The test that governs all of it#
Never buy the expensive thing because it’s expensive. Buy the one attached to a memory, a milestone, or real craft.
That single rule does more work than the list. A watch bought at fifty, or after a brutal year, or when a business finally worked, means something every time you look at it. The same watch bought on a Tuesday because you could is an accessory.
The nine#
A dream car. Porsche 911, a vintage Mercedes, an old Bronco, a classic Mustang. Cars stand in for freedom more than any other object. A fixer-upper is the underrated version — you get the car and a few years of learning what things are actually made of. Renting or borrowing counts if buying doesn’t.
A watch tied to a milestone. The price range here is enormous and mostly irrelevant. What matters is that it marks a chapter. The Cartier Tank Louis is the usual grail for good reason.
A bespoke suit. The suit is the souvenir; the process is the purchase. Choosing cloth, arguing about details, being measured, waiting. Navy, charcoal, or mid-grey unless you have a specific occasion asking for something else. Made-to-measure is a perfectly honest step down.
One flight at the front of the plane. No need to pay the sticker price — points, card rewards, and asking about upgrades get most people there. The revelation is usually smaller than expected and lands anyway: even premium economy on a long leg back from Europe is enough to reset what you think a flight is.
A trip built around a memory rather than a price. The Orient Express across Europe. Wimbledon, the Monaco Grand Prix, the Masters, a World Cup match. Something you’d have been at rather than somewhere you’d have stayed.
One slightly irrational hobby purchase. Golf clubs you don’t need. A camera beyond your ability. The justification is that it gets you outside, or making something, or learning a skill for no reason at all. Unnecessary is the feature.
A meal worth saving for — after research. This is where price fails hardest. Two hundred dollars at a well-known steakhouse can buy a small steak and four pieces of asparagus and an evening you resent. Expensive and worth it are unrelated variables. Read before booking.
A pair of handmade shoes. The best-value thing on the list, because you stand in them all day. One good pair — loafers, oxfords, derbies, Chelsea boots — outlasts and outclasses twenty factory pairs, and teaches you what patient work feels like in the hand.
A real piece of art. Not an investment and not a Picasso. A signed print, a limited-edition photograph, a vintage poster, something found at auction. The only requirement is that it’s genuinely yours in taste rather than chosen to match a sofa.
Why the tenth changes everything#
Nine self-rewards in a row is a shopping list with a philosophy stapled on. Add a tenth — the gift you’ve always meant to give someone — and the whole thing reorders itself.
Sending a parent somewhere they’ve talked about for thirty years and never been. That’s the same money and a different feeling entirely, and most people who’ve done both will tell you which one they think about more.
It’s also the honest check on the other nine. If none of them would be improved by someone else being there, they might not be trophies. They might just be purchases.
A few small things to try:
- Pick the one item that maps to a milestone you can actually see coming, and start saving on purpose.
- Research any expensive meal before booking it. Fifteen minutes saves the whole bill.
- If you’re choosing between two, choose the one with the better story attached.
- Decide who your tenth is for.
