Privilege has nothing to do with how hard you work

version of this essay was published as part of my monthly newsletter a couple weeks back. Find other archives and join here to get updates like this first.

Privilege has nothing to do with how hard you work, or even what you deserve.

Among the many complexities we are confronting in our fist-flying, partisan online discourse, this is a translation issue. If you’re telling someone they’re privileged and you can’t understand why they get frustrated or tune you out, pause for a moment. Likewise, if you’re someone who has been called privileged and don’t understand why they ignore how hard you work, stop to consider.

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Don’t wait for things you think you deserve

version of this essay was published as part of my monthly newsletter several weeks ago. Find other archives and join here to get updates like this first.

When I think about mistakes I’ve made, one of the common causes of my blindness that led me there is entitlement. I thought something was going to happen because I deserved it.

Not because I had done the crucial work of understanding that outcome was good for all involved. Not because I worked to get a clear agreement or that I negotiated for it by offering something someone else wanted. No.

When I’ve really gotten something wrong, when I’ve been blindsided or made a miscalculation, a lot of times I just plain thought something was coming my way because I perceived I was owed it. Maybe I thought I had put my time in or I thought I was close to the person with power. Sometimes I admire the idea of how good for me it would be if this happened, or my friends tell me how great it would be.

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It’s hard to hate up close

A version of this essay was published as part of my monthly newsletter several weeks ago. Find other archives and join here to get updates like this first.

A mentor of mine said in a meeting recently: it’s hard to hate up close.

It’s really not in our nature, she said. Distance (including the anonymity of the web and the imprecision of written communication) is so often involved in conflict, both big and small. So the message is whenever you’re in conflict, you need to get as close to the source of that conflict as you can.

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Journalists: what do you love first, the Reporting or the Writing

A version of this essay was published as part of my monthly newsletter several weeks ago. Find other archives and join here to get updates like this first.

One of the first questions I ask younger reporters when I meet them is which is their first love: the reporting or the writing. Storytelling, as the form is euphemistically categorized, is very old. The ways we report and write, too, have old origins, but their forms adapt with the times. They change constantly. I bet your industry has a similar kind of split, subtly different pathways to the professional work.

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I am motivated by fear

A version of this essay was published as part of my twice-monthly newsletter several weeks ago. Find other archives and join here to get updates like this first.

Someone asked me recently what was the biggest motivator for me to start a company, and I told him it was fear.

That’s true, if still somewhat self-deprecating.

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Don’t mix up censorship with civility

A version of this essay was published as part of my twice-monthly newsletter several weeks ago. Find other archives and join here to get updates like this first.

Censorship is about content (you can’t say this or that). Civility is about tone (you can’t say this like that).

Attribution bias virtually guarantees that we are sure our tone is appropriate for all circumstances. If we use vulgar language or overly fatalistic language, it’s because we are on the right and just side of a cause. If someone with whom we disagree does this, they are proving just why they something short of civil.

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New Sincerity is the answer to snarky post-modern web culture

A version of this essay was published as part of my twice-monthly newsletter several weeks ago. Find other archives and join here to get updates like this first.

I’ve been struggling a lot over the last couple years, and of course particularly in the last six months, with how mean the social web can be. How mean we are to each other. And how naive I sound to others when I think we can be something else.

This has gotten me into reading about the New Sincerity movement of the 1980s that then got a major boost of attention in the 1990s by beloved and troubled writer David Foster Wallace. It’s what I’ve been searching for.

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