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What I Use: Hotmail and Exchange for Email

In the first episode of the Windows Weekly podcast this year, I once again discussed some technology-related resolutions for the New Year. From a high level, these resolutions were no different than in years past: I'm always seeking to refine and adapt, and be more efficient. But this time around, I'm determined to be truly ruthless and aggressive. And some of my choices--such as dumping Microsoft Word for Evernote for day-to-day writing--will surprise some readers.

I'll be writing about that decision soon and responding to the many questions I've already received. Before that, however, I'd like to tackle another related issue, that of email consolidation. This is part of an ongoing effort, as you may know since I wrote a series of several email consolidation articles last summer. But with the New Year here, and several months of experimentation behind me, I think I'm ready to settle into a new way of doing things.

First, if you haven't done so, please do check out my email consolidation series. This consists of the following articles:

Long story short, there are many ways in which to consolidate multiple email accounts, and while the articles above are somewhat exhaustive, they don't cover related--and arguably as important--topics like contacts and calendar consolidation. Someday.

For now, let's just look at email. Here, as in other areas, my needs are likely quite different than yours. That is, I need to stay current on what's going on in the industry with regards to such things as cloud computing, web-based email services, and the like, so I have accounts (sometimes multiple accounts) at all the major players: Microsoft, Google, Yahoo, Apple, and so on. For the past several years, however, I've had two main accounts, if you will, two accounts that I use regularly. One, my work (Penton), account, I can't change: It's on Exchange 2010 and I've been accessing it through Office Web App, which works well. The other, to this date, has been on Gmail. But that one is changing.

I've hailed Gmail in the past for its efficiency and streamlined UI, and those accolades still stand. But one of the other differences between my needs and yours is that I cover technology generally, yes, but Microsoft and its products more specifically. And Microsoft's consumer-oriented Hotmail service has been improving in leaps and bounds this past year, a fact that has apparently escaped the attention of the technocrati and general public alike. And in many ways, most ways, it's actually caught up to Gmail. In fact, in some ways, it even does things better.

There are other reasons for me to adopt Hotmail. I'm an enthusiastic user of both Windows Phone, the Xbox 360/Xbox LIVE, and Zune/Zune Music Pass, and all of these products and services revolved around the same Windows Live ID ... ie. my Hotmail account. So there's one less extra thing to configure, or worry about. It's already something I'm using every day.

More to the point, perhaps, if you can accept that Hotmail has achieved a certain parity with Gmail, then my previous stance of routing everything non-work-related through Google's email service no longer makes sense. After all, I'll definitely be writing about whatever Hotmail- and Windows Live-based improvements come down the pike, but I rarely cover Gmail updates, and even then would do so with a short blog post at best. It's time to move to Hotmail.

So I've switched from Gmail to Hotmail. 

What's interesting about this, to me at least, is that it didn't require much work. Using the methods described in those previously written email consolidation articles, I already set up Gmail as my central (non-work) email account using the forwarding method described in Email Consolidation: How To Forward Email To Other Accounts. So to access all my personal email from Hotmail, all that was required was to configure Gmail to forward its mail to Hotmail, and then configure Hotmail to also be able to send mail as Gmail, so I could do that when needed.

Also, since I'm forwarding email around, and can respond to email from other accounts as if I were literally using those accounts, no one needs to even know I've changed. Those people that have my Gmail account in their contacts list can just keep using it. Everything still works.

So that's pretty much done, though there are a few other related issues.

The first is dealing with contacts and calendar. Importing contacts into Hotmail was a simple affair, actually, and Hotmail provides a handy web-based wizard for making that happen. As for calendars, Hotmail's Calendar, offers a few options. I can subscribe to my Google Calendar, providing a link to previously-created appointments that is available while I make all new appointments in Hotmail Calendar. Or I can export my Google Calendar in iCS format and then import that in Hotmail Calendar, so I can modify previously created entries if needed. Right now I'm experimenting with the former approach, but I may move the whole thing over. We'll see.

The second is Office 365. I can't ignore Microsoft's amazing cloud-based service, which provides not just Exchange Online-based email, contacts, calendar, and tasks, but also SharePoint Online and Lync Online functionality for just $6 per user month. Office 365 offers excellent compatibility with Windows Phone, too, which is a huge plus.

I considered centralizing my personal email accounts around Office 365. But there's just one problem: The web-based interfaces for Office 365--which I'll be using--are virtually identical at this moment to what I'm getting through my work-based Exchange account. So it would be just another instance of Outlook Web App in day-to-day use, and as Hotmail changed and evolved going forward, it would be hard to test that in a real world way. So I'm going to keep using and paying for Office 365, of course, but with a tertiary domain, so I can keep an eye on that. But my main accounts will be Hotmail and Exchange. (If it weren't for all this email testing and the side issues around my Windows Live ID, I'd probably just use Office 365. It's that good.)

In many ways, the notion that a guy who writes a Windows-oriented web site would use Microsoft email solutions may not seem all that shocking. But honestly, I've had nothing but good luck and efficiency with Gmail, and this migration is perhaps more monumental than you may believe. That's fine. And while I'm not necessarily saying that anyone else should switch from Gmail to Hotmail, I am saying that Hotmail is a lot better than you're probably willing to believe. And based on what I've seen and can guess about Microsoft's consolidated future, it's only going to keep getting better. 
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