Millennials of a Certain Age

If you, dear reader, are a Millennial of a certain age…then this is for you. I promise not a single word was written by AI. Just my decrepit, aged Millennial brain. Maybe something of value lingers among the years.

Millennials are in a tough spot. In a way, we always are. We’re in the prime years of contribution while society undergoes massive, accelerated disruption. For many of us, these disruptions are not positive and we know it.

The world we grew up in fades faster every day. A bunch of nerds and financial mercenaries have plundered the quality of life we came to know. Technology, the promised democratizer, has exacerbated wealth disparity and balkanized our communities. Dynastic politicians have been replaced by bipartisan keyfabe clowns who openly plunder our resources. Mental health is deteriorating at scale. We aren’t even fucking anymore. Life wasn’t supposed to be this way. Mufasa told us that everything the light touches is our kingdom. The shadowy place was beyond our borders.

Elbows out, ladies and gentlemen.

I only speak for myself. I’ve spent the last few years making mistake after mistake stemming from what I consider a Millennial mindset. I’ve spent a lot of time considering this mindset. In this piece I’ll cover 1) what it is 2) why it’s important but flawed and 3) what I did about it. This is only what’s worked for me and it’s mostly about thinking. Feeling is another topic entirely.

*What is the Millennial Mindset?* If you’re a Millennial you already know the answer. “Work hard, good things will happen, the moral arc of history bends toward justice.”
** We were told and sold that going to college would yield a good job¹, that globalization and the ‘information super highway’ would lead to prosperity and that hard work alone leads to good outcomes. That may have been true at one point. I believe it was. It is not true anymore and that’s causing a lot of cognitive dissonance.

There’s good reason to have once held these beliefs tightly; millennials were raised in the pleroma of the neoliberal world order. Every single day preceding September 11th, 2001 was a gift to the human experience. Even witnessing and intellectually understanding the realities of institutional rot, I struggle to internalize it. I saw a world where institutions presided over order and growth; just look at my parents! My childhood! It worked and maybe it’ll work again, I hope.

*Hope is not a strategy* Having had these positive experiences is exactly what will lead us out of this rut. We are, for instance, the only working-age generation left that has the bicameral experience of a world rich with abundance and a world descending into scarcity. (Would love to include GenX but I can’t find them.) Our values are inherited from a world that worked, on average, well. If we want the world to work well again, we need to hold on to the parts that worked and evolve the rest.

The issue in our mindset is that big chunks of our identity require society to uphold promises that will never be fulfilled. In the absence of those promises, many are left wondering who, exactly, we ought to be.

This kind of retrocausal attribution happens all the time; think of the lucky entrepreneur who strikes gold, only to tell the tale that it was all due their hard work. Of course it was the hard work. It has to be; the truth that life is mostly random and utterly uncertain is too hard to hold. Instead, we derive meaning from current events which we then apply backwards to our own stories. We’re like boats being driven by our wakes. E.g. Good outcomes infuse your path with meaning. A decent job says you made the right use of your time. A growing economic pie means you trusted the right people. If society fails to deliver on any one of these, it challenges deeply held beliefs about how we exist in the world.

It’s not uncommon or unhealthy to live with some outsourced beliefs. We’re introjected at birth from teachers, parents, employers, friends and politicians. But as some of them let us down, the imperative for articulating and holding a principled, independently reasoned point-of-view becomes more urgent. Many of us can sound like we’ve done that work, but I tend to notice a generational anxiety undergirding it that betrays a desire for the validation our upbringing conditioned.

These beliefs are soaked deeply in the minds of millennials . They’re not only the values that endure from how we were raised, they’re familiar. Even misery can feel friendly when it’s familiar.

The other big challenge, for everyone, is today’s intensity of uncertainty. This intensity is a function of economic unpredictability, the pervasiveness of low-trust interactions and the cultural acceleration created by rapid, society-wide deployment of new technology. I see this in my own life and hear it from friends across all walks of life. It’s cross-generational and cross-demographic. The one exception may be the Boomers who paradoxically face a different set of problems as the generation that spawned some of these issues.

Like every generation before us, we need to adapt. Here’s what’s worked for me.

”Hi, I’m a millennial and I don’t know how to think".”
Essentially I had to admit the possibility that I didn’t really know how to think for myself. Instead, most of my thinking has been agreement. My opinions were therefore reasoned out of the relationships that served me. It could have been work relationships. A partner or parents. Maybe communities of identity. Whatever it is, it wasn’t independently reasoned. And because I hadn’t roamed the wilderness to earn those thoughts, I didn’t understand how to reason backwards from them. It made life feel easier, even normal. The old world worked hard to reward us for agreeing with it. The new world doesn’t reward agreement; it demands a point-of-view.

*Point-of-view* A point of view is not a talking point. When I say point-of-view, I mean a clear frame with unique elements that include:

• Defensible mental model: A mental model means you’ve organized a set of theories about how the world works so that you can anticipate how things will work in the future. A very simple mental model might be, “The house always wins.” If you believe this, you will make your bets in a very specific way and avoid many other types of bets. Another example might be, “European craftsmanship is the best on the planet.” If you believe this (and you should) and can afford it, you will prefer clothing or cars made in Italy. A mental model isn’t something you arrive at; it’s something you start from. In this way, every observation and experience ought to feed a mental model that helps you operate in the world by being a better predictor of outcomes.

  For Millennials, a mental model is often, “I’ll work harder and good things will happen because I will be recognized for my effort.” This is outdated. The paradigms of work have changed. Working smarter is more important than working harder. This is especially true with AI. In many cases, too, being aware of sharp elbows is more important than looking for an extended hand. Maybe always true but not as transparently so.

• Contains tension, turns many things down: A good point-of-view says ‘yes’ to one thing while saying ‘no’ to many other things. Let me say this loudly to the Millennials in the back who were taught to be agreeable: a good POV means you disagree and debate.

  An example of this might be, ‘Automation is good and should be pursued maximally.’ This means you are saying no to human labor, the sanctity of meaning many find in their work and the social fabric that underpins economic productivity. Someone who believes this may believe automation is good because it’s a yes to human leisure and the liberation of human time for better endeavors. Nobody knows the answer yet, but the POV votes for one thing and against others.

• Contains theory of the mind: A good point-of-view has anticipated the motivations and reactions of those it will encounter such that it will survive them. Politicians are good at this because holding elected office requires leaders to meet disagreement without conceding their POV. Theory of mind is similar to a mental model in that it’s about how well you can simulate and prepare for reaction.

  You’ll find ToM anywhere debate is practiced. Courtrooms are a great place to see it because lawyers anticipate their opponents’ arguments and advance frames that defeat or diminish the importance of competing frames by virtue of their structure, not just their substance. It took me a long time to learn that distinction. For example, if you prevail in a courtroom with the frame of moral justice, and the other side had advanced a frame of legal technicality, then you will win even if the details of the law are against you. Structure over substance.

• Contains status: POVs establish status by virtue of the fact that you have to successfully defend it in the world. Success means someone else will lose. This isn’t about who is a better person or who has more value. That’s above our pay grades. This is about the competition of ideas. Some people will hold winning POVs; others will lose. If you feel uncomfortable with any one of these, you’re likely a Millennial.

Those are just four of the elements I’ve been used to test my own thinking. Very often my thinking is insufficient and I have to further develop an aspect of my ideas. This is a good thing. Iteration means you are reasoning independently.

*No One Way* Part of the challenge is that there isn’t any one way you should move forward. That’s an obsolete mindset. Old programming. You have to create your own. That’s hard work at midlife.

I wrote this because I’ve made a ton of mistakes and I’ve had this conversation with many 40-something Millennials who all share the same befuddled confusion on why they aren’t where they want to be and how to move forward. These are the things we talk about.

I don’t know the answer because there is no answer. Life is empty and meaningless until you realize that you get to infuse it with your own well-reasoned meaning. What an amazing gift. Go do it.

Eat, Love, Pray
This isn’t about self-care or finding your bliss. I’m talking about self-authoring logical and internally consistent beliefs about you and the world in which you exist so that you can take another step more confidently. By definition, that kind of work ought to increase the connection between you and your community, not result in trotting off to Southeast Asia to find yourself. I’ve done that. Turns out that wherever you go, there you are!