James' World 2

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Kim Scott had one thing to do that day. She was going to price her product. It was the year 2000, she was the founder and CEO of Juice Software, and she had blocked off her whole morning to make this decision.

The moment she stepped off the elevator, she was met by co-worker after co-worker who needed and wanted to talk to her — one about a health concern, another about his kid excelling at school, another about a disintegrating marriage. She comforted, celebrated with, and listened to each one in turn. She didn’t, however, price the product.

“For a minute I thought, this is where the assholes really have the advantage,” says Scott. “But that’s not right either. Good managers give a damn.”

This is just one piece of advice Scott discovered during the last 20 years and has carried with her through leadership roles at some of the biggest and influential tech companies in the world. Most recently, she advised Dropbox and Twitter. At First Round’s recent CEO Summit, she shared what she believes to be the most important management lessons she’s learned.

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My Management Lessons

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The first self-described self-help book was published in 1859. The author’s name, improbably, was Samuel Smiles; the title, even more improbably, was Self-Help. A distillation of lessons from the lives of famous people who had pulled themselves up by their bootstraps, it sold millions of copies and was a mainstay in Victorian households. Every generation since had its runaway bestseller, such as How to Live on 24 Hours a Day (1908), Think and Grow Rich (1937), or Don’t Sweat the Small Stuff (1997). 

By now, the $11 billion self-help industry is most definitely not small stuff. Yet when you strip it down, there’s very little new information. After all, we were consuming self-help for centuries before Smiles, just under different names. Roman emperor Marcus Aurelius gave tweet-sized advice in Meditations; so did Benjamin Franklin In Poor Richard’s Almanack. Even self-help parody isn’t new. Shakespeare did it with Polonius’ “to thine own self be true” speech in Hamlet: basically a bullet-point list from a blowhard. 

The 21st century has seen a measure of self-awareness about our self-help addiction. There’s the wave of sweary self-help bestsellers I wrote about, such as The Subtle Art of Not Giving a F*ck. They hover somewhere between parody and dressing up the same advice as to their forebears in earthier language. More recently, there’s a trend you might call meta-self-help: books in which people write about their experiences following self-help books, such as Help Me! (2018) and How to Be Fine (2020), based on a similar self-help podcast By the Book. 

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A small selection of centuries-spanning advice.

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“I want to reassure people,” I announced grandly on Instagram the other day, “that it’s easier to change behavior than you think.” With anxious friends facing a massive change of life in the face of coronavirus, I wanted to spread some calm.

The reason I’d started dispensing “wisdom” like some nautical soothsayer was that I gave up a much-loved job at the Guardian three years ago to pursue a simpler life on my tiny sailboat. I ended up crossing the Channel to France, sailing down the Atlantic coast to Portugal, into the Mediterranean, through Spain and Italy to Greece. It’s the slowest life imaginable, traveling at a walking pace, completely immersed in nature. I sleep freely in secluded bays, by white beaches, fish and octopus swimming below me. I’ve sailed with dolphins and whales, woken to horses galloping on deserted beaches in southern Italy, and anchored by castles and cathedral-like cliffs. It is magical and it is nourishing.

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Photo by kieferpix / Getty Images.

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