Dear Friends,

If there has been a unifying theme to this weekly newsletter since I started ten months ago, it has been to look back at changes over the past 25 years since I graduated from high school to imagine the next 25 years until I retire. There is a term for this stretch of life between 40 and 65, of course, and my fellow “elder millennials” are getting our first taste of it.

But I don’t feel middle age. I relate entirely to Jennifer Senior’s essay in The Atlantic, which describes why, after a certain point, “you always feel 20 percent younger than your actual age.” Though 53 in biological years, Senior says she is suspended at 36 in her head. But she didn’t always feel this way:

I felt 40 at 22, when I barely went to bars; I felt 40 at 25, when I started accumulating noncollege friends and realized I was partial to older people’s company. And when I turned 40, I was genuinely relieved, as if I’d finally achieved some kind of cosmic internal-external temporal alignment. But over time, I rolled backwards.

That’s me! I was an old soul in a young body with mostly older friends … until the past few years when I started to feel younger, look older, and hang out with mostly younger friends. [Footnote: Surely this has something to do with not having children. Increasingly, I’m hanging out with folks in their early 30s and mid-50s — on both ends of peak child-raising.] In my head, I’m in my mid-30s. But then occasionally, I am startled to discover that the middle-aged, graying man staring back at me is my own reflection.

This is the first of a two-part newsletter about the Millennial midlife transition. First, I want to look at what has changed about society in how Millennials experience midlife today compared to how our parents, the Boomers, experienced it 20-30 years ago. Then in part two, I pull out my vulnerability pen to share some reflections about how I am changing as I settle into midlife with the hope that you might relate to some of it, and maybe it will even prompt a conversation.

Basically, in part one I show a lot of graphs to argue that we should, on average, be complaining less. In part two, having complained about complaining, I try to get in touch with my feelings to chart a path toward a meaningful midlife transition.

The myth of the broke millennial

It’s boom times for cultural commentary on Millennial middle age. [Footnote: From Bloomberg: “Poor, busy millennials are doing the midlife crisis differently.” From Insider Magazine: “Millions of millennials could soon enter a midlife crisis. But they're going to spend and divorce less — and value experiences more.” Mashable warns its mostly Millennial audience that we are entering our “decade of despair.” Harper’s Bazaar has a whole series of middle-age commentary under the most generic of headlines: “40 is the new 40.”] Rising above the din, it was Jessica Grose’s essay for the New York Times that went viral: “Millennials are hitting middle age — and it doesn’t look like what we were promised.” If there was a “promise” about Millennial middle age that didn’t come to fruition, Grose blames the bestseller from 2000, “Millennials Rising: The Next Great Generation”:

What the authors could not foresee was that there wouldn’t be just one crisis. There would be a series of cascading crises, starting the year after their book was published. There was the fallout from the dot-com bubble burst; then there was Sept. 11, followed by the Great Recession in 2008; then came the political chaos of increasing polarization, the specter of climate change, and finally, the Covid pandemic.

That is quite the 20-year stretch! No wonder (AT)Anne Helen Petersen and (AT)Jill Filipovic were inspired to write bestsellers at the end of 2020 to explain, respectively “How Millennials Became the Burnout Generation” and “How My Generation Got Left Behind.” You know the story even if you haven’t read the books:

But do these claims about Millennial misfortune truly hold up? In this month’s Atlantic, Jean Twenge debunks each of the above four bullets:

In fact, “by 2019, households headed by Millennials were making considerably more money than those headed by the Silent Generation, Baby Boomers, and Generation X at the same age, after adjusting for inflation.”

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“Millennials’ homeownership rates in 2020 were only slightly behind Boomers’ and Gen Xers’ at the same age: 50 percent of Boomers owned their own home as 25-to-39-year-olds, compared with 48 percent of Millennials, hardly a difference deserving of headlines or social-media memes.”

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