What was your first boss like?

Note from the Author: This is the 3rd Question my daughter sent me to answer for her and my other three children and grandchildren. I have to admit I kind of went wild with this one an answered more than about my first boss. Read it and you will understand.

Dear Samantha;

Rather than answer your question as one question I have decided to tell you about my first three jobs and my first three bosses.  This will not include the paper route that I had at age 10 because it was only 2 hours per day (4:00 AM till 6:00 AM) and I was helped by my dad.  I think this job paid me about $7.50 per month and I had to deliver papers 5 days per week.  I don’t even think about that job anymore.  So, let me start by telling you about my first real job (or what I’d consider as my first real job).

My First Real Job

I really don’t remember my first bosses name … but I do remember him and the job.  He owned a gasoline station that was about 2 miles from my home.  I was about 12 years old and lived at Sterling Estates Trailer Park in Justice Illinois.  His gas station was a small building and his drive only had two gas pumps … Regular and Ethyl (called premium today).  I worked for him for about 2 months one summer.  And when I say “I worked” I mean just that.

I would have to be there by 7:00 AM, when he opened and was not allowed to leave until about 6:00 PM when he closed.  My job as his assistant was to make sure that every car that came in for gas – regardless if it was a fill-up or a dollar’s worth (yea you could get about 4 gallons of gas for a buck back then) – my job was to make sure that every window and mirror on the car was cleaned.  I would use a spray bottle of Windex and paper towels (and I’d better not use too many paper towels). 

There were many times, especially with pickup trucks, that I’d have to use a step stool to reach some of the windshields and rear windows.  I was never allowed to “Pump the Gas” or “handle the money.”  Child labor laws at the time – I was told – would not allow me to do those things.

I used to enjoy lunch time because my boss would always buy me a hamburger and a Coca-Cola from the bar down the road (about a half mile away) that I would have to walk to and get and bring back to him.  If I remember right the cost was 75¢ and he would always send me with $1.50 for him and me.

At the end of the day my dad would come get me at 6:00 PM (he’s also the one who took me there) and the boss would give me $2.00 in cash and send me on my way … only to start again in 13 hours.  I was paid every day, and I liked that – though I had very little time to spend the money I made.

My Second Real Job …

Hole 1 Edgewood Valley Country Club

My second Real Job was that as a Caddy at Edgewood Valley Country Club in LaGrange Illinois.  The picture above is the first hole (a par 5) on that course today.

Back in those days (I was 13 years old) we could only caddy during golf season which was from about May through September/October when snow was not on the ground.

Caddies did pretty good during the summer months and because I had to ride my bicycle to the golf course, I could only work when school was out between June and August.

This was a ride of about 5 to 6 miles and would generally take me about 30 minutes to get there on my bicycle.

My Route to the Golf Course

Remember I was only 13 and at the time a very skinny and scrawny 13.  Many of the golf bags I had to carry took everything I had to loop 18 holes.  Back in those days’ caddies were called “Loopers.”

If I remember correctly the fees per round were $2.50 for 9 holes and $4.00 for 18 holes.  It did not take me long to figure out that I’d prefer two 9-hole rounds to one 18-hole round.  In addition to these mandatory fees to the caddy, the members – if they were nice and we were good and did not lose to many of their balls – would pay us reasonable tips.  The front 9 was easier to walk (less hills) than the back 9 and the pay was 50¢ more.  In addition – Doctors and Lawyers would play 18 whereas their wives would play 9.  Doctors and Lawyers would tip $2.00 to $3.00 and their wives would tip $4.00 to $5.00. 

So, for 9 holes … the golfers were usually much prettier and much freer with the money.  I could make $13 to $15 for two 9-hole rounds vs. $10 to $11 for 18 holes with Ugly Fat Men trying to walk up and down the hills of the back nine after wearing themselves out on the front 9.  Back then Electric or Gasoline powered carts were not available for individual play unless you were an individual who could afford your own and the course would allow you to use it.  They preferred walking and caddies.

But the truth was, back then I hated golf so this job only lasted one season and I was on to bigger and better things.  Again, I have no idea who the boss was or what his name was.  I just showed up … was assigned a golfer and their golf bag and off I went.  I would do two 9-hole rounds on most days – get on the ole bicycle and head back home before dark.  I did like the fact that again I got paid every day I worked without having to wait a week or two for the money.

My third (and best) job as a child …

At the time I did not think of myself as a child … but I was.  I was 14 years of age and decided to apply for work at “Playland Amusement Park” which was right next door to the Mobile Home Park we lived in (Sterling Estates).

Playland Park was located in Willow Springs which at that time was unincorporated and the area is considered Justice, IL today. The park was located where the Sterling Estates Mobile Home Park at 9300 W 79th Street is today.

Only a maintenance building remains today which continues to be a maintenance and storage building for Sterling Estates.

The park was a kiddie park operated primarily by the Rocco family. The Rocco’s are perhaps best known for being the developers/manufacturers of the Flying Scooters ride. This park was a small showcase for Bisch-Rocco’s kiddie and adult rides.

There were also a number of ride concessionaires in the later years, some who moved here when Riverview closed. Riverview was a large amusement park in the city of Chicago that closed down sometime in the early to mid-1960s due to the need for housing or office buildings.  Playland Park itself was somewhat boomerang-shaped and looked more like a fair than an amusement park with dirt and gravel walkways, and no landscaping. The front and original section had mostly kiddie rides while the back was expanded into more adult rides in the 1960’s.

Overall, there were 30-40 rides in the park. The park closed quietly in 1979 with pressure from IDOT (Illinois Department of Transportation) expanding roadways, Sterling Estates desire to buy the property and competition from Chicago’s newest parks — Marriott’s Great America and Old Chicago.

Map shows where the park used to be

As this map shows … we lived on Oak Lane and at the time Playland Amusement Park was just a street or two over.  Since the closure of the park, it looks like Sterling Estates (which is still there) has grown to take over the land it was on.

The man I worked for and looked to as a my first “Mentor” was a guy by the name of Gene Heland.  Gene was about 40-45 at the time and a “chain smoker.”  I remember he smoked Camels and Lucky Strike and neither had a filter.  I remember when Gene caught me smoking my Winston’s he laughed at me and asked why I was smoking a cigarette with a Kotex on the end of it like some girl.  I learned to smoke Camels!

Next are a few of the pictures of Playland Amusement Park I was able to find on the internet for this piece … then I will get back to my Boss.

This is an Ariel view of the park.  My first job was taking care of the Pony Ride which had two locations.  The upper part of the picture is the barn where they were housed and my job was to shovel pony crap and keep it clean and take the ponies to and from the pony ride in the lower part of the picture.

Ariel View of Playland
Sign showing way to Park

The picture above is the sign that directs people from the main road to the park.  The clown was the popular “Bozo the Clown” from the 1960s.

Here’s a mother with her child on the back of “Toby” – one of our most loved ponies.

Tobie with Child Rider and mom watching child

After running the ponies for a while, I was allowed to run the Swingin’ Gym as pictured below. Truth be known I was probably switched from the Ponies to the Swingin’ Gym because I could not keep the ponies corralled at night and they kept getting loose and going into the trailer park next door where they damaged many gardens. I think it started costing my boss too much money … but he didn’t fire me.

Swingin’ Gym

This was one of the few rides that did not require electrical power or gas power.  The power for this one came from the rider shifting their weight back and forth to get the big basket to swing around the hinge at the top.

Looks like this dad and daughter just got off the Swingin’ Gym or the Bullet next door.

Assume it is dad with daughter or Uncle with Niece.

This was our Roller Coaster and I can tell you back in the day it looked a lot bigger than this.

I think they called it the Cyclone

Our great Concession Stand served the best Hamburgers and Hot Dogs in all of town (and actually the only hamburgers and hot dogs in the town at the time). 

Playland Concession Stand

This was the cost of the tickets at Playland (entry into the park was free).  However only the Kiddie Rides could be ridden with one ticket.  All other rides required 2 tickets or more … and the best rides it was four or five tickets to ride. As inflation caused prices to increase over the years, the cheap skates who ran the park would not change the price of the tickets … they would just require more per ride. I guess it was less expensive to repaint the # of Tickets Required on the signs by the rides.

I’ve Got a ticket to Ride …

The ponies or the Swingin’ Gym was not my favorite job at playland.  I will tell you what that was in a moment … but first let me tell you about my first real boss my first Mentor.

My First Mentor …

Gene Heland was the first boss and mentor that I remember to this day.  He always treated me fairly and paid me well (I thought).  I would do anything for this man who would not only teach me new things but would tease me and help me to build my self-confidence while growing up.  As I mentioned in previous articles, I was always quite shy as a kid.

Gene had a little note book he’d carry in his pocket to keep track of my hours.  He’d pay me every Friday night at the rate of $1.00 per hour, which was the Federal Minimum Wage back then.  He would pay me for doing and for learning or just being there.  What I mean is that he did a lot of the carpentry work and painting for everyone who owned rides or concessions in the park.  I’d help him with the upkeep and even if we were going to the lumber store for lumber … he’d pay me for riding along in the truck with him.  When we had nothing to do, Gene would teach me how to fight.

Gene (as I was always allowed to call him) would get upset with the owner of the park who made me call him Mr. Rocco.  Gene looked at everyone – regardless of age – as an equal.  There is no way he’d call the 80-year-old park owner (or his 40-year-old son) Mister.  It was always Rocky or Rocky Jr (and I don’t believe the younger Rocky was really a Jr.).  If the Rocco’s needed police help in the park for a rowdy bunch of guys (of which we had many and many were my friends), they never called the police … they called Gene.

Gene was not a big man by any stretch of the imagination.  He stood about 5’7” but he was rock solid and never met a man he would not go up against … or a group of teenagers he would not grab by the neck and march out of the park.  If their dads came to complain – it would only happen once because Gene would be on them like “flies on manure.”  I’ve seen him bloody … but I never saw him quit – he just had no “quit” in him.

When Gene was not working in the park – which was seldom – he was a volunteer fireman and EMT. He was also a certified scuba diver and assisted the police on many drownings in Lake Michigan and other waterways of the greater Chicago area.

Gene was married to a beautiful woman named Jackie and together they had three young daughters (no sons) and both tended to treat me as the son they never had.  During the months from the time the park opened till it closed (April – September) from the time I was 14 till the time I went into the Military I was with him constantly.  If not at the park, then at his home helping him paint and fix up his house.  Much of this home work was done after the park season when Gene and his family would not go south (to Florida) to run other Amusement Parks.

At the age of 16, when I could legally deal with money, Gene decided to allow me to get off the pony ride and Swingin’ Gym and work a game booth.  The game I ran was Tic-Tac-Doe and you can see my booth in the picture below (Yellow Arrow):

My Tic-Tac-Doe Booth

The game that Gene Designed (Sorry I could not find the actual game online) was similar to this:

See Information Below on how Ours was different

We did not call it Tic-Tac-Toe because we were not concerned with the balls being in a straight line or diagonal (and we used baseballs).  We called it Tic-Tac-Doe because each of three squares (rather than circles) were either Red, White or Blue (yea, Gene was a patriot that loved the colors of our flag).  The idea was to toss and land three balls into the same color.  The person tossing the ball was about 7 feet away from the box where the squares were located.

We would sell park patrons three balls for a quarter.  The more quarters they would spend the more points they would accumulate (if they won at all).  Based on the value of points they could select prizes (mostly stuffed animals) of varying sizes.  I remember one win (1 point) would get a person a plastic whistle, fancy plastic straw (back then most straws were paper), key ring or some other cheap prize that probably cost Gene 10¢ at the most.  Once they got into 5 points or more, they would have enough to get a small teddy bear or something similar.  If they got to 10 points then they were into the really big teddy bears, tigers or other stuffed animals.

Commission …

When Gene decided to let me consider running a game, he held our first “man to employee” meeting.  This is kinda the way the conversation went.

Gene:  It is time you make a career choice.  I can give you a raise from $1.00 per hour to a wage of $1.50 per hour for the same job that you now have (I knew this was 50¢ greater than the minimum required wage).  In a typical 70-hour work week (the park opened at 1:00 PM and closed at 9:00 PM and all workers had to be there 1 hour early and leave 1 hour later), you could make up to $105 per week.  Or, I can let you run one of my booths and you could earn that much in a matter of 2 or three days – and probably that much on a Holiday.  However, there would be some days that you may earn far less.

Me:  How does this work?

Gene:  I put you in a booth with $100.00 of bank in your money apron.  At the end of the night, we count what you have in your apron.  If it amounts to say $500 you just made a profit for the company of $400.  I will give you 25% of that $400 which would be $100.  That would work out to about $10.00 per hour for a 10-hour day.

Me:  Damn man, that sounds good to me.

Gene:  I have to warn you, you are not going to have $400 days every day.  Some days you may only pull in $25 so your cut would only be $6.25 which would only be about 63¢ per hour … and you need to understand that up front.

Me:  What’s the downside? 

Gene:  You may end up earning less than you are making now; and once I hire someone to replace you on the rides, I can’t take away his job and give it back to you.  However, you could do much better than you are now because it would be like you are running your own business.  It is going to require you to come out of your shell and put yourself out there in the public.  You are not going to draw people to your game by being quiet.  You will have to yell at them to come give your game a try or they will likely just walk on by.  These guys want to win some stuffed animals for their girls but they want to be entertained while they do so.  They will not waste time on a shy person who is afraid to bring them into the game.

Me: (thinking to myself – the worse that happens is that I lose and will have to go find a new job, perhaps with the Rocco’s) … Okay, it sounds good to me.  I like the idea of running my own business.  When do I start?

Gene: (While handing me a money apron with $100 in it); Right now, because I’ve already hired someone to replace you on the Swingin’ Gym.

Self Esteem & Self Confidence

I gotta tell you, the going was not very easy that first month.  I was not making much money at all.  Probably about $10.00 per day when I was lucky – and if I’d kept the hourly job, I would have made $20 per day.  My dad was not very happy with me either considering that I was bringing less in and had to rely on him more.

But after awhile I gained some Confidence and Self-Esteem.  I learned to get out of the booth and walk the midway screaming to the top of my lungs … “Bring the little lady in and get her a big Teddy.  I’ll give you 3-balls for a quarter.”  Or, “Come on man … let’s be a winner for her today … 3 balls for a quarter will make you the winner of her dreams.”

Yep, I became a hell of a “carnival barker.”

Once I got them hooked and got them to start winning – or at least trying to win – if they were close (say two balls in one color and one in another color – I’d sell them the 4th ball for $1.00 more (I mean after all it was my business).  Of course, I would not offer the extra ball for a dollar until they had blown through $5 or more and was close to winning with more than 1 game under their belt. I remember on the 4th of July that year I brought in over $750 and was given a big fat pay day of $187.50 for the days work.  Another thing I really liked about this deal was that we were paid every night and not once per week.  Also, I could call my breaks as I wanted to and not as anyone thought I should have them.  I just had to turn the booth over to someone else and they operated out of their cash apron and not mine.  I rarely took breaks (unless there was some good-looking girl I wanted to talk to and get to know).  I thought I was a “big shot” indeed.  How many other kids my age could walk around the park with hundreds of dollars in their apron?  Not sure I’d do that today, though.


This job truly taught me to be an entrepreneur who appreciated the good things of a capitalistic system. I remember going to purchase the stuffed animals one Monday Morning with Gene.  We drove down to skid row (a place where drunks slept in the streets) and parked in a secure parking lot. You did not want to leave a vehicle unattended unless it was in a secure lot in that area of town. 

We walked into a huge warehouse where stuffed animals were being manufactured by low skilled workers – many homeless or disabled.  They too were probably working for minimum wage or less. I remember I was amazed that the big teddy bears and tigers were going for as little as $1.50 each and the plastic whistles and stuff was like 15 for a dollar.  We bought a truck load of stuff.

After putting the new stuff up in the games, the old stuff was taken to the Salvation Army (the sun would fade out the material the stuffed animals were made from) and donated for charity which gave Gene a tax write-off.  He was actually donating the old stuff for retail cost that he was picking up at less than wholesale cost.

I was amazed that we could spend $1.50 for a Teddy Bear and sell it to some poor Joe or Joanne for up to $20 if they decided to spend that much to try to win it.  Heck if 20 people played for $2.00 (8 games) each and won nothing [which was highly likely] that was $40 for a chance to win the $1.50 item. 

There is an old cliché out there that people think the “games in the carnival are rigged.”  They really are not.  It’s just the chance to really win any of them big is so slim.  It’s all chance.  I could win two out of ten times (and I ran the game). I could do this both looking at it while tossing the balls and while tossing the balls behind my back.  If I could win 2 out of 10 times and needed 10 wins to get the big teddy bear … I’d have to play 50 games to win 10 times. At a quarter per game that would be about $12.50 for a product that costs us $1.50.

Then, there were people who could win ten times in a row and walk off with a nice prize by only spending $2.50 (though that happened very few times).  But still the best they could do is spend $2.50 for an item we paid $1.50 for. It was all chance – but at the same time it was capitalism at its finest. I actually liked it occasionally to get one of these in my game. It brought in more people wanting to try when they had just witnessed a winner, without me having to yell out to them.

I can tell you the most money made in an Amusement Park is the money made in the gaming concessions (kinda like a casino today) and not the money made on ticket sales for rides.  People would spend $10 to $20 for ride tickets and $25 to $100 trying to win a stuffed animal at various games.

I am very thankful for Gene Heland because without him, his wisdom, his guidance and his friendship I would not have made it in the financial services industry (which is all sales and commission paid work) and be where I am today. He taught me to be confident, competent, outgoing, friendly, and fearless. He also taught me about our free enterprise system and capitalism we have in America. I learned more from this one man than I could ever learn in a school system. I learned things that mattered.

I went into the military in 1969 and came out in 1972 and worked one more season for Gene and his lovely wife Jackie in the summer of 1972 right after getting married. Our friendship was as solid as it ever was. After that season, Gene and his family moved to Florida permanently and I lost track of him. I doubt that our paths will ever cross again now that I am 70 and I am almost certain he is no longer a part of this world, but I surely wished they would.

I do remember that I would get so tired putting in 10-hour days, 7 days per week and always looked forward to this song (go ahead click on “to this song”) … which was the parks closing signal to all patrons and employees. It’s also my closing signal to you. I do hope you have enjoyed these memories.

7 thoughts on “What was your first boss like?

  1. Bronwyn Libelle

    Hi Jerry,

    I just loved hearing about Playland Park. I shared with my Mom and we had a giggle about having gone there when I was a little girl. It seems my Mom remembers I was afraid of the ponies when I went to ride them.

    I hope you and your family are doing well. I miss having you at work. You definitely spiced things up… in a good way. ??

    Sent from my T-Mobile 4G LTE Device Get Outlook for Android ________________________________

    1. Bronwyn, my dear friend, how has it been going. I am so glad you liked my story about my first three jobs and one of my most important bosses. I had no idea your mom and you went to Playland. Where did you grow up at. By the way … are you on Facebook. If so, please look me up and friend me. I will promise you this, if you will keep reading — I will keep writing since I love to do it.

  2. Mary Hopper

    Yet again, another great story! Too few kids these days have learned how to be responsible and earn a buck with hard work. You’ve done well for yourself and I’m sure you make your family proud. KUDOS to you for doing so back then, and sharing those experiences with us now!

    1. Oh Mary, thanks so much for reading my story of my first three jobs. I love writing my memories and since I am sharing with the kids and grandkids I just thought some would be good to share with friends (and strangers since my blog is public). You keep reading and I promise to keep writing as long as the good Lord allows it.

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