➺ January 8, 2026

Hey {{ first_name | Neighbor }}. On this day in 1996 the Baseball Hall of Fame announced that absolutely no one had been inducted. The trouble wasn't that there weren't worthy players, but that there were so many – Phil Niekro, Don Sutton, Jim Rice, Tony Pérez – that none got the required 75% of the vote. Jim Rice, who drove in more runs than any other player for 12 years in a row, didn’t get in until 2009.

This is all to say that talent isn’t relative. We just compete like it is. – AB

➺ Until You Get Punched in the Face: The big finding of The Financial Planning Survey so far: Lots of us are calling audibles. Participate to receive the results.

➺ On That Note: A quick shoutout to our sponsors at Domain Money for offering each Upper Middle reader a free 30-minute financial planning sesh. Definitely wouldn’t kill some of you….

A.I. Doesn’t Get Retirement.

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That’s why you need Domain Money’s financial intelligence. Their CFP® professionals look at:

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What we’re drinking about while talking.

STATUS ➽ Bad Intentions
Why look so closely?
Last week, Twitter co-founder Biz Stone and Pinterest founder Evan Sharp launched Tangle, an "intentional living" social media app pitched as an antidote to the social “devastation” caused by.... Biz Stone and Evan Sharp. Invite-only because of course, Tangle prompts users to declare an intention for the day¹, then to log how it went, publicly demonstrating their interiority. The pitch reveals the choice now facing most people who spend their time online (which is most people): Live an unexamined life mediated by algorithms or an over-examined life mediated by tight feedback loops.

Tangle sounds like LiveJournal, but has more in common with Strava or Oura, which quantify basic human activities in service of "intentional living." But intentional does not have to mean optimized. Asked how he wrote so well, E.B. White famously quipped: “I don’t look under the hood.” That's intentional living too.

TASTE ➽ Fantasy Island
Why is Tommy Bahama still a thing?

On Monday, Grub Street filed an incredulous dispatch from the Tommy Bahama restaurant in Midtown East, which has apparently become a power-lunch spot for private-equity associates and vice presidents who sense that ordering steak frites at Le Bilboquet might seem unseemly in the current economic climate. The optics of upper-middle-market tropicalia are apparently better. But the premise of the article – that Tommy Bahama is a brand for dads summoning up the courage to snorkel – is unfair. Founded in 1993 by Ralph Lauren alums, the brand undeniably traffics in postcolonial nostalgia and midweight, nipple-forward quarter-zips, but it also makes really good furniture. It has for a while.

Tommy Bahama poster beds, chests, and dressers lean toward teak and Caribbean colonial, which is plantation style with plausible deniability. The combination of bad clothes and good furniture makes Tommy Bahama something unique: a brand that appeals to risk-on financiers, risk-off SPF-50 index-fund guys, and the if-you-know-you-know décor crowd. Their social circles may not overlap, but their piratical fantasies do.

MONEY ➽ L7 Battle Royale
Why is Amazon having workers apply jobs they already have?
In late 2025, Amazon cut 14,000 corporate jobs then submitted WARN filings notifying California, New York, Washington, and New Jersey of plans for mass layoffs later this month. Now, the comapny has revamped its Forte self-review system. Going forward, Amazon will demand that employees enumerate their “accomplishments,” defined narrowly as “specific projects, goals, initiatives, or process improvements that show the impact of your work.” The play here is obvious: CEO Andy Jassey is using a formal system created out of thin air to justify breaking an informal covenant with his workers – that they'll keep their jobs if they do them – before a rug pull that's already on the books. He's not moving the goal posts so much as eliminating the most of the space between them.

What comes next is a collective rush toward quantifiable work that will pit L6s and L7s against each other rather than against C-level officers watching from the cheap seats. Employment, which used to be the baseline, will become the prize.

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People who produce complexity consume simplicity.

A senior vice president of operations walks into an antique store.

She has time before dinner and no intention of buying anything. The store has the skunk weed smell of wood polish. She pokes a Chesterfield sofa and fondles a bored-looking ceramic spaniel. Then she spots a ladder back chair next to a tole side table. It’s tall with a woven rush seat and has been given pride of place. She reads the tag hanging off the side: “Enfield Shaker Chair Circa 1830. $1,800 $1,450.” The price seems obscene², but the chair is special. She’s longed sensed a person can only prioritize making one thing at a time – a product or a profit. She imagines the man who made the chair – some humble bearded ascetic – chose the former. 

She doesn’t buy it because it will match her Danish modern coffee table or her Noguchi lamp or the Eames lounger her husband bought six months prior as an “investment.” And she certainly doesn’t buy it because she needs it. 

She buys it because, when she sits in it, she feels a specific kind of relief. The great project of her professional life is reducing roles to ever smaller, more measurable tasks and responsibilities. She creates complexity in service of savings. Naturally, she craves simplicity. But she can’t afford to be simple; she can only afford simple things. She buys the chair because she’s jealous of it. It’s imbued with a feeling she doesn’t have.

It’s fulfillment. The chair is not the product – much less creator – of a workflow so splintered that participants cannot derive meaning from their work much less imbue the object of their work with meaning. The chair has quintessence, an it-ness derived by from the fulfillment of its makers. On some level she knows this, though she’s good enough at rationalizing her work to hide her moral injury from herself. 

She brings the chair back to her apartment, pulls it up to her IKEA desk³. She googles the Enfield Shakers and is surprised to learn that no one artisan built the chair – that the Shakers ran what was, at least by the standards of their time, a massive manufacturing business: furniture, seeds, brooms, herbs. They divided labor. Posts were turned in batches. Slats were cut separately. Seats were woven in a special room built for that purpose. She wonders who handled their ops.

Lots of people. She finds out the Enfield Shakers created an ops org consisting of “trustees” and “deacons” who handled the “temporal affairs” of the community while true authority remained with a small, charismatic ministry that derived legitimacy not from efficiency but belief. Management was custodial rather than extractive, bounded by doctrine and accountable to a moral vision. Initially, complexity was only allowed to the degree it did not interfere with purpose, making the work feel empty or cruel. Profit was less an orientation than a byproduct of the “Hands to work, hearts to God” religion doctrine. 

She toggles between the article and LinkedIn. A former colleague has posted about “operational excellence in a tightening market.” She clicks back. She reads a quote from an Enfield Shaker eldress: “In any community fitly joined together there must be many who are inconspicuous, but who [provide] for the solid substance without which the wholesome community could not exist. To be a person of that sort is worthy of one’s ambition.”

She leans back a bit, using Siri to transcribe the quote into her journaling app. The chair creaks, but doesn’t give. It feels as though she is being given permission to produce simplicity in response to the complexity of the world. It’s a nice feeling, but not a new feeling. Years earlier, when interest rates were near zero, she worked at a software startup where more time and focus went toward refining the product than profiting from it. It was SaaS, sure, but those years were some of her best. She produced simplicity and consumed complexity – largely in the form of second dates.

The startup failed. Rates changed. Ce’st la vie. There was more money in management, and abstraction so she leaned into documentation and goal setting: OKRs, RACI docs, KPIs.  She got a job and then a promotion and then an office with a door. She went in eyes open. She’s read her Barbara Ehrenreich – “through a careful analysis of the production process, the complex and intellectually demanding work of the craftsman could be broken down into simple, repetitive motions to be divided among less-skilled workers” – but she also has to pay rent.

She keeps reading and learns that as the number of trustees and deacons among the Shakers grew, the community shrank. It’s strikes her that workers – congregants, really – didn’t leave because of money. They weren’t there for the money. They left because they no longer felt fulfilled. When supervision replaced shared belief the system began to fail.

She wonders what her coworkers would do if they weren’t in it for the money, if her company was a spiritual project. She concludes, uncomfortably, that they would either force her out or leave themselves – that her work would become a barrier to their fulfillment. Then she reads that many of the deacons left before the rank and file, not wanting to undermine a project that had deep meaning to them.

She sympathizes. Her work has meaning to her. Deep meaning. Of course it does. There’s just a distance between meaning and fulfillment. That distance is measurable in the time she spends at retreats and in therapy and, sure, shopping. It’s measurable in how much a producer of complexity will pay for simplicity – a bit of relief, a few pieces of polished wood.

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MOVE FORWARD (IN A CIRCLE)

When FDR enumerated the Four Freedoms, he did not clarify that freedom from want does not mean freedom from wanting a Breville toaster, a room with a private pool, and a more attractive spouse to dip in it. Being free of that kind of wanting would require being free of the exquisitely calibrated algorithms that feed images and videos of a lifestyle just out of reach.

The feeling that drives grasping and grinding—working toward a fantasy of weekends in Vail⁴, the odd dinner at Carbone—is more aspiration and competitiveness than greed, but still a strong enough spice to bitter a lobster bisque. The good news is that it almost inevitably produces an enviable lifestyle. The bad news is that the lifestyle belongs to someone a few floors up. Nevertheless, the cycle continues.

[2] It’s not. The reason Shaker chairs are priced so high is that they’re beautiful. Things that are subtle and beautiful can cost more too!

[3] IKEA may be the best modern equivalent of a Shaker Villager. It used to be Zappos when they tried to get rid of hierarchy and implement holacracy. Those were the days.

[4] Go hang out in Gold Hill and ski El Dorado with the stoners. That’s how the West was won.

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