Being a “learn-it-all” will get you way further than being a “know-it-all”

🎂 We forgot to mention this last Friday, but the Medium Newsletter is officially 1 year old, meaning it can sit up without help and understand the word “no”
Issue #260: journalism’s “chilling effect” + why you should write actual letters
By Harris Sockel

Somehow, we’ve been sending this newsletter every weekday for a whole dang year! If you’ve been here since the jump — or discovered us any time over the last year — thank you.

To celebrate, I want to revisit one of my favorite issues. It touches on the theme of simply keeping something going for a while — through success, failure, bad days, and good days. It centers on a story by former Microsoft engineer Dare Obasanjo, who remembers life inside the company after Satya Nadella became CEO in 2014. Nadella had risen through the ranks for 22 years after beginning as a humble engineer in 1992. By the time he assumed the CEO mantle, Microsoft was “dead” — or at least that’s what Y Combinator founder Paul Graham was saying. In 2007, Graham argued that the rise of Google’s web apps (Gmail, mostly) and Apple had turned Windows into an obsolete tool “for grandmas.”

“Microsoft’s biggest weakness,” Graham wrote, “is that they still don’t realize how much they suck.” In other words, they were complacent — and Graham wasn’t wrong about this. Obasanjo remembers: “Despite failure after failure, many people… acted like we were the best thing since sliced bread because we had Windows & Office, two of the most successful software products ever built.”

One lesson: Overcoming success is sometimes harder than coming back after failure. Finding the will to make mistakes, to be weird, to learn something from scratch even if you might be terrible at it — that’s hard if you’ve just built a legendary product like Windows! Nadella fought complacency by taping mantras about “growth mindset” to whiteboards in every conference room (“learn from criticism!”). He sponsored the “largest private hackathon on the planet” to help everyone think like entrepreneurs again. Arguably, it worked. Microsoft finally developed cloud-based software like Azure, and its valuation now rivals Apple’s. A few strategic investments (GitHub, LinkedIn, and, most notably, OpenAI) made the company newly relevant.

Turnaround CEO Philippe Collard (he’s turned around 3 companies in 10 years!) builds on this idea in a more recent Medium story. He writes that a leader’s primary job is to help people “face reality” with equal parts humility and optimism, which is key after a big win. Obasanjo’s primary takeaway from living through that era at Microsoft is, I think, applicable to both life and work: being a “learn-it-all” will get you way further than being a “know-it-all.”

💃 Also today…

• Music critic Mariel Ferragamo on Cowboy Carter’s revolutionary legacy: “Pop culture has largely treated country and hip-hop as if they’re magnets that repel each other.” Not anymore.
• I love this essay by (almost) 70-year-old burlesque performer Tris Harkness — it’s basically an ode to being yourself. “In journalism, there’s something called the ‘chilling effect,’” she writes, “which occurs when people censor their own writing even before they’ve been told to in order to stay out of trouble. And a chilling effect happens in life, too.”
• S. Bear Bergman — one of the five founders of the first gay/straight alliances — lists all the very tangible things you can do right now to support your trans and nonbinary friends, the most important being not to succumb to panic yourself, and to be thoughtful with the links you share. Instead of sharing news stories that provoke anger or resentment (even as a way to show you care), “send us nice trans articles: awards, accomplishments, book reviews, whatever you see that’s NOT the news.”

✉️ Your daily dose of practical wisdom

A handwritten letter to someone you care about, Rachel Syme believes, is “probably one of the most closely read documents you’ll ever compose in your lifetime.” (The Molehill)

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Edited and produced by Scott Lamb & Carly Rose Gillis

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