I, T, or semicolon: What type of professional are you?

And where Deep Work fits into this framework

I woke up last Saturday to an e-mail newsletter, challenging not one, but two of my deeply-held beliefs. The subject was “Semi-Colon Shaped People” and the sender was Venkatesh Rao, one of my favorite contemporary thinkers. Rao was challenging my beliefs of the virtues of T-Shaped Individuals and Deep Work.

I’ve often spoken about striving to be a T-Shaped individual (including here, with Patrick O’Shaughnessy) My embrace (and borderline evangelism) of Deep Work has even frustrated some of my friends as I’ve created extremely strict and precise boundaries around huge chunks of my life (not to mention tons of hacks to fight distraction). As a result, I’m typically unresponsive to texts/emails and significancy limit my meetings each day. So how do I feel when my one of my internet man-crushes states:

“I personally find T-shaped people boring.” Venkatesh Rao

Source: Venkatesh Rao Breaking Smart e-mail newsletter

First, from “I” to “T”

First, some definitions. An I-shaped individual (an “I”) is someone who’s highly specialized, an expert. A “T” is someone who can specialize (the stem of the “I”) but also can go wide (the horizontal stroke). Charlie Munger refers to them as expert-generalists and an example could be the CEO of Goldman Sachs, Lloyd Blankfein. Blankfein was a commodities trader before he ascended to oversee Goldman Sachs in its entirety.

Personally, my departure from finance was driven by the desire to be less of an “I” (i.e. a hedge fund investor) and more of a “T” (i.e. an entrepreneur who needs to understanding product, management, sales, and more).

Rao argues that “T”s are like their namesake Tetris piece — they “interlock” well into a broader system, be it large corporations (and their respective org charts), academia, and, more broadly, society. Because “T”s are so structurally sound, they play nice with one another — from which arises a strong sense of belonging.

From T to Semi-Colon: A Messy Exploration

I strongly believe that work, companies, and economies are being fundamentally changed by technology and our ensuing interconnectedness — and we’re only in the early innings. Examples abound, ranging from 55 people building a company worth $22 Bn (WhatsApp), viral ice dumping and ALS breakthroughs (Ice bucket challenge), and even (gasp!) the US presidency (I’ll save you the links ?).

Many knowledge workers are unprepared for this change, both in skills and in mindsets. And this is where Rao’s semi-colon comes in:

The tl;dr is that you have an anchor (the dot) and a general area of exploration (the curvy tail). But Rao’s special sauce is the space in between the two, where messy exploration takes place. Here, people look at you like you’re crazy, things are unfinished and undefined, and — unlike a “T”you cannot cleanly explain to your peers what you do.

The Canary for Messy Exploration: Google Docs or Microsoft Word

Here are a few examples to highlight this messiness and how it makes people extremely uncomfortable. I recently spoke to a friend, who went from a Fortune 500 company to a late-stage start-up. This involved moving from Word to Google Docs — no big deal, right? Not exactly. The tension he felt in a Google Doc world, was that documents were truly living (and dynamic). There was no closure, to the point that he felt the need to “freeze” certain changes by converting them into PDFs. You see this dichotomy in Slack vs. E-mail as well. Closure, finality… PDFs — yet the world is changing too quickly for finality to be a relevant goal.

Kanye West — King of Messy Exploration?

Take another sillier, but relatable example: Kanye West and his release of The Life of Pablo. I’ll spare you the details, but here’s how he released it. In bits and pieces across Spotify, Soundcloud, TIDAL, iTunes, tweaking songs/track lists/album names via social media, and “debuting” the album at the Livestream at his fashion show.


Pundits called it a disastrous release — but I say, does it really fucking matter? The album is Microsoft Word, and Kanye was iterating and experimenting his way towards a final product, well, that was never really finalized. (I’ve listened to it close to a hundred times and have no idea what the album is.)

My guess is that Rao would describe this album release as explorer’s chasm — Kanye’s messy space between the dot and the curvy tail.

Messy Exploration in Finance (umm, I mean Bitcoin)

Many of my finance friends have been hit by the crypto-bug and have asked “What’s the best book on the topic?” (I’m told Digital Gold is a good starting point). But my brief conversations in the space indicate this messy exploration is not happening in books — it’s on Twitter, Reddit — but even more on Slack and other communication channels.


Microsoft Word. Albums. Books… seeing a trend?

My own journey in the Explorer’s Chasm

Personally, my explorer’s chasm has been one of the most rewarding parts of my two year journey as an entrepreneur — but I’ve struggled (particularly in the early days) with the sense of belonging that Rao describes.

It’s extremely hard for me to answer the question “What do you do” (which many feel is a bullshit question). The closest thing I have to a “job” is my work as Quartz’s Entrepreneur in Residence; I am self-funding a podcast and e-mail newsletter; I’m writing a book proposal; and I make silly videos on Snapchat. This is not easy to explain at a cocktail party with my fellow finance buds. This used to be a huge source of self-doubt and confusion — after all, our society loves clean labels. (Another thinker, Tiago Forte coined the term Full Stack Freelancer.)


Not only has my “work” been a messy exploration, but so has every aspect of my life. When I travel to a new city, the majority of my meetings are with friends I’ve met on Twitter. My “work day” is both 24/7, yet I’m able to have dinner at home every night. I spend over half of my time learning about technology and media from people half my age. And many strangers, contribute over $1,100 a month (via Patreon) to fuel the growth of RadReads.

And what about Deep Work?

The more I reflect on Deep Work, I realize that it ultimately comes down to personal preferences. But it must be accompanied by a deep sense of self-awareness. I know that I cannot write and create, if I’m constantly responding to texts and Tweets — so I’m very rigid about this. FWIW, I wrote this with my laptop WiFi off, in two pomodoro sittings. (I also believe that the tech giants’ incentives are deeply at odds with consumers’.) Others, like Rao, derive creativity from this constant interaction, the collective mind — and by all means they should continue to do this.

But please, be honest with yourself — if you’re trying to create something special and are arguing with someone about COVFEFE — you may be deceiving yourself about the role of technology in your own work process.

So what kind of person does this make me?

Sorry to disappoint, but I’ve eschewed labels for a while now, and I guess I won’t recommit now. It’s more instructive to understand approaches and the mindsets required for them to work. One of those mindsets, abandoning the need for conformity and belonging, has been a personal game changer. And for now, deliberately messy seems to be working best for me.


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