Economic Lessons from the Screwtape Letters

The Screwtape Letters and time is a circle

Last week in San Francisco, I saw Nick Cave in concert. We stopped in the Green Apple Books before the show, mostly because I have a habit of treating bookstores like oracles. I’ve been trying to find something that speaks to me, something that makes sense of the bleakness and blandness, the constant hum of fear and uncertainty that understandably seems to be everywhere right now.

A big part of my job is reading, over the past few months, everyone has converging on the same emotion: fear. Articles about the Music King and Cartoon Network and John Deere - peel back the words, and they all say the same thing: things are bad. things are scary. things are spiraling.

They’re not wrong! Every time we seem to recalibrate toward less uncertainty, there’s another ReTruth or policy proposal. There is increased talk of suspending habeas corpus and imprisoning human beings who never violated immigration law and DOGE is trying to kill surveys.

The only thing the government can completely agree on seems to be things like the Senate voting unanimously to pass the No Tax on Tips Act1. This is happening as the House completely disagrees on the very complicated One, Big, Beautiful Bill which will reduce federal tax revenue by $4T over the next ten years, according to the Tax Foundation, and allow for a $4.5T increase in the deficit.

Moodys, one of the three rating agencies, downgraded US debt last Friday, in the face of ever-expanding spending and interest payment ratio problem, and the unwillingness to address it for decades. The bond market responded, with the 30Y Treasury jumping above 5% (which is the bond market’s way of screaming “please address your budget problems we are worried about the future”). This is all happening at the same time that Japan is losing total control of their bond market which, if not contained, could lead to cascading effects across the world.

So yes, the spiral feels real. I’ve felt it, too. It's hard to stay present when the present has been hollowed out into a scroll. When certainty becomes consumption, and consumption replaces meaning.

So, at the bookstore, I found a slightly battered, used copy of one of my favorite books, The Screwtape Letters, C.S. Lewis’s incredible fictionalized correspondence from a senior demon, Screwtape, to his nephew, Wormwood, on how to sabotage the human soul. The terrain was familiar - Screwtape loved talking about anxiety, fear, distraction, and the slow hollowing of the self.

“It is funny how mortals always picture us as putting things into their minds: in reality our best work is done by keeping things out.” - The Screwtape Letters

In Screwtape, evil doesn’t arrive through fire and fury. It creeps in through ease, comfort, and optimization. Screwtape wants to nudge people into passivity as a way of capturing their souls. Let them scroll. Let them spend. Let them smooth away all friction until they wake up hollow and can’t remember why.

“The more often he feels without acting, the less he will be able ever to act, and, in the long run, the less he will be able to feel.” - The Screwtape Letters

As I was reading it, and reflecting on now, it increasingly felt like we are in a version of Screwtape’s Economy. On each page, there is a lesson, ranging what we do versus what happens to us, the focus on the future instead of the present, the rot of letting feelings fester, how distorted reality can become from manipulation of truth, a spiritual economy built on slow erosion.

So I want to explore rejection, convenience, and a lack of surprise through this lens - building a bit on my friction piece, but through the eyes of CS Lewis, and the lessons we are eternally learning about what an economy is beyond money.

Rejection

David Brooks recently dubbed Gen Z “the most rejected generation,”:

• Harvard gets 54,000 applications. It accepts 1,950.

• Goldman Sachs receives over 315,000 applications for 2,700 internships.

• The average knowledge-worker job posting now receives 244 applications — more than double 2019 levels.

• Students regularly apply to hundreds of jobs - just to maybe get one callback.

Brooks writes about the world of ‘competitive exclusion’ (rejection as a way of life) and quotes research showing its long-term psychological toll: less empathy, more aggression, lower self-control. Rejection threatens our core needs - belonging, agency, competence. There is some financial nihilism baked in. He writes:

She told me that none of her friends are doing long-term thinking or saving for a mortgage. The world seems so radically unstable to them that they’d rather enjoy what they can today than sacrifice now for some possibility that may never come to pass two decades from now

But mostly, it’s a lot of young people trying very, very hard in a world that isn’t making any room for them.

“Indeed the safest road to Hell is the gradual one—the gentle slope, soft underfoot, without sudden turnings, without milestones, without signposts.” - The Screwtape Letters

Part of it is a feature of convenience. Online applications were meant to democratize access. But when everyone can apply, no one gets seen. In removing that friction, we unintentionally created seemingly infinite supply which is handled by algorithmic culling - and there is no real feedback loop, no human warmth, no dignity in the process (Brooks calls it the seventh circle of Indeed hell). And that sort of rejection is now the default condition of economic life.

“One young man told me the system caused him to value security and stability above all—to find a place where he wouldn't be vulnerable to the next rejection.”

This is what Screwtape would call a slow erosion of spirit. Humans in a perpetual state of anxiety, constantly questioning their worth, experiencing rejection not as an occasional setback but as the default condition of existence.

I’ve been watching Lauren Greenfield’s Social Studies series2, featuring a group of teens going back to high school post-pandemic, and following them through the world as they navigate parties and school and being young.

One girl built her entire life around getting into Stanford. She has a podcast on health and wellness, took college classes at UCLA, has a perfect GPA, volunteers, is a yoga teacher - basically, has a resume that should glow and levitate off the application stack. She got rejected. She got rejected from her other ten choices too.

To see that happen - to see almost ten years of dreaming get completely and totally crushed, and to know that rejection might be what she faces the rest of her life is devastating. The hard work didn’t pay off in the way she expected, and there is no real answer to it, because of course Stanford can't accept everyone! They’re Stanford! Of course companies need to filter somehow.

The system makes perfect sense on paper. But we've built an economy that functions as an industrial-scale rejection machine, and then we wonder why young people seem anxious, risk-averse, and increasingly detached.

When you combine this constant rejection with the pressure to maintain a perfect digital presence, you get a generation caught in an impossible bind: expected to pursue opportunities aggressively while simultaneously protecting themselves emotionally from the near-certain rejection that follows. It's exactly the kind of spiritual fatigue that Lewis warned about - the quiet, whimpering despair of perpetual inadequacy.

“Satan and his devils want a whole race perpetually in pursuit of the rainbow's end, never honest, nor kind, nor happy now, but always using as mere fuel wherewith to heap the altar of the Future every real gift which is offered them in the Present.” - The Screwtape Letters

And we might have to just rethink all of this. Rejection can be recalibration. One of the best ways to get wealthy in the US is to own a medium-size regional business, as reported by the WSJ. They are boring and lucrative and many of their owners are retiring. The shiny path of perfection might be the endless path of rejection - but there are alternatives.

Convenience

Meanwhile, life has never been easier to outsource as I wrote about a few weeks ago. You can get a burrito, a dopamine hit, and a loan in mere seconds, and certainly it has no repercussions… right?

According to the National Restaurant Association’s 2025 report, 75% of restaurant traffic is now takeout and 60% of Gen Z and Millennials are ordering more takeout than they did last year. Klarna, the buy-now-pay-later giant, recently partnered with DoorDash to let you finance a burrito. But their losses are mounting, with defaults up 17% year-over-year.

Who could have seen this coming! Buy-now-pay-later apps are bleeding cash as users default on $12 tacos. Convenience is infrastructure now, and a great cost.

This is the Convenience Contradiction that I’ve written about before in regards to dating apps: the more we optimize for effortlessness, the less resilient we become. And the more fragile our systems get, the more anxious we are, so of course we reach for even more convenience to soothe ourselves.

What Lewis understood so clearly was that small choices, repeated daily, shape our character more profoundly than dramatic one-time decisions. He would see our convenience economy as a perfect trap because it slowly takes away our capacity for meaningful effort.

What happens when we remove all friction from consumption?

• Well, the meal that arrives at our door through three layers of intermediaries (the app, the delivery person, the restaurant) creates no social ties, requires no planning, and leaves nothing behind but packaging waste.

• The entertainment that streams directly to our devices based on "what you might like" removes both the joy of discovery and the possibility of being challenged by something unexpected.

Even our financial decisions have become frictionless through buy-now-pay-later services! We're no longer forced to confront our economic reality at the present (something that’s been happening since the rise of credit cards). Instead, we can continuously defer that confrontation, pushing it into a theoretical future where we'll somehow have more capacity to deal with it.

Screwtape would feast here, with that slow untethering from reality. The irony is that this convenience was supposed to free us for deeper pursuits. With food delivery, we wouldn't waste time cooking; with algorithmic entertainment, we wouldn't waste time browsing; with frictionless finance, we wouldn't waste time budgeting.

But free us for what, exactly? The promise was more time for meaningful connection, creative pursuits, deep thinking - exactly the things that require effort, patience, and resilience, the very muscles that convenience has allowed to atrophy.

Surprise

One of my favorite recent reads is Felix Gillette’s Cartoon Network’s Last Gasp. It’s an incredible moratorium on an incredible studio that shaped a lot of weirdo kids into who they are today. It respected art, respected time, and certainly respected the viewer.

Now it makes reboots! In a recent interview, one Warner Bros. exec summed up the new approach to Cartoon Networks new growth strategy:

“The easiest way for me to do [make money] now is to do it with our really beloved IP.”

The easiest way to make good business sense is to exist in the past, to keep telling the same stories, of course, of course, of course. This shift from originality to optimization is systemic. Across media, the algorithm wins. I wrote about Mr Beast a few months ago but the youtubification of everything is here. Dave Perell captures it well:

Lewis would recognize this too! When everything becomes interchangeable, measurable, marketable, we lose the very quality that makes culture meaningful beyond utility - its ability to communicate values!!

The convenience economy makes all elements of life predictable that shouldn’t be predictable. Lewis would see this death of surprise as spiritually catastrophic. The unexpected discovery, the challenging idea, the story that doesn't go where you anticipated - these are the experiences that expand our humanity, the collective consciousness, all the things that we feel and touch and see.

But algorithms don’t really like surprise. The data never recommends true novelty because novelty, by definition, lacks historical engagement metrics. So we get this weird version of the illusion of choice while the cultural diet narrows to what is "safe." Cartoon Network once gave us shows like "Adventure Time" and "Chowder" - creative risks that expanded what animation could be. Now they're retreating to Barney reboots. When we optimize for the "easiest way," we lose the beautiful, difficult paths that lead somewhere new.

We want him to be in the maximum uncertainty, so that his mind will be filled with contradictory pictures of the future, every one of which arouses hope or fear. There is nothing like suspense and anxiety for barricading a human's mind against the Enemy. He wants men to be concerned with what they do; our business is to keep them thinking about what will happen to them. - The Screwtape Letters

Same Problems, Different Time

What Lewis saw, and what we’re now living through, is the spiritual cost of systems designed to make everything easier. Rejection isn’t a weird glitch in the economy, it’s the default. Convenience isn’t a consumer preference, it’s a coping mechanism. The absence of surprise isn’t just a creative choice, it’s now a byproduct of optimization. And all of it chips away at our capacity for presence, for agency, for wonder.

And not to get too abstract here in my economic newsletter - but rejection, convenience, and absence of surprise are all economic questions. When enough people choose friction over convenience, markets respond. We're seeing early signs of this: the (slow) revival of independent bookstores, the rise of deinfluencing, the growing market for durability over disposability, especially as the economy turns.

These are emerging from the simple recognition that the frictionless life is ultimately unsatisfying. Even the secular, modern, economic soul hungers for something deeper than convenience!

The economic problems (fiascos?) that dominate our headlines, from debt ceilings to bond market freakouts, are following same pattern. Our financial systems have also optimized for short-term convenience at the expense of long-term resilience.

The Moody's downgrade shows that even our most sophisticated economic systems eventually face the consequences of deferred friction. Screwtape would celebrate that our national balance sheet as operating on the same principles as our DoorDash accounts - the constant deferral of necessary difficulty.

Once they knew that some changes were for the better, and others for the worse, and others again indifferent. We have largely removed this knowledge. For the descriptive adjective ‘unchanged’ we have substituted the emotional adjective ‘stagnant’. We have trained them to think of the Future as a promised land which favoured heroes attain—not as something which everyone reaches at the rate of sixty minutes an hour, whatever he does, whoever he is. - The Screwtape Letters

Lewis would remind us that true happiness never came from eliminating difficulty but from facing it with purpose. He would remind us of a lot of stuff, but mostly he would probably point out that rejection erodes but can recalibrate us, some convenience robs, surprise is joy, and that true hope requires a little friction. Etc.

Thanks for reading. :-)