Yep, I'm almost 50
coming out of my middle-aged closet
In part of my brain, I am still 23 — twinkish, fresh out of college, and brimming with infinite possibilities. Back then, I lived in an English basement apartment in Washington DC’s Dupont Circle, drove a boxy red 1991 BMW, and was debating between grad school and starting a business.
In reality, I have creeping crow’s feet, rapidly spreading salt-and-pepper hair (which I kind of like, to be honest), dated cultural references, and a long trail of lived experiences. My 30th high school reunion came and went, and some of my Mormon classmates are already celebrating their first grandchildren. Oh my heck!
I am middle-aged. I can no longer deny it.
Ever so gradually, my self-image is coming around to my midlife reality, like a prolonged software upgrade with periodic glitches. As if to stomp out any lingering delusions, I recently bought my first pair of reading glasses. They sit on my nose like an imperious king on a throne, declaring, I hereby crown you an older person.
In a few months, I’ll turn 50 and, damn, I am embarrassed to admit it. Psychologically, approaching 50 feels harder than approaching 40 ever did. It’s like coming out of the closet as an old person. While it’s tempting to LARP — role-play — as a younger me, it seems more honest to own my age. When Boomers say stuff like “70 is the new 40” and cling to power too long, Biden-style, I realize that’s not the path I want to take.
Turning a half-century-old forces me to confront certain realities: I’m getting older, I’m mortal, and I haven’t made much of a dent on the world. It’s like the middle-age version of twink death, a loss of physical appearance and identity as “young.”
And yet I like myself at this stage of life. There’s something grounding and settled about life beyond midlife crisis. In shoe terms, it’s like Top-Siders. In house terms, it’s like a Craftsman with a large front porch: comfortable, functional, and stylish in its own way. Inwardly, I feel more content, humble, and self-assured, even as outwardly my life remains a work in progress.
My 20s and 30s were “work hard, play hard” years that were fun, focused, and productive. But my 40s have been wandering wilderness years. The decade began with the death of my brother, and it felt like I’d been thrown into a fog of uncertainty and lack of purpose. Drinking became a problem. I took a political turn that became toxic and traumatic. I treated my professional life like a sailor exploring new lands, resting on my laurels as a post-exit entrepreneur, unanchored by a clear vision of where I wanted to go.
At 42, I became a dad, an experience that brought me an unexpected sense of purpose and joy. It was something I never imagined possible when I was 23 and coming out as gay. Parenting reshaped my identity as I navigated my neighborhood, stroller in hand, embracing this new chapter. Yet, during the Covid pandemic, like many parents of toddlers at the time, I struggled and fell into a period of depression. In the summer of 2020, we moved out of Washington, DC, and over the past four years, I’ve been on a journey of recovery, growth, and settling into a new, “school dad” phase of life.
So yeah, my 40s have been a time of tectonic internal shifts. Navigating grief, mistakes, and questions of purpose has brought me greater humility, acceptance, and wisdom. I’ve come to recognize my smallness in the universe. I now understand that contentment is, at its core, an inside job. I try to be a good person for my own soul — realizing it’s more important to like the guy in the mirror than to impress anyone else. Clout, social status, and LinkedIn-profile achievements don’t hold the same sway over me. The idea of attending a fancy gala makes me feel more nauseous than excited, unless it involves a charity or people I care about.
The economist David Blanchflower studied the relationship between happiness and age across 132 countries, producing the now-famous “happiness curve.” This U-shaped chart shows that happiness dips to its lowest point in midlife before rising again, with peak unhappiness occurring at age 47 in the developed world. Jonathan Rauch, a friend and well-known writer, explored this phenomenon in his book The Happiness Curve: Why Life Gets Better After 50, noting: “aging equips us to be happier and kinder, even as our bodies get frailer.” When I saw Jonathan recently, I shared how I’ve struggled in my 40s, and he told me I’m a textbook case.
At 49, I feel like I’m finally beginning to ascend the midlife crisis dip, clawing upward as if it’s the Half Dome at Yosemite. Writing essays has been part of this, a way to process moments of self-doubt, reckoning, and rediscovery. It is breathing oxygen into my lungs, reminding me that I can be funny, creative, and playful — that I don’t have to take myself so damn seriously.
Midlife isn’t just about decline; it’s also about renewal. I’m old enough now to see the cycles of life for what they are. I’ve lost things: my brother, some ambitions, the illusion of infinite time. But I’ve gained, too: resilience, perspective, and a deeper appreciation for what I have. A family. There’s something liberating about reaching an age where I can say, This is who I am, and let the chips fall where they may.
So yes, I’m middle-aged, pushing 50, and — for the most part — okay with it. There’s really no alternative other than death or denial, so I might as well come out and own it. Count me out as a Dorian Gray gay. If the happiness curve is right, the best may be yet to come.
As always, thanks to for draft feedback!
I think you’ve made a dent in the world Jeff. You helped me a lot. If I matter then you matter!
OMG! How similar we all are. I am 70 now and remember feeling everything that you describe at turning 50. I am happier now than I ever have been but I can't say that becoming invisible, seeing my greying hair and wrinkled skin and dealing with friends popping off intermittently has been easy. Mortality. Its quite a big one to really deal with but you have no choice and eventually you get to a place where you live with it and experience nirvana at the same time. thanks for your writing. I love reading you.