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When I first became an advisor, most of my training focused on mastery of quantifiable opportunities and risks. My studies oriented me around the familiar risks in later life: market crashes with less time to recover, inflation that pinched affordability, tax attrition, and healthcare / long-term care costs.
However, I’m seeing another risk emerge—one that doesn’t show up in a Monte Carlo simulation and seemingly strikes at men disproportionately. It involves struggles where the risk isn’t running out of money. It’s running out of identity. It’s the collision of:
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Retirement from a career
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Real and perceived changes in identity
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Raging social media
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Divisive politics
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The modern manosphere
I’m seeing this more than the stereotypical male midlife crisis behavior (affairs/sports cars/impulse spending). It’s less obvious but potentially more dangerous and self-destructive.
I’ve observed intelligent, accomplished men shrink psychologically after decades of being builders, creators, leaders, and family men. Their identities were anchored in usefulness. But then they find their careers over, their children grown, parents dying, and social calendars emptying—not to mention emerging health issues.
Into that vacuum steps a new villain.
Man vs. algorithm
I wrote last week about the Boredom Retirement Plan, one defense against the risk I’m now describing but I haven’t seen previously named: the algorithm.
The algorithm doesn’t care whether you’re conservative or progressive. It doesn’t care whether you’re watching cable news, YouTube, X, TikTok, or podcasts.
The algorithm has only one job: keeping you emotionally activated. Attention is profitable. And nothing captures attention like convincing someone that they’re losing something: your country, masculinity, status, relevance, future.
I’ve watched accomplished men slowly become full-time consumers and peddlers of outrage. Men who once built businesses now spend six hours a day forwarding articles. Men who mentored young professionals now argue with strangers online. Men who solved real problems now consume endless commentary about problems they’ll never personally solve.
Psychologists have long understood that uncertainty creates anxiety. The attention economy has simply industrialized this insight by figuring out what mental levers to pull to activate us. And this activation can fill up space in a life where new purpose could fit.
A quick sidebar: I always hesitate to generalize by gender. For an older generation where women had not yet entered the workforce for the better part of their working years, I’m still seeing this issue more among my 70+ year old male cohort.
The fourth retirement risk
Readers of Age Against the Machine know I often divide people into three broad camps.
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Planners: They prepare early. They build margin. They think ahead.
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Procrastinators: They know what they should do. They simply keep delaying it.
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Crashers: They ignore reality until reality makes the decision for them.
For years I’ve used that framework to describe financial planning, healthcare decisions, estate planning, and aging. I’m wondering if this applies to identity as well.
Identity Planners understand that retirement isn’t simply leaving work. It’s entering another purposeful identity. Mentor. Volunteer. Grandparent. Teacher. Board member. Coach. Community builder. I’ve noticed that Identity Planners constantly add new identities before the old ones disappear.
Identity Procrastinators assume they’ll figure it out later. They’ll volunteer someday. Travel after the thing. Develop new friendships eventually. Learn something new when it feels right. Then “someday” arrives faster than expected.
Finally, there are the Identity Crashers. I worry about them the most. Unlike Retirement Crashers, many Identity Crashers are financially prepared for retirement. Emotionally, however, they are not ready, and what I am seeing is that some accidentally retired from “becoming.”
The warrior’s second battle
One of my favorite human observations comes from Bushido, the code of the samurai.
“The bravest are the tenderest, the loving are the daring.”
I come back to that line often because it quietly dismantles one of the greatest myths about masculinity.
Young men often define strength by conquest. In today’s world, that’s money, status, influence, recognition, and expertise.
Older men, by contrast, have an opportunity to redefine strength by contribution. The “code” changes:
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Can you mentor without controlling?
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Can you lead without needing credit?
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Can you become curious again?
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Can you celebrate someone else’s success as enthusiastically as your own?
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Can your identity expand instead of contract?
The idea that youthful strength and vitality mature is found in plenty of cultures. Marcus Aurelius wrote that gentleness was not weakness but one of the highest expressions of strength. The samurai believed compassion mattered precisely because it came from someone capable of violence. Indigenous warrior traditions across the world often judged a man not only by what he could defend, but by what he chose to protect.
However, in the algorithm world, this approach is not the one that gets amplified. And I think this really impacts the Identity Crasher men who don’t make the connection that they can continue to contribute.
The masculinity market
I’m far from the first to articulate that the male attention economy is built on something many traditional institutions have forgotten. Men are hungry for meaning. Unfortunately, too much of today’s algorithm marketplace sells identity the way processed food sells nutrition.
Fast. Addictive. Emotionally satisfying. Spiritually empty.
Much of it promises to restore masculinity by making men perpetually angry about being misunderstood, being victims, and being under attack. The formula is politically flexible. While a disproportionate amount of attention is spent on the effects on younger men, I’ve come to realize that older men (like me and even grayer) are susceptible as well–although for different reasons than younger men.
The greatest irony is that many of the men I see in a triggered agita spent their careers solving extraordinarily difficult problems. After retirement they can feel like they are sidelined to become spectators rather than participants. Consumers rather than creators. Commentators rather than contributors.
Then the algorithms convince them they’re warriors, re-kindling their desire to “get back in the game.” What it’s really doing, though, is quietly turning them into audiences.
David’s promotion
One client—I’ll call him David—showed me another path. David sold the business he’d spent thirty-five years building.
The first year looked successful from the outside. Golf. Travel. “Putting his feet up.” But also the podcasts. 24-hour news. Social media. Even though his financial situation was rock solid, his mood was deteriorating.
Every conversation drifted toward what was wrong with America, younger generations, technology, or politics. As the years passed, I simply could not get him off his algorithm-sounding topics. I’m not minimizing serious conversations about serious issues in the world today, but I’ve been around the block enough to recognize when conversations move away from purposeful and productive and appear symptomatic of something that I hadn’t yet found a name for.
Then something changed at the beginning of 2026. He began mentoring first-generation entrepreneurs through a local nonprofit. He volunteered to teach financial literacy classes at a community college. His daughter asked if he would coach his grandson’s baseball team. Eventually he joined the board of a regional charity—not because they needed his money, but because they needed his judgment.
He gave me a clue about his mindset shift when he told me recently, “I didn’t like who I was right after I retired. I started to sound like all of my angry friends and crackpot family members. I guess I needed to get bigger, not smaller.”
That transition from an Identity Crasher to Identity Planner helped David flip his warrior mode from youthful conqueror to elder contributor.
Algorithms are attacking the potential to be the male elder we need
There’s this whole content space that I love and embrace about intentionally growing into the Chip Conley version of the Modern Elder, among other great models of affirmative aging. There are many models and many positive voices, and they organize around ideas like shared wisdom, inner peace, legacy, stewardship, self-sufficiency, all the things. I’m not going to repeat them here because others are exploring the space to great effect.
Most of the best ideas about positive aging involve identity expansion. Allowing and accepting yourself to be different from and more than who you were when you were younger.
My first observation is that this can be harder for older men, particularly those who have had some success in their working years.
My second observation is that these accomplished older men are more vulnerable to the algorithmic hijacking of what could be a normal and healthy expansion of their identities. Of course they rarely consider themselves vulnerable. However, I’ve seen that sometimes they are the least likely to be immunized from the information economy that monetizes their attention. Among other reasons why, they might have a more limited number of roles / identities coming out of their working years and the algorithm is filling up empty space.
So I’m going back to my Planners / Procrastinators / Crashers framework for a reminder:
Planners prepare for their future, and now I’m including the planned intentional development of non-career roles and identities.
Procrastinators keep waiting to discover who they’ll become. And with their iPhones always on, there is a danger they can slip into Crasher territory.
And some Crashers, even if financially secure, could wake up one morning not just retired but unwittingly hijacked. The algorithm becomes a parasite of the Crasher’s attention, sapping reserves meant for finding new purpose.
It’s that lack of purpose, that vacuum that happens when older men feel they are no longer useful, that allows the algorithm to thrive among Gen-Xers and Boomers. It’s more important than ever to encourage them to contribute, to make a difference, to find a new identity that makes them feel as useful as their previous ones. That’s how, to quote David, they can get bigger, not smaller.