The Two Big Questions
The order—and the answers—matter
The other day I was speaking with someone who works at a creative agency, and we hashed over a familiar lament. They mentioned that the people she works with are really focused on designs that look cool.
At this point, you may be thinking, Uhh, why is that a problem? But I immediately knew what they meant.
When you are a creative (I abhor using this title, but have yet to come up with anything better) there are two important questions that you must ask when evaluating your output:
Does it work?
Is it cool?
The ideal scenario, of course, is that the answer to both questions is, “Yes.” But if only one question can be answered in the affirmative, it is way more important that it be the former. Too often, however, we judge work by the answer to the latter.
I’m not trying to be a wet blanket. I’ve spent a good chunk of my life in the quote-unquote Cool Economy™, and my career goal whenever anyone asks is simply, “make cool stuff with cool people.”
Like I said, the goal is always to check both boxes. But it’s important to put first things first. While the hard part is front-loaded, it’s much easier in the long run to create work that works first and then figure out how to make it cool than it is to reverse engineer something cool into something that works.
But cool should never supplant solving a problem. When we create, there is a job to be done. This isn’t for sh*ts and giggles or to impress our friends. And sometimes doing that job effectively means doing it in an uncool way. That’s a feature, not a bug. Being able to recognize when that’s needed—pride and cool points be damned—is the mark of a real creative leader.
At the risk of sounding like an afterschool special, you may find that not focusing on cool may end up being the coolest thing of all.
How Six Italian Brothers Shaped the Story of New York
This is a great story about the unsung heroes behind some of New York’s and the world’s most recognizable sculptures. The Piccirilli brothers carved iconic totems such as the lions outside the New York Public Library, the figures above the New York Stock Exchange, and the Lincoln Memorial. While much of their work involved executing the designs of others, they were more than highly skilled craftsmen, they were artists in their own right. —Justin
Invest Like The Best — Justin Mares
I’m an occasional listener of this podcast, but was drawn in by my increasing desire to become even more radicalized about “The US Health Crisis.” After having read Justin’s piece about the “Food Compass” in Pirate Wires last year, I hoped this episode would be similarly astonishing. It was. So much so, that I reached out to Justin to see about doing some work together for his new company, Truemed. —Andrew
Toro y Moi - Sandhills
There is a genre of YouTube that I really appreciate for one specific and regular use case: having something on in the background while reading a book or surfing the web. Ideally, these are mellow tracks with a visual component that greatly enhances the experience over just listening to the audio. I threw this on last weekend while Just a Friend, JD1818, and I sat on my couch (also a rec btw) and talked about life. It earned a “this is really nice” just around the four-minute mark. —Andrew
Glerups Leather Sole Slippers
After some time away, a link Andrew sent me got me to re-sign up for the Blackbird Spyplane Substack. While I still find some of the language a bit tedious, I was pleased to see that these slippers got a co-sign. I’d owned and loved a pair for many years that I received as part of a press junket. Then when I got a dog, he chewed them up in one of the biggest clichés ever. After making do with some ill-fitting holdovers from Armor-Lux and Ugg, I recently re-upped on Glerups and am so glad I did-slash-kicking myself for waiting so long. —Justin