When to Filter

Email filters seem like a bit of a power-user feature. These are things like “if an email is from this address and contains this text, apply this label and automatically archive it.” It’s pretty cool that we can do that, and I’d wager most clients support some version of that. 

At the moment, I use about a 50/50 split between Gmail and Google Inbox. Gmail has filters. Inbox does not. I don’t miss them though, the bundling in Inbox does good for me. And if I need a filter, I can always pop over to Gmail and create one.

I recently saw this:

That sounds like it saves Julia a lot of grief, which is great. It makes me think though… wouldn’t cutting those emails off at the source be better? Hm. Maybe, maybe not. It boils down to if it’s useful to have those emails in the archive or not. Perhaps it’s useful to be able to search for a person and see when you had meetings with them in the past (or future, I suppose). If that’s not ever useful, then I’d see about getting the calendar you use to stop sending those emails. After all, you wouldn’t fight junk email by setting up a million filters, you unsubscribe from them.

So I suppose… only filter if:

  • You have no control over the source of the email, and need to exert some control after it arrives.
  • You don’t mind getting the email, but you don’t need to see it. It’s useful in search.
  • You like doing fancy workflow things, like automatic labeling or prioritization.

If you’re using filtering to trash stuff, try to cut it off at the head instead.

Crossing the Barriers

Hey Chris, just shooting you a text here to let you know I emailed you about that stuff we talk about on the phone. 

It just doesn’t feel right, does it? I’ll admit, sometimes I don’t mind. Like if it’s a real estate agent whom I’ve told I want to be kept very up to date on everything going on. But usually, it’s pretty far up the obnoxious scale.


I don’t want a Direct Message (DM) on Twitter about the email you sent me. I don’t want a phone call about that same email. I don’t need a email about your phone call. I don’t need a Slack message about your text or for you to stop by in person about your phone call.

All these are crossing the communication-type chasm and feel like a violation of trust. We’ve already communicated in one way. There is already proof that I use that communication type. I’m an adult person who has already communicated with you and if there is some breakdown there, there is a reason for it that can’t be solved by jumping chasms.

The primary reason is that my trust in you drops a ton the second you do it. You don’t come across as a go-getter, you come across as needy and desperate, and that’s not a good look on anybody.

You know how I pick which communications of any type I respond to first? Whatever ones I feel like. The ones I think have the most potential and feel good. Make me feel good, not chased.

Not to mention, confusion:

I don’t answer *all* my email.

Of course not. There are people like Daniel Jacobs out there:

You don’t deserve my time, Daniel Jacobs. You demonstrated no understanding of me or the site you are asking about. That’s a terrible way to reach out to someone. I’m quite sure you are a real person and this tactic gets you enough leads or whatever that you’re doing just fine.

But I’m not going to talk to you Daniel Jacobs. I know just by the smell of this email you are not a good person for me to work with.

Caffeinate your highs, not your lows

The Productivity Cycle by Alex Sexton is a wonderful article that has stuck with me over the years. There is a bunch of it that is about caffeine consumption. Alex cites actual research and provides context, so definitely read the article, but the gist of it is this:

Consuming caffeine in time for it to affect you at the exact peak of your “focus wave” effectively makes the highs higher, and the lows lower. The rich get richer, while the poor get poorer. It’s like the sad state of our socioeconomic classes, except not awful, and for brain power!

Rather than using caffeine to fight off being tired, just be tired. But when you’re bouncing back and going into a high-energy period, that’s when you caffeinate, to make a productive period even more powerful. 

I thought of this as I was considering how I pair energy and tasks. If I’m working on something extraordinarily hard, I’ll consider caffeinating a high. If I need more average hours to knock out a lot of stuff that just takes time, I’d consider caffeinating a low.

Work on what you feel like

I realize not all of us have the freedom to do whatever we feel like doing all day at work. But assuming you have some wiggle room on what you do and when I find letting your mood dictate that is a recipe for a productive day.

I have a variety of things I can be doing that I’d consider productive:

  • Coding
  • Emailing
  • Organizing
  • Designing
  • Writing

And, being a human being, I have a variety of ways I’m feeling. There are infinite ways I might be feeling, but to boil it down to some large practical buckets:

  • Fresh
  • Average
  • Tired
  • Toast

If I was going to pair up those activities for me, it might be something like:

  • Fresh: Writing & Emailing
  • Average: Designing & Coding
  • Tired: Organizing 
  • Toast: Go home

I’m not good at writing (email or otherwise) when I’m not quite fresh. It’s mentally taxing, and the stakes for how well I do it are high. I’d rather capture my most energetic and fresh moods to do writing. 

Once that has worn off, I can settle into regular tasks like designing and coding. Once I’m pretty wiped, I can do low-effort low-stakes tasks like organizing and cleanup. I might knock off the easiest emails that require no written reply. I might organize my todo lists. I might clean up internal documentation and planning documents and calendars. 

Then once I’ve really had it, I gotta just shut the laptop. That used to be harder, but I’ve gotten better at it. I suck at everything when I’m super tired. I imagine most of us do.

When not to email yourself (2 minute rule)

I have a major habit of emailing myself. I don’t consider it a huge problem really, but it is just dumping something at my future-self to deal with without much structure. So I’ve been weaning myself off it. 

I use Things for my to-do lists, which are structured, and have due dates and context. So if the thing I’m emailing myself really belongs there, I put it there. 

But more importantly, there is a good chance the thing I’m emailing myself is a tiny, tiny thing. It’s a reminder to do something else, like “text the landlord about the drawer.” It seems silly thinking about that, because writing myself an email about that takes about just as long as writing the dang text itself.

I forgive myself to some degree, because writing to yourself is very low-stakes. Communicating with another person is higher-stakes. You need to make sure you understand yourself exactly what you are saying and then make sure you say it in a clear way. It’s not every second of the day you’re in that headspace. 

Still. I’m trying to use the Getting Things Done-rooted 2 minute rule. If the thing takes less than 2 minutes to do, just do it. That includes actually writing the email and not dumping it on future-me. So far so good. I prefer keeping those tiny-weenie things off actual to-do lists, lest they become more overwhelming than they really are.

You get good at what you do

You work at an ice cream shop and scoop ice cream cones by the hundreds? You’re gonna get good at it. You’ll get a feel for the scoop and how it grabs the ice cream. You’ll get a feel for how big you need to make the scoops depending on what you’re doing with them. You’ll get to the point where you do it as fast as it should be done. It’s a small art.

I’m sitting in a coffee shop right now and it’s clear these baristas got good by making coffee drinks.

Heck, even if you watch TV all day, you’ll get good at it. You’ll know what’s on when. You’ll know when to surf and when not to. You’ll know to extract as much satisfaction out of that TV as is damn well possible while you stare at it.

It helps if there are stakes though. Say you throw darts at a dartboard three hours a day. You’ll probably get better, but you won’t get as good as you would if you were competing against people during those three hours trying to beat them.

Forgive the crassness, but I have an uncle who once said he’s been peeing several times a day for his whole life. He could pee into a bottle 5 feet away and not spill a drop. It almost stands to reason, doesn’t it? Us male-parts-havers should be pretty damn excellent at aiming we’ve been doing it for so long. But of course, we aren’t, as we’re told by cute little signs in public bathrooms. We don’t get better because the stakes are low and, frankly, the controls just aren’t there.

I’m fond of music analogies as well, as someone who’s essentially been a life-long student of playing stringed instruments. I’m not amazing, but I have some skill I’ve hard-won. It came from doing it, a lot, and from a lot of angles. An instrument in hand, practicing or playing with people. But also some level of immersion in it. Listening to and loving the music of people playing in the style I’m practicing. You don’t get to say hey it’d be neat to play to banjo, buy one, and practice your way to proficiency alone. If you don’t actively listen to music with prominent banjo, you’re doomed.

Email, too, of course. You’ll get better at it by reading and writing a lot of it. Especially if you care about keeping yourself up to date and communicating strongly.

Gmail Tips

Vaishnavi Rao has a couple of Gmail-specific email productivity tips. I didn’t know about the Google Labs feature for viewing sender legitimacy. That seems like a good one to have on. 

If you haven’t heard of it, the “Send & Archive” is a massive one. It’s a default setting now after spending many years as a Labs feature. The idea is that you type out an email response and can both send and whoosh it away from your inbox in one swoosh.

And hey, I was just poking around in some of my Gmail accounts… the new look is pretty great, I wonder why we don’t have that for GSuite accounts yet?!

Double Opt-In Email Intros

Reposting from my other blog, because this blog is way better for it. 

You know those “introduction” emails? Someone thinks you should meet someone else, and emails happen about it. Or it’s you doing the introducing, either by request or because you think it’s a good idea. Cutting to the chase here, those emails could be done better. Eight years ago, Fred Wilson coined the term “double opt-in intro”.

This is how it can work.

You’re doing the vetting

Since you’re writing the emails here, it’s your reputation at stake here. If you do an introduction that is obnoxious for either side, they’ll remember. Make sure you’re introducing people that you really do think should know each other. Like a bizdev cupid.

You’re gonna do two (or three) times writing

The bad way to do an intro is to email both people at once. Even if this introduction has passed your vetting, you have no idea how it’s going to turn out. There is a decent chance either of them or both aren’t particularly interested in this, which makes you look like a dolt. It doesn’t respect either of their time, puts your reputation at risk, and immediately puts everyone into an awkward position (if they ignore it they look like an asshole).

Instead, you’re going to write two emails, one to each person you’re trying to introduce. And you’re not going to reveal who the other person is, except with non-identifying relevant details and your endorsement.

They do the opt-ing in

If either of the folks are interested in this introduction, they can email you back. Give them an easy out though, I’d say something like “if for any reason you aren’t into it, just tell me so or ignore this, I promise I understand”. If you don’t make it easy to blow you off, it’s your just transferring the awkward situation to yourself.

If either of them isn’t into it, it doesn’t matter. They don’t know who the other is and there is no awkwardness or burnt bridge.

If both are into it, great, now it’s time for the third email actually introducing them. Get out of the way quickly.

It’s about more than awkwardness and reputation, it’s about saftey


Just because you have someone’s email address in your book doesn’t mean you should be giving it out to anyone that asks. Better to just assume any contact info you have for someone else is extremely private and only to be shared with their permission.