Most of my favorite writing is about uncertainty — I find it interesting because it actively avoids conclusions, pushing the onus back on the reader to form their own. Yet in my brain, I prefer the opposite; I want to have everything squared away and explained, a complex web of earned understandings that I can relay at a moment’s notice. One of my least favorite feelings is when I find myself running my mouth about something I have no business talking about — it feels as if I’m walking along a teetery plank where any interjection could cause me to fall and look stupid/shallow.
This discomfort is taken to an even greater degree when discussing feelings — but the fear there isn’t so much of looking stupid, it’s of being rejected and/or not receiving enough love in return. Sharing big feelings feels like walking on a glass bridge above a large ravine — you want to believe it will hold your weight but as soon as you start moving, your shifting point of view blurs any sign of the bridge, leaving you with nothing but memories of the structure to steady your anxious mind. Will you float or will you freefall? Only the beholder’s response will tell.
It’s surprised me how many of the shameful parts of myself I’ve unearthed from walking above such ravines have turned out to be exactly what the right people love. Anyone who finds your uncertainty threatening is immediately disqualified. Unconditional love has an inherent integrity to it — a special sort of invisible material that gives you something to stand on while staring straight at things you couldn’t before. In the same way I like writing that isn’t self-assured, I’m learning that there are people who will love the fact that I can’t always explain myself, and enjoy beholding when I do.
Instead of a conclusion, I have an observation: people are perplexing mysteries who can never be fully aware of their own plots. Why is there such a beautiful quality to seeing that in another, while a tragic feeling when we find it in ourselves?
Links
The Earnest Ambitious Kid's Guide to Investors (essay)
Frank fundraising advice for folks who’ve never raised before.
The Rogue Investor's Guide to Venture (essay)
Notes on what I’ve learned about VC these past two years.
Gene Pool Engineering for Entrepreneurs by Vinod Khosla (guide)
An incredibly tactical guide on hiring from the recruiting king himself.
Smart and Elicit by Ross Levine and Yona Rubinstein (paper)
Research on the persistent qualities among young entrepreneurs.
The B Lane Swimmer by Holly Witteman (essay)
“The truly great researchers are generous and friendly; so are many of the middle of the roaders. Those who have something to prove… and who feel like they aren’t quite managing to do it, show definite aspects of being B lane swimmers.”
The Billionaire Who Wasn’t by Conor O'Clery (book)
On Chuck Feeney, who made billions as a founder of Duty Free Shoppers Group and then gave it all away via his foundation, Atlantic Philanthropies. Insanely interesting — you don’t have to enjoy business books to get something out of this.
An Ambitious Woman after the End of Ambition by Jill Filipovic (essay)
Nothing new, I just like hearing how other women think about this topic.
The Third Thing by Donald Hall (essay)
"Third things are essential to marriages, objects or practices or habits or arts or institutions or games or human beings that provide a site of joint rapture or contentment. Each member of a couple is separate; the two come together in double attention.” Tim Keller echos this!Fan Fiction by Tavi Gevinson (zine)
The ““fictional”” email exchange at the end between Tavi and Taylor Swift says a lot about each of their markedly different perspectives on the role of art.
Pain & Surprise by Annie Kreighbaum (essay)
Annie was responsible for Glossier’s voice in the early days. Her writing now is both poetic and pithy, a good example of uncertainty being given its proper space.
Tolerating Unknowns Will Make You Stronger by Heather Havrilesky (essay)
Very good advice for type A people attempting hard, ambiguous things.
Black & Gold by Sam Sparro (song)
This song is silly good, even 16 years later.
Parting thought
Whatever you now find weird, ugly, uncomfortable and nasty about a new medium will surely become its signature. CD distortion, the jitteriness of digital video, the crap sound of 8-bit - all of these will be cherished and emulated as soon as they can be avoided. It’s the sound of failure: so much modern art is the sound of things going out of control, of a medium pushing to its limits and breaking apart. The distorted guitar sound is the sound of something too loud for the medium supposed to carry it. The blues singer with the cracked voice is the sound of an emotional cry too powerful for the throat that releases it. The excitement of grainy film, of bleached-out black and white, is the excitement of witnessing events too momentous for the medium assigned to record them.
thats lovely molly, i really liked how you put in words some things i have been thinking about lately, especially this: “One of my least favorite feelings is when I find myself running my mouth about something I have no business talking about — it feels as if I’m walking along a teetery plank where any interjection could cause me to fall and look stupid/shallow.”
thank you, i enjoyed reading this bit before going to sleep
thank you for painting such vivid images of bridges and planks in these emotional analogies.. I couldn't help but visualize the Golden Bridge in Vietnam that's shaped like two hands, holding up the pedestrians. Those hands feel like the metaphorical support of the folks who embrace our uncertainty and vulnerability.
wonderful parting quote as well - now i'll think about all the current mediums and what quirky things I see in their futures