on having enough

this is my beautiful life.

In the 1980s, when I was a young man, the median age at which people were able to buy their own home was 32—just out of my reach. Now it is 54. The goal line moved while the Boomers were playing the game. The problem is even worse for those younger than I.

We were all promised that if we worked hard and played by the rules, a day would come when we could relax and enjoy ourselves for a meaningful period of our lives before dying—called retirement. With the judicious exercise of a little fiscal discipline during our working lives, we could enjoy a time when our needs are met and demands are few. Sixty-five was the rule-of-thumb age when all that would probably happen for Boomers.

Now I am faced with deciding whether I have enough money to retire in a society that seems to never have enough of anything. Bumper stickers and magazine ads tell me I don't have enough money to retire, I'm not young enough for Sydney Sweeney, I am not muscular enough to be seen shirtless, I can't climb enough stairs to keep my cardiologist from scribbling down notes after he asks that question.

I don't produce enough dopamine to enjoy working, I don't show some people enough respect, I'm not suspicious enough of others, I don't read enough, I don't watch enough TV or movies, I don't know enough new music, I'm not buying enough wine, I don't eat enough greens, I'm not getting enough steps in.

I'm not getting enough sleep, I'm not doing enough work, I don't dress nicely enough, I don't hug trees enough, I don't get out enough, I don't know enough about the Cowboys' chances this year and man, I really don't love Jesus enough.

How am I supposed to know when I have enough of anything?

Well, I've had enough of this.

Social Security and Medicare. What delightful euphemisms these were. Keeping your place in society as you age, and being cared for medically. Those notions feel so safe and warm. The programs themselves don't actually make you feel safe or warm, but they do have really nice names.

Money doesn't make me feel safe. People do. My sense of security comes from my personal and community bonds, not money. If I can't pay my rent, I really don't give a fuck about the effect that has on the well-being of the private equity shareholders invested in the corporation that houses me.

I pay my rent so I can stay connected to the community I live in and to the people in my life. Losing my apartment would disrupt those connections—that's the real threat to my security. I don't care much about the things in my apartment beyond their utility in maintaining my bonds to other people.

So, in retirement I will prioritize strengthening my existing social bonds, both community and personal, and forming new ones. That helps me answer questions about where I should be.

In my distress, have I been obsessing over the wrong things? I have been trying to answer an unanswerable question—do I have enough money to live an unknown period of time in an increasingly uncertain future? What is enough money? One dollar more than you spend? The question misses the point.

The real question is: will I have enough friends if I stop going to work? Will I still feel connected to a community?

Fortunately, my answer to that question is fuck yes. I will have to develop some new habits to stay in touch with a handful of people from work if I stop going there (but I've seen them all outside of work for some reason, so those new habits won't be that novel).

I have been investing for my retirement my entire life.

I have been sometimes investing in, sometimes neglecting and periodically robbing my shamefully tiny 401(k) since I started it in the 1990s. I thought my poor performance as a financial investor was a problem. I realize now I was moving investments from one place (the bank) to another (my friendships). Over the years I have only robbed my retirement accounts to fund trips to see important people for meaningful reasons.

I've come to realize that I'm set for my retirement from healthcare because I've been investing heavily in my friendships for decades. I feel like a friendillionaire. I am definitely rich in social connections—most of you are reading these words. You reside all over the US, here in NYC, and in various other parts of the world. I'm a success in this regard.

This realization makes my uncertainty about money so much easier to tolerate. Of course, it is still possible that I will run out of money, but it seems far less possible I will run out of friends. Having friends can get you through a time of no money better than having money can get you through a time of no friends.

Yes, I stole that line from a 1970s stoner axiom about weed, but it applies just as much. As I ponder the relief that this shift in thinking brings me, I think of the notion of cruel optimism. Lauren Berlant wrote a book with this title.

Cruel Optimism

Cruel optimism is the condition that exists when what you want, or the pursuit of it, hurts you. Berlant illustrates this by writing about "the good life fantasy"—the promise that diligent work and playing by the rules will enable financial stability, job security, political and social equality, and durable intimacy.

My father was 28 when he bought his first home. His new wife (my mother-to-be) was 23. His Navy career had ended not as planned; he was working as an engineer in the defense industry. His family wasn't helpful—he did this all on his own, with money he had and could borrow affordably. His family wanted him to stay home and participate in the family grift (his father was an ethically-compromised sheriff in rural Texas) and they resented his desire to go to college, feeling as though he was taking a superior, snooty attitude by wanting more education. He was kind of the Michael Corleone to his brothers Santino and Fredo.

My parents' home, before I was born, was in a comfortable part of southwest Dallas. They had me about seven years into their American Dream marriage. When I was a toddler they bought a larger house with a larger yard on a creek about a mile away. Dad was 38, Mom was 33. It was a bigger, nicer house, in a better neighborhood, close to the elementary school I would attend. This was that promised upward mobility in action. John F. Kennedy was president.

The American Dream was working out for them except for the parts about a happy family, a stable home life, and durable intimacy with a spouse and kids who adored him.

My mother told me later (I have no idea why) that they decided to have me to save their marriage. That didn't work either. In fact, my parents having a child was a significant problem for all three of us. Five marriages for each of them followed my birth—three of them to each other.

I doubt they would have married each other three times without the desire to avoid the public shame of a broken family (a prima facie failure of the American Dream), which was still a thing in the 1970s. Without a child, they could have just gone through their breakups and reconciliations without involving the courts and lawyers. They could have kept their swinging single friends, Mom could have easily gone to college (her secret desire at the time), and led an unconventional yet more serene existence. They could have been that fun, childless couple who can't seem to live with or without each other.

Believe me, that would have been better (yes, I know I also wouldn't be here, but this is a counterfactual thought experiment, not a manifesto of desire for nonexistence). They both would have lived happier lives if they had patterned their life choices using a template other than the American Dream.

For my parents, the American Dream was cruel optimism. The idea that they should continue to invest in a plan that was never going to work for them was what caused most of their problems as I was growing up. My father had a substance abuse disorder; my mother had a personality disorder. They both went untreated, though my father did stop abusing alcohol when he was my age (mid-60s).

He stopped because his last partner, whom he wanted to marry, required it of him. He also had to profess faith as a Catholic. I have no idea if he sought annulment for his previous four marriages. She ended up marrying him for his money, and when he died she succeeded in seizing a sizable portion of the money my father wanted me to inherit, which would have enraged him.

But I digress. Instead of finding fault with the world around them, my parents should have sought help for their serious psychosocial disorders. These conditions seriously disrupted both of their lives and mine, repeatedly, and also weren't entirely of their making, nor were they something they could fix alone. Both of my parents were abused as children (in different ways). This was likely responsible for part of their intense lifelong bond to each other.

They lived in Dallas, Texas in the 1970s. Help was available, but going to a shrink was not part of the template for the American Dream. Attending AA meetings and professing powerlessness over alcohol was viewed as a character deficit. Being "in therapy" or openly professing alcoholism meant you were perhaps dangerous, maybe untrustworthy and possibly unemployable. Who puts on that T-shirt?

Norman Rockwell didn't paint people on the therapist's couch; Jerry Lee Lewis didn't write honky-tonk ballads about enjoying tea and cookies with friends on Saturday nights. To live this way would have meant giving up the plan that they convinced themselves they should follow to be happy—the American Dream.

The optimism they had—the notion that if they worked hard, saved money, raised a family, and played by the rules everything else would work itself out—was what kept them from simply looking at their lives and doing what needed to be done.

Flawed as they were, they would have wanted me to take a lesson from all that. As difficult as it was to be their only child, I am taking that lesson.

A More Concrete Example

I have a more concrete example of cruel optimism.

Until my last move in May 2024, I have always made a place in my home for houseguests. Maybe I only had a couch that folded into a bed, but I was always ready for someone to come and stay at my place.

At my previous home, I devoted an entire room to this. I bought furniture, bought the supplies I would need in the kitchen, the extra towels, etc. I spent about $1,500 buying things I did not use or need so that I could host guests. Never mind that I almost never have houseguests. That fact did not enter my mind. I needed to be ready for houseguests to enjoy this home. This was the cruel optimism: I have friends, I visit my friends, surely they will visit me.

In the twenty-four months that I lived there, two people spent the night. For the $1,500 I spent on furnishing and enabling the guest room, I could have put them up in the best hotel in the area, taken them out for the most expensive dinners, and still had a few hundred dollars in change.

Not only that, I would have saved all the time I spent and trouble I went to setting up the guest room, and I would have had an extra room in my home to enjoy as an office or studio. When I moved, I gave away all of that furniture. My new place did not have a guest room.

The real value I got from spending that $1,500 (as well as the additional expense of taking the time and energy to both set it all up and to tear it all down two years later to donate to charity) was realizing that I do not need a place for guests in order for me to enjoy my home. In fact, where I live now has a lovely bed-and-breakfast within walking distance should that need arise while I am here.

Cruel optimism cost me that money and expense. Is it costing me my retirement now?

I am thinking hard about that. What guarantee do I have that working longer and having bigger numbers in the bank means I will enjoy the rest of my life more than if I just get started on doing what I want to do now?

None. Nada.

What guarantee do I have that getting up each day in the morning to sit and write until I can't anymore will make me happy? Well, I did that for the month of November 2014 to write my first book. I was happy as a pig in slop.

I know what makes me happy. It isn't the American Dream.

Thanks, Mom and Dad. I learned.