My first experience with “failing forward” on the job took place during the summer of ’86.  A few of my high school friends had landed jobs as valets at a private beach club on the Long Island Sound.  The club’s general manager was looking for an extra valet parker so I hitched a ride with them one morning and landed the job.  The job requirements were fairly simple, even for an 11th grader:  Show up early.  Be ready for the morning rush between 7:30am and 10:30 am.  Get to know the members by their last names.  Sit around during the middle of the day while the members were swimming and playing cards.  Be ready for the afternoon rush between 4 and 7 pm.  Remember where you parked their cars.  Be friendly and don’t let them wait too long in the afternoon sun for their cars.  My pay:  $1.85 per hour plus tips.  (Valet parking is all about the tips.)

My crew consisted of about 6 guys, including a few of my high school friends.  We would wake up at the crack of dawn, cruise by a deli and grab a breakfast sandwich and a Gatorade, and show up at the club at an hour when the only ones there were the GM and the maintenance crew.  The job itself was easy for anyone with a decent personality and a driver’s license.  For me, there was one issue, though  It was the eighties and a lot of members owned cars with manual transmissions.  When he hired me, I told the GM that of course I knew how to drive a stick shift.  In reality, I had never driven stick in my life, so, I asked my friends for help.

During the middle of the day, while the club members were sunning by the pool, I’d grab a set of keys to a BMW or a Jaguar and go for a driving lesson.  My friends were also 16 or 17 years old and their driving lessons consisted of just two pointers: “see that third pedal on the left, that’s the clutch, step on it before you shift gears” and “here’s the order of the gears: up 1, down 2, up 3, down 4, up 5”.  I would start the car, shift into 1st, let go of the clutch, and the car would stall.  Third pointer:  “When you let go of the clutch, make sure you step on the gas.” So I would shift to neutral, step on the clutch, start the car, let go of the clutch, and step on the gas.  The car would lurch forward, so I’d hit the brakes and the car would stall.  Our lessons would last for two or three failed attempts followed by laughter from my friends.

We never got caught during our driving lessons.  Managing the morning rush wasn’t the issue either;  we knew which cars were stick as they pulled into the driveway, so my friends would always take them and leave the automatic transmissions for me.  The problem was the evening rush, when the members came out to get their cars.  Even worse was during holiday events, when guests whom we didn’t recognize came out to retrieve their cars and we didn’t know who owned which car.   People who wait a long time for their cars can get testy.  When the kid who took 15 minutes to get their car pulls up driving 3 miles an hour in 1st gear , and stalls as he pulls up in a $70,000 BMW, people can get really pissed off.  I lasted for about three weeks before the GM relieved me of my job.

When I got into the GM’s air-conditioned office, he told me, “I need another guy in the back, another Cabana Boy.  So grab your stuff and get back there.  The other Cabana Boys will teach you the ropes.”  That was it…  my first job promotion!  I thanked the GM and went back to the valet parking guys to share the news.  My friends there were surprised, and a couple of the other guys were pissed off.  I didn’t share the GM’s reasons with the guys.  Truth was, I didn’t know his reasons for certain.  But, I had a pretty good idea that the GM knew what was going on and so he put his worst driver (me) in a role that was a better fit (waiting on and talking with the members).  It was a lucky break for me.  Oh and my pay in the new job:  $2.05 per hour plus tips. (It’s all about the tips.)