I don’t know who will win. And I wouldn’t trust anyone who feels overly confident that they do. Right now, it seems like Trump has something like a 51% chance of winning. Ok. Would you flip a coin that has a 51% chance of landing heads and say, mid-air, that it’s going up to be heads? No. But, of course, if it does land heads, you’ll spend the next four years saying I knew

Probability easily becomes astrology during an election year. Rather than take the numbers for what they are, we tell stories to secure ourselves against the uncertainty. 

A Donald Trump win could backfire on Republicans. Nobody can do Trump like Trump (just ask Tony Hinchcliffe), but thanks to Trump’s vice-grip on the Republican party, so many wannabes are going to try. So far, that hasn’t proven to be wise. 

Two things are true at the same time: Trump is the most important figure in American politics over the last decade. And he was also 80,000 votes away from losing to Hilary, who crushed him in the popular vote; he got smashed in the midterms in 2018; lost to Joe Biden in 2020; and then, from the sidelines, watched just about all his chosen candidates get rocked in the 2022 midterms. (JD Vance was the only candidate in the seven statewide general election races that were funded by Trump's PAC to win.) 

What makes Trump Trump isn’t his policies. Ezra Klein has a great audio-essay on Trump’s uniquely manic disinhibition, with the main takeaway being that what makes Trump special is that he has absolutely no filter. You’re always getting the raw Trumpian stream-of-consciousness, delivered with zero regard for its consequences. Other politicians, even Vance, all have a filter. You know they’re not saying exactly what’s on their mind. And so long as that is true, Trump will remain a singular, irreplicable figure. 

The bottom line: Trumpism has not proven to be a winning or repeatable strategy for anyone other than its namesake. A Trump win now could guarantee Democratic wins in the mid-terms as well as 2028. 

Kamala skeptics and critics underestimate the “Democratic team.” I think this goes back to Biden. Voters know when they’re voting for the Democratic ticket that they’re really voting for the Democratic team. Thus, they’re less interested in Kamala’s individual positions and policies. They don’t envision her as a savior the way Republicans view Trump. 

Because of that, I actually don’t think her top-line messaging (I’m not Donald Trump) has been that bad. In this election, as in the last, you’re either voting for the China Shop or you're voting for the bull, in which case, the China Shop should simply remind you — bulls can’t be tamed. 

Personality and temperament have never mattered more — which is why I do think Kamala still could have done more media before the final push. Voters don’t necessarily care about the specifics of your policies, but they do want to know who you are

Hope springs eternal, even in defeat. I hear so many progressive thinkers and friends saying that if Kamala loses this election, it will at least lead to a “reset” in the party. Really? It’s still going to be the same donors, constituents, elected officials and media figures spearheading the Democratic machine. What makes you think they’re going to look critically in the mirror? A far more likely reality is a period of infighting and scapegoating followed by, inevitably, more of the same. After all, we were promised a reset after 2016. Instead, we got the oldest President in American history. 

If Trump loses, I think he runs again. He seems to like campaigning much more than governing. And it’s the easiest way to keep his spot “on-stage” in our 24/7 media spectacle. 

We’re all consuming too much election content. This election has been a toss-up since July and will remain that way until the end. Nobody is changing their minds at this point. All the cards have been dealt, each side is all in. There’s nothing most of us can do but wait. And yet, many people (including myself) are spending hours a day reading about, thinking about, and talking about the election. All this frenetic, unproductive activity — for what? A sense of control? A sense of agency? 

It’s not going to change (as) much (as people hope/fear). And in fact, the more apocalyptic the rhetoric gets, the more I’m convinced very little will change.

Whatever you fear most about each candidate — it precedes, supersedes, and will certainly outlast them. The complacency, careerism and inscrutability of Kamala. The madness, disinhibition, and joylessness of Trump. Neither will do what they promise to do. Kamala can’t save our institutions from their bloated ineffectiveness. Trump can’t destroy them, either. 

My base case for the near future of America is basically more of the same: stagnation, stasis, and spectacle. Ever-worsening apathy, division and hand-wringing. 

The same issues we have now will be there in four years. Our cities will look the same. We’ll still need more housing. We’ll still be having the same cultural fights. The great stagnation will continue, in other words. A pending sense of doom compounded (and offset) by local governments that can hardly fix a pothole on budget and on time. 

What I’ll remember from this cycle: Silicon Valley’s rightward turn. I’ve written about this elsewhere, and on the surface, I still think it’s astonishing that so many smart venture capital types are supporting a candidate who they would never do business with. They wouldn’t trust Trump to run a startup, yet they fetishize his ability to bring the federal government into line.

For so many years, it seemed like Silicon Valley went out of its way to ignore DC. Now they’re venturing into politics with an engineer’s mindset, believing there’s a simple, elegant solution to every one of our nation’s problems. That’s how you end up with this ridiculous notion that Elon will somehow zero-based-budget the entire Deep State, or that RFK is going to single-handedly oversee an agricultural revolution. 

All Silicon Valley sees in DC is inefficiency – but they don’t know why things are inefficient. They assume these people are just bad at doing their jobs, and that if they had an accomplished private sector champion in charge, they’d be able to magically fix our healthcare system, procurement process, national debt and more. They are nerds who don’t understand how a complicated social system — with a near-infinite list of stakeholders — works. This isn’t something you can solve with code or by going “Founder Mode.” 

You either die an intellectual, or live long enough to become another partisan. I have no problem with Elon and David Sacks and other so-called “contrarian” thinkers supporting Donald Trump. I take very seriously the American ideal that everyone should be allowed to vote for who they want without fear of physical or political repercussion. But I’ll never take either Elon or David Sacks all that seriously again, having seen them totally jettison critical thinking in favor of pure partisan jeering. 

Humility and doubt are hallmarks of true thinking, while partisanship forces you to make a religion out of your bets. There’s no intellectual hedging allowed. 

Both candidates should disappoint you. That doesn't mean you can’t have one you prefer. But disappointment is the best barometer for ensuring you’re awake. It means you’re not being seduced by our deeply-wired need for saviors and salvation. 

The choice should feel practical, uninspiring, and boring. Less like the Super Bowl and more like picking a dentist. It’s important to pick a good one. But then you should go back to the parts of your life that actually have meaning, and where, if you’re lucky, focused and patient, you might actually make a difference. 

I’m voting for Kamala. Simply to protect for the downside. I don’t expect much from a Democratic administration, but I’d prefer not to have another four years in which the President has to be talked out of shooting missiles into Mexico while watching TV for eight hours a day.

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