Why I skipped the Hey Free trial and why it made me think about my email setup

Yes, I confess, I jump on the hey train of these never-ending tweets, posts, and whatever. But I have such a small audience that I don’t contribute to the hype.

But seriously, this post is just 30% about Hey. I tested it, and I liked the stuff, I was not too fond of things and decided not to pay. But Basecamp has a lot of good points about email setup. Which ones these are and how I changed my setup is the subject of this post.

The before setup

I was not unhappy with my mail setup. As an email provider, I used Google (Gmail and GSuite) for five different email addresses. Why five? Well, they appeared over time with new projects and ideas. But only two are essential for me.

As a client, I used Spark on all devices. What I liked about Spark is the smart notification and the intelligent clustering of personal (important) messages, notifications, and newsletters. The apps are well designed.

Because I was not unhappy, I was not sure if I would do the Hey free trial. But I am also a product person, so of course, I would do the free trial just to see how they approach the email topic.

Basecamp is well known for its opinionated products and methods. So I was expecting that they try new stuff.

So I watched Jason Fried demoing Hey and narrating why they choose to do things. That was the final step for me. Sure, I wanted to try it.

The Hey test

I was not in the early batches, so it took roughly some days until I got my invite. So I spent some time watching Basecamp vs. Apple and the waves it created on the Twitter.

Then I got my invite. timo@hey was already taken. Good, I was expecting this.

What I liked in Hey:

Deciding that I don’t want to see emails from this sender is deliberating. I hate to unsubscribe because 90% make it too hard. So I just want them to disappear. It brought me much joy to merely put my thumb down on emails that I was annoyed with (yes before I could simply set them on spam, but I didn’t).

Having all trackers blocked was something I liked as well—also, the little icon showing me, whose trackers have been prevented.

The idea that my emails are in a place where no ad algorithms will run was excellent too (but I lived with that for a long time)

What I didn’t like in Hey:

The client itself. I need too many clicks to do stuff. There are some keyboard shortcuts, but not enough for me. During the training, it’s easy to push messages into the feed and paper trail. After the training, I miss the options on the top.

I don’t own it. Well, I did not before. But with Hey, I some kind decided that privacy is more important to me than before.

And I am annoyed by the term “imbox” because, for some part of my brain, it’s a typo.

My new setup – the aftermath

So I decided not to sign up for Hey. But thinking about email and some of the useful features started a thought process. So I did the usual, some research.

These were my goals:

  • Have a way to set emails on ignoring
  • Move emails out of Google in a more privacy-aware space
  • Block trackers
  • Filter important messages

Step 1: The email service

The search for a new place for my mails was not too complicated. It boiled down quickly to two options: Protonmail or Fastmail.

I had tested Protonmail before and was not 100% happy. But at that time, there was no way to use a client on your Mac, only the web interface. Now they have some kind of bridge technology that lets you use any client.

But the whole experience was not great. Migrating my old emails looked time-consuming. Too many hoops to jump through.

I read a lot about fast mail from Reddit people who were happy with the service: easy setup, smooth migration, and reasonable costs.

So the decision was between more work, lesser experience but an email in a Swiss bunker or less work and emails in lay down Aussie server.

I went with Fast Mail.

After setting up two email accounts and migrating all my old emails, I can say: So far, it was straightforward. They have a migration service that lets you connect to your emails (Google in my case) and then copy them.

Step 3: Ignoring and filtering emails

As said, I can simply set emails to spam, and they will disappear. But now comes my psychology: it’s a bit unfair. It’s not spam, and I signed up for most of the stuff. It’s just that our time together is over. And most of them give me a hard time to admit this (let me simply unsubscribe). So I wanted the ignore feature.

Luckily I didn’t have to look too far. I already tested Sanebox at some time in the past (thanks to some podcast ad). Unfortunately, I can’t recall why I didn’t keep using them. I guess that it was the costs (99/annually). But Hey prepared now this price tag.

The second thing why I didn’t care in the past was the kind of acceptance of the mess. Like when you have an untidy room. If you are the kind of person, you start to ignore it. But still, it does something on a deeper level. Because when you clean and tidy up, the relief is visible.

So I went back to Sanebox, activated it on top of my new email accounts. Sanebox immediately is applying its magic.

I get a black hole folder, where I can simply dump stuff I don’t want to see anymore. Sanebox keeps my essential messages in the inbox and puts the rest in a SaneLater folder (like the feed in Hey).


Final step: The email client

As I have said, I was happy with Spark. But now getting down the privacy road, I thought if there is maybe something with a more privacy focus.

This research was the hardest part. Most of the clients put their effort into looking nice. But none of them on privacy (or I didn’t found the option).

Clients bragging with a “see who read your email” featured were filtered out immediately.

I was close to going with Thunderbird when I read a post that Airmail has a privacy and tracking blocker feature in the settings. Not active by default.

Some time ago, I used Airmail, and I liked their quick actions. But they had no smart inbox, so I left for Astro and then for Spark.

But with Sanebox, I don’t need that smartness in the client.

So Airmail was the first candidate for the test.

But after three days I switched. The major problem for me was the search. I haven’t found some emails I later found on the server. Maybe when I would have spent some time on the settings, I could figure it out.

But I just tested #2 on my list: Canary Mail.

Canary claims end2end encryption, but don’t ask me about the details here. When I have more time, I might look at how this works. PGP is also built-in, but I rarely use it. But I can switch off all tracking options in the settings. I have not tested yet if there is still tracking stuff is sent.

In general, Canary works well. Search is finds everything I looked for. I can customize the sidebars to make the sandbox labels more prominent.

One thing to keep in mind: With Sanebox notification for emails, don’t work correctly. Most of the time, you get a notification about a mail that SaneBox then puts into the SaneLater or SaneNews folder. So basically, a notification I don’t care about.

So I did what I should have done a long time before: switch off notifications for emails.


Does my switching make sense? I will see it. The emails are tidier now. I killed three mail addresses I didn’t use and replaced my generic Gmail with a custom dechau.net domain(something I had on my list for ages).

Let’s give it some more weeks, and I will write a catch-up.

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