End of Mailplane?

I was a little sad to get this email:

I’m a Gmail user and I really like the Mailplane tabbed interface for doing email on different accounts. There are alternatives (like Shift), but it sounds like all the apps similar to Mailplane will be affected by Google’s changes which they say are trying to fight man-in-the-middle attacks.

But I’m not that sad. I’ll find a new workflow. It won’t make me worse at email.

On the Gmail mobile apps, I can be logged in to multiple accounts in one app and then use the “All Inboxes” feature to see them all at once. I’d like to see that come to the web client (I’m not missing something, right? You can’t do that on the web?).

I’m also thinking Firefox Multi-Account Containers might be a fairly easy way to replicate it. I just have doubts it will be as nice as a dedicated app just for this. For example, I really like how I can just close the whole damn Mailplane window and it doesn’t unload the apps, it just hides the window, and I can bring it back to the exact state it was in just be clicking the icon in the dock. Browsers don’t really work like that. I’d have to more explicitly Command-H hide. Oh well, just some new muscle memory to build.

The One Way

You know what’s a weird email archetype? The one way.

It’s when you get an email from someone that very much wants to tell you something. Maybe they read something you wrote. They saw something you made. They cross paths with some part of your life. They type it all up and send it to you. You get it, read it, and respond to it, but then never hear back ever again. That email they sent was a one-off one-way anomaly.

One-ways feel weird because email is this highly established two-way street where communication flows easily both ways. But in this case, it behaves more as they sent you a letter with 123 black hole avenue as a return address.

If that’s the intention of the email, the respectful thing is to say so.

No need to reply to this email. I probably won't see/read the reply if you do, because of [insert legitimate reason here]. 


Get well-written AI-generated rejection emails that reduce your writing time by 95% so you can focus on the things you love.


Hi (Founder name),

Thanks for waiting! We had the chance to sync up internally after our conversation.

I personally find what you're building awesome, but unfortunately, we're struggling to gain conviction as a result of some of the metrics, but it's great to see a significant improvement since launching.

This is the only thing that matters for you to be a multi-billion $$ business.

Best of luck with the round. Here’s a Medium article we wrote that might be helpful.

(Your name)

Don’t want to

You don’t have to level up to this, you can just say it.

I mean, you probably can’t to your boss, but you can say this to all those other emails you get where you don’t have any particular obligation.

If you think that “I don’t want to” is a bit harsh, you can be honest but still soften it. I told someone the other day, while delivering a “no”, that I’m trying to wrestle some of my personal time back. That’s true, I am. That way it prevents them from reading in between the lines that you don’t want to because you they suck or their thing sucks.

If you think that, don’t answer at all. This is email. While I think answering things is generally good and I’m broadly against bridge-burning, you don’t owe random people asking you for things responses.

My Trust Issues with Small Businesses and Custom Domains

I got a referral the other day to a physical therapist that is good with backs. A literal paper business card. This email was something like this:


Now I’m an indie-web kinda guy for the most part. I’m all about people owning their own websites and taking control over their little slice of the web. And yet. My trust level with random small businesses managing their own email on their own domain is super low. I get this little twang of distrust when I have to type in an email address like this.


Their email was busted.

It could have been anything. They could have let their domain name lapse. The DNS (MX) records could have gotten screwed up somehow. They could have been trying to move to GSuite, for example, and gotten those records wrong. They could be moving hosts and something got funky. Who knows.

That stuff is complicated for me, and I’ve been working on the web for decades.

That’s why even though I like the idea of doing as much as you can yourself on the web, I think using a managed email service is a smart move for most. Even if you do “do it yourself”, you’re leaning on so much rented technology anyway, it’s not that different.

If I see an email like: small-business@hotmail.com – all my doubt is gone on if they are actually going to get that message or not. Heck, I even prefer just seeing an email like that on the website itself (rather than a contact form), because the contact form is just one more bit of technology that can go wrong.

I get the desire to have email on your own domain as well. “It looks more professional” I was just told the other week by someone I was helping out with a website. But there are other pokes too. Like if that small business uses MailChimp, MailChimp will literally tell you that your “from:” email address should be your own domain, not something like Gmail.

The middle-ground for me is using my own domain, but using Gmail on top of it. So I still have to deal with MX records, but once it’s set up correctly, I just never change it. It works for every company I run and every project I have that has a custom domain and email.

Email is not dead.

Interesting little landing page from Jordie van Rijn with lots of statistics and links to articles about email. All evidence points to:

  • Tons of people use email (more than any other communication tool)
  • Email isn’t dying, it’s growing.
  • People prefer it, particularly in business in business and marketing.

So many links in there to read. Like The Triumph of Email from Adrienne LaFrance in 2016:

Over the course of about half a century, email went from being obscure and specialized, to mega-popular and beloved, to derided and barely tolerated. With email’s reputation now cratering, service providers offer tools to help you hit “inbox zero,” while startups promise to kill email altogether. It’s even become fashionable in tech circles to brag about how little a person uses email anymore.

I think now in 2021 that last sentence isn’t as true as it was in 2016. I don’t doubt that most people don’t like email, but as nobody is even close to unseating it, it may be settling in that we might as well get good at it.

The Expectations of `cc`

When you “cc” someone on an email, what are the expectations?

The least you can do, is nothing. You just add additional recipients to the email, and expect them to understand what you meant by adding them to the thread. Depending on the group dynamics, different things can happen. If I’m your boss and I do that, you might be a little confused or annoyed, but the expectation might be that you read the thread and try to understand how you fit in. If a random stranger cc’s me on an email, I might be so unmotivated and unincentivized to guess what you are doing that I just archive it.

It’s more common to see a short inclusive statement. “Adding Bob and Julie to this thread!” a party-planning email thread might include when some other form of communication has confirmed that indeed, Bob and Julie can attend the party. That might not add any clarity, but at least it’s acknowledged.

If you’re going for complete clarity you might either:

  1. Include text in the email that acknowledges any new people cc’d, why, and what your expectations for them are.
  2. If that is awkward or distracting, cc them, but use another communication channel to do those same things. (“Julie, I cc’d you on the email thread about the party. Nothing for you to do there, I just wanted you to have the list of addresses in there in case you need them for the labels.)

I’d shoot for clarity no matter what, but I admit it’s a weak point for me to assume people know what I mean when I cc them (or forward things for that matter).

And another thing! Is there any implied difference for when you actually use the cc function of email, or when you just include them as a new recipient in the to field? My gut says people don’t even notice generally, an email in the inbox is an email in the inbox.

Unfortunate Warning

I visited my mom this week. We got her a new computer. MacBook Air. One of the new M1’s. Very neat. She loves it so far. As she was setting it up, she went for a new @icloud.com email address. The first thing she did with it was email me at my @gmail.com address. And behold:

That’s a little unfortunate isn’t it? My own mother looks like spam to Google. I get loads of email every day from people I don’t know and very rarely see a message like this. But my own mother emails me and somehow that looks suspicious?