Got my chips cashed in

By The Deadhead Cyclist

For Week


Truckin’ is perhaps the best known song in the entire Grateful Dead repertoire. Indeed, only Touch of Grey ever climbed to a higher position on the Billboard “Hot 100” chart (Touch of Grey reached #6; Truckin’ topped out at #64 in December, 1971). As with all Grateful Dead tunes, the deeper meaning of the lyrics is found in the metaphors – I call them “Deadaphors” – and Truckin’ is overflowing with “Deadaphoric” references that beg for deeper exploration.

The very title and first word of the song, Truckin’, cannot be defined literally, as the tune is, of course, not about driving a truck or hauling materials from one place to the next. Rather, the term, “truckin’,” is a Deadaphor for life on the road, depicted in the list of colorful, creative references and defining characteristics of some of the American cities the band visited while on tour. Expanding on this concept, “truckin’ ” can be taken as a broad description of the way each and every one of us makes our way through life, meeting the challenges we face one day at a time as we “get back truckin’ on.”

But it is the remainder of the first line of the song – “got my chips cashed in” – that is the cream that rises to the top (metaphor intended) of the chart of fascinating Deadaphors in this tune. References to card games are in no short supply in the lyrics of Grateful Dead tunes. Songs like Loser (“If I had a gun for every ace I have drawn”), Deal (“Watch each card you play and play it slow”), Me and My Uncle (“You know my uncle, he starts a friendly game”), and Dire Wolf (“The wolf came in, I got my cards, we sat down for a game”), challenge us to observe the deeper psychological meanings implicit in the games we play with our fellow human beings, and Truckin’ follows suit (emphasis intended) with this striking pattern.

For anyone who has played Blackjack, Poker, or any other card game where chips are used to represent various denominations of money, it is well known that recognizing the right time to walk away from the table and cash in those chips is as vital a skill as knowing when to raise the bet, bluff or double down. And, of course, possessing a flair for figuratively cashing in one’s chips during the course of our life pursuits is similarly essential to a successful life.

When I was 25 years old, I was working at my first “real job,” selling copy machine toner (the black ink used in xerographic copying technology) in a setting that was represented to me at the time of my interview as a “telemarketing firm,” but was more commonly (and accurately) characterized at the time (also metaphorically) as a “boiler room.” The sales pitch – most often made to someone in an administrative position – typically with no actual authority to make purchasing decisions for the company – was completely fabricated. We called it the “Switched Machine” pitch:

“One of my customers in (___name of same city as prospect___) had the same copy machine as you, and they switched machines without informing me just before I shipped their regular order of toner. Rather than shipping the toner back to my warehouse and then out to another customer, thereby incurring double shipping charges, I can send it over to you at a tremendous savings.”

Another sales pitch was even more dishonest, but very effective. It was called the “New Girl” pitch, and was used when there was a new administrative employee:

“I was supposed to get back to (___name of the “new girl’s”  predecessor___) to send out the regular order of toner today. I guess since you’ve taken her place, the order should be sent to your attention.”

The biggest problem with this job wasn’t the dishonesty, though. The main issue was that I was making more money than I had even made before, and had become intoxicated (often literally, as there were certain “substances” that were liberally available in the workplace) with the ever increasing pile of “chips” accumulating in my bank account. Faced with the dilemma of continuing on the path of profitable deception or cashing in my “chips” and “truckin’ on,” I eventually chose the latter option, sublet my apartment, loaded my Martin D-41, a Coleman stove and some other essential camping gear into my 1964 VW Bus and headed “down the road feelin’ bad.”

This week’s Deadaphor – got my chips cashed in – speaks to the way we choose to transition from one job to a better one, from one relationship to another, from one stage of life to the next.

Make no mistake: This was a “Hippie Bus” through and through – right down to the platform bed with cotton futon, the large speakers (driven by a Blaupunkt cassette stereo), and the paneled interior, replete with ubiquitous leather trim, including cassette-sized pockets that lined the cab. The Grateful Dead, Steely Dan, the Beatles, Bob Marley and the Allman Brothers Band were the most often heard sounds emanating from within my new home on the road and at many campgrounds around the country. And the lasting memories and life lessons from this “trip” are astonishingly vivid today, decades later, as I ponder another call to cash in my chips.

Upon returning from visiting 22 national parks in the U.S. and Canada and moving back into my apartment, I found myself in need of a new supply of “chips,” and took a job in the advertising business. It appears I made the mistake of “blinking,” because suddenly I find myself 42 years down the road and facing the prospect of cashing in my chips again. I’m talking about the Big R, AKA Retirement, and I know I’m not alone: Many “Old School” Deadheads have written to the Deadhead Cyclist since I published my first book and shared with me their stories. Given that the “Band Beyond Description” cashed in its chips more than a quarter-century ago, it stands to reason that many of us “Classic Deadheads” (those who were there at the beginning, or close to it) are now looking at retirement, the ultimate act of cashing in one’s chips.

As the Deadhead Cyclist, I have been preparing for this transition for many years by developing my passions, and my ability to continue enjoying them. For me, that means keeping in shape as a cyclist, baseball player, musician and author, both physically and financially. Cashing in one’s chips requires not only having chips to cash in, but a reason (or series of reasons) to do so.

This week’s Deadaphor – got my chips cashed in – speaks to the way we choose to transition from one job to a better one, from one relationship to another, from one stage of life to the next. Ideally, this should be done smoothly, with great care, and in such a way that the passage is made as skillfully as the famous segue from Not Fade Away into Goin’ Down the Road. If done correctly, any trauma is minimized, and the before and after are connected in a way that is almost seamless. This requires planning, sensitivity and creativity.

Think about the times you have made the decision to get up from a table that is no longer working for you as it once did and to cash in your chips. What changes ensued and how were they executed? What did you learn from the past that can be helpful in informing future transitions?


Perhaps even more importantly, when have you stayed at the table too long and failed to cash in your chips, only to pass up other opportunities? Believing in yourself means finding the place of inner knowing and trusting your instincts. I knew it was time to quit a job that was no longer serving me; and many years later I now sense intuitively that it’s time to cash in my chips once again and devote myself to the other pursuits I have been developing for the past several years.


Only you have access to your sense of inner knowing. It is your best friend, and easily a better ally than the even increasing pile of chips you have grown accustomed to building. Choose boldly the “path that is for your steps along,” and let your intuition rule over fear.

Concert of the week in Grateful Dead history: January 30, 1978 (Listen Now)

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