I recently wrapped a move off of various email platforms to FastMail. As I wrapped this up, I tweeted

Google services dropped:
☒ Calendar
☒ Contacts
☐ Email

The last one is today’s project.
— Jason Verly (@mygeekdaddy) September 1, 2014

The response I got back on that was surprising since I thought I was the last kid on the block to make the move.

So why did I make the move? It's funny how the little things get under your skin. The most recent thing that has been under my skin has been my email, contacts and calendars. Over time I've picked up several email accounts, some them by choice and some of them by force. I sat down one night to do a weekly review and realized how ridiculous it was to have slog through multiple accounts. So I created a project that had a very simple outcome...

Move email to single account

Gaining my sanity

Looking around at the various accounts I had I orignally thought it was pretty straight forward decision to push everything to Google. Gmail synced nicely on my iPhone and could be setup easily on my Mac for contacts and calendars. As I started settling in I got a quick terms of service update from Google. It's funny how fast we ignore the terms of services or user agreements computer companies throw at these days. We eagerly hit 'Yes', 'Ok', or 'Accept' without really know what we're getting ourselves into. On a whim I actually sat down and read through them. This is the section that got me:

When you upload, submit, store, send or receive content to or through our Services, you give Google (and those we work with) a worldwide license to use, host, store, reproduce, modify, create derivative works (such as those resulting from translations, adaptations or other changes we make so that your content works better with our Services), communicate, publish, publicly perform, publicly display and distribute such content. The rights you grant in this license are for the limited purpose of operating, promoting, and improving our Services, and to develop new ones. This license continues even if you stop using our Services (for example, for a business listing you have added to Google Maps). Some Services may offer you ways to access and remove content that has been provided to that Service. Also, in some of our Services, there are terms or settings that narrow the scope of our use of the content submitted in those Services. Make sure you have the necessary rights to grant us this license for any content that you submit to our Services.

Huh...

I had just gone toe to toe with a group that had "borrowed" a photo of mine and I was a little more sensative to the idea that Google could also "borrow" my content. I had legitimate concerns that if I emailed a great shot of mine to share with my family, it looked like Google to grab that picture and use it for themselves. That was not something I was willing to put up with for free email.

What I was looking for

So I set off to look at alternatives other than the big three (Gmail, Yahoo, Hotmail) with some specific requirements:

• I wanted to be able to use one of my personal domains with the mail host to have the exact email address I wanted.
• The service had to use standard IMAP so I didn't experience the same issues I ran into with Gmail.
• The service had to include an address book for my exported contacts and synced to my iPhone and Mac.
• The service had to include an calendar that could be viewed and updated from my iPhone and Mac.

I looked at using the email serviced provided by my hosting company, but some of the key items were missing and I wanted a solution that segregated my personal information.

What I found

After looking around I decided on FastMail. While I didn't find all my requirements with FastMail, I did find a lot of things that made me feel good about my choice:

• FastMail uses a secure connection for everything. If you want to browse their pricing options or review their support information, you will be on a https connection. So now I know I'm on a secure connection from start to finish when I use their web based mail client.
• FastMail of course has email, but it easily allowed me to use my custom domain for email addresses. In addition to the custom domain, they also allow for aliases on your primary FastMail account. So now when I need to give an email address out publicly, I can give them my "spam" address and have mail rules move messages to a separate folder for less frequent review.
• FastMail offers both Calendars and Contacts. Calendars are CalDav format and sync easily with my Mac and iPhone. Contacts are available in the web based mail client, but they don't have a way to sync to my Mac or iPhone. While Contact syncing was originally one of my requirements, it wasn't a make or break item.

Bonus features

Beyond the features that had to be met, FastMail has some additional features that make it stand above

• Web Client: The web client from FastMail was the surprising bonus. When you open the web client you don't feel like it's a web page. The client has keyboard shortcuts, folder management, and great search capabilities.
• Personalities: Personalities was another bonus feature that was extremely helpful while making the switch - in fact it still is. From the FastMail help:

A personality allows you to send email and make it appear to come from a different 'From' address. For instance, you can setup a 'Work' personality and an 'ISP' personality, and send email and make it appear to come from those addresses.

So while I was transitioning to my inbox on FastMail, I could continue to converse with people as if I was on my old email. Look for more on this functionality soon.

• Sieve Filter Language: This is the untapped potential of FastMail. FastMail has a visual app (kind of like smart lists in OS X) to setup mail rules in the web client, but FastMail also allow users to setup mail rules directly in a scripting language called Sieve. This can lead to some powerful rules on the ways you want to manage your incoming email. ²

Final Setup

After the move to FastMail I found I had to tweak a couple of things in my setup. Here's how everything has settled down at this point:

Email: My email setup is pretty simple since it's down to one inbox.

• iPhone: I use Dispatch for email because it can so easily hand off messages to other apps, like OmniFocus. In fact I use Dispatch on my iPad too because of the its great handoff features.
• Mac: I use Mail.app as my default email program. This is temporary until I can move back to Outlook when I've finally closed a few more accounts.

Calendar: Calendars are one of the items I had to switch up to meet the real world.

• Personal Calendar: This is on FastMail with syncing back to my Mac and iOS devices. I use Fantastical on my Mac and iOS devices.
• Shared Calendar: I have shared calendar with my family and that resides on iCloud. Ditto again with Fantastical.

Contacts: Contacts was one of the items I had to compromise on.

• FastMail: Contacts on FastMail are used for mailing in the web client and a "backup" of my contacts.
• iCloud: Since FastMail Contacts don't sync back to my Mac or iOS device, I've put them into iCloud. Apple seems to be the least likely of the big three to potentially spam my Contacts list and has made sense to keep them there for integration with other core OS X and iOS apps. ¹

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Update 2014-09-17: As I was writing this post, Gabe and Erik did a great job breaking the ice on FastMail with their latest Technical Difficulties podcast. It's an easy listen for another perspective on moving over to FastMail.