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[November 24, 2024]

This looks gerat!
How typos, AI and a six-million-dollar banana freed me from perfectionism

* * *

Typos.

I make them. All. The. Time... 

Ask anyone I work with. Slack, with its low stakes, high velocity, only makes it worse.

Am I careless? Lack attention to detail? Don't know how to write? Don't proofread?

I actually care about writing - clear, cogent writing - deeply. I fixate on commas. I fret over split infinitives. When someone misses a gerund, part of me dies. Don't get me started on Capitalization.

I care about clear, polished writing so much so that I spent a great deal of my life caring deeply about how it appeared when communicating to others.

I care about communication, about projecting ideas, emotions, but for a long time, I also cared about the projection of image.

But the typos persisted.

I type quickly. I often hit send quickly. (Yes, I proofread). Auto-correct isn't a help. I recently messaged a colleague in response to a request, "Your ask is sensible" to which I sent "Your ass is sensible."

I went to fancy schools, won fancy awards for getting fancy grades. But with a foundational liberal arts education (more on the importance of that later), came an obsessive fixation on achieving and projecting perfection.

TL;DR; perfectionism (stress the "ism"). Perfectionism is when the communication of ideas is drowned out by the communication of image. A terrible partner to a lifelong typo-holic.

The one thing I've learned is this: perfectionism destroys growth. It destroys personal growth, it destroys businesses, it destroys ideas, it destroys people. It took me nearly 40 years to discover this.

I'm a history student who became a spreadsheet junkie (more on how that happened later). Like with the gerunds, I would obsess over spreadsheet formatting. If someone gave me a poorly formatted spreadsheet, that little siren that goes off in Uma Thurman's head in Kill Bill would go off in mine.

A junior investment banking career compounded the problem--obsessing over PowerPoint bullets, pie chart formatting, fonts, sensitivity tables. Read Sweating Bullets about the founding of PowerPoint btw. Back then, it was called 'attention to detail' (and certain career death if you didn't have it - although footnotes would always somehow absolve you of blame); but really, it was perfectionism and, for me, it was the single biggest blocker to my own growth.

Then I watched the banana.

> What is up with you and this banana, Nigel? My team hasn't heard me shut up about it for three days now.

Something about watching a $0.60 bodega banana sell at an art auction for $6 million - 10 million times its intrinsic value - hit me like a ton of bricks. Not another meme or an instagram moment, it may have been one of the most clarifying experiences of my life (and, yes, my wedding and births of my kids are right there ). The banana said something about the reality and value of projecting image - particularly in the age of AI.

AI is on the brink of becoming the most consequential technological shift of our lifetime. But more than the mind-bending tech behind it, the awesome computational brute force that enables it, AI's key ingredient is not GPUs, nor nuclear power, nor the great lakes of proprietary data, it's this: English.

OK, let's call it, more inclusively, language. A trained model is nothing without a prompt and prompt is the required input for the systems to generate an output. 'Prompt engineering' is fancy, tech-speak for language. Clear language has never been more important than it is now. (I have forced Orwell's Politics and English Language on virtually everyone at my company).

    
    
[Figure 1: "DALL-E's Banana"]

I'm a geriatric millennial, some call us Xennials. I grew up with MS-DOS, Windows 3x then CompuServe, then AOL IM. I managed to survive college pre-social media and pre-camera phones (thank the Lord). The iPhone came much much later.

I love historical metaphors - the more bonkers the better. I love irony. I enjoy hitting the Popeye's at the 125th St Metro-North station after leaving the Sotheby's Contemporary Art Evening Sale.

I call several places home - New York, Alabama, DC, Paris... I strongly believe that every Buccee's location should be on the National Registry of Historic Places.

I help lead a business combining investing, fintech and the art market, the most intellectually engaging venture of my career, and one with the potential to be a generational enterprise that redefines its core market - a market that literally creates and builds value from images.

So this looks gerat: where a $0.60 banana is my madeleine, I try to keep typos to a minimum, and I plan to write about trying to overcome perfectionism...

└─ How laziness made me an spreadsheet, then a python junkie

└─ How can a CFO have low number memory? Hint: the most bonkers images you can think of.

└─ Why trying to sound smart is the dumbest thing you can do.

└─ What does a civil war battle have to do with online payment systems?

└─ What the horse-drawn reaper has to do with learning by doing?

└─ LinkedIn posts are so lame: How LinkedIn enables the worst forms of perfectionism

└─ How AI will destroy Python

└─ The contemporary art market: The book club where (almost) no one read the book

└─ AI as thought partner: Not just for haikus anymore

└─ What horse racing taught me about life and markets

└─ Intellectual curiosity (that the killed the cat)

└─ How Nigel's spreadsheets pro tips are completely ridiculous (and necessary)

└─ How Airtable taught me everything I needed to know about database theory

└─ My advice to Gen Z: Never work remotely (if you can help it)

Frank Zappa always reminded others he wrote music for himself, so this will start out as a story for me to read (and maybe I'll inflict it on my wife).

I always tell people at our company that I'm trying to fire myself from jobs I know other people are better at. This is a story of how I'm firing myself from trying to be perfect - and it won't be.

(Oh, and I'm sure people will ask whether the AI wrote any of this. More on that later too. It was definitely part of it, but it's my writing.)
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