Never Enough
written on July 21, 2026
Two recent stories about Silicon Valley are hard to read without wondering if everyone involved has lost their mind. Once a place that celebrated “the crazy ones, the misfits and rebels who saw things differently,” it now seems to have found a new kind of crazy that isn’t born of rebellion but fear of falling behind. Everyone is chasing the person ahead of them, with little time to remember where they meant to go.
One story talks about a couple that earns a combined $550,000 a year and still feels behind because someone at Anthropic might buy the dream house first. The husband asked his wife to take over almost all parenting so he could spend days, nights and weekends becoming his company’s top user of AI. And she did.
The other story covers a founder who has Claude review her first dates and tell her whether she was engaging and empathetic enough, thanks to recording every single one of them. Two people meet and afterwards, rather than talk to the other person or trust her own judgment, one of them sits alone with a machine and asks how well she performed.
Technology was supposed to make room for life but instead for more and more people life is slowly being rearranged around AI. People fear being replaced by machines and respond by giving those machines more of their judgment, attention and time. And for what? Every “saved” hour is returned to a race with no finish line.
If the valley shows us what it means to live in the future, perhaps falling behind is not the worst thing that could happen. Maybe we need the misfits who know when to stop. Who leave a conversation unrecorded. Who play with their children without agents running in the background. Who can admire another person’s success without feeling diminished by it. Who find peace not by getting ahead, but by no longer needing to.
