When to Sunset Goals and When to Expand Them
Make Unreasonable Requests that Aren’t

Misadventure: Al Jarreau, No Money, Needing a Ride Home

This is a true story of a misadventure from 35 years ago that has impacted how I think about success today (in good and bad ways). In 2005, I attended an Al Jarreau concert. As I soaked in every word he sang, I remembered the night I was first introduced to his music. I was about 20 years old and in a pickle caused by my drunk roommate.

I was living in Florida at the time. My roommate and I went to a club to dance. We were both broke and nursed our drinks for hours. The drinking age was eighteen at that time. We went our separate ways in the club after a couple of hours. I preferred to be on my own and she was more of an extrovert. I got alarmed, however, when it I couldn’t find my roommate thirty minutes before closing time. I circled through the club several times, checked the lady’s room, and looked for her in the parking lot. She’d left - probably with the cutest-guy-in-the-world-du-jour.

The bad thing about this situation was that she had driven us to the club. And I didn’t have enough money for a cab. Ft. Myers didn’t have public transportation at this time, either. I was stranded well beyond walking distance to my apartment.

After brainstorming options, I knew I’d have to ask someone—a stranger, because I didn’t know anyone left at the club—for a ride home. I didn’t want to make a request that seemed like it was more than I intended (no quid pro quo, if you know what I mean).

I observed a well-dressed middle-aged man at the bar. He seemed poised, pleasant, and not yet drunk. My nerves made my face go flush as I walked up to him. He smiled, but it was a reserved smile like perhaps he was surprised I was approaching him (maybe he thought I was a prostitute?). I explained my situation as humbly as possible—party-animal roommate, no money, apartment across town—and told him I needed a ride. He was gracious, sweet, and agreed to help me out.

I worried that he might not be as nice as he seemed—people are often no what they seem—but didn’t have a Plan B. This happened before people had cell phones, so there was no way to call or text a friend or family member for help.

Unimaginable, I know!

We left the bar and walked through the thinning parking lot. The man pointed toward the passenger side of his car, which was a Mercedes two-seater convertible. He got in, unlocked the doors to let me in, started the car, and put down the top.

Remember, I was twenty. I was thinking what I now know are highly illogical thoughts like how even if this guy was a perv, it might be worth some trouble to get to hang out at the riverfront mansion I imagined he owned. The car was cherry, so it was reasonable to assume he owned an enormous house and boat. And maybe a helicopter.

As we got onto the parkway, he turned on the built-in cassette player (cassettes were hot then, having just replaced the 8-track player in cars). What did the man play?

Al Jarreau.

“Mornin'” and “Boogie Down” filled the air and my head with their complex and upbeat vibes. Fast car, cool breeze, and jazzy tunes. It was unlike anything I’d done or heard, and I was hooked.

The man didn’t say a word during the drive, although he smiled a few times when he noticed I was enjoying the music. I leaned back in the passenger's seat and soaked in the experience.

This was success.

As he reached my apartment parking lot, I thanked him, and we parted ways. I never knew his name, just that he was a gracious man who had impeccable taste.

Fast forward to today. When I need to feel successful or nudge myself out of a mental funk, I play jazzy tunes in my car, windows down, and let the breeze carry my hopes and intentions through my breath and body. And if I’m in a tough spot, I turn up the Al Jarreau. It works every time.

We all have metaphors for success—things, places, or situations emblematic of how we want to live. It’s helpful to reconnect with these experiences and explore why they resonate. I mentioned that this experience affected how I’ve thought about success in good and bad ways.

The good is obvious, I think. That music is evocative and can lift our moods and energy. The right song can make us smile.

The bad is likely obvious, too. That having a Mercedes and lots of money equals success. While this might be true for some, it depends on how we define success (an important topic for another day!).

At twenty, getting stuck at a bar because I didn’t have a car or enough money to call a cab shaped my view of the man’s success. He seemed to have it all, and I wanted a life like I imagined he lived. That’s the kicker, right? My imagination. All I saw was the outfit, the car, and the cassette tape. For all I knew, he might’ve been unhappy or lost. He was drinking alone. Or he might’ve been in town to close a lucrative new deal and was heading back to his blissful life on his private island.

I’ve written a lot about the power of small actions (the Butterfly Effect) and this is an excellent example of how a particular moment can reverberate in ways that change who we are, how we define success, and how we live.

We all play the role of Lisa-at-twenty at some point.

And we’re also the-man and have the privilege to transform how another person perceives their world.

I’m glad I experienced this mini-misadventure. Al Jarreau died in 2017, but he remains one of my favorite singers. “Mornin'” and “Boogie Down” are magical songs.

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