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Navigating the failed promises of managed email platforms

Published: at 02:06 AM

Email. Sigh. Where to begin?

Forget it. I’ll spare the diatribe. Everyone’s experiences with email is pretty consistent…it sucks.

I’ve fell for the bait a few times. Almost 20 years ago it was Google swooping in with a solution to the mess that Hotmail, Yahoo, AOL and others had created. Gmail was fast, easy and best of all, it filtered out all the shit.

Fast-forward several years, and Gmail became the same bloated, spam littered email services that it had replaced. The difference was that you didn’t get the spam in your inbox, the spam surrounded the rest of your life on the internet because of the data Google collects.

I’m not an anti-ads. I’m not anti-data-collection. I think these are genuinely useful pillars of the internet when there is alignment. The problem with Gmail has always been that the data Google learns about me via my email doesn’t make my internet life better. It just makes it more annoying.

I tried iCloud email for a hot second. The spam filtering was hot garbage.

In 2019, Jason Fried & David Heinemeier Hansson of 37Signals & Basecamp began a crusade against the state of email and the direction it was going. They teased that they were going to fix email. I was intrigued. Months later they launch with the promise of fixing email.

It has tracking blockers, an out of the box triage system, and interesting ideas on how to prioritize the way you consume email. It was also an email host & client rolled in one, but without all the bullshit of previous services

I signed up immediately.

Hey, like it’s founders, is incredibly opinionated. I appreciate that about good products. Hey is truly a good product, for some people. The only problem I had was the opinions broke 25 years of email muscle memory.

Dear Hey, it’s not you, it’s me. I’m just not a good fit for the product, but I truly applaud the effort. So, I cancelled my subscription

I’ll never fall for the fully managed email service promise again. One way or another, the convenience they offer creates too many tradeoffs that aren’t worth it for me.

Email should be simple. I just need something that I can point my address at to send & receive email. I want to use it on a mac & iPhone, and be able to access via web when necessary. It needs to be fast & reliable. I need to be able to organize it for some fairly simple workflows I have. It needs to be secure. It sounds simple, right? has all of the familiar features & workflows I need, without all the cruft. I can point my domain at it to send & receive email. I have it connected to my mac & iPhone email clients via IMAP. It’s fast & reliable. I use labels, masked email aliases & rules to organize.

As a bonus, it also has a simple calendar & contacts system baked in. Best of all, Fastmail embraces openness through common protocols, including the modern JMAP protocolthat they are helping to pioneer.

I moved over to it about a year ago, and I’ve quite honestly embraced email again for the first time in years.