Years ago, in the dark ages of the internet, my father paid for a dial-up connection, as many did in those days. He made use of the e-mail account provided with that service for his small business. He still does, its the e-mail on the business cards hes been handing out for years and years, what is listed for his business in industry directories, etc.
This means that for all these years after he moved on to better and faster internet services, from other providers, he has continued to shell out for this dial up, purely for the e-mail. This seems rather wasteful, considering you can get a nice gmail account for free.
The account is an atteleportdotcom address, a small ISP that was bought out years ago by Earthlink. He uses Outlook to check his emails. I'm well versed in backing up and exporting all the archived emails and the address book from Outlook, so my question is could I set him up a gmail account and import all that stuff, and then set it up so that emails to that old address are forwarded to the new, free one, without paying for the old one?
Or would it be a longer, more painful change over with new business cards, updated directories, mass mailings to his address book informing them of the change, etc?
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No. If you no longer pay for the old address you won't retain access to it and will then not be able to set up any kind of mail forwarding for that address.
I'd suggest what MushroomStick/matthasaproblem said. Just forward the mail now, update his business cards to the gmail address, and continue paying for the old email for 3-6 months. Send a message about updating his email to all current customers, and make sure he uses the gmail for all communication to current/new customers so that they have the new address. After a few months, the bulk of customers should be using the updated address and you can cancel the old account.
This. Domains are extremely cheap and look a lot more professional. Also, as my own general rule, don't host mail with your ISP.
A couple of reasons. Owning your domain name means you get to keep your address, wherever it goes (and can set up a webpage if you choose to do so). Not hosting with your ISP saves headaches if you change providers or your provider changes on you - gmail/godaddy/etc isn't likely to go anywhere.