Way back when,
someone at WeTransfer bought me a desk sign. Engraved. Proper effort. It read:
“Don’t ask me. I don’t know.”Apparently I say it a lot.
Enough for it to become a thing. Enough to stand out. Which is odd, because we’re supposed to know. Or at least appear to know. Or know adjacent. Or now — use ChatGPT in real time so that you definitely know. Or can convincingly fake it.
Because not knowing is stupid.
Or lazy.
Or weak.
Or a career-limiting move.
There is so much I don’t know. Can you imagine knowing everything? Would that be the equivalent of being a neurological billionaire? Hang on — is that how Elon feels? Shit, I think it is.
Is that the origin story of a megalomaniac?
Is omniscience just untreated narcissism with Starlink?
We’ve reached a cultural moment where not knowing is treated like a failure. Everyone has an answer — publicly, instantly, convincingly. Hot takes before thinking. Verdicts before questions. Certainty as performance.
Not knowing is the silence nobody wants to hear.
The playbook is knowledge.
We must know how to act.
How to perform.
The ingredients for a great film are.
How to write a top-ten bestseller.
How to build a company and sell it for $1bn.
How to write a top-ten hit.
How to sleep with 1,000 men in one night?!
There is a playbook for everything now.
Slides for the soul.
Frameworks for feelings.
Bullet points for meaning.
And yet — there is one thing we can be absolutely certain of.
We will die.
But what happens after that?
No idea.
Which is interesting, because we prepare obsessively for everything except the one event with a 100% conversion rate.
We meditate.
We journal.
We biohack.
We optimise sleep, purpose, productivity, gut flora.
We enrich life, curate joy, architect meaning.
But prepare for not knowing?
Barely. Actually, never.
Here’s my advice for 2026.
There will be no Google Maps when we die. Nope. And no Waze either. (Apple Maps might be there — it died a while back.)
No turn-by-turn directions.
No “people who liked this life also enjoyed…”
ChatGPT will not help us write the playbook for the afterlife.
There will be no deck.
No onboarding flow.
No FAQ.
Just a sudden and deeply inconvenient realisation that we cannot playbook this shit. Doh!
And if we don’t practise not knowing before that moment — if we don’t build some muscle memory for uncertainty — our generation is going to absolutely lose its mind. More! Can you even begin to imagine what that will look like?! Actually, this might be the game plan to resolve the ageing-population issue.
Imagine it:
A cohort raised on answers, metrics, certainty, optimisation — suddenly faced with the ultimate unknown.
No tools.
No search bar.
No Claude.
No ChatGPT.
No Gemini.
No Sam.
And let’s hope to f*ck, no Elon.
No workaround.
Just us.
And silence…
So maybe “I don’t know” isn’t a weakness.
Maybe it’s rehearsal.
Maybe admitting uncertainty isn’t intellectual laziness — it’s existential strength.
Because if you can’t sit comfortably with not knowing now, death is going to be a real shock to the system.
And frankly, I’d rather practise early.
Wishing you and your loved ones a very prosperous — and very, very unpredictable — 2026.
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Commercial break.
This 💌 was brought to you by
Momotaro, an app for focus developed by the uber-talented
Orlando F. Ruiz (fka Laszlito Kovacs), because your brain needs 23 minutes to refocus after a distraction. Every notification costs you momentum. Simple.
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For anyone new to the letter—here’s a handful of things I’ve enjoyed lately.
Legend:
🧁 = Light / Easy
🦪 = Dark / Challenging
Books
Oskar Schell, a precocious nine-year-old genius-type, grapples with the devastating loss of his father in the September 11 attacks.
A genre-defying graphic novel that mashes memoir, history, and social commentary around… ginseng. The author draws on his childhood in rural Wisconsin, where he and his brother worked on the family’s ginseng farm, earning a dollar an hour and spending it on comics — a formative experience that shaped his life and craft.
Recommended to me by Deirdre O’Callaghan, the infamous photographer and author of The Drum Thing. Part memoir, part cautionary tale, The Dirt stands out for its brutal honesty and outrageous anecdotes, capturing both the allure and the cost of the rock-star lifestyle.
The greatest playbook never written. A playbook about not being a playbook by an author about a company you might have heard of.
Podcast
🧁
Louis Theroux I had the pleasure of meeting Louis two weeks ago, and it didn’t disappoint. This episode is Jimmy Carr × Louis Theroux. Jimmy touches on deliberate transgression, comedy as one of the last “safe spaces”, the importance of play, and his role in the service industry — being paid for the attempt, not the jump.
Not a podcast but a Patreon radio programme, hosted by Owen Cutts. Energetic and entertaining.
TV & Film
🦪
One battle after anotherWithout doubt Leonardo DiCaprio’s best performance in years, Sean Penn’s most worrying, and a typically unfaltering supporting role from Benicio Del Toro.
🦪
The Ice TowerMarion Cotillard is perfect casting for the role of an Ice Queen. This is a joy to watch, with each frame in itself a piece of art.
A film from inside the mind of Pablo Escobars hippo. Come on!
Sarabande & The Supporting Act Artists (past and present)
I helped to establish
The Supporting Act Charity and sit on the board for Sarabande. Both have a similar mission to support emerging talent.
🧁
Daisy CollingridgeDaisy is a graduate of the Sarabande foundation and in part thanks to the WePresent team will be taking over Time Square on 13th March 2026. If you happen to be in Time Square at midnight drop by…
Jet is a 2025/2026 Sarabande artist. Clearly an incredibly talented jewellery designer, I am very intrigued to see how her craft develops during her time at Sarabande.
Bina was selected by Ciara and Curly Media for
Drop School and was also recently the recipient of a grant from The Supporting Act c/o Will Smiths donation.
That's it. Thanks for reading. If you have any suggestions please email me. In fact just email me anyway :)