of my experiences. I would have moved on no matter what because of economics. But knowledge of that on the front end makes the outcome on the back end go completely different. And that smoothing of transitions can make business life completely different.

As for the Cubs, I was happy for them. My former boss was a purest. He loved the designated hitter in high school but hated it in the pros. I am an old Houston Buffs and Colt 45s guy. That made me a Cubs fan. I think he would have been also.

We’ll get back to examining states soon. Until then, good luck and good hunting.



Related articles

The Fisher Law Office is known for its experience in asset protection, business counselling and development, business succession planning, estate planning and probate administration. Annapolis attorney Randall D. Fisher has practiced for over 20 years, is licensed in Maryland, Texas, Wyoming and the District of Columbia, and has clients all over the country. He maintains the highest peer review rating for ethics (AV Preeminent) by Martindale-Hubbell, and is a sucker for long walks on the fairways.

If you need legal help, or just want to find out how he is doing at eliminate his slice, find out how to reach Randy via or find him at, on Twitter @thefisherlawoffice, or at

3 views0 comments

Recent Posts

See All

How the Wizard can “Make Your Mark”

I just had a potential client contact me about how to trademark their business. This is a common question for business attorneys from business savvy clients who don’t want to get tripped up by not dot

Use of LLCs for holding real estate: Pros and Cons

I read a colleague’s recent blog today about the pros and cons of using a Limited Liability Company (LLC) to hold investment real estate. It seems to be a popular topic because I spent last evening di


bottom of page