Washington, DC is about as far as you can get from San Francisco and still be in the continental United States. The 2,800 miles between them symbolizes more than a physical separation. For many young Americans, they are two very different potential paths to the future; two very different ways to think about possibility, advancement, and the pace of change itself.
I should know. My academic research on how Congress functions and my work with the Subcommittee on Modernization afforded me a unique view into the institution’s and Washington’s inner workings. Now I am based in San Francisco, adjusting to a life among the builders out west.
On any given day in DC, I could find myself at a happy hour with friends working at think tanks, federal agencies, and on the Hill as Staff Assistants, Schedulers, Legislative Correspondents, and if they were lucky, Legislative Assistants. These titles carry weight in the Capitol but mean little elsewhere. We would talk about who is moving up, the newest Hill gossip, and what the latest is with China. The rhythm of advancement is measured, hierarchical. A Chief of Staff in DC is someone who has spent years, sometimes decades, earning political wit and institutional knowledge. Age and experience are not just valued — they are prerequisites.
On any given day in San Francisco, I might find myself at a poker table with three software engineers from FAANG companies, two startup founders (one with $3 million in seed funding, another running on savings), a venture capitalist, and someone who just burned out from their own startup and joined a later-stage company. At least one person at that table holds a title like Founder or Chief of Staff — roles they secured not through decades of ladder-climbing but through having an idea worth betting on and the audacity to try. But ask anyone at the table what their startup does and there’s a pretty good chance of hearing five minutes of jargon that translates to “we’re still figuring it out.”
I have never met so many young people obsessed with poker. Maybe it’s the noticeably skewed male-to-female ratio in this city, or it could just be that they have money to burn. But I think it is something else: poker rewards calculated risk-taking, pattern recognition, and the ability to read what others cannot see. These are the same skills that define success here.
In San Francisco, taking risks earns you respect. The Bay’s famous fetishization of risk has evolved from big tech’s “move fast and break things” approach and settled into the religion of the grind. People glorify fifteen-hour work days, “coding houses,” and sacrifice.
Calculated risk may mean leaving a $250K job at Google to join a pre-revenue startup as employee number eight, taking a 30% pay cut for equity that might be worth millions or might be worth nothing. It means spending nights and weekends building a prototype before knowing if anyone wants it. It means betting on yourself, on technology’s trajectory, and on your ability to create something from nothing. The downside is bounded; you can always get another job because the ecosystem expects failure as part of the learning curve and admires the entrepreneurial drive to try. And the upside, well, is potentially unlimited.
In DC, it’s almost the exact opposite. The two-year election cycle hangs over everything — staffers in political offices can do everything right and still find themselves out of a job because their Member lost. It is hard not to become risk-averse when the ground shifts beneath you every two years. Off the Hill, institutions are wired to avoid risk through bureaucratic organization. Rather than facing sacrifice to make a risky move with a potential big payout, many in DC sacrifice and accept below market compensation to avoid a risky move. This might mean a Hill staffer staying with a Member whose committee assignment is not ideal rather than gambling on a lateral move to another Member’s office or a think tank researcher waiting to see which way the political consensus is shifting before publishing on a contentious topic. The most adventurous risk might be leaving a secure position to join a newer nonprofit with uncertain funding, or leaving a safe senior Member’s office for one where the Member could lose in two years.
Risk in DC is not just financial — it is reputational, political, relational. Unlike in SF, where failure is expected and recoverable, there is no ecosystem to catch you. And right now, the stakes feel higher than ever. Federal layoffs have gutted entire agencies, senior staffers are competing for junior roles just to stay employed, and the ladder that young people once slowly climbed has fewer rungs than it used to. So people stay careful. They stay safe. They wait their turn. But that caution is not just careerism — for many people, it is the price of admission to rooms that have never had someone like them in it before. They came to Washington because they believe in something: because an issue touched their family, because they wanted to work in government since they were kids, because they are the first from their community to ever have a seat at the table. The careful moves, the patient waiting, the small tasks — these are not signs of timidity. They are how you stay near the work that you came to Washington to do.
This difference shapes everything. The poker table in SF is not just about wealth, it is a reflection of a culture where risk tolerance is a core competency. These engineers are not gambling recklessly; they are practicing the same skills they use when deciding which features to build, which technical architecture to bet on, or which company to join. The happy hour in DC reflects a different kind of calculation entirely. Congressional staffers, policy analysts, and advocates alike, are reading political tea leaves, gauging whose star is rising, and whose policy priorities align with the shifting consensus. It is strategic, it is careful, and it is constrained by the reality that the policy world is small.
This cultural divergence has profound implications for how we govern in an age of rapid technological change. The gap between what young people view as possible in each city directly reflects the gap between technological innovation and government modernization. In SF, the ambient assumption is that most problems can be solved, most systems can be rebuilt, most limitations are temporary. The question is not whether something can be done but how quickly. In Washington, the ambient assumption is that most problems are intractable, most systems are immovable, and most changes take years of coalition-building and compromise. The question is not how quickly but whether it is politically feasible.
This is not to romanticize either city’s approach. DC’s emphasis on experience and relationships creates stability and prevents naive policy mistakes, but it can also calcify into gatekeeping and resistance to necessary change. SF’s celebration of youth and velocity creates breakthrough innovation, but it can also produce reckless disruption and burnout culture.
Nate Silver, in his 2024 book On the Edge, maps similar terrain — tracing how the gambler’s mindset runs through Silicon Valley’s founders and financiers, set against the risk-averse world of credentialed institutions. I had not read Silver’s work when I first wrote these observations down, and when a colleague pointed me to it, I took the convergence as something like confirmation: when two people arrive at the same diagnosis independently, it is probably not a coincidence. Where we part ways is on the question of stakes. His book is ultimately about understanding this world and what it can teach us. This newsletter is about what happens to democratic governance if the distance between these two cultures keeps growing — and what we stand to lose if nobody closes it.
The challenges facing democratic governance — from AI regulation to digital infrastructure to cybersecurity — require both the velocity and ambition of Silicon Valley and the legitimacy and deliberation of Washington. We need policymakers who understand that the pace of technological change is not slowing to meet government’s timeline. We need technologists who understand that “move fast and break things” is not acceptable when the things you are breaking are democratic institutions.
Washington needs to recognize that its young people arrived with the same conviction and potential as their counterparts 2,800 miles away — but where SF channels that energy into calculated bets, DC’s culture of risk aversion can wear it down before it ever gets the chance to matter. When caution becomes the only option, you don’t just slow things down. You lose the people who believed in the institution most.
Really fascinating -- excited for this newsletter
Caitlin, this is so well done and beautifully written! DC misses you!