Margaritaville is a mirage

The joy is the work, not getting to the finish line

Have you ever been to a Jimmy Buffett concert? It's quite the experience. Buffett's fans, christened "Parrot Heads," of which I have long considered myself one—even if I haven't been to one of his concerts in the better part of twenty years—know how to have a good time.

Buffet's music is fun. The perfect feel-good, sing-along, summertime, country/rock/Caribbean anthems.

And while the crooner is still an amazing showman, even at the ripe old age of 73 (how did that happen?!?)—everyone knows that the real action is not in the performances themselves, but in the parking lots beforehand.

In every city the aging pirate appears, Parrot Heads transform concrete jungles into Caribbean dream worlds. Pickup truck beds become hot tubs. Minivans are re-imagined as tiki bars. Soccer moms sport grass skirts and coconut bras, while middle manager dads shed their ties for Hawaiian shirts, and of course leis, everyone's got leis. Most importantly, there is plenty of Corona, Red Stripe, you guessed it, margaritas, to go around.

It's all about enjoying life. Living care-free. Kicking back and relaxing.

That's the idea that Buffett sells.

And it's something that most people have too little of in their lives, so they're more than ready to indulge in this little bit of escapism every time Buffett comes to town.

The dream is to live like Jimmy does. You just need a million bucks, a white sand beach, and a cold beer.

Of course, Buffett is not the only one to sell this dream. Kenny Chesney sells it. Zac Brown sells it. And countless others have and will continue to do the same.

In many ways, this idea of sitting on a beach and drinking a beer has become the American dream.

It's become the goal. The finish line that we're trying to get to.

I used to have this dream myself. If you asked me in my early-20's what my life's dream was, it probably would have involved a beachside tiki bar somewhere in the Caribbean.

But then I grew up and got old and boring and... well, you know how it goes.

But I've also come to realize that the "sitting on a beach with a beer" dream is a mirage. It's hollow. There's not much to it.

Don't get me wrong, sitting on a beach with a beer is wonderful. I enjoy it when I get the opportunity. In fact, in these days of face masks and quarantines, nothing sounds more appealing to me right now than that. But I no longer dream of it as some ultimate finish line.

This idea of getting to a finish line where we do... well... nothing... has been advertised to us for a few generations now. But in fact, the concept of retirement—where we no longer have any responsibilities and are free to "enjoy life"—is a new one in the grand scheme of things.

Before the 1800's, there is very little evidence of retirement as a widespread concept.

And it makes sense if you think about it. Prior to the Industrial Revolution, our societies were mostly agrarian, and you couldn't really just walk away from your farm at the age of 65 and call it a career. Of course, life expectancy was lower then, too. The statistics can be misleading as they'll tell you that life expectancy was between 35 - 40 years in the early-1800's but astronomical infant and childhood mortality rates skew the data. In reality, if you made it to 21, you most likely could expect to live into your 60's, maybe 70's if you were lucky. Still, not a tremendous amount of time to enjoy the fruits of your labors.

German Chancellor Otto von Bismarck is widely credited with inventing the modern concept of retirement back in 1889. In an effort to address the country's chronic youth unemployment problem, good ol' Otto von B decided to pay those 70 and older to leave the workforce.

Later on, the U.S. addressed the issue by finding a clever way for workers to fund their own retirements (or more accurately for younger generations to fund older ones)—and Social Security was born under FDR in 1935.

Throughout the rest of the 20th century, the concept of retirement was heavily promoted to Americans and became an accepted part of the culture. While many of those in the 65+ cohort resisted the idea along the way, a few things made it more palatable:

  • the development of retirement communities — growing more amenity-rich by the year

  • the proliferation of air conditioning (especially central air in the 1970s), which made warmer climates more tolerable/desirable

  • the ubiquitous availability of television — which helped to pass the time (sorry, no comments this week on CNN or Fox News... enough politics!)

For many, retirement became an attractive idea. And it's easy to see why. Growing industrialization and corporatism meant more economic growth and jobs overall, but those jobs weren't always the most fulfilling ones. When you're on an assembly line or stuck in a cubicle from 9 to 5, that beach and beer start to look mighty attractive.

So that's where the American workforce focused its attention. On getting to the end. To the finish line.

Entire industries popped up to support this—from ever more senior living communities to the invention of the 401k in 1978. Society bought into the idea of getting its workers to the end.

And it all went swimmingly until a funny thing happened.

People got to the end—and while they had counted down the days leading up to it, when it actually became their reality, many of them found it... well... disappointing. And disorienting. And even depressing.

It turns out, they needed more than golf courses, beaches, and afternoon cocktails to make them happy.

They had no responsibilities. No place to be. No clock to punch. They had freedom!

So why then did depression rates skyrocket? Why did suicide become increasingly prevalent among retirees?

Well, it's complicated.

But it has a lot to do with purpose, identity, and community.

We tend to hugely underestimate how much of our own identities are tied up in our careers. When I quit my Wall Street job eight years ago and moved to Charlotte, I had no idea how much my identity would be impacted. After being gainfully employed for my entire career until then, being unemployed did not feel like freedom. It felt scary and disorienting. It was humbling, to say the least, and that was a situation I brought upon myself! Think of what it feels like after having been gainfully employed for 40 or 50 years. Disorienting to say the least.

We also tend not to appreciate how important it is for us to feel like we are adding value. When you go from a busy career where you feel like you are NEEDED and where the entire place would come crumbling down without you, to being "free," there can be a significant letdown. It's hard for us to see this when we're buried in work and complaining about unreasonable colleagues, but we humans have an instinctual drive to add value, and when it's not happening, it can eat us alive. Throughout our careers, we get into grooves where we know we can add value—where we feel confident in our purpose. But when those careers are over, it's not always clear how we can contribute. And that can lead to self-doubt and even depression.

And then, of course, the idea of community cannot be ignored. Even as I sit here typing this in my home office away from the rest of the world, I realize the value of community. Of relationships. Some thrive on this more than others, but much research has been done on longevity—and outside of obvious factors like tobacco use, one of the key determinants of a long life is the extent to which a person remains engaged socially. It turns out that work provides that social engagement for many of us, and when it's gone, it can be disorienting, and again, even depressing.

So why am I spending all this time knocking the traditional idea of retirement? Well, it's not to guilt anyone who is enjoying or planning to enjoy their retirement in the traditional sense. But rather to put forth another way of thinking about it.

And that is simply this: Retirement, in my mind, is not a finish line.

It's not a destination that we get to and say "Okay, I'm done." But rather, it's a halfway point of sorts.

If you think about it from a financial perspective, one way to define retirement is the point at which you no longer need to spend time on tasks you HAVE to do, but rather, you get to spend time on the tasks you WANT to do.

This means different things to different people. For some, what they really want to do may be charity or volunteering. For others, what they really want to do may be earning an advanced degree, teaching, or even becoming an expert-level player in a sport. 

Whatever it is, if we want it to feel rewarding, it should:

  • give us an opportunity to feel like we are truly adding value, and meaningfully contributing to an important cause

  • give us a sense of identity—a way to describe ourselves and what we "do"
    By the way, this is actually important. It’s not just semantics. If you have to answer the question “What do you do?” with “Well, I used to…” then you have an identity problem that you need to address because whether you like it or not, you’re basically now saying that you no longer “do” anything of value (or worth mentioning)

  • give us opportunities for social interaction

But for many, it's even deeper than this. As we age, we start to think about legacy. And we think about spending our precious time on what really matters. Again, the specifics here are personal. But most of us need to do more than pass the time. We need to be part of a greater cause. And by believing in something bigger than us, we have that reason we need to get out of bed in the morning and get our work done—yes, even in retirement.

As I think about this from the perspective of someone who is halfway through his traditionally defined “working years,” I'm not interested in waiting until 65 before doing important work. Do I have to work for financial purposes today? I sure do. But can I find time to work on the projects that have greater personal importance to me? Well, I making time right now at 9 pm on a Wednesday night after my kids have gone to bed. Because for me, this newsletter is that project. Maybe in a year or two years, it will be something else. I don't know.

One thing I do know is that I need to better define my bigger causes. I need to think about what is truly important to me and what value I ultimately want to leave behind. What "dent I want to make in the universe" to use Steve Jobs' words.

This is what I'm going to be thinking about in the months ahead. And this is what I'm going to slowly but surely start spending more and more of my time on.

Retirement in the traditional sense of the word is far off for me. And to be honest, I don't want to get there. But retirement in the "financial freedom" and the "work on what I want to" sense is pretty attractive. And I want to get there as soon as I can.

I don't know. What do you think? Am I crazy? Is it really all about golf and cocktails? Pull up a chair next to me sometime on a white sand beach, and we'll have a beer and talk more about it… and maybe listen to some Jimmy Buffett.


Notes: What do you think about the retirement graph? I drew it myself… If you didn’t buy my book, you missed all the cartoons I drew. Think I’m kidding? I’m not. And interestingly, I’m not that good at drawing cartoons.

Okay, here’s a parting gift for you for making it to the end. Three of my favorite Jimmy Buffett songs:
One Particular Harbor (live)
Bama Breeze
Southern Cross (cover, live)

Photo credit: Sean O. @