The virtue and private sorrow of Boomer Man
and why I'm not ready for him to leave
This is part 3 of a four-part exploration of the inner life of men of different generations.
Part 1 - late Millennials
Part 2 - Gen X
Part 3 - Boomers (this essay)
Part 4 - Zoomers
The trait that stands out about Boomer Man is how genial he is. He makes small talk with the Ethiopian lady who rings him up at Trader Joe’s, compliments his neighbor’s summer landscaping, and makes funny faces at small children on airplanes and in restaurants. He goes out of his way to help elderly people, which at this point means people five years older than him. He was socialized in the softer, more civilized norms of 1950s and ‘60s America, and it shows.
As I write about Boomer Man here, he represents a composite of many boomer men I know and not any specific individual. Examining him with empathy is complicated because it brings up some of my own psychological baggage. My dad is on the oldest edge of boomer men, and we do not have a good relationship. After years of strain, I ended contact with him following my brother’s funeral nine years ago. It’s a long story.
On the other hand, my partner is on the younger side of boomers, and we have a great relationship even though it is unorthodox in some ways. My dear friend Steve and countless other friends, mentors, and contacts are boomer men as well.
Notwithstanding these positive relationships, my daddy issues and petty generational resentments sometimes rear their head. So as I study this composite Boomer Man, I have to take a deep breath first. Some of the baggage I exhale includes the little boy in me that wants his approval. Or an assumption that his generation has played life in “easy mode” compared to my own. Or jealousy that he has a pension, or that he bought his multimillion-dollar home for 12 raspberries in 1981. It feels pathetic admitting all of this, but it would be weird and unfair to project my issues onto him.
Thankfully, Boomer Man doesn’t notice my baggage-clearing breath. Why would he? Outwardly, everything is hunky-dory in Boomer Man’s world. Everything is peachy-keen. His world is Mayberry, and he is Andy Taylor. Never mind that today’s world is far from Mayberry, and he is not the town sheriff.
But beneath Boomer Man’s Howdy Doody geniality lies a well-concealed sorrow. Boomer Man would rather not look at it. He treats it as a secret. Within this sorrow is a begrudging awareness of his mortality, unresolved questions about his legacy, fears about the future, and fragments of a spiritual crisis. When these emotions surface, Boomer Man dispels them by verbalizing how grateful he is for his life — for his family, career, marriage, and home. He lights up when he talks about his grandkids, noting his good fortune.
Health issues are creeping up on Boomer Man, as they are with many of the boomer men in my life. It may be a heart issue or a knee replacement or a progressive disorder. Boomer Man actively addresses these issues — and thank God for modern medicine! — but he realizes his time on earth is slipping away. He says with a quivering lip that he could die tomorrow and feel satisfied. In conversations, he repeats sentences like: Time marches on and Getting old is better than the alternative.
Boomer Man sometimes wonders: What is my place in the world now? He occasionally feels as though his relevance is slipping away like sands in an hourglass, bringing with it a sense of vulnerability. His closet mirrors this liminal sense of identity, filled with clothes he no longer wears — the light blue Brooks Brothers shirts, leather shoes, dark suits with full cuts, and ties hanging like award ribbons from another life. He realizes he should give a lot of it away.
Then again, Boomer Man is definitely not done. Sure, Boomer Man likes golf and savors his free time, but he is not retired. He is not a retiree. He has projects. He’s involved. People still thank Boomer Man for the ways he’s helped them, how he’s touched their lives. Boomer Man is a giver, not a taker. He still has a lot to offer the world, and this is true.
Among my boomer men friends, many remain highly impactful. They chair boards, make valuable introductions, and undertake innovative projects. Some still work; others incubate businesses, write, or invest. For some time, I was an anti-gerontocracy crusader, a stance partly intended as a middle finger to my dad. I still believe it is a problem when 80-year-olds refuse to give up power (see Biden, Trump, Pelosi). However, I’ve had to add nuance after coming to appreciate how valuable boomers can be as tribal elders, even into their late-60s and 70s. There is nothing better than a “good boomer” who skillfully operates at his altitude.
Regardless of whether he still works, Boomer Man’s natural habitat is in his living room or office, where he sits in his comfy chair reading the newspaper like Ward Cleaver, his coffee mug within arm’s reach. Cable news plays in the background, and he flips between CNN and FOX News. He’s not conscious of the cable news noise pollution, which is a source of tension between me and some of the boomer men in my life.
When I moved to Florida several years ago, I befriended several boomer men who watch Fox News religiously. In hushed tones, they would share political hot takes that, to my ears, sounded like recycled ideas from rightwing Twitter a decade ago or even from The Stanford Review in the ‘90s. Jeff, did you hear about the latest woke excess in schools! With some vanity, I imagine a supply chain of ideas emanating from my past political peers, through Tucker Carlson and other Fox hosts, and onto these freshly radicalized, Trump-supporting Fox Boomers. An old version of me would’ve seen this as a victory, a conquest of boomer hearts and minds. But the new me is taken aback because time has marched on and my perspective has evolved. It’s like being a fashion designer and seeing your trendy collection from a decade ago show up in Kirkland-brand clothes at Costco, except with the weight of politics.
Because of these dynamics, I sometimes need to establish boundaries around politics with Boomer Man. When he wants to say something about the latest cable news segment, I have to remind him: I saw that on Twitter four days ago. Or, Can we not talk about politics? I do that a lot online. This doesn’t mean Boomer Man lacks new or intelligent insights — he often has them. It’s just that his approach to political discourse is different. Cable News and Twitter are the Mars and Venus of political media.
Boomer Man views his childhood as straight out of Norman Rockwell, even if it was tough. He grew up watching Mickey Mouse Club, Sky King, Captain Kangaroo, and Roy Rogers. He cried during Lassie. He was shaped by Vietnam and Watergate, Woodstock and the Partridge Family. He remembers when Neil Armstrong planted a foot on the moon, when bell bottoms were cool, and when Reagan was first elected.
As Boomer Man looks at the world today, he sees beauty and grace and yet feels troubled by a world that seems to be spinning out of control. What kind of society is he leaving his kids and grandkids? How will they navigate the challenges ahead? It is not his fault he was born during the greatest stretch of peace and wealth creation in history. Will he leave the world a better place than he found it? He thinks about this question a lot, even though it’s largely out of his control.
Steady, reliable, and a Good Citizen™, Boomer Man’s greatest fear is becoming dependent on others. He’s always been the provider. It doesn’t occur to him to ask for help, and the idea of it conflicts with his identity. Boomer Man knows he needs to learn how to receive, how to surrender. But now is not the time for that, not yet.
In the abstract, I sometimes feel Boomer Man is holding things back and grow impatient with his continued presence on the world’s stage. But when I consider the boomer men in my life, I have to confess that I don’t want them to go. They are holding things together much more than holding things back. I value them. I’m not ready to lose the connection to "Leave It to Beaver" America that they represent to me.
The truth is, I need Boomer Man. Maybe we all do more than we are willing to admit. And yet, when Boomer Man does eventually ride off into the sunset, I know I will be ok. I know we will carry on. Kemo Sabe will be gone but never forgotten.
Special thanks to for pushing me to make this essay more personal.
I am a Boomer. Staying engaged and fighting via local politics to preserve the peace and prosperity for my grandchildren. Paradoxically I have been shocked to be reviled by the woke Millennials, even the ones I raised, but am finding allies among Gen Z. God only knows whether my young Grandchildren will ever comprehend my love and concern for them as their parents poison their minds with hate because “inclusion.” I feel like you nailed the Boomer zeitgeist. We were inculcated with love of God, country and family. We were free range kids- no helmets or car seats. We organized our own games and agreed on the rules. We trust easily and anger slowly. I don’t think we are the generation that had it the easiest. I would apply that to our children, the participation trophy generation. I blame us for contributing, through our coddling, to the narcissism that pervades the culture today.
As an 87 year old born in 38 I remember WW2 and Benefited from wealth generated during the 60s, I see bits and pieces of myself in your essay. I saved all my ties, but gave away my wingtips. Am saving 3 Brooks Brothers suits for my son Sebastian. Have a house full of art, books, that my three sons will have to divi up.
My health is great, but the country’s is not. The Constitution is being shredded, and FBI, JD, and court system and being politicized.
Thank you for describing for me where I am too.