I do this for my son. I use iCloud, but set it up with a custom domain for him. I send him an email every month on the date of his birthday (he happens to be bo

I do this for my son. I use iCloud, but set it up with a custom domain for him. I send him an email every month on the date of his birthday (he happens to be born on the same date as me, just a different month, so I get to send him an email on my birthday once a year as well). It’s easy enough to backup through IMAP as well, so I’ll do that until he’s old enough to take charge of the domain himself. This can off course be done with Gmail as well, I just didn’t use that because I already use iCloud and they have free support for custom domains (and I like the idea that my emails to him won’t be scanned for ads or whatever), so I can switch to another provider later if needed. I draft the emails in my journal software and use that the print out a paper copy as well, which I use to read to him at bedtime (he’s just over two right now). I keep to a pretty strict format: One large image I think he’ll like to look and then the text, which I usually end up editing before I print so it fits on the facing page.