Good Work—Edition Nº 12

A hand-curated newsletter devoted to exploring how we choose to spend the 90,000 hours that will make up our careers.
Courtney Nash
▪︎ 6 minutes read time

🎶 Help by Weaves

The damage that you have inflicted heals over, and the scarred places left behind have unusual surface areas, roughnesses enough to become the nodes around which wisdom weaves its fibrils.Nicholson Baker*

I call up strangers on the internet and ask them to talk to me.

That’s what I told my mom I did for a living over 10 years ago, when I started my job as an editor at O’Reilly Media, and I’m still doing it today. I started my career in acquisitions, where my primary job was finding authors to write books, and then chairing conferences that sometimes brought in outright famous people. I became a gregarious asker, not just of questions, but of help.

  • “Is Site Reliability Engineering really a thing? Why does it matter; who is doing it?”
  • “I saw your fantastic talk on distributed tracing, would you be interested in expanding it for our event later this year?”
  • “I’m trying to get in touch with [semi-famous person], would you happen to have any contacts who can help me get introduced?”

Initially, I was terrible. My emails and Twitter DMs to people I wanted to meet were wandering, sloppy, and almost intentionally avoided getting to the point. But I got better at it the more I stumbled through, and eventually I grew to love approaching strangers. And I was surprised how often people were more than happy to talk to me, provide some form of help, or—if they were unable—to connect me with someone else who could. That’s always my #1 tip when asking someone for something: if they can’t help, ask them to refer you to someone they think can. People are mostly really nice, and want to help! I still have to remind myself of this sometimes.

Cultural anthropologists have long argued that reciprocity—the practice of exchanging things for mutual benefit—is a uniquely human trait. In theory, this mixture of selfish preservation with tribal altruism enhances our likelihood of survival. In The Origins of Virtue, Human Instincts and the Evolution of Cooperation, Matt Ridley surveys recent sociological research on the topic and writes:

“Trust is as vital a form of social capital as money is a form of actual capital…Trust, like money, can be lent (’I trust you because I trust the person who told me he trusts you’), and can be risked, hoarded or squandered. It pays dividends in the currency of more trust.”

Asking someone for something is an exercise in trust. That’s also what makes it perilous territory for many people. Forging a trustworthy connection requires vulnerability, which paves the way for rejection, and rejection can be painful. In fact, the very same parts of your brain that process physical pain also get in on the party when you feel emotional pain, including rejection.

The most important thing I’ve figured out about asking people for nearly anything is that there is always a moment when you’re going to feel uncomfortable. It’s like stage fright—even seasoned performers still get it, they’ve just learned how to acknowledge it and not let it get in their way (and know it usually means something great is about to happen). That discomfort comes from the corner of your mind that has framed photos of all your junior high outfits, audio recordings of cringe-worthy work presentations, and an unredacted transcript of that one time you said what you really thought to your Uncle Robert in front of everyone at Thanksgiving. Turn the lights off, shut the door on that room, and remember that most people really do want to help.

Asking people is a muscle—you have to build it, and then keep using it. You might be working up to some big things to ask for, like fundraising for your company, a promotion, or help with a gnarly, complicated work project; if asking is scary for you, start small. Pick someone you’re almost certain would help, be very specific about what you want, and approach it as forming a connection, not completing a transaction.

What would you ask us here at Holloway?

This Week


  • Sarah Peck’s Medium post on asking for help was so popular that she ended up turning it into an eBook. It has some of the most comprehensive and practical experience I’ve seen on the topic of how to ask people for all kinds of things, big and small.
  • Jia Jiang’s talk about his love story with rejection is delightful. In order to get better at handling rejection, he undertook “rejection therapy” and set out to ask as many people as possible for some pretty ridiculous things. The crazy thing? People said yes to all of them.
  • A few very specific things can go a long way when asking for something. HBR lays out a few such cues, or “reinforcements” to make your requests more successful.
  • How to ask better questions, according to some surprising Harvard research.
  • As usual, there’s an appropriate xkcd comic for awkward human conversations.

That’s Good Work for this week. Looking forward to what’s next.

Courtney and the Holloway Team

Good Work is written and curated by Andy Sparks, Courtney Nash, Dmitriy Kharchenko, Hope Hackett, Joshua Levy, and Rachel Jepsen.

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