The Caddy

The real title of today’s offering is Every lesson I have used in my personal and business life, I learned as a caddy.  Now that title is longer than some of my blogs, so I shortened it to keep fingers from going numb as I typed.  A more frightening component of this title is that I have PowerPoint slides and an entire presentation based on this very long title.  I will spare you the brilliant oration causing multiple, time consuming standing ovations that occur when I present this live. Okay maybe more sitting ovations. Okay less ovations more looks of pure bewilderment hoping eventually I would get off stage.

During my WiFi free childhood, getting a job was a marker for independence.  I am not suggesting children moved out of the house at age 10 because they got a paper route, but I am suggesting that having your own money at a young age contributed to the local economy, especially in the candy area of the local general store.

After quitting my Globe and Mail paper route, I walked to the Oakville Golf Course and began my career as a caddy.  This was a decision with a clear financial upside.  Caddying had the potential of doubling my weekly salary. 

Caddies needed to show up at the golf course around 6:00 a.m. First caddy to show up was the first caddy out on the course.  2ndcaddy arriving was the second caddy out and so on.   On the weekends there were often 10 to 15 caddies waiting behind the pro shop, and most of them would get employment that morning.  More ambitious boys would hang around and get an afternoon bag.  I was so young I would use a pull cart and not carry the members bag until I got a little older and a little stronger.  The lessons from that period of time were universal and many have become the subtext of best selling books in the business section of bookstores.

Clear Expectations

At the end of every round, the member would fill out a caddy card to justify their payment.  On that caddy card there were more than a dozen criteria to measure the performance of the caddy.:  “Rake sand traps” “Stay quiet” , “Tend the Flag” “Clean clubs” etc., were all clearly displayed on the caddy card, to help the members assess the quality and skill of the young boy.  Every Caddy was aware of the expectations of the work. As we all learned later, with awareness comes responsibility. Caddies were slowly managing their financial potential.

Measure Performance

There were three levels of caddies at The Oakville Golf Course. The caddy card for “C” caddies was yellow, the caddy card for “B” caddies was pink and the caddy card for “A” caddies was blue.  “C” caddies received $2.50 for 4 hours of work.  “B” caddies got $3.00 and the coveted “A” caddies received $4.00 a round. Members were allowed to tip, and that was a pretty regular occurrence.  As you climbed up the caddy corporate ladder, with measured performance, you earned more money.  In caddying as in life.  Experience matters.

Develop Working Relationships

As time passed certain members would ask for certain caddies, and violate the standard order of 1stcaddy 2ndcaddy behind the pro shop. I became the steady caddy for Don Green and had guaranteed work three times a week.  A relationship of trust developed.  My eventual “A” caddy status gave me new confidence.  I could “club” Mr. Green.  I would share “You should use your 7 iron here” and a conversation occurred and collaboration on the course became the new norm.  Mutual trust was the anchor for this growing working relationship.  

Manage your Manager

The Oakville Golf Club will turn 100 years old this year. In those 100 years they have only had 5 Head Golf professionals.  Les Louth, Jack Davidson, Dave Clayton, Bill Bevington and recently Matt Maiola.  I have known all of these gentlemen.  (I recently visited The Oakville Golf club so I could claim I met every pro)  After caddying I worked in the back shop, cleaning clubs, eventually working in the pro shop for my entire time I was in school.  The three club professionals I worked for, Jack Davidson, Dave Clayton and Bill Bevington could not have been more different in approach and personality. I learned very quickly that whatever is important to your boss, will become important to you.  All of these men were highly principled and fair to their employees.  I honoured their unique approaches and worked hard to fulfill their individual expectations.

Adapt to Change

My early days of caddying were highlighted by getting to caddy for the Baillie brothers.  Aubrey and Frank Baillie golfed every Saturday and Sunday morning and paid their caddies $5.00 regardless of the caddy ranking.  Caddies would celebrate when they were selected for their bags.  This worked out well until the Pro Shop began investing in Electric carts.  That technology changed the caddy’s future forever.  I started cleaning clubs for free knowing that if I was going to work at the club, I had better change my job description.  Jack Davidson noticed my free help to the back shop and eventually hired me as the back shop club cleaner.


Caddies were given permission to play the golf course early mornings as long as they were off the golf course by 8:00 am.  I cannot tell you how many times there were 20 caddies on the first tee before 6:00 a.m. to ensure all 9 holes were played before 8:00 a.m. Earlier I mentioned Les Louth, the original Head Professional at the Oakville Golf Club.  He lived across the street from The Oakville Golf Club and had a lifetime membership at the club because of his decades of contribution.  Well Mr. Louth would walk the course every morning and would give caddies free golf lessons as they played .  He showed proper grip, swing plane, stance and other tips for free to ever 11 year old playing early morning golf.  He volunteered his time because that is what the good ones do.

Life Isn’t Fair

The club championship was the pinnacle of financial opportunity at the Oakville Golf club.  For that weekend caddies would get a bag and make more then $20.00 dollars for the weekend work.  One year I got to caddy for Cliff Post, Sandra Post’s (LPGA Major champion) dad, and he was a superb golfer.  He was a character and a wonderful man to know.  That weekend he finished 2ndin the club championship and while other caddies received their $20.00 bill, I got $6.00 for the weekend work.  It was simply an oversight by Mr. Post who later compensated, but at the time I was devastated.  I did not complain, pout or have a caddy temper tantrum.   I learned one must deal with disappointment with maturity and grace even when you are twelve years old and this painful lesson has served me well.

The 90 \10 Inverse Rule

During the 12 years I worked at the Oakville Golf Club the greatest lesson I learned has repeated itself in every organization I have worked for.  90% of the members I had the pleasure to work with were decent, kind, modest and virtuous human beings.   10% of the members were absolute unpleasant people.  Complaining about their clubs not being clean.  Complaining about their tee times. Literally complaining about everything.  Now I learned discretion and will not name these people, but every member knew who they were.  This 10% of the people caused 90% of the problems at work.  That ratio has proved consistent during my work and family life. 

The People

Finally this simplest life lesson I learned.  Reflecting back at my time at the Oakville Golf Club and my over thirty years in the corporate work world, one truth has never changed.  It is never the work you remember.  It isn’t the projects, the deadlines, the occasional promotions or even the annual financial bonuses.  No it is always the people you remember.  This is not an original idea, but it is an accurate one.  When I think about the Oakville Golf Club I smile, because of the wonderful people who shaped my life.  The greens keeping staff, the kitchen staff, the other caddies and the members.  In this current Covid19 world we are constantly reminded about this universal truth.

I have more thank exceeded my typical 1000 word count with this blog.  90% of you will forgive me, demonstrate empathy and understanding for my wordiness. As for the other 10% … F$^k  em!

Cue the Blong: More painful life lessons…


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