Hey friends, happy weekend! A few quick housekeeping notes:
October journaling prompts are here.
My recommendations for what to read, cook and try this fall.
And I’m currently offering my biggest discount ever—don’t miss your chance to lock in an annual subscription for 50% off, forever! Discount good through Sunday.
You don’t have to look far to find regret. It shows up in small, almost imperceptible ways: in the way someone talks about their past, in the routines that feel like obligation rather than joy, in the quiet envy of people who took risks they didn’t. Regret is rarely dramatic. It accumulates slowly, like sediment at the bottom of a river, until one day you realize the shape of an entire life has been determined by what was left unsaid, undone, or avoided.
We like to tell ourselves that the people who didn’t live the lives they wanted simply “missed their chance.” They married the wrong person, took the wrong job, or stayed in the wrong town. But when you start looking closely—at relatives, mentors, strangers, even yourself—the patterns become hard to ignore. They’re not random at all. They’re repetitive. Generation after generation, people are tripped up by the same quiet forces, dressed in different clothes but leading to the same result: a life that feels smaller than it could have been.
The reasons are rarely glamorous. Most people don’t fail to live their lives because of one catastrophic decision. They fail because of a long series of small decisions that slowly calcify into identity. They don’t protect their time. They keep saying yes when every part of them wants to say no. They let their self-respect be outsourced to institutions, bosses, parents, or peers. They fear change more than stagnation. They ignore the quiet warnings from their body, their gut, their dreams. They tell themselves they’ll “get around to it” later, believing that time is generous when it isn’t. And perhaps most tragically, they believe that sacrifice will eventually be rewarded simply for being sacrifice, even if it’s never attached to a larger purpose.
Sacrifice without direction is just slow-motion self-abandonment. That’s the part no one warns you about. You can pour decades into an idea, a job, or a relationship without realizing you’ve been paying into an account that doesn’t exist. The people who end up feeling most hollow at the end of their lives are rarely the ones who tried and failed. They’re the ones who kept postponing their own lives because they were scared. Scared to make the wrong choice, to risk instability, to want something different and not know how to get it. So they stayed. They waited. They told themselves the time wasn’t right.
Avoidance is another thief. Over time it stops looking like avoidance and starts looking like personality. “I’m just not the type to travel,” “I’m bad with money,” “I’m not artistic.” These are often just convenient names we give to fears or undeveloped parts of ourselves. By the time someone reaches their sixties or seventies, these stories can be so entrenched they feel immutable. Yet if you scratch the surface, you’ll often find a moment—sometimes decades back—when that person knew they wanted something else but quietly decided it was unrealistic, or selfish, or too late.
If you’ve been around my work for a while, you know how much I love a good mental model—practical thinking tools that help us make sense of the world and navigate it with a little more clarity. One of my favorites is called the Regret Minimization Framework, coined by Jeff Bezos back when he was deciding whether to leave his stable finance job to start what would eventually become Amazon. He imagined himself at age 80, looking back on his life, and asked which choice he’d regret more: trying and potentially failing, or never trying at all.
If you’re not familiar with Bezos beyond the headlines, it’s worth zooming out for a moment. He didn’t just launch Amazon—he reimagined how the internet could work. He started in books, but what he was really building was infrastructure. Fulfillment centers, logistics systems, cloud computing. It wasn’t glamorous at the start, but he saw far enough into the future to know where it was heading. The risk for Bezos wasn’t failure—it was regret.
Mental Models for People Who Actually Want to Think
You don’t need to be smarter than everyone. You just need a better way of seeing.
When you look at people who seem genuinely content in later life, the differences are striking. They’re not the ones who got everything right. They’re the ones who stayed in contact with themselves. They found ways to take small risks even when it was inconvenient. They created boundaries before burnout forced them to. They didn’t confuse self-sacrifice with virtue. And they learned, often the hard way, that regret isn’t a one-time feeling. It’s an atmosphere. You build it or you don’t.
The good news is that seeing the pattern is half the work. When you recognize that these forces are predictable, you also recognize that they’re interruptible. Protecting your time doesn’t have to be dramatic. Saying no doesn’t have to burn bridges. Checking in with yourself regularly doesn’t make you self-absorbed—it makes you honest. Even small acts of clarity compound over time, just like avoidance does. Writing things down, for example, may seem trivial, but it’s one of the simplest ways to catch yourself before you drift. It turns vague dissatisfaction into information you can actually work with.
That’s why I keep journaling. That’s why I keep writing. That’s why THE DAILY 5 exists. Because regret, when you zoom out, is just a feedback loop that never got intercepted. And when you catch the loop early enough, you can still change the story.
The point isn’t to panic or overhaul your entire life. It’s to pay attention now, while you still have options. To notice which habits are quietly shaping your future self. To ask, before another season slips by, whether you’re living a story you chose or one you defaulted into.
If there’s a lesson in watching people age into regret, it’s that no one is exempt from these patterns. You can be intelligent, hardworking, or well-intentioned and still end up living someone else’s life. The only real defense is awareness—and small, repeated acts of self-alignment.
You don’t need a new life. You just need a better relationship with the one you’re already building. And today is a great day to begin again.
—S
PS: I currently have this album on repeat, x
