Thinking About Email Consolidation Strategies

Like many of you, I have multiple email accounts. Like some of you, I have far too many email accounts. And in keeping with my desire to simplify wherever possible, I've been thinking a lot about the best way to consolidate these accounts into more manageable groups. And there are a couple of general approaches that may make sense.

First, and perhaps most important, if you do find yourself with too many email accounts--and that number will vary, depending on your perspective--do consider closing some of the less frequently used accounts. This isn't an approach I can necessarily take advantage of myself--I need to test different account types for work purposes--but most people should be fine with two or possibly three accounts at most.

(Why not just one? One of the basic tenets of email security is that you need a secondary account from which to recover your primary account. After all, what happens if you put all your electronic eggs in one basket, so to speak, and some enterprising hacker seizes control of that account? Two is the minimum, even for people who only care about personal accounts.)

Once you've culled your account list down to something manageable, the next step is considering your access strategies. That is, yes, you could access these accounts individually--via web interfaces, native Windows applications and/or native (or web-based) mobile apps--though that's probably only a viable strategy for those with two or possibly three email accounts.

But what about consolidating them? This is the approach I need to take because of the sheer number of accounts I access. Doing so manually, account by account, would be tedious.

There are two basic ways to consolidate multiple email accounts. You can consolidate at the cloud level--using a single, master account to collect email from multiple services--or at the client level, where you use a single Windows application (and/or a single mobile application on a smart phone or other device) to access multiple, separate accounts from a single interface.

But of course it's not really that simple either.

Which of these general strategies you'll want to adopt, and which of the sadly numerous options you'll want to choose in either scenario will vary according to your needs, and to the types of the accounts you've chosen.

For example. After years as a Gmail user, I've decided to turn to Microsoft email solutions, and will be utilizing new primary email accounts for each, one for work, and one for personal use. On the work end, I'll be using a new email account, [email protected], which is hosted on an on-premise Exchange 2010 server. And Exchange comes with various advantages over competing solutions, of course. But it also comes with some interesting disadvantages as well, not the least of which is client email choices: You can only use Microsoft Outlook or the web client, OWA (Outlook Web App), from a PC.

For my personal account, I'll be using some form of Hotmail account, though I haven't decided yet which one to use. (And in this case, you don't really need to know anyway, since readers should contact me through my work account.) Hotmail comes with its own advantages and disadvantages as well, of course. I can pick from hotmail.com, live.com, and custom domains (using Windows Live Domains), so I'm not stuck with what work gives me. But PC client access is limited to Microsoft clients in Windows (Windows Live Mail or Outlook), or the web client, which is decent. Hotmail also has some issues with consolidating multiple Hotmail-based accounts on the server side (which is to say you really can't do this with Hotmail, a fact I find inconvenient).

When choosing between email services, you may want to use different account types. And an examination of the available choices would be a complicated and long article in its own right. That's because each email account type comes with various advantages and disadvantages of their own, and your needs will all vary from mine. (Does this topic warrant a separate, long form article? Probably.)

So I'll be using Exchange and Hotmail. But I'll also want to access my other accounts. And as noted above, I have a few basic choices there, or even a mixture of these choices. In Windows, I could simply opt to use Outlook for everything, since Outlook is universally compatible with all email accounts and has a decent multi-account interface. On the flipside, Outlook is also added bloat, another thing I'll need to install and configure on each of my PCs, and that goes against my general simplicity mantra. (I could also access work accounts from Outlook and personal accounts from Windows Live Mail, which also offers a decent multi-account interface. But this is yet another layer of complexity.)

Or, I could consolidate at the cloud level. That is, I could set up my master personal account to pull all my email from the other accounts. (Or vice versa; many email accounts can also be configured to forward any incoming messages to another account.)

This makes a lot of sense because you only have to do it once and you'll then have less to configure on the client side (if you use a native email application in Windows) or nothing to configure at all, going forward, if you access the email account's web interface. Doing so does come with some downside, however. For example, let's say you consolidate three accounts through Exchange but want to use Outlook to send and receive email. Outlook will have no understanding of the collected accounts, so you won't be able to (easily, at any rate) send mail from those accounts. But if you send mail from the OWA web client, this will work just fine.

Mobile device access is another consideration because the type of device you choose--really, the OS it runs--will determine the experience you receive with different email account types.

I happen to use Windows Phone and will be doing so going forward. Fortunately, both Outlook and Hotmail are first-class citizens on Windows Phone, meaning that the device natively supports all of the functionality of these account types, including not just push-based access to email, but also contacts, calendars, and now tasks (in Mango). But some other account types are less well supported on Windows Phone. For example, with Yahoo! Mail, you can only get email access, and not contacts or calendar. Any limitations like this can and should contribute to your decision about how to consolidate, and with what accounts.

Complicated? You bet. In fact, I've been almost obsessing over this stuff lately, and I'm still not 100 percent sure how I'm going to handle it. But if you're curious, my own email nightmare breaks down like so:

As noted before, I have a primary work email address, [email protected], that's based on Exchange 2010. But I also have a second work-type address, for the Windows 8 Secrets book, that's based on Office 365. And while my primary personal account will be some form of Hotmail account, I currently have three Hotmail-type accounts, including a hotmail.com address, a live.com address, and a custom domain that utilizes Windows Live Domains. I have a Gmail account and a separate Google Apps account, the latter of which also utilizes a custom domain name. I have a personal account that's not tied to any of the major providers. And I have a Yahoo! Mail account and a Facebook account, the latter of which doesn't yet utilize standard email clients, but still has an email component I need to check regularly. That's 10 accounts.

(Update: Actually, it's 11. I forgot about my MobileMe/iCloud account. Ugh.)

While I haven't settled on a final plan, I'm going to keep the two work accounts separate and access each individually in Outlook on the PC and via individual mail accounts on Windows Phone.

For the personal accounts, some form of consolidation is in order. I noted previously that Microsoft does not allow you to consolidate multiple Hotmail-type accounts; instead, you can only "link" them, which I've done. But that doesn't help with my consolidation needs, and they will remain separate in the cloud. This means I need to consolidate them in the clients I use, Outlook on the PC and the Mail app in Windows Phone (which in Mango supports linked inboxes).

Further complicating matters, it may not make sense to consolidate some of my accounts anyway--like the Google Apps account and my Windows Live Domains-based account--because they are there for testing purposes, and automatically pulling that mail into another service would be contrary to the point of the accounts. (Most likely, I'll consolidate them in the cloud regardless, as it's still possible to use them from their native interfaces when testing.)

What this all adds up to is some mixture of cloud- and client-based consolidation. Which is too bad, because it also means I'll be spending a lot of time configuring email clients anytime I reinstall Windows or reset my Windows Phone. This isn't the way I like to spend my time, and it's not something I recommend to others. So please, do yourself a favor, and consolidate your email accounts intelligently, jettisoning those that simply don't make sense.

Note: This is a big topic, of course, and I've only touched on the surface of something I'll be working on for months to come. There is much else to touch on, including the differences between how Microsoft email services and Microsoft email applications handle email organization and management. Perhaps this is a ripe area for future examination. In any event, let me know what your own email strategy is. Given the complexities, especially in the different ways in which you can access email, there are certainly many ways to handle this. And it's very likely I've missed something.