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So there’s two reasons for this post. The first is that I was going through my list of those miscellaneous ideas that you can do at some point in the future that would be fun or helpful (hopefully) but that you never quite get around to, and I saw something on there that seemed like it would be quick and maybe hopefully useful to someone.
The second one is that, by the deadlines that I personally have set, today is the last day to publish a blog post that will make it into the June newsletter and if I put something out then I will have two blog posts in a newsletter for the first time since October 2022 (I need to blog more).
Anyway, I was going through my to-do list and in the section of “miscellaneous ideas for the future” I saw something about making a diagram of how the three systems of Domain of One’s Own work together. It’s something I have to explain a lot when training new admins, and while I feel like I’ve got a pretty good handle on the overarching metaphor by now, training usually focuses on each system’s user interface and what admins can do with that system, so I always worry I’ve skimped on making sure they’ve got the full picture.
To that end, I made a diagram.
This was very much something I saw on the list and went “Hey, I could do a pretty version of that in the future given a couple of days and some dedicated resources, or I could do a functional version of that right now using Google Drive’s weird photomanipulation-ish drawing platform.” And functional now is better than pretty later.
So, voila: The Diagram.
Hope I didn’t hype it up too much.
Is this accurate? That’s gonna be a strong “maybe.” But it’s close enough for our purposes, it only took about twenty minutes, and I got this blog post done in time for the Roundup deadline, so I’m going to call this a win.
It’s definitely not perfect. Looking at it now I’m thinking of all the little adjustments that I want to make, both in the text and in the design. But like I said back in October, sometimes you have to let perfection go.
Also, it’s here as a PDF too I guess, since Google Draw also offers that as an export format.
Coming off of Reclaim Open, one of the things I’m thinking about is online resources for self-teaching beginners. When we were interviewing people for the documentary, we asked people what they were glad the internet had now, in the present, that it hadn’t had in the past. And a lot of people — not everyone, but a lot — talked about how there’s a plethora of learning resources for beginners on just about any subject. Which got me thinking about the learning resources that I’ve used and the tutorials I’ve tried to follow.
There are so many things that I want to learn. I’ve got a post in the works about teaching myself to draw. About a month ago, I hit a milestone on my Duolingo streak (800 days!). I used to practice guitar, though I’ve fallen out of that habit in the past year. For a while I was experimenting with some of the beginner guides to Unity. I have an abundance of tutorials and resources on various topics bookmarked — a beginner’s guide to Ruby on Rails, Codecademy, HackerRank, etc. — which I’ve used… at some point in the past. I keep a list of topics to research that only gets longer and longer.
All this, and I still feel like a dabbler in everything. Part of it is that I’ve put aside topics for long periods of time (almost everything except Duolingo, honestly). That’s naturally led to skill atrophy and forgetting what I was doing, which means difficulty picking up where I left off. But for the one thing I have stuck with, I don’t feel like I’m getting any better — my Italian is beginner-level at best, with a poor grasp of grammar and difficulty remembering vocabulary when I need it.
So I’m thinking: what are the differences in the resources I’ve looked at? What do they require? Where do they go together, and where do they fall short?
The framework I’ve got in my head right now for self-teaching is structured vs unstructured learning resources.
Structured resources are things like Duolingo or Codecademy, a series of tutorials designed to build on each other. Unstructured resources are more like the Youtube video tutorials that exist for drawing or guitar, and their related practice tools (guitar tab websites, figure drawing photo banks).
Structured resources are designed methodically by one group in a way that emphasizes logical progress from point A to point B to point C. There’s a general focus on fundamentals first, then building up to more advanced concepts, with exercises designed to practice each new topic. The exercises are usually short and easy enough that lessons can be completed in 5-10 minutes max, to encourage making learning a routine and habitual practice. The focus is on progressing through the course.
Unstructured resources means that there’s a wide range of sources from various unconnected groups, which all specialize in different topics. Learning is self-directed, since there’s no clear path connecting everything, and there are few if any pre-built exercises (a given resource might have 2 or 3, but none of them hang together). Learners can focus their studying in their weakest areas, or specialize in the topics that most interest them, and the lack of pre-built exercises means that their learning goals shape what they’re working on — which means that there’s more intrinsic motivation to learn, since they’re tailoring their practice to their own interests. The most common advice I hear for people who want to learn guitar is “Pick a song you like, and learn to play it.” There’s simplified versions of just about every song out there so beginners can learn the most basic version, and once they have that, they can try something more advanced. It’s learning by doing.
With structured learning, there’s issues of pacing, attention span and motivation. Short, easy lessons are designed to keep attention and build routine, so you can do a little bit every day, but if you do only a little bit every day it might feel like you’re taking months or years to get anywhere. That damages motivation, which is doubly bad because you’re working towards proficiency but not a specific intrinsic goal; that makes it extra-hard to measure progress.
Curated and designed exercises may also not be right for all learners, or self-structured online learning may create certain pitfalls. For example, one major issue I have with Duolingo is that because of the way its lessons are structured, there’s no way to have exercises strengthening true composition (written or spoken). There’s options for translating back and forth between your native language and your target language, but there’s nothing along the lines of “Write a paragraph about your favorite book” or “Talk about your most recent vacation”. That’s a major barrier to fluency, since being able to read and listen in your target language is only one half of communication, and it’s the less challenging half.
With unstructured learning, though, you still get pacing, attention span and motivation issues. This time the issue is that it’s hard to know how much time to spend on certain topics, and where to start or how to build on them. Dumping time into something while feeling like you’re stumbling in the dark trying to figure out what you need to do next is a sure way to damage motivation, which can in turn make your attention focus elsewhere.
Exercises for unstructured learning can also feel repetitive, since your resources only give you a few. Everyone says the way to get good at drawing is to practice figure drawing, which is true — I have definitely improved as a result — but I don’t know how to vary it up to keep learning fresh or which details to pay attention to in order to practice most effectively. And if it’s not repetitive, it’s chaotic — everyone has an opinion, and everyone disagrees. Who do you listen to, and how do you cut through the noise and really decide how to spend your time?
This is a long way of saying: I’ve never learned to teach, and I don’t know how to learn to learn. Because self-structured learning is way different than learning in a classroom, or in a group, or with a mentor. There’s no external framework to keep you accountable, or to provide feedback, or to provide any of the other benefits that come with a learning community.
When it comes to self-directed learning, there’s so many principles I keep hearing about — resilience, goal-setting, failing forward, varying your practice, etc. — but all the resources I’ve found assume learners are coming to them with those principles already well-developed, and that all that’s left is the skill-building section.
Which makes sense! Teaching your learners how to self-teach before teaching them what they actually came to learn, is an absurd thing to ask. But for pretty much everything I learned in school, I learned from other people; I almost never got practice teaching myself.
So there’s a lot of beginner-friendly resources out there. And they’re great for if you have one or two specific things you need to learn. But for people starting in total ignorance who want to work their way up to overarching mastery, how beginner-friendly are they really?
So to start — this isn’t a formula. Or, the blog post might seem like a formula, or a checklist or something like that, but really what it’s meant to be is a distillation of a lot of things that I don’t actively think about when I write emails, turned into something explainable. So maybe it’ll seem like a checklist. Who knows.
Basically: I thought I would sit down and parse out what background processes happen habitually/instinctively when I write a professional email (or any message generally). It’s not meant to be prescriptive, but if the tips are helpful, awesome.
Also, to be clear, none of the scenarios or people I mention here are real.
Before you even get started writing, safety first.
What does “safety first” mean here? If I’m writing an email, it means that I draft the whole thing and add the subject line before I put in the email address I’m sending it to. Theoretically I should add attachments before that, but usually attachments are the very last thing I remember to do. If I’m responding in our ticketing system, I toggle the word processing box from external reply to internal note. (This turns the whole box background pale yellow. I don’t draft anything if the box isn’t yellow).
The reason for this is, I don’t want to send it prematurely. If there’s no email address, it can’t be sent; if it’s an internal note and I do record it early, worst case scenario I copy/paste it back in and keep drafting.
(Okay, I don’t do this for low-stakes emails or tickets. But for high stakes ones, you bet. Or I draft it in a word processor. I don’t like sending unfinished emails.)
Write the whole thing first. Don’t worry about phrasing, don’t worry about terminology, just hit every point that you need to hit.
If you don’t have the word you want or the numbers you need or something like that, don’t go looking it up right now, put it in brackets (eg, “Please make sure you’ve filled out your skydiving waiver by [WHENEVER IT’S DUE]”). and come back. I recommend [square] or <pointy> brackets, they’re easier to CTRL+F search for and find fast.
If you’re saying something vague or nonspecific and you want to be more precise, or if you don’t like the way you phrased something but don’t know why, bold it and come back later. Or mark it in brackets. Just do something so it’ll be easy to find when it comes time for revisions.
Speaking of which, revisions!
Once you’ve hit all the important points you need to hit, go back and grab the terminology and numbers you were missing before. The reason we do this now instead of during the first draft is to keep the flow of the writing while drafting and not get sidetracked.
After that, let’s move on to phrasing. Are you being nonspecific? Is something just kinda off? What’s going on?
If you’re being nonspecific, take a quick check why. For me it usually comes down to a couple of things: a) I’m leaving out relevant details because they seem obvious, like something the person would already know; b) I’m leaving out details because I don’t know them and I don’t want to get it wrong; c) I have to deliver bad news, and I don’t wanna.
None of these are good reasons to be vague. (There are good reasons to be vague. We’ll get to them in a minute.)
If your phrasing just feels off, nothing related to the details, then you just have to parse out why. For me, I often get antsy when I write something that’s sort of kind of broadly true but not actually 100% universally correct (like, “Everyone loves chocolate cake, so we should get that flavor.” Maybe they do or maybe they don’t, but I don’t know that). Once you know why you don’t like something, you can rephrase it to smooth over the rough patches. (“You all know how popular chocolate cake is. That’s probably a good choice for the party.”)
None of the things I’m saying are universal rules. Can’t reiterate that enough. In any case: sometimes it’s okay to be vague.
Sometimes the phrasing of something feels clunky, but it’s accurate and clear and you don’t have time to fix it. If it’s doing its job, then sometimes that’s good enough.
Alternatively, maybe you don’t have news yet (or aren’t sure of the details), but the message is urgent or it’s been waiting for a long time. If that’s the case, sending a quick “Hey we haven’t forgotten about this and we’re still working on it” message is better than saying nothing, even if you don’t have anything specific to report. You can always come back with the details once you have them.
In general, I recommend going for more detail when you can, but that’s not always an option. Sometimes you can’t wait for the time it’ll take to get answers — you want to get a message out today. Or maybe going deep into the technical weeds is going to confuse the person you’re talking to. Or maybe you want to keep some things private for now, even if they’re relevant.
That’s all fine. In cases like that, the detail you want to provide and need to provide is a matter of judgement.
Take tech stuff. If you can give an informative but general overview of the relevant facts (“We’ll be planting flowers on the moon starting Monday at 10am, which will require us to set up a really long hose.”) you don’t need to go into details that don’t pertain to the person you’re talking to (“We’ll be planting the gardenias in the Ocean of Storms on the moon Monday at 10, which will require a 23 thousand kilometer long hose that we’ll be connecting to a pump in Lake Superior.”). If the person you’re talking to isn’t doing any planting and doesn’t have to set up the hose, it may be worth it to skip those details.
Or you need to get that message out, but you don’t have news yet. “I know Kimberly has been working on arranging transport to the moon, so I’ll be checking in with her today to see if there are any updates to pass along.”
Or even something that’s not really their business, like, “We borrowed the hose and the pump from your least favorite neighbor.” It doesn’t matter where you got the hose, what matters is that you got it. Bringing up the neighbor they hate is just going to cast a shadow over the important part: you have the hose, and now you can get to work watering those moon gardenias.
This section is going to be a long one. We’ll tackle the scariest one first.
I told you we’d get back here! Here we are.
Delivering bad news is the worst. It’s gonna make the other person unhappy, which both feels bad and can be intimidating if you think they’re going to react poorly. It stinks. But sometimes, you just have to do it.
So, for starters: does this cloud have a silver lining? People want to get something, especially if they’re losing something else. So instead of thinking about why the news is bad, think about why the news is happening.
Let’s try this. You’re a birthday party clown, and you have to tell your clients, “I’m not going to be making balloon animals anymore.” Why aren’t you?
So, here we go:
“I’m not going to be making balloon animals anymore. Doing this will use less rubber and lower each birthday party’s carbon footprint, but even beyond that, this change will give me the opportunity to develop my juggling skills, something many people have asked for. I’m excited to be able to offer a juggling act at parties from now on.”
By focusing on the positives that come from this change, you’ve reframed a thing people won’t like (they don’t get balloon animals anymore) as a thing that benefits them (they get a juggler instead) and add a nice little bonus that will make them feel good (their birthday parties will have lower environmental impact).
That said, sometimes news is just bad, and there isn’t a great way to spin it. Either someone might get scared, or someone might get mad. You don’t always know they will, but depending on the type of news, you can prep your tone according to what you expect the worst case scenario will be.
If the news is scary: Sympathize! Let them know that you understand why they’re worried, and let them know potential ways that you or they can address the problem (without caving).
“I definitely understand how stressful a lack of balloon animals can be. However, I do offer juggling with balls, pins and swords depending on what would work best for your party. As another alternative, I’ve worked with another clown who’s very talented with balloon animals, so if balloon animals are vital to your party, you can reach out to them and see whether they’re available to perform.”
(And then provide your friend’s professional contact information, of course.)
If they just won’t like it: Sometimes you just gotta say, “Tough.” Not in so many words, but really — sometimes someone’s going to get mad, and the best thing you can do there is to acknowledge that they’re frustrated and then patiently reiterate your boundaries.
“I understand your frustration, but owing to the reasons I mentioned, I can’t continue making balloon animals at this time. However, I may be able to offer some alternatives.”
(And then give some options — probably the same ones you’d give in the previous example, honestly.)
In general, people just want to feel heard and taken care of. So acknowledge how they’re feeling, and then let them know they aren’t totally screwed.
Of course, sometimes people don’t listen. If you’ve made your case and offered options, and they still won’t meet you in the middle, you tried your best. At that point, there’s nothing wrong with a polite, firm, “No.”
Sometimes people ignore you. It’s really annoying, and you need them to do something, or to answer your questions, and it happens. You can be polite and firm in your reminders; I recommend also being detailed, unless you’ve given those details very recently, because people forget things easily. So here’s an example:
“Hi Cheryl,
Hope you enjoyed your weekend. I wanted to follow up here given that the deadline to rent a pony is coming up in about two weeks, on April 19th. Do you have a timeline for selecting your pony? Alternatively, do you need anything from me, like color or breed recommendations?
Remember that the pony rental agency doesn’t accept checks, so you’ll need to pay by either cash or credit card. If you have any questions for me, please don’t hesitate to ask. Have a great day!”
Let’s break that down.
Sometimes people continue to ignore you after you’ve sent multiple polite reminders, and it’s really, really annoying. This is important, dammit!
So let’s bring in the big guns.
If you’re losing patience & they will be able to see CC’d parties, copy in someone in your company or your department who they know has authority (or who they think has authority). Our ticketing system doesn’t let people know who’s CC’d, so in that case you may want to mention, “I’m CC’ing in my boss Sotirios, who may be able to help you with any higher level questions you have.” Note that your boss doesn’t need to actually participate as long as the person you’re talking to knows they’re on the thread, but if they still don’t respond and it’s really important, then your boss can step in smoothly.
If you’re really REALLY losing patience and their boss, or a person in their department with more direct power to do what you want, isn’t on the thread, it may be appropriate to CC that person in. This is not a first resort. Bringing in their boss means both pulling someone new into an email thread they probably don’t want to deal with, and showing the boss that the person you’ve been talking to hasn’t been fulfilling their responsibilities.
If you do this, do not use that email to be rude or pushy, or to point out all the things the other person has done wrong. Be polite, be firm, reiterate everything people need to know, but don’t call people out. You’ve already escalated the conversation, and at this point being a jerk will reflect poorly on you.
In general, I send an email that follows similar principles to the last one I sent, though maybe a little shorter — the email history will have the details included.
“Hi Cheryl,
Just following up on that pony rental. Since the rental deadline is coming up on the 19th, I wanted to check in and see whether you had a timeline on when the pony will be picked, or whether there was anything you needed from me to make that happen. Let me know if so — I’m happy to help.”
Sometimes people are jerks, or they’ve ignored you for the fourteenth time, or they’re making you feel like an idiot and that pisses you off. It’s fine to write emails while angry, but don’t send them like that.
If you know you’re angry while writing the email, get a sanity check from a second party before sending it. You can’t always do your own check if you’re in that headspace. Just let someone know, “Hey I’m getting really frustrated & want to make sure this email doesn’t convey that (to an inappropriate degree)” & ask them to take a look.
Note: When I say “to an inappropriate degree,” I mean that it’s fine to convey (not outright state) “The way you’re speaking to me is unacceptable, and you need to stop.” There are politer ways to phrase it, which is why you should ask for a second opinion, but if you write something angry and then try and soften your tone, it’s possible to soften it too much and risk surrendering your boundaries. It’s important to be polite, but it’s also important to stand up for yourself.
And on that note: you don’t necessarily have to apologize! Maybe you want to soften some bad news, or compensate for being angry, or you’re otherwise worried about how your message might be received. If that’s the case, you may be pretty apologetic while drafting. THIS IS NOT ALWAYS NECESSARY, and it can even feel crummy while you’re writing.
Look for places where you are being apologetic or deferential, & decide whether they’re necessary. Even if the situation does warrant an apology, you can keep it to one, maybe two if things are really drastic. But you don’t have to grovel throughout the email. You are allowed to be confident in what you’re saying.
And hey, sometimes there are people that you just can’t win with. And that’s fine. That’s not on you. There are people who will take your words in the worst possible faith, or be short and impatient and skirt the border of being rude without ever technically crossing a line in order to make you feel like you’re the bad guy, and that is not on you and you don’t have to take that.
Don’t write your emails angry, own your actions if you did mess up, try and give people the benefit of the doubt, be sympathetic in a difficult situation, but if someone is being rude & refusing to work with you, you don’t have to apologize just to try and keep the peace. Just because they’re mad doesn’t mean you did anything wrong.
Jumping off of that pushover check: urgency in someone else’s tone doesn’t always mean the situation is actually an emergency. Sometimes it just means that they’re stressed. In those cases, firing off a quick, “I understand your concerns, and I want you to know that we’re looking at this,” is a good call. This goes back to a core principle: making sure people feel that they’re being heard and taken care of.
However, whether there’s actually a fire that needs putting out is a matter of judgement. When you’re talking to someone who’s close to a problem, their worries may be making them feel like something is the end of the world, even if what’s going on is not time-sensitive and it’s definitely going to be okay.
Remember that even if someone’s stress is making you feel like you should be dropping everything to work on that problem, it may not be the case. There’s an important difference between being responsive, understanding and helpful, and rearranging your priorities because someone else’s stress is stressing you out in turn.
To make sure all my terminology is clear (hey, gotta put in those details), “SPaG” stands for Spelling, Punctuation and Grammar. This is just about the last thing you do, because if you go back and redraft something, you’re going to have to do another SPaG check once you do. Get the whole thing written and then check the spelling.
This one is honestly pretty self explanatory, since it’s not as intuition-based as everything else I just said. So:
This is the place for the important takeaways and the stuff I couldn’t fit in anywhere else.
First, repeating and rephrasing things that people have said to you makes them feel heard, which makes it easier to help them. (For example, responding to “I’m worried about how many cars will be on the rollercoaster…” with “Regarding your concerns about the number of rollercoaster cars…”). Try to do this before jumping into technical details.
Make sure you know what people want to be called. I’m always hideously embarrassed when it turns out I’ve been using the wrong name (or the long name, if someone goes by a nickname. You can edit this in some systems, like Gmail or our ticketing system, and I particularly try to do this in our ticketing system, since it also future-proofs this for other people.
Once you’ve written your draft, take a second to step back and make sure you’re not making assumptions about what they know. If you’re worried about being too clinical, you can always cut detail later.
If you’re dealing with a known tough cookie, it may also be worth taking a step back and trying to read what you’ve written in a bad-faith light. Having another person take a look can be a huge help, especially since you’ll want to include accurate, honest details so they can’t misinterpret the facts, while not putting in unnecessary info that might confuse or derail the conversation.
I said at the top that I didn’t want this to be a prescriptivist checklist, and I mean it. A lot of this stuff is written as instructions, but take them or leave them as you need. Some of it you may already do instinctively; some of it will become easier and easier with practice. Some of it may not work for you, and that’s fine.
Anyway, I’m done revising this. That’s all, folks, and happy emailing!
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