I moved to fastmail earlier this year. Honestly, it took a full day of updating all my accounts on every site that used my email. It helps to have a password manager to keep track of progress.

Since then it's been pretty good. I keep my old gmail as an additional account on my email client to track things I've missed, but it's been surprisingly little.

I moved to fastmail. Biggest pain was all my filters that I ported to their rule syntax and still manually maintain. I believe they have a better way to do this 5+ years later, but that is my experience.

1. Get Fastmail 2. Forward all your email from gmail to Fastmail. Use this time to update your contacts, etc. 3. After 30 days disable gmail forward. You will probably keep the email address for spam.

For Calendar - you can have fastmail pull your gmail calendar. Keep that in place to help transition recurring meetings to fastmail, and then eventually you can sunset that too.

Do invest in your own domain name so that if you need to leave fastmail in the future you can do that more easily.

I would definitely recommend using 2 email addresses. Pick one for your important stuff and another for spam (give this out to merchants and what not). Protonmail works but there are others. Also realize that you are not going to self destruct if you miss an email from migrating as long as you cover the most important contacts. It can actually be a good spring cleaning exercise.

I use Tutanota.