Bootstrapping and Other Useless Advice

Boomers At The End of Time

Few topics get people riled up as much as boomers and their “tough love” advice to the younger generations. A large portion of the derision comes from their cluelessness regarding how society has shifted under their feet and the contempt of their tone. This isn’t unique to boomers, as every generations eventually loses the ability to grasp changing mores like they were in youth, and often retreat to a more comfortable atmosphere where such changes can be ignored. The difference from other generations is their lack of cognizance in realizing this and their confidence in vacuous thought patterns. As an older millennial, I was blessed to know many in the Silent Generation, and while a lot of them talked themselves up, they didn’t tend to give abstract advice. You wouldn’t hear platitudes, grandstanding, or the absolute confidence that what worked for them would work for the next generations. They had a personal code of honor, but knew that didn’t always translate to success.

I want to caveat the mindset below is a general archetype. There are plenty of people past their 60’s that aren’t the type, though the plague of this worldview has infested that age group heavily. If you are a subscriber in this age demographic, it’s very likely this doesn’t apply to you. My subscribers, especially my paid subscribers, are far more intelligent, handsome, and charismatic than the general population. It is also true, however, that everyone has dealt with this sort of person, and often they are not even that old.

Talk to many boomers, and the self-confidence they have it all figured out is nauseating. While the incessant whining of much of the younger generation is also irritating, the conversation is not bolstered by older generations who aren’t willing to acknowledge the collapse in social trust and economic prospects that will likely make Gen-Z the first generation in a century to have a lower quality of life. The irony is the more successful the boomer in his career, the more unwillingness there is to understand these changes. It can’t be forgotten, though, that many boomers did rise to great things, and many showed enormous skill and work ethic in achieving success.

During a recent graduation ceremony the school’s founder, an older gentleman who built it as a passion project, gave the usual spiel about the graduating students being the future. It was pablum, but nice enough. As a graduation present he gave each student a copy of William McRaven’s book, “Make Your Bed”. Curious, I grabbed an extra copy and read it. It was a short, breezy, one hour read. I chuckled most of the way through, as it might as well have been titled, “The Final Boomer Boss”.

McRaven was no slouch. He was an accomplished SEAL who made combat jumps and ran the operation that killed Bin Laden, ascending all the way up to being a Four-Star Admiral. He later served as Chancellor of the University of Texas System. The book was an expanded version of a speech he gave to college graduates. I have nothing but respect for his credentials, and he seemed to be overall a good person, but man was his advice dogshit.

What was clear reading this book was, like most successful boomers, McRaven was a company man through and through. Amusingly, his one career setback was being pushed out of Seal Team Six for being too much of a square. In McRaven’s defense, he was likely in the right given some of the notorious characters there. The title of the book “Make Your Bed” was based on his military training where an impeccably made bed was harshly enforced by his superiors. Because the military said it was important, he assumed it important also, and the work involved in making sure the coin bounced off the sheets well was a sign you accomplished a simple task, and were therefore ready to start the day. The lessons were as follows.

• 1. Start Your Day With a Task Completed

  2. You Can’t Go It Alone

  3. Only the Size of your Heart Matters

  4. Life’s Not Fair - Drive On!

  5. Failure Can Make You Stronger

  6. You Must Dare Greatly

  7. Stand Up to the Bullies

  8. Rise to the Occasion

  9. Give People Hope

  10. Never, Ever Quit!

Now I understand that this is supposed to be a small, pithy, easily digestible book and not a grand treatise, but is this the best a four star admiral can give? It could be forgiven if he went into more depth to say something unique, but most of his success was this straightforward and the ensuing description added little to no nuance. He entered the military, did what he was told, suffered setbacks like a parachuting accident that left him immobilized for a year, but slogged through the hard times and was rewarded by the institution. Reading the book, there was only one instance where he implied the system screwed him over, but even then everything fixed itself up in the end.

Still, the book’s subtext was teaching other lessons. Instead of taking the lessons above, below are the actual lessons he was teaching, and anyone fifty years or younger will realize why they don’t work anymore.

• Work Hard and You Will Be Rewarded

  Trust the Institutions

  Make Your Values Applicable to Everyone

  Smooth Out the Rough Edges of Life

  Believe in Pleasant Half-Truths

  The Boomers Figured It All Out

The Silents and previous generations tended to fall into two camps. There were the ones who would talk of their life in vivid detail, especially war stories. The other would say nothing about their life, especially their war experience. The ones who talked did so in a more rough, personal way. They say they did X because of their code, or talked about the circumstances that led to their decision. The boomer generation likes to talk more in universal terms, that the basis of their decisions rested on rock-solid principles applicable to everyone in every circumstance. While the boomers often pride themselves on fighting the man, they were actually the most aggressive advocates of trusting the system.

A lot of the book pertained to his SEAL training, where there is a clear success and failure state. Swim over to the island in time and you succeeded. Set the detonation charge in the right place and you succeeded. There were clear orders with clear victory objectives. When one works in a high-trust society, this is how things work. Whether in the military of the most mundane of jobs, there are objectives for you to complete and the agency to get them done. When a society disintegrates, one has to deal with more unspecified expectations, more politicking, and more double-speak regarding what you are supposed to do.

While I’m sure McRaven was avoiding throwing people under the bus, one gets the impression throughout the book that the leadership he received was impeccable. There never seemed to be a bad actor who wanted to use him for personal gain, nor was there an aspect of the system that seemed to be dead-set against him. There was never a word about bean-counters who made him jump through nonsense, nor dealing with a sadistic or corrupt superior. If they said you were going to get a marshmallow if you persevered, you would get a marshmallow.

Even his advice about taking risks rested solely within the system’s metrics. His example dealt with an obstacle course and the risk of going head-first to get a faster time. And this was after he was told to do so. In his example of life not being fair, his example was a drill sergeant that made him do additional workouts just to instill that message. Never is there the message that the system itself might screw you over, that it would be an impediment to success. There is just total trust.

The most amusing portion of the book was recounting his encounters with Saddam Hussein under the chapter “Stand Up to the Bullies”. You could feel the seething he never broke Saddam, and the dictator had an aura that terrified everyone around him even when in handcuffs. Even worse was the hypocrisy, since it was clear he verbally and likely physically mistreated Saddam long after he was no longer a threat and was awaiting a show trial. He was a war on terror advocate through and through, and even after seeing his adversary was different than the caricature in his mind didn’t update his priors.

While Saddam clearly was a ruthless ruler, you got none of the ambiguities and conflicts of an imperial power forcing its will half-a-world away. When reality did not comply with your good vs. evil paradigm, you forced reality to conform with your mind. While McRaven tried to belittle the reader’s view of Saddam through his unkempt cell and bed, Saddam came across as far more formidable than McRaven, and I think the old Admiral knew it. “Stand Up to Bullies” indeed.

While there is little direct political pandering, McRaven had the classic idealism of equality and freedom that lionized the civil rights revolution. He was gung-ho about the war on terror bringing "emancipation” from the clutches of such people as Saddam Hussein. He is a true believer through and through. He believes in setting the same rules for everyone, and no one should be judged on a different scale. He praised Nelson Mandela, Martin Luther King, and other secular saints with the same piety an Orthodox Priest bestows the name of St. John Chrysostom. The values did not just correlate to his culture and place in time, but was universal to all places in all times. His worldview showcased the all-encompassing secular religion of the American Empire. He wasn’t fighting for a distinct people, but a value system.

Anyone who lives in our current age knows that working hard doesn’t necessarily mean success, and especially not if you follow currently laid out rules. Strivers are finding their prospects dwindling by going the standard elite college route the current system recommends. The institutions are increasingly unable to do their job, and constant roadblocks inhibit anything from getting done. We have become deracinated and out once universal values are being used against us. It’s very clear the boomers did not have everything figured out. I don’t have to go into detail. We’ve all seen it.

Everywhere At the End of Time

As I have entered my forties, I’ve experienced all the obvious pathologies of aging. I’m having trouble keeping up with the young bloods on the Racquetball court, my weightlifting has to be more reserved to avoid injury and, most frustrating of all, my ability to learn new things has receded. I’m finally checking off a bucket list item of playing a musical instrument proficiently, and can’t help but notice my kids progress much faster than me with equivalent practice times. Their minds are simply sponges. As the political climate has rapidly changed, it has required conscious effort to analyze and understand the new situation without relying on older mental models of ten years ago.

It’s not a coincidence that most people’s political viewpoints ossify in their thirties and forties, becoming encased in a moment of time. In a world not engulfed in rapidly transforming cultural and political realities, this was still fine. There was also an understanding that you’re too old for this shit, there needed to be a passing of the guard, and make the transition from leader to the more humble role of passing down practical knowledge to the ascending patriarch, playing with the grandkids, and hoping you don’t turn into a burden.

This isn’t universal, and while Trump does a lot of boomerisms, even in his eighties he can pivot. You can see the mental toll it takes though. Everything is just harder. You must resist receding into the same thought patterns. You want to fall back to the security blanket of the tried and true, and mental fatigue is a constant burden.

When you believe you figured it all out, not just in your lifetime, but every lifetime, the humility that is supposed to come with old age gets thwarted. No matter how accomplished you were, and no matter your mark in history, you have to accept fading into the twilight in order for your people to continue on. In our current youth obsessed society, there is no transition to becoming a respectable elder. Instead we have a gerontocracy having trouble coming to terms with their own mortality.

In a world of systems and universal abstractions, the boomers were the first American generation that didn’t see themselves as a distinct people in a distinct time, but a sort of immortal pantheon of gods who figured out the mysteries of existence. The Civil Rights revolution was a permanent artifice of the cosmos, the system that treated them well would never fail, and the high-trust society they lived in was forever regardless of its inhabitants. Sure, there would be bumps here or there, but the foundation was immovable. Just follow the pleasant sounding platitudes and you will be fine. McRaven’s book distilled this into its essence.

Unfortunately, this sort of unmooring from time and place isn’t the output of an enlightened mind, but dementia. As human beings, we can use certain universal concepts as a sort of guiding light, but our actions always have to be placed in the context of what we see with our own eyes. Nostalgic “lessons” don’t work when the conditions in which they worked don’t exist anymore. That doesn’t mean they’re completely wrong, but they are missing some critical subtext.

Stage 2 dementia is explained as “the self realization and awareness that something is wrong with a refusal to accept that. More effort is made to remember so memories can be more long form with a little more deterioration in quality. The overall personal mood is generally lower than the first stage and at a point before confusion starts setting in.”

Note how this pertains to current discourse, and not just to boomers. There are a plethora of Millennials and Gen-Xers that act like this online. They refuse to engage with political realities. They run to talking points from over a decade ago. They have a hazy, idealized version of the past that they can’t link with current realities. They know something is deeply broken but wring their hands about someone doing anything about it that’s not according to internalized “rules”. Unfortunately, it only gets worse from here.

At stage 3, “We are presented with some of the last coherent memories before confusion fully rolls in and the grey mists form and fade away. Finest moments have been remembered, the musical flow in places is more confused and tangled. As we progress some singular memories become more disturbed, isolated, broken and distant. These are the last embers of awareness before we enter the post awareness stages.”

This is where we reach political incoherence. I would argue many online pundits have already entered this stage and have written the same cycle of articles talking about the terrifying resurrection of The Austrian Painter or how the Free Market will save society for years. The talking points are separate from whatever is being discussed, used as talismans against people who are impervious to its magic. They only have vague recollections of what once was but no idea of how such the society actually worked.

Then we see stage 4 through 6, a point of no return, and all is lost.

When you see such a person, whether it be your grizzly political pundit or your dad, the right reaction to such degradation is not anger, but pity. They are not going to change. Just as the agony of dementia can only be contained, not cured, you’re not going to cure someone unable to see reality anymore. Eventually we won’t be able to catch up either. While I personally hope to be a better beacon in my old age, I can’t guarantee it. It’s a constant battle we are destined to eventually lose. The ravages of time comes for us all.

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