Laugh - All Of Life Is Fun



James L. Cowles

(c) Copyright 2025 by James L. Cowles

 
Photo by Jopwell at Pexels
Photo by Jopwell at Pexels
 
Have you ever given thought to fun you have had on the job? What’s that you say – you don’t remember any fun? Sorry to say, I had never given it much thought, but as I began thinking about writing a few humorous stories from my past, I began to realize that many funny things have happened to me in my work life. In fact, I’m surprised at how much humor I remember from my workplace, and how much more fun it made my career. The truth is, there were days when I was saved by my fellow employees and their humor. A good laugh can cure most any problem, and I’m betting you feel much the same as me about that. Here are just a few of the stories that come to mind from my time at work, but I have many more. I hope you find them entertaining.
 

I will begin with my career in the insurance business, and if those words, “insurance business,” doesn't make you shy away, keep reading. It was a unique time in my life and it was downright enjoyable as well. Instead of expecting relatives to become my first customers, my company  sold “fringe benefits” (insurance policies) to small businesses, both owners and employees. Believe me, I know my relatives appreciated that. First, however, I think I should try to give you an idea of what my job requirements were, so you will see why humor was so helpful to me. Many of our specialists, including myself, were Chartered Life Underwriters (CLU), which is a designation earned through ten college courses in insurance. It’s a little tough to study and earn a degree, while also working every day, but we claimed to be experienced professionals, and thus we were expected to earn that designation. So, while some were enjoying life during evening, or weekends, I was often studying.

You might think my business would be way more serious than most, but I didn’t find that to be true. The one thing that helped our business the most was the endorsement of business trade associations. Most Kentucky associations were actively seeking insurance benefits for their members anyway, and we were able to design and implement several benefit plans for member firms, using the power of numbers. Later in my career, I became a Senior Vice President and Regional Sales and Marketing Director, and as such, I serviced our trade associations and managed their benefit plans. Now, don’t get discouraged; we will get to the humorous part soon, but I hope these details will prepare you for the funny stuff.  At one time, we had almost every trade association in Kentucky as customers (9 or 10 of them), and I routinely worked with their insurance committees, especially when medical plans were renewed. We also offered a service of enrolling new employees as they became eligible to enroll in their employer sponsored program, but we could only afford to do so when the employer was paying a good portion of the benefit costs. Those customers also received annual “benefit communication” to their employees, reminding them of how much their employer was contributing toward the cost of their benefits, and how those plans benefited them. Of course, this often gave us opportunities to sell additional, payroll deducted benefits.

Our approach helped pay for the work we did for our employer-customers, and it allowed employees to have all their benefits as payroll deductions with their employer. We had additional discounted and guaranteed issue plans available, saving the employee more money, and even allowing some who were not insurable to provide plans for themselves and their families. We went above and beyond on this, being sure to note how much the employer was paying toward benefits, as well as financial information about social security and workers compensation.

As you may have already gathered, it took quite a large staff to accomplish our goals, and another of my jobs later in my career was to manage that staff, which required hiring and firing. Oh, man; imagine the fun I had with that; but that's an entirely different story. Our account executives were the most experienced of our sales force, making calls on business owners. In other words, they called on business owner members and sold the association programs that were endorsed by the trade association insurance committees. It was easy to talk with most members, using the phrase, “I’m calling on behalf of your (fill in the blank) Trade Association.”

We did indeed had a large staff (50 or more) who did the very hard work of selling, enrolling, communicating, and servicing the association benefits for employers, and to employees, one on one. The field personnel who enrolled new employees were called, Account Representatives, and they had to be ready to enroll new plans, new employees, and new programs as they were sold. As brokers, we had many insurance carriers covering employees in almost every client’s business. In other words, we might have five to ten insurance companies in a corporate program, depending on the benefit plan the employer had approved. Each one of the insurers in a program had their own applications, so perhaps this helps give you a picture of how much work it took to sell and service clients.  A lot of paper was necessary.

That’s the last of the somewhat technical information I intend to provide in this story, and at this point, if you’ve read this far, and have decided to keep going, I know you will be glad there will be no more of that kind of stuff. In fact, from here on out I’m going to give you the lowdown on more of some of the humor in our business; the kind of things that are bound to happen when you have so much on your plate. My Lord, when I look back at all we had to do, I thank God for the humor we enjoyed from time to time.

Maybe my writing should have started here, ignoring all the explanation of what we did, but I think it gives you a better picture of what we were dealing with. Let’s just say we were bound to make mistakes, so we were always looking for something to lighten our load. Now, some of what I am going to tell you simply happened out of stupidity, the silliness that befalls us humans; let’s begin at the beginning.

TRAINING
When you have such a major undertaking, you know you are going to have to receive a lot of training, and I came aboard as an innocent, inexperienced AR (account representative). Yes, we were the ones who had to do all the dirty work of completing applications for every insurer involved in covering the employees in an employer sponsored program. Part of our role was to explain to each employee how a benefit works, thus all of us inexperienced folks had to attend a week of classes in our home office, in Nashville, Tennessee to learn about the programs we provided. We were called rookies, amongst other things, and we were the low life of the sales force, occasionally fitting into the “dumb and dumber” category. A good sense of humor was a definite requirement.

This initial training week began smoothly enough, but the night life in Nashville often called, making the training days a little tougher; turning to late night honky-tonks and such was not very conducive to learning, but no one was watching us at night, so…. Here are a few examples of what occurred during the free hours of training.

ALAN
Our company thought it was good to double up hotel rooms, you know, so we could get to know our fellow agents a little better, at least that’s what they said. Of course, it saved the company lots of money, but they didn’t tell it that way. We figured that out all by ourselves. Now, I have never been much of a drinker, but the peer pressure among the class of account representatives made that part of life’s journey essential, at least a time or two. I was rooming with my new, good friend, whom we shall call Alan, and man, was that ever an experience with alcohol I shall never forget. One of those nights during our week in the home office, I decided to stay in the room after dinner. I should say, I needed to stay in my room, to try to catch up on something important to the learning process, restful sleep! I remember being fast asleep when Alan came in that night, and I think it must have been at least 2:00 or 3:00 a.m., if not later. Of course, he had to wake me and fill me in on the adventurous time he had that night, something I would rather not have heard, and as he slurred his way through it, I kept nodding and dropping off to sleep. Alan was a talkative guy, so it was not okay with him when I didn’t respond. He shook me a time or two, and began talking louder, probably thinking that would make me more attentive. He was wrong; I just faked it. Anyway, at some point, he abruptly stopped talking and ran into the bathroom, and I thought whatever he had drunk was about to come up. Instead, he ran back in quickly to continue his story, which again, I didn’t want to hear. My luck had run out. Now, get this. He was suddenly drinking a fresh can of beer. I’m still lying there half asleep, pretending I’m listening, and then I began wondering where he got that cold beer, so I interrupted and asked him, “do we have a refrigerator in our restroom (?).” “No,” he says, so I say, “where’d you get that beer?” “From the toilet,” he says. “From the toilet,” I say? In the toilet, dumbass, in the toilet tank,” he says. “And there’s a six pack in there. Want one?” I politely said, “Hell no. I just want to sleep.” “Alright, alright. Don’t get your panties in a bunch,” he says, and he finally lets me go back to a peaceful sleep, while he sits drinking his beer.

The next morning, I’m up bright and early, shower, shave and dressed, ready for breakfast, and Alan is still asleep. Payback time!”  “Alan, Alan,” I say, as I shake him. “What, what the hell,” he says. “You are going to be late, dude. You’d better get your rear in gear, if you want some breakfast.” “I’ve got breakfast in there in the toilet tank,” he says, and he’s serious. He made it to class on time, and even though he had beer on his breath, he looked damn chipper. Unbelievable…

We were warned there would be a test on the last day, Friday, so Thursday night, as I go over my notes and reading material, Alan is ready to hit the town again, and doesn’t crack a book. Nothing. But as he is changing clothes, he keeps saying, “Ask me a question, ask me a question. Make it a hard one and let’s see if I can answer it.” So, I play his silly game, and ask him a very technical question about life insurance. He answers it perfectly. He continues to bug me, and I continue asking him questions, with him preventing me from going over the material so I can be ready for the damn test. Here’s a guy who took no notes, didn’t crack a book, an insurance policy, nothing, and he scored perfectly on the test. I got 90%, but this guy who went out partying every night, and only came to breakfast the first day, drank his breakfast from a toilet once, scores 100%. He had to be at a genius level.

There were many other training sessions over the years, and many stories to go with them, but in addition to my story about Alan, several stand out in my memory. They don’t stand out because of the incident, but rather, the person with whom I experienced them. I’ll call the guys involved, Roger, Mickey, Frank, and my favorite pal, Tom. He was Best Man at my wedding.

MICKEY
In Mickey’s case, he was a good friend I worked with, but never roomed with. He told me this story, and had me on the floor, in stitches. Mick was an old country boy from Eastern Kentucky. He was a high school football star, playing with reckless abandon throughout his short career. He didn’t play in college, primarily because his doctor advised against it. He was so reckless on the field, most games he would get knocked out. We’re talking, out like a light. Winning was important to Mick, and he knew two speeds back in the day. Fast and faster. Work hard and you win was his policy, and to do so, like most country boys, he went to bed not much past dark, and awoke before the rooster had even thought about crowing. You know the type, always rested and ready, up so early and happy to see the cows and milk them; it made me nauseous. His story goes something like this. The company put him in a room with a guy who was considerably different than him. The fellow, we’ll call him “David,” had only one eye, and the other was glass, but it looked pretty good, except it seemed to follow you no matter where you went. If you looked back as you walked away, I swear, it followed your movement. Creepy! He also liked to party, so, much like the first story, Mick was fast asleep when David was just coming in, at almost the time to get up. Mick always got up before daylight, and did so that morning, as usual, but David, like my pal, Alan, also wanted to talk when he came in after a night on the town. Mickey had a switch. Turn it off, and he slept, turn it on, and he was bright as a new light bulb. So, David wore Mickey out with conversation at two or three o’clock in the morning. It would have been fine if David had stayed out one more hour, or so, but he messed up Mickey’s sleep pattern, so Mick couldn’t get his eight or nine hours of sleep in. Mick needed that sleep. Anyway, as Mickey told it, he just wasn’t himself that morning, primarily because of David’s attempt to tell him what all he had done the night before. Mickey was so polite; he would never have thought of telling his new friend to “shut it!” David, of course was fast asleep by the time Mick arose and went into the bathroom. I can’t make this as funny as Mickey did when he first told me this story, but here goes. He said he did what he always did when he got up every morning. He always had a good long pee, then he would wash his hands with warm water, then turn the cold water on, and splash it on his face with both hands. Afterward, he’d drink a glass of cold water, and he was good to go. The only difference was he was half asleep because of David. This morning, as he looked down for a glass to get his water, in one of the motel glasses already full of water, an eyeball was staring back at him. He said, the first thing he did was reach up and check each eye with his hands. “I didn’t know David had a fake eye,” he said. I had never really met him until he came in so late that night. I thought, could this be my eye?’ I had to check to be sure.” We laughed about this for years, most especially when we had meetings at the home office in Nashville. It was one of many Holiday Inn stories.

ROGER
This next story involves me again. Seems I was often the brunt of someone’s ill-conceived plan. At any rate, I knew Roger from previous training classes, and like Mickey, he was a Kentucky boy, only he was from Western Kentucky Coal country. You know, “Mr. Peabody’s coal train done hauled it away,” country. John Prine, may he rest in peace.

Roger and I found ourselves at another Nashville training session, and they chose to put us in a room together. This had to be more advanced training, because Roger and I had been trading places all year as the leading salesman in our agency, so we were both experienced guys. That's exactly why they put us together; they loved the competition. Every sales organization does this, if they are smart.

Roger, living in Madisonville, Kentucky, didn't have much opportunity for nightlife, so he had to make up for it during those Nashville sessions. On the other hand, it was my intent to work my way into management at some future date, and I had learned that upper management looked all of us over when they had the opportunity, and being fuzzy brained during a training session was not a good thing for the more serious minded. At any rate, I remember that Roger “went out on the town” and, not only that, but stayed late. For me, I figured one drink was enough, then I'd relax, head back to the room at a reasonable hour, and turn in.

Roger rolled in about 3:00 a.m., or so, and of course woke me up, saying, "hey Jim, get up and let’s go get some “Crystal burgers.” Crystal burgers are about the same as White Castle, a favorite in the Louisville area. I was just awoken from a sound sleep, and right away I told him that wasn't a good idea. Crystal stayed open all night, and he could have picked up a package on the way back to his room, as he drove down Murfreesboro Road to the Holiday Inn, but no, he didn't think of that. Well, maybe he did, but was not sure he could maneuver through the drive-thru without wrecking. I was sure he hatched his plan as he was driving back – he could just get me to drive him, and maybe even order for him. He kept pleading with me, and it was then I realized how drunk he was. I imagined him thinking about getting back to his room, and the only thing he could do was get in his car, start it, and hope it could find its way back to the Holiday Inn. He was lucky, and so were others who may have been out at that hour of the morning.

Roger kept insisting I get up and dress, so we could go to Crystal, and I kept insisting he get his rear end in bed, but he wasn't listening. Instead, out of the blue, he said he was going to call his wife and tell her much he loved her and missed her. I tried to talk him out of that, too, because she would know he had been drinking, but he was already dialing, and the next thing I hear is, “How is my old sweet cheeks doin,’ darlin?” I was entertained for the next few minutes by several catty remarks, none of which I want to include here. I’ve never laughed so hard in my life. She was sweet about being awakened, and told how much he loved and missed her, but I know she was embarrassed to know I was listening to one half their conversation.

Well, Roger finished up with his phone call, hung up, and said, “Why aren't you dressed; now get dressed!” Again, I told him to shut up and go to bed and that’s when he got me. He said, “I don't need you to go with me, hell, I'll go by myself!” Now, he had not sobered up even a little, so I was not going to let him drive. He was so drunk that an accident would not have hurt him; I was more concerned about other poor innocent souls who might have the misfortune of being run over by him. Yes, you guessed it. I finally had no choice. I volunteered to go for him.

When I got back, wouldn’t you know, he was dead to the world. I shook him, but couldn’t wake him, but I was tempted to stuff the burgers down his throat, with the likely affect of choking him, and deservedly so. I was happy to note, they did not go wasted; Roger ate them, cold and greasy, the next morning. He looked a bit peaked all day, and skipped lunch altogether. I smiled throughout the day, every time I caught his eye. I also made a big decision that day; I was committed to beating him sales wise, and indeed, ended up being leading Account Representative that year. I am not bragging about that, because without his antics that night, he probably would have beaten me. I had to get even, so I remembered that night every time I sold a policy. Thanks for the memories, Rog.

JIM
It was company policy to send a new person out with someone who had been through training, but I found that some people, even though they were letting you come with them, had no intention of sticking with company policy. This took place the first week I was with the company, and almost caused me to have second thoughts about staying. Jim was someone I would never have hired if I had been doing the hiring, but they said he sold a lot of bibles door to door when he was in college, and that touched our then, regional manager’s heart; he too had sold bibles when in college. I had only been with the company a few days when my manager said, “Go with Jim today. He has some enrollments to do, and you will pick up some pointers just watching him.”

Now, let me tell you a little more about Jim. He was from eastern Kentucky, and I don’t mean for that to be a stigma, but he was one of those guys whom you could put a Brooks Brothers suit on, and he would still look sloppy. The back section of his tie was longer than the front, and was a little below belt level. Sloppy. He had a little pooch on his belly which caused his shirt to pull out, and almost expose the entire front tail, plus his stomach. His blond hair was in disarray, but the worst thing came after we were in his car on the way to the sales call. This is when he cued me in on his approach to sales. He said, “talk to a customer in a whisper, which forces him or her to move closer to you.” He said then you smile as you give your sales pitch and begin filling out the application before the customer has agreed on anything. He said it worked for him most every time. I think he was still selling bibles, at least in his mind. When we arrived at our call, Jim walked in like he owned the place, and got several employees to stand against the wall. If I remember, there were five, maybe six, new employees, all females. Jim proceeded to talk softly, and he was right; the ladies couldn’t quite make out what he was saying, so were leaning in. Somehow, he suddenly got the brilliant idea that he would get the employees to fill out their own application, which of course would save him time. He enrolled all those ladies in several programs, with little or no explanation of what they were buying, or how they worked. He was having fun, at least until the owner of the company came in and overheard part of his spiel, and threw us both out of the business.

I knew we were supposed to meet with each employee, one at a time, and explain each benefit in an understandable fashion, but Jim had told me to keep quiet, so I did. I was new and green, and he broke the rules. I had serious reservations about what I had gotten myself into. I was thinking that an agent needed to stick to company policy, but if they let everyone do as they please, I didn’t want to be a part of it. The showdown came when we returned to the office, and our manager asked me to come into his office and shut the door; he wanted to know how the call had gone. He could tell I was hesitant, but he insisted I tell him how it went. You can imagine how I responded, but when I told him the owner kicked us out, he didn't budge. I suggested he talk with Jim about the call, but he said, “No, no, I wanted you to tell me about it, because I value your input, and a third-party observation is best in these situations. He asked, “What would you have done differently?” Later on he told me the owner of the business had called him and told him what had happened. My new boss knew he could lose me over the incident, and wanted to assure me that was not the way we did business.

Jim didn’t last long in our organization. My call with him was indeed startling. It shook me up, but I soon learned we had a much more meaningful approach, and I’m glad I didn’t make a hasty decision.

FRANK
I want to tell this story because it is about a senior officer in our company. Funny things happen to everyone, but sometimes you never hear a good story because a person is too embarrassed to tell on themselves. Frank was not that kind of person; in fact, he'd rather laugh at himself than anyone else.

My company was one of the largest insurance brokers in the world, and Frank eventually became its chief executive officer. Our U.S. headquarters was in New York City at the time, and Frank was living in Nashville, and traveling to New York for senior meetings. I don't recall the hotel he was staying at, but suffice to say, it was one of the best and biggest. As Frank tells it, he slept in his jockey shorts. He simply did not like to be encumbered by pajamas, but didn't want to sleep in the bare either.

As many hotels do, one of the benefits offered him was a newspaper at his door every morning, in this case of couse, it was the Times. He was there all week, and every morning he would get up early to read the paper before showering and going down for breakfast. However, one morning he opened the door to get his paper, and it wasn't there. He said he said a curse word under his breath, but looking across the hall, he saw a paper lying in front of his neighbor's door. He was still in his jockeys of course, but he was sure he could grab that paper and make it back to his room before the door slammed shut. He was wrong.

So here Frank stood in front of his door, a senior officer of our company, wearing only his jockey shorts. But he did not hesitate; he tucked the paper under his arm and headed for the elevator. He said he didn't see a soul until he arrived on the first floor, and he proceeded to say good morning to several people, including several attractive, smiling women. He nodded each time, smiled and said, “Good morning, have a nice day, now.” The front desk offered to find him something to wear, but he refused, and only wanted another key to his room.

Frank was a southern gentleman, born and reared in Nashville, and had you been one of those he met that morning, you would have heard a pleasant southern voice wishing you good morning, and have seen a sincere smile from someone who was not the least bit embarrassed.

TOM
This next story is my last in this series, and the shortest of the ones I have told, but it’s one I love more than any other. Tom was the Account Executive to whom I was assigned when I first got into the business. I enrolled all the employees in his new business and existing customers for him; we called a new group, a “case.” and he trained me how to make calls on employer association members with the objective of selling a case, which could have contained any number of benefit plans. . I recall my very first lead call to a member of one of our trade associations. It was a Pepsi Cola bottler in Louisville.

For weeks I was with Tom when he made this kind of call, and he was with me that day, allowing me to lead the way. During the weeks and days leading up to that fateful day, we role played, and he shared with me the serious objectives of that first call. In the Pepsi parking lot, we again discussed our objectives, and he asked me if I was ready. I think I probably said, “No, but let's do this anyway.” So off we went, headed for the front door of Pepsi Cola, a plant containing around a hundred employees. What a reputation I could begin building if I sold this.

As we neared the front door, I noticed the entrance had a corridor with doors at both ends. Something many buildings have, to keep the heat or A/C in. One set opens automatically, and when they close, the lobby doors open to let you in. Just as the first set of entrance doors closed behind us, Tom passed gas. Not just a little either. The distance between doors was sufficient to get more than a good whiff, and I turned to Tom and said, “Did you just fart?” He grinned, and I broke up laughing. When the lobby door opened, I was still laughing; maybe it had turned into a big smile by then. I was completely at ease when we reached the receptionist, and the call could not have gone more smoothly. We met our objectives of getting employee data and there was good interest in what I had offered. As I recall, Tom ultimately had himself a new client. Of course, he did most of the preparation for the final presentation, but I know he was proud of me. So was I.

Tom was a special guy. He sensed the tension I was feeling as I got ready to make that call, broke that tension for me, maybe by happenstance, but I think he planned it. He made me laugh. I always remembered that the best thing you can do on a sales call is relax, and above all, smile.

I have many more stories, but I will save them for now. Thanks for hanging out with me and allowing me to share a laugh or two.


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