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.

Nick Douglas’ “How to Ask for Advice Over Email”

Great list:

  • Spend 95% of your time researching the person you’re emailing, and 5% writing the email.
  • Introduce yourself quickly but specifically, and ask specific questions.
  • Ask one or two questions. Not three! You’ll feel like adding a third because your email looks too short. It’s not.
  • Google your questions first.
  • Don’t offer to “hop on the phone” as a compromise. That’s not a compromise, it’s a threat.
  • Say “Even one sentence would be great.”
  • Novelist Tao Lin came up with this one: Tell the recipient it’s OK to ignore your email. Not just to say no, but to completely ignore it.
  • Say thank you.
  • As soon as you’re ready to send, find and delete at least one sentence.
  • Send and move on. Never “follow up.”

Email Statistics Report

This company The Radicati Group, Inc. produces “quantitative and qualitative research on email, security, instant messaging, social networking, information archiving, regulatory compliance, wireless technologies, web technologies, unified communications, and more.” Looks like one report will run ya about $7,500, but they publish summaries, including the email one. It has some interesting stuff in it:

In 2015, the number of worldwide email users will be nearly 2.6 billion. By the end of 2019, the number of worldwide email users will increase to over 2.9 billion. Over one-third of the worldwide population will be using email by year-end 2019.

Over the next four years, the average number of email accounts per user ratio will grow from an average of 1.7 accounts per user to an average of 1.9 accounts per user

As in, most people have 2 email addresses.

In 2015, the number of business emails sent and received per user per day totals 122 emails per day. This figure continues to show growth and is expected to average 126 messages sent and received per business user by the end of 2019.

They say “consumer email” continues to grow as well, but mostly because of stuff like notifications and not so much “interpersonal communication.”

“It’s going to get worse before it gets better.”

Quinn Norton for the Atlantic:

Email has changed since [the 1970s], but not much. Most of what’s changed in the last 45 years is email clients—the software we use to access email. They’ve clumsily bolted on new functionality onto the old email, without fixing any of the underlying protocols to support that functionality.

The article is mostly about the efail stuff and how it’s apparently inherently bad that email can be HTML because it brings the vulnerabilities of web browsers to email clients. Fair point. Pretty impressive that those protocols and such haven’t changed for half a century. What’s the HTTP/2 of emails going to be?