…such an interesting observation…it makes me want to dig even deeper into the effects of pop culture on out leaders…musk and trump are such standouts here…musk was so obsessed with becoming the king of all memes that he bought a meme factory to run and concurrently some say Trump’s initial idea to run for president was spurred from the failed negotiations of another apprentice season…as a straddler millenial gen-xer i worry not only about the existentialism but also the nihilism…i feel like we have spent three decades playing “nevermind”…even the new alternative radio station on every FM dial continues to play decades old grumbly flannel songs…are we fighting for our future or against it?…with Elon i continually wonder…if the goal is to save mankind on mars because the earth is in danger why wouldn’t we try and save earth instead?…great read Jeff!!…
Thanks brother, appreciate you and your feedback ALWAYS. Those are great questions. I think decoding the cultural programming of leaders is key. Writing this forced some realizations I had taken for granted, like our grandiosity and relationship with existential risk.
Hi Jeff, I thoroughly enjoyed reading this. It’s very well written and had me captivated the entire time! Not surprisingly this topic has been on my mind a lot. Many people around me seem to think that this is just politics, it’ll swing back around again soon enough, but I wonder at what point we might risk catapulting out of this normal pendulum trajectory, causing lasting damage / hurl towards the ‘end of the world as we know it’. (I’m a bit ashamed of doom and gloom thinking like this, the world will always be changing to be different than we know it of course, hopefully also for the better, but still). In any case, what an enjoyable read, thank you for that!
I wonder if the « swinging of the pendulum » in politics is just down to demographic shifts of generations. Old ones die off and new ones come of age. Gen X delivered the election to the Republicans this year, but the Gen Z age bracket had the largest shift compared to 2020. Boomers were relatively progressive and raised progressive millennials the latter being more economically populist due to lack of Cold War exposure. Gen Z in contrast are the children of Gen X, raised on similar values but more cynical in our outlook. There’s been talk of Zers looking for $500k to feel secure and I think it’s because we came of age during the time of cancel culture and want the ability to financially endure a true cancellation (ie survive being unemployable for a large part of our life)
Yeah great questions. I learned a lot by looking at my cultural programming, and it's a good exercise for decoding leaders in general. I do think politics is downstream from generational and demographic shifts as well as a function of inter-elite competition. The Gen Z shift toward Trump was dramatic. You are correct to spotlight that. It would be interesting to dig into that to understand. I'm pretty clueless about Zoomers, though I tried here :) https://jeffgiesea.substack.com/p/letter-to-zoomer-men-resist-nihilism
Also it may not be necessarily a Gen Z shift toward Trump, but just more Zoomers being at voting age. 18-29 polling would reflect the youngest millennials and oldest Gen Zers in 2020 but be almost entirely Gen Z now. If you count Gen Z as 1997-2012 which is what I generally see, the shift isn’t even complete. 2026 will be the first election where 18-29 age group is exclusively Gen Z and 2030 will be the first year where all of Gen Z can vote. I’m using the 18-29 age bracket since that’s what polls use even though it doesn’t line up with generations
Before this election. I thought I was a minority (very conservative) but that seems to be not the case for men and even the women are trending right too. I hope it doesn’t turn excessive but it’s nice to not feel like millennials part two because I think our interests are not necessarily the same.
All this to say I feel less alone post election, but also need to empirically reevaluate some of my views of people.
Excellent writing and a well-crafted essay. I'm a Gen-X'er. I started my first business at 23 before there was such a thing as the "freelance economy," and I sold my last one almost 30 years later with lots of failure inbetween. I resonate with much of what you said. I'm neither a fan of Trump nor Musk. I make Peter Thiel's Zero to One book mandatory reading for start-ups I invest in, or when someone asks me to "mentor them," I tell them to read Zero to One and then return to me. They never do. I might disagree with Thiel's politics and worldview, but his thoughts on business are worth considering. I also push all the founders of my early-stage investments and my entrepreneurial scholarship winners to sign a "Founders Agreement," which is a moral rather than legal agreement to donate a portion of their "some-day-earned" wealth to charities. The more we can shape philanthropic giving as a status symbol of success, even if that is also driven by ego and hubris, the better. I'd rather have two newly wealthy entrepreneurs compete over who has given the most to charities than who has the biggest yacht. Thank you again for contributing and working on topics few people have discussed. Well done!
"Ultimately, the Gen X relationship with existential risk is a double-edged sword. On one hand, our hero complex drives us to tackle humanity’s greatest challenges. On the other, our generational grandiosity blinds us to unintended consequences and leads us toward recklessness.
The stakes today are undeniably high — climate change, advanced AI, bioweapons, Trump, geopolitics. But broligarch boldness and braggadocio alone won’t save us. Navigating existential risk demands something more: humility to recognize our limitations, collaboration to bridge divides and reveal blind spots, and courage to confront the unintended consequences of our own ambitions.
As Gen X broligarchs flex power, the future hinges on whether we can transcend our hero complexes and embrace these traits. If we’re not careful, the drive to save humanity could become the wrecking ball that destroys it."
This would ring true today...if only we weren't so risk-averse and utterly obsessed with safety and harm elimination as a Society these days.
This is more of a feature and not a bug than you think. The feminization/HRing of Society has sent us entirely too far in the risk-avoidance direction, and we're reaping the pathologies of that excess.
I'd say there's a healthy dialectic between tech acceleration and safety in America, though it's more risk-averse than I'd prefer. At least we're not Europe.
Agreed. It's not hard to imagine a scenario where we overlook risk too much; the correctives that came out in the late 60s and 70s were needed to overcome the risks incurred and hazards realized of the late 40s through the early 60s. But we've swung too far the other way and it's handcuffed our nation in our ability to do the needful.
Europe is a mess and there's a reason their GDP has been flat since the Great Recession.
All true. The risk issue is complex because there is black swan tail risk, on top of normal stuff. I'm not sure we know how to manage that type of risk.
Interesting article Jeff. I’m more interested in politics rather than generational differences and movement. In a population of 350M 175M voters rejected the 8 years disaster of Democratic Party anti constitutional dictatorship. Trump maga messaging was needed to educate the masses that California/NewYork Democratic Party management, Open Borders, judicial system liberalism, girls have penises education, was improper and not the desired direction for the country as a whole.
In a large democracy it’s the majority that counts when electing a leader. Our problem in the US is that there is a very large uneducated number of voters.
As a single Gen X woman, I have yet to meet an available Gen X man who is not a narcissist. In fact, I have observed that most Gen X men do not even date Gen X women. Divorced Gen X men date/marry millennials and younger - a true sign of insecurity and narcissism. Even those who consider themselves on the "spiritual path" might need a checkin to what you have called out as "...middle-child narcissism — cleverly disguised but raging beneath the surface." This is leaving behind a generation of Gen X women who are actually working on themselves with no partner to grow with. Thank you for the article, I am researching for an upcoming podcast on Baby Boomers & Gen X.
Couldn’t agree more, this is excellent insight on what specifically brewed amongst our generation’s men that (combined with other factors) led to us being such a mixed bag. We’re “the greatest entrepreneurial generation in US history” but also “the boomerang generation” for how many of us were so neglected we struggled to get on our feet & had to move back in with parents.
I see, thanks for clarifying. The boomerang effects you mention are really interesting, especially considering that many Gen Z have Gen X parents. I see what you mean.
…such an interesting observation…it makes me want to dig even deeper into the effects of pop culture on out leaders…musk and trump are such standouts here…musk was so obsessed with becoming the king of all memes that he bought a meme factory to run and concurrently some say Trump’s initial idea to run for president was spurred from the failed negotiations of another apprentice season…as a straddler millenial gen-xer i worry not only about the existentialism but also the nihilism…i feel like we have spent three decades playing “nevermind”…even the new alternative radio station on every FM dial continues to play decades old grumbly flannel songs…are we fighting for our future or against it?…with Elon i continually wonder…if the goal is to save mankind on mars because the earth is in danger why wouldn’t we try and save earth instead?…great read Jeff!!…
Thanks brother, appreciate you and your feedback ALWAYS. Those are great questions. I think decoding the cultural programming of leaders is key. Writing this forced some realizations I had taken for granted, like our grandiosity and relationship with existential risk.
...it's really sharp Jeff...great work...
Hi Jeff, I thoroughly enjoyed reading this. It’s very well written and had me captivated the entire time! Not surprisingly this topic has been on my mind a lot. Many people around me seem to think that this is just politics, it’ll swing back around again soon enough, but I wonder at what point we might risk catapulting out of this normal pendulum trajectory, causing lasting damage / hurl towards the ‘end of the world as we know it’. (I’m a bit ashamed of doom and gloom thinking like this, the world will always be changing to be different than we know it of course, hopefully also for the better, but still). In any case, what an enjoyable read, thank you for that!
Thanks Esther. Good to know others are thinking about these issues.
This is making me reflect on my own Generation Z.
I wonder if the « swinging of the pendulum » in politics is just down to demographic shifts of generations. Old ones die off and new ones come of age. Gen X delivered the election to the Republicans this year, but the Gen Z age bracket had the largest shift compared to 2020. Boomers were relatively progressive and raised progressive millennials the latter being more economically populist due to lack of Cold War exposure. Gen Z in contrast are the children of Gen X, raised on similar values but more cynical in our outlook. There’s been talk of Zers looking for $500k to feel secure and I think it’s because we came of age during the time of cancel culture and want the ability to financially endure a true cancellation (ie survive being unemployable for a large part of our life)
Yeah great questions. I learned a lot by looking at my cultural programming, and it's a good exercise for decoding leaders in general. I do think politics is downstream from generational and demographic shifts as well as a function of inter-elite competition. The Gen Z shift toward Trump was dramatic. You are correct to spotlight that. It would be interesting to dig into that to understand. I'm pretty clueless about Zoomers, though I tried here :) https://jeffgiesea.substack.com/p/letter-to-zoomer-men-resist-nihilism
Also it may not be necessarily a Gen Z shift toward Trump, but just more Zoomers being at voting age. 18-29 polling would reflect the youngest millennials and oldest Gen Zers in 2020 but be almost entirely Gen Z now. If you count Gen Z as 1997-2012 which is what I generally see, the shift isn’t even complete. 2026 will be the first election where 18-29 age group is exclusively Gen Z and 2030 will be the first year where all of Gen Z can vote. I’m using the 18-29 age bracket since that’s what polls use even though it doesn’t line up with generations
Good point
Before this election. I thought I was a minority (very conservative) but that seems to be not the case for men and even the women are trending right too. I hope it doesn’t turn excessive but it’s nice to not feel like millennials part two because I think our interests are not necessarily the same.
All this to say I feel less alone post election, but also need to empirically reevaluate some of my views of people.
Hello Jeff,
Excellent writing and a well-crafted essay. I'm a Gen-X'er. I started my first business at 23 before there was such a thing as the "freelance economy," and I sold my last one almost 30 years later with lots of failure inbetween. I resonate with much of what you said. I'm neither a fan of Trump nor Musk. I make Peter Thiel's Zero to One book mandatory reading for start-ups I invest in, or when someone asks me to "mentor them," I tell them to read Zero to One and then return to me. They never do. I might disagree with Thiel's politics and worldview, but his thoughts on business are worth considering. I also push all the founders of my early-stage investments and my entrepreneurial scholarship winners to sign a "Founders Agreement," which is a moral rather than legal agreement to donate a portion of their "some-day-earned" wealth to charities. The more we can shape philanthropic giving as a status symbol of success, even if that is also driven by ego and hubris, the better. I'd rather have two newly wealthy entrepreneurs compete over who has given the most to charities than who has the biggest yacht. Thank you again for contributing and working on topics few people have discussed. Well done!
Thanks Chris, appreciate your kind words. "Zero to One" is excellent — a philosophy book disguised a business book. ;)
"Ultimately, the Gen X relationship with existential risk is a double-edged sword. On one hand, our hero complex drives us to tackle humanity’s greatest challenges. On the other, our generational grandiosity blinds us to unintended consequences and leads us toward recklessness.
The stakes today are undeniably high — climate change, advanced AI, bioweapons, Trump, geopolitics. But broligarch boldness and braggadocio alone won’t save us. Navigating existential risk demands something more: humility to recognize our limitations, collaboration to bridge divides and reveal blind spots, and courage to confront the unintended consequences of our own ambitions.
As Gen X broligarchs flex power, the future hinges on whether we can transcend our hero complexes and embrace these traits. If we’re not careful, the drive to save humanity could become the wrecking ball that destroys it."
This would ring true today...if only we weren't so risk-averse and utterly obsessed with safety and harm elimination as a Society these days.
This is more of a feature and not a bug than you think. The feminization/HRing of Society has sent us entirely too far in the risk-avoidance direction, and we're reaping the pathologies of that excess.
I'd say there's a healthy dialectic between tech acceleration and safety in America, though it's more risk-averse than I'd prefer. At least we're not Europe.
Agreed. It's not hard to imagine a scenario where we overlook risk too much; the correctives that came out in the late 60s and 70s were needed to overcome the risks incurred and hazards realized of the late 40s through the early 60s. But we've swung too far the other way and it's handcuffed our nation in our ability to do the needful.
Europe is a mess and there's a reason their GDP has been flat since the Great Recession.
All true. The risk issue is complex because there is black swan tail risk, on top of normal stuff. I'm not sure we know how to manage that type of risk.
Interesting article Jeff. I’m more interested in politics rather than generational differences and movement. In a population of 350M 175M voters rejected the 8 years disaster of Democratic Party anti constitutional dictatorship. Trump maga messaging was needed to educate the masses that California/NewYork Democratic Party management, Open Borders, judicial system liberalism, girls have penises education, was improper and not the desired direction for the country as a whole.
In a large democracy it’s the majority that counts when electing a leader. Our problem in the US is that there is a very large uneducated number of voters.
As a single Gen X woman, I have yet to meet an available Gen X man who is not a narcissist. In fact, I have observed that most Gen X men do not even date Gen X women. Divorced Gen X men date/marry millennials and younger - a true sign of insecurity and narcissism. Even those who consider themselves on the "spiritual path" might need a checkin to what you have called out as "...middle-child narcissism — cleverly disguised but raging beneath the surface." This is leaving behind a generation of Gen X women who are actually working on themselves with no partner to grow with. Thank you for the article, I am researching for an upcoming podcast on Baby Boomers & Gen X.
Very compelling generational observations and arguments.
Thanks Andrew
Couldn’t agree more, this is excellent insight on what specifically brewed amongst our generation’s men that (combined with other factors) led to us being such a mixed bag. We’re “the greatest entrepreneurial generation in US history” but also “the boomerang generation” for how many of us were so neglected we struggled to get on our feet & had to move back in with parents.
Thank you for linking my related article!
Thanks Liz! I like your perspective and look forward to reading more of your work.
we love our new oligarchs, a lot
we love our new oligarchs, a lot
thanks Jarlis, you can be honorary Gen X :) Btw, this is an interesting insight —
« The "fall" of Silicon Valley, and California more broadly, is a major undercurrent of the Trump movement »
How does this relate to my article?
I see, thanks for clarifying. The boomerang effects you mention are really interesting, especially considering that many Gen Z have Gen X parents. I see what you mean.
Thanks. I confess I don't understand Gen Z, but I did take a shot at writing to them here: https://jeffgiesea.substack.com/p/letter-to-zoomer-men-resist-nihilism