Having been on the internet since before the world wide web existed, I’m familiar with the woes of email in the cloud. In the early days of the web, I had two email accounts: fcmail (fortune city mail) and juno. Fcmail was my primary and juno was my secondary and junk mail account. At some point in the dot-bomb area (I think it was later 2000), fcmail suddenly disappeared, never to be seen again.

I had lost all my email, contacts, etc. In the days of slow computers and slow internet connections, it took time to have multiple backups and I didn’t have one. I was well aware of the risk, but I was still pissed. Then not too long after that, my juno account mysteriously didn’t work at all, although it seemed like it should have. Again, I was pretty annoyed. At some point I believe in early 2001, I registered for a Hotmail account to become my primary and began using that exclusively. My logic was that since it was owned by Microsoft, it was less likely to disappear literally overnight. I kept trying my juno account every few months and sometime years later, it mysteriously started working again, but all my prior email was gone. It still works now. Later in the 2000s my gmail account became my primary.

My Hotmail account then fell mostly to the wayside, but was still used from time to time for family email. Now, Microsoft has come out with an outlook.com premium where for 20 bucks, I can use my own domain (which I have multiple of), have five email addresses on the domain, an ad-free webmail, and a number of other family sharing features. That price raises after March 31 to 50 bucks I believe and is a yearly subscription. I signed up for it with my own domain and after testing it for a day, I was sold on the fact that the new email would become my go-to address. In fact, the gradual transition away from my gmail account as my primary will almost certainly occur this year.

My Hotmail account isn’t actually gone, though, it still works too and is integrated right into my address in use on outlook.com premium. That is part of what sold me on it in such a short time – everything simply worked as advertised when setting it up and my Microsoft hardware at home (Surface Book and Xbox One) immediately took the new domain login without any issues whatsoever, as did Outlook on my Android phone. That’s quite a coup for Microsoft, as it is as seamless as google, without quite as much invasion of privacy as google (though there’s still far more than I would like). This comes after I’ve been using Microsoft’s OneDrive on a regular basis and the Office 365 application ecosystem appears mature enough to actually be quite useful. And dare I say it…Edge isn’t nearly as bad as Internet Explorer used to be. Bing still sucks though, but I bet as google keeps censoring more and more stuff via their algorithms and Bing improves their algorithms, Bing will become a player at some point.

Connecting to my outlook.com premium account through my Outlook 2016 was relatively easy too (but I had to use POP3 for some reason), although I did that only as an easier way of going through my 16 years of messages, deleting the junk, and archiving off others. Now my inbox is clean. That can’t be said for my gmail account, however, and some major work will need to be done on that as well.

Looking through my Hotmail, the earliest surviving email (I had cleaned up the account a little bit a couple years after I got it) is a humor chain email from 5/11/01 that is still very relevant today:

RULES FOR WORK

1. Never give me work in the morning. Always wait until 4:00 and then
bring it to me. The challenge of a deadline is refreshing.

2. If it’s really a rush job, run in and interrupt me every
10 minutes to inquire how it’s going. That helps. Even
better, hover behind me, and advise me at every keystroke.

3. Always leave without telling anyone where you’re going. It gives
me a chance to be creative when someone asks where you are.

4. If my arms are full of papers, boxes, books, or supplies, don’t
open the door for me. I need to learn how to function as a paraplegic
and opening doors with no arms is good training in case I should ever
be injured and lose all use of my limbs.

5. If you give me more than one job to do, don’t tell me
which is priority. I am psychic.

6. Do your best to keep me late. I adore this office and
really have nowhere to go or anything to do. I have no life beyond
work.

7. If a job I do pleases you, keep it a secret. If that gets
out, it could mean a promotion.

8. If you don’t like my work, tell everyone. I like my name to be
popular in conversations. I was born to be whipped.

9. If you have special instructions for a job, don’t write
them down. In fact, save them until the job is almost done. No use
confusing me with useful information.

10. Never introduce me to the people you’re with. I have no right to
know anything. In the corporate food chain, I am plankton. When you
refer to them later, my shrewd deductions will identify them.

11. Be nice to me only when the job I’m doing for you could really
change your life and send you straight to manager’s hell.

12. Tell me all your little problems. No one else has any
and it’s nice to know someone is less fortunate. I especially like the
story about having to pay so many taxes on the bonus check you
received for being such a good manager.

13. Wait until my yearly review and THEN tell me what my goals SHOULD
have been. Give me a mediocre performance rating with a cost of living
increase. I’m not here for the money anyway.

My earliest surviving “real” email from my friends folder is somewhat interesting from a historical perspective. That email came from a friend on 09/12/2001, a day after the 9/11 attacks. We had been set to fly that weekend to Michigan for a wedding. After giving directions to his house, he wrote:

I’m still waiting to find out if the flights will be grounded. Don’t know just yet. If they are grounded, how do you guys feel about driving?

We ultimately were forced to do the 14 hour one-way drive then the ferry to Mackinac Island, then turned around for the drive back a day later.