While I still have a public @gmail.com email, I recently moved off of Google Workspace (or whatever it's now called) and haven't had any real issues with the replacement set of tools. I want to talk about why—and how it relates to systems thinking—as well as what I did.

Anyone Remember POP?

I signed up for Google Workspace a long time ago to handle email for my naildrivin5.com domain, which is my primary home on the Internet. I love the way GMail works, and as long-time POP and IMAP user, it was a breath of fresh air. Email is the center of my digital life and the primary tool I use for organizing information. GMail felt tailor-made for me.

Over time, I grew heavily dependent on Google Calendar, but also used Docs quite a bit. The only other Google service I used was Google Voice, which was initially a free way to have a phone number I could use in situations where I had to provide a real number, but knew I'd be getting a ton of spam and sales calls.

Why Leave All This

Google, despite running one of the most popular email services in the world, is not in the email business. Yes, I pay $5/month for Google Workspace, but the reality is that they will never care about me as a customer. I read one too many posts on Hacker News where some ML-model inside Google canceled their account with no way to reach an actual person for explanation, remediation, or data recovery.

The relationship between product design, engineering, and customer support is something I explored in "A Framework for Product Design Beyond the Happy Path". In this case, the relationship between myself and Google is lop-sided. I'm getting a ton more value out of them than they are to me. And that's a huge risk.

I use email as a repository of information that I don't know if I'll ever need. For example, I can find a weird charge on my bank statement, search my email for the amount of the charge, and come up with a receipt that explains what it is.

My calendar is also my lifeline to organization. I cannot remember appointments at all, and rely on the calendar. I manage my parents finances and healthcare and let me tell you…unhealthy people in their late 70's have a lot of doctor's appointments. There's just no way to manage them without a calendar.

The thought of waking up one day and having it all gone without any way to get it back, and no way to get support, was unsettling. I realized that my core workflows—systems I rely on to navigate my life—heavily depend on a company with no interest in provide the tools I needed.

Could I find alternatives that provided the user experience I needed, with a more equitable relationship?

Fastmail

Fastmail (referral link) provides web mail and calendar. They are renowned for having good support, based on people and not machine learning. Their web UI is snappy and met my needs.

I ported my Google email into it to try out the search. All of my search use-cases worked and worked quickly. The Web UI has keyboard shortcuts, and provides archiving (instead of deletion).

Fastmail's calendar system is standards-compliant and synced perfectly with Fantastical, which is my primary UI for all things calendar. It works with invitations from other Google users, so I could have the same workflow of accepting calendar invites directly from email and seeing them on Fantastical.

The only three downsides I've found are not deal-breakers:

• Fastmail's Web UI requires full page refreshes at least once a week. Google's only required it about once a month.
• Fastmail's spam detection isn't quite as good as Google, but I heavily curate and triage my inbox, so it's no big deal to mark messages as spam. I also triage my spam folder for false positives, so this is no problem.
• When an invited calendar entry is updated, Fastmail's calender does not seem to be notified. This is slightly annoying, however I have also experienced this between Google Workspaces, so I'm not sure there is a solution here. I just let people know that they need to email me with any changes.

Could Fastmail capriciously cancel my account without warning and without allowing me to contact support? I guess, sure. But this seems far less likely. Charging people for email is what they do. Charging people for email is not what Google does.

Other Stuff

Most of my ad-hoc writing that would be in Google Docs can live in Apple Notes, and most of my ad-hoc spreadsheets can be in Numbers. I do maintain a few shared docs and sheets, so I migrated them to my @gmail.com account. Losing them would be annoying, but not the end of the world.

Google Voice was trickier. I strongly considered porting it to a cheap flip-phone and pay-as-you-go plan. I wanted to keep the number, since it's a DC prefix. I decided to make this part of the migration more of a project, and decied to port it to Twilio and take programmatic control over its behavior.

Twilio's "Studio" product is a no-code tool that gave me what I needed. Texts sent to the number would be forward to my real phone number and phone calls would go straight to voicemail, with a transcription and recording emailed to me.

Porting the number and getting approved for sending SMSs took several weeks, but once that was done, here is the flow I have:

Initially, "Incoming Call" went directly to "EmailVoiceMail", however I started getting a lot of calls from a real person who I think had the wrong number. So, I added a check for the number and, if that guy called me ("ThatOneGuy"), it instead delivered a message "You have the wrong number". Neat!

Owning The Tools of Your Core Workflows

Maybe you don't care about email, but let this be an opportunity to think about the tools and services you do use that are critical to how you operate your life. Consider the relationship you have with those vendors. Is it equitable? Do they make their living by selling you the tool or service? If not, you may be in a risky situation that you should consider re-evaluating.

Unless otherwise noted, my emails were written entirely by me without any assistance from a generative AI.