At the risk of sounding trite, the best thing to do is get started.
Remember, you don’t have to turn off your old account and it’s not going to start bouncing emails immediately. So you don’t have to do this all in one day, or one week, or even one month.
(For ease of discussion, I’m going to talk as if you are moving from Gmail to Fastmail, because that’s what I did, but the process is pretty much the same no matter what you are moving from and to. I’m also going to assume that your new domain is “jaketheo.com” just for the sake of discussion.)
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Get your domain working at “Fastmail” (new location destination). Make sure it has a rock-solid random, unique password and two-factor enabled.
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Most email providers will let you create an ‘alias’ or use “plus addresses”. For example, if your email address is “jake@jaketheo.com” you might also be able to receive emails as “jake+gmail@jaketheo.com” or just “gmail@jaketheo.com”. Create one of these aliases or test to see if you can use the “plus address” system. Let’s assume “jake+gmail@jaketheo.com” for the examples going forward.
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Once you know it’s working, create a filter from ‘Gmail’ that will send a copy of all of your incoming messages to your “jake+gmail@jaketheo.com” address. Why?
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Because you can easily filter all of your “jake+gmail@jaketheo.com” emails to a specific folder. When you find a new email in that folder, you know that’s a sender who needs to be updated.
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Also, from that point on, you will have a ‘backup’ of all of your email messages sent to ‘Gmail’ at ‘Fastmail’. You can have ‘Gmail’ keep a copy, just mark it as read so you’re not reading the same email in two places.
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Now, think about those 250+ addresses, and find the small subset of them that are connected to anything financial (bank, PayPal, credit cards, Amazon, Apple ID). Any account you would be horrified if you were locked out of or if someone else was able to access, that’s your starting point. There’s going to be a lot fewer than 250. There are probably fewer than 25. Change those first and update them in 1Password. You can do that in a couple of hours on a weekend while you’re watching TV. Getting locked out of your credit card account is much worse than getting locked out of your Netflix account.
Create a new “signature file” for jake@jaketheo.com that says something like:
Please note! Effective immediately, I am no longer using my old email address
jaketheo@gmail.com. Please update your address book/contacts with my new email address or else I may not receive your email.
Ok, yes, technically it’s very close to a lie, because you haven’t blown up your old email address, but you need to get people’s attention that this is something they need to act on now otherwise, they’ll put it on their “someday/maybe” list which is another word for “probably never”.
Start sending that out at the bottom of all of your new emails. People who care will see it and act accordingly. A startling number of people use autocomplete and will keep sending emails to whatever address comes up when they start typing your name. But most people will just ‘reply’ to whatever address you email them from, so as long as you email them from that new address, they’ll eventually catch on, whether they realize it or not.
And if they do send an email to your old address, you’ll see it in the special folder on your new ‘Fastmail’ account, and you can email them back and say “Hey, I’m glad I saw this, but just as a reminder, my new email address is jake@jaketheo.com.”
You probably don’t need to tell all of your contacts this information. Like the small handful of ‘crucial’ accounts, you want certain people to be sure to have this information. For the rest, you can tell them the next time they email you and you respond from the new account with the new “signature” at the bottom of the email message.
Do you really need those? I mean, maybe you do. Maybe you delete all unimportant emails and have thousands of important emails left over. But the majority of the email that I get is not all that useful after a week or so. There are exceptions of course: software licenses, epic poems from your high school sweetheart, that really funny email that your friend from college sent.
Again, unless you plan to shutter the old account, you’ll still have them in that account. What would be the worst thing that would happen if you lost access to them?
Personally, if it’s in my “Keep” mailbox or it’s got an IMAP “flag” set, it’s an important email. Most of the rest are not.
But let’s assume I’m wrong. Let’s assume that you need 100% of all the old emails that you have. You have two options:
A. Download and archive them locally using something like EagleFiler or Horcrux or Mail Archiver X.
B. Transfer them to your new account.
Horcrux has a feature to help you do that. Your new mail service probably has a way to do it too. It probably won’t require you to sit there and drag thousands of emails from one IMAP folder to another. It will probably be something you need to setup and then let it run.
Q. How do you eat an elephant?
A. One bite at a time.
(Note: Please do not actually eat an elephant.)
I hope some of this was helpful. The hardest step is the first one. Once you get started, it’s much easier to continue. Until you get started, you can’t make any progress at all.