Avoiding public discourse traps: a case study from Calendly, Twitter, & me

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PC: Ibrahim Asad. I thought a calm sunset beach photo suited this post.

Are you familiar with Calendly?

It’s a tool that looks for free periods on your Google calendar and makes them available for others to book in 15, 30, or 60 minute sections. The UI for someone who has clicked your Calendly link looks something like this:

It’s popular among folks who struggle with the back-and-forth of making plans; you send one link to everyone (or post it somewhere), and it becomes fast and easy for folks to plan on spending time with you.

Instead of an email chain, making plans is two clicks! And it does work pretty beautifully as long as the Calendly portion of the Calendly person’s Google calendar always contains 100% of their commitments and they rarely need to shift their schedule around. In particular, it does a great job in cases like the example above: a conference organizer team scheduling proposal consultations on specific mornings.

In practice, people sometimes try to use it as their all-access booking tool for their professional and personal life. That tends to work out poorly for the folks doing the booking because that case breaks the two conditions for Calendly working well:

  1. The Calendly person’s Google calendar always contains 100% of their commitments: People know they have things, like a grocery store run or a workout or dinner with their mom, that aren’t on their Google calendar, so folks book over that time on Calendly and then the Calendly person cancels.
  2. They rarely need to shift their schedule around: when something comes up and the Calendly person needs to shift things around, often the Calendly bookings are the things on the calendar that are surprises to them. So those bookings get caught in the crossfire more than other commitments.

In practice, then, when someone is using Calendly un-judiciously, the Calendly can end up being an extremely unreliable means to book time with them. If you force someone to lay eyeballs on their calendar while making plans, those plans are much more likely to hold. A Calendly tends to just offload the work of managing a person’s schedule volatility onto other people (“Sorry, I’m actually unavailable then. Please use my Calendly link again?”). That doesn’t respect the bookers’ time. It’s not a good use of the tool.

This blog post isn’t about Calendly.

It’s about an argument that broke out on Twitter in January of 2022 about Calendly. Specifically, it’s about the way people treated each other in that argument.

Feel free to go have a look yourself; I’m not going screenshot hunting because I never want to see a single word of it ever again. The conversation somehow very quickly devolved into a lot of adults who have Extremely Online Brands about empathy being absolute shitheads to each other. 

Not lemmings. Not children. Adults who are semi-famous on the internet for being empathetic people. I watched people with executive positions and thousands of followers post tiny brain memes about the people they didn’t agree with.

The person who posted this has built their business and brand on “tech to help marginalized people.” And yet, not liking Calendlies? Psh, must be an ego thing, and they probably have tiny brains to boot! Haha! Hilarious!

I don’t care that it’s Twitter, the cafeteria of the internet; these people have influence. You don’t get to just abdicate responsibility for how you use your influence because you’re in the cafeteria. You wanna do that, make a private account and post your kiki to your friends. This is the public internet. These people have employees and people who depend on them. What are the chances they implicated one of their charges in these memes? 

This is about how to disagree with people.

There’s a good rule of thumb to keep in mind when it comes to some of the words we use while disagreeing. 

“I don’t get blahblahblah” is a vulnerable, brave thing to say when talking about, like, a technical concept that one might be judged for not already understanding.

“I don’t get blahblahblah” is an asshole thing to say when talking about a lived experience that many people are actively trying to explain to you. 

People seem to understand this when it’s them in the group doing the explaining. A LOT of the people I saw slinging this were, it’s gotta be said, in marginalized groups, so I know they get the concept of “it sucks to explain your experience and immediately get back I Don’t Get It” 

But I watched people double down.

“I truly, honestly, GENUINELY from the BOTTOM OF MY HEART DO NOT UNDERSTAND why ANYONE would EVER want/not want to use Calendly, and I HAVE TRIED”

Gurl, you have not. I’ve seen 19 crystal clear explanations zing by since I started my percolator to make my morning coffee. 

And I get it. I understand that people got way down the evidently very slippery slope of shitposting before they figured out that anybody who disagreed with them had some legitimate concerns.

Honestly, I have some tough love for y’all: I expect the slope of shitposting to be a lot less slippery for People Who Are Semi-Famous on the Internet for Empathy.

I expect People Who Are Semi-Famous on the Internet for Empathy to have some ability to address their own defensiveness before they muzzle sweep their own charges with their memes.

See, public discourse is a skill.

And we do that skill the same disservice that we do every other inclusion skill by ramming it into this tiny can labeled “just try to be a good person, OK?”

It’s not just about trying to be good. I could try to be good at CrossFit all the live long day, and if I don’t do my drills, I will still suck at CrossFit.

I have to learn to disambiguate the separate skills that I need, that I don’t have, and work on them as their own specific, technical things deserving of my time and attention.

Fostering an inclusive environment requires several rather difficult skills, and we don’t talk about them. That’s how people who are theoretically good at this can be so bad at this.

It’s why folks can get to manager and director with such underdeveloped capacities for theory of mind. Nobody teaches that to them. Nobody mentions it to them. So they walk through the world thinking as if everything in it is for them, personally.

It’s how someone can ask so plaintively and sincerely for feedback and then lash out when they receive it. They’ve never developed the skill of receiving feedback.

And it’s how someone can speak so eloquently from their experience of marginalization and then, on an axis where they’re the favored demographic, turn around and act the same way they so often preach against. Turns out, when you’re the marginalized group, you don’t need inclusion skills. You need coping skills, and maybe cunning, to get around other people’s lack of inclusion skills. You need inclusion skills when you’re the dominant group. And wishing that the dominant group had inclusion skills when you’re in the marginalized group is not the same thing as having inclusion skills yourself.

So, as a first step to developing those skills, consider whether your use of “I don’t get X” is co-opting the language of vulnerable bravery to be an asshole to people who are actively trying to help you get it. 

OK. Let’s take a breath, because I haven’t even said the spiciest thing I’m gonna say yet.

The discussion presented Calendly as an accessibility tool.

That’s fine. I agree with that presentation.

The presentation came with a corollary: because Calendly addresses an accessibility need, not only is its use unassailable, but also the arguments and behaviors anyone defending its use are unassailable. 

Now, this right here ain’t the case.

The thing about accessibility needs, folks, is there are lots of reasons people might have ’em, from disability to neurodiversity to, straightup, family obligations.

Sometimes, accessibility needs are mutually exclusive. 

An example I hear a lot is the movie watching example: deaf folks need captions. Some neurodivergent folks find captions prohibitively distracting. Neither party is, in fact, The Boneheadest Possible Version of Evil Incarnate. 

And when we talk to each other like somebody is, we go backwards from any kind of thoughtful or inclusive conversation where anybody is gonna learn anything.

With Calendly, people brought up conflicting accessibility needs. The most common one I saw was ‘I need Calendly because ADHD.’

OK. So what Calendly does, you see, is it assumes 100% commitment to a specific time/place of multiple parties with no conversation. It doesn’t take too much thought to figure out how that could itself be an accessibility impediment:

  • Someone’s got dependents & something might happen.
  • Someone’s mental health shifts from day to day.
  • Someone’s got a maybe-appointment in the malebolge that is American health insurance. 
  • Somebody works 24 hour on-call in medicine, disaster relief, or software infrastructure.
  • Someone who you want to schedule time with, who is willing to meet with you and to whom you have sent your Calendly, is themself very in demand.

So maybe it takes a conversation to figure out how to plan, and that’s not an ableist act against people with ADHD. 

I get it. Marginalized people are tired of having to argue for their right to accommodation and/or existence. Reaming each other over mutually exclusive needs instead of approaching the conversation with curiosity and creativity makes that problem worse, not better. This is, fundamentally, why we don’t like Cop Shit, right?

Cop Shit is “Who do we punish over this? Who do we remove from the conversation?”

What we want is “How do we include everybody, especially folks who are historically excluded, in the conversation?” 

Success with that requires slowing down.

It requires devaluing witty zingers and the Internet Points they earn.

It requires shouldering the inconvenience of genuinely trying on another perspective, and accepting the possibility that we could be wrong. 

And to be honest, if one finds oneself creating a meme designed to denigrate other people, that’s probably a sign that we’re in the not responding productively to the discourse. 

Okay, Chelsea. But how do we do that?

Once upon a time, I talked to you about the skill of critiquing someone else’s work. Engineers don’t learn this skill the way artists do. I suspect that contributes heavily to the way engineers act online about things. But there’s another contributor: the way people act online in general.

Here’s the first thing, and I think it’s the hardest to sit with: I humbly submit that you think it’s other people, but actually, it’s also you.

Tweet credit here goes to Jennifer Tu. My general tweet reshare philosophy is: take all screenshots of someone else’s tweets without their screen name in it to make it anonymizable, present it anonymously, and add credit back in if it contributes to the conversation.

Let’s talk about why this is hard and how to do it well.

I suspect you’re going to hate what I’m about to suggest. It’s not my snap reaction either, and I have had to train myself to do it. But it’s worth it because ultimately what we’re doing, as that tweet explicitly states, is learning to treat thoughtful people we trust differently than we treat people who we already agree take up a dangerous amount of space online.

Because y’all, I hope it’s really f**king easy to distinguish people with a humanitarian track record from Nazis.

So, I want to acknowledge the things that make it harder.

And I’m warning you, this is not going to be fun to read.

1. The internet in general, and social media specifically, is structured to reward people for pithy zingers.

A pile-on is a chance to get a zinger in, and you can do it guilt-free if there’s a veneer of belief that you’re punching up. A guilt-free dopamine rush is hard to resist.

2. It’s easy to assume something is true if a lot of people are saying it, or if someone we generally believe says it.

“I saw 4 people on my timeline/someone whose opinion I admire call out this group for caving to grifters => That group is definitely caving to grifters!”

3. Internet discourse moves fast and, frankly, white supremacy culture indoctrinates us into a sense of urgency that SCREAMS at us that the WORLD will end if WE, PERSONALLY, do not act RIGHT NOW!

I wrote about that here, if you care.

Now, I want to address the complications with each of those things.

1. I’ve watched people with 10 years of advocacy work get piled on over a bad tweet. That discourages people from participating in conversations about ethics, because they see what happens if you get known for that and then fuck up.

2. A lot of people can be wrong at once. Even somebody you like can be wrong about something, especially if they temporarily also forgot that a lot of people can be wrong at once.

It’s a truism in community work that, in the absence of information, people will assume the worst possible story about what you did.

And we laugh about it, but it definitely makes community work less attractive, especially for—uh—exactly the kind of people we want doing it.

3. I know it’s hard to remember this, but I encourage trying because it’s wonderful news:

The world actually gets no closer to ending because you took a minute to ask some questions, or look at someone’s track record, before you mouthed off on the internet about it.

And that step—a step woefully often skipped, I’m afraid—is what makes “approach with curiosity, but also punch Nazis” so much easier.

Why? Because…

…it gives you the context to realize “Wait a second. This assumption I’ve made about this person based on this one thing I saw is actually incongruent with literally every other thing they’ve ever said or done for their whole adult life…”

“…something doesn’t add up here.”

If you’re reading this, I know that voice is inside you. Every thoughtful, caring person has it.

But it’s easy for the thrill of the pile-on, the wash of internet consensus, and the crushing sense of urgency to scream over it and drown it out.

You have to listen for it.

It is hard. It is especially hard when we insist on condensing the awareness-to-action pipeline into 5 seconds. We have to not do that. We have to slow down and ask ‘Wait. What does the little voice say?’

“I have always known this person to care. What am I missing here?”

And that takes skills that we usually have not developed, or have underdeveloped.

So, at the risk of sounding like I’m tooting my own horn, I have specifically made the effort to observe, study, and develop some of these slippery skills, and then install handles on them for your benefit. Here are some of those, which I hope will help you.

Critique, The Internet, and You—about critiquing things people make

The feedback series—about critiquing the things that somebody does

The listening series—the one I’d say most people think they need the least and actually need the most

One comment

  1. I appreciated this post, and this was my favorite part:

    “Like any other inclusion skill, it’s not reducible to “just try to be a good person, OK?” There are a lot more specific sub-components, and we don’t talk about them. That’s how people who are theoretically good at this can be so bad at this.”

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