Should I Switch to Gmail?

I’m struggling with a question. Should I switch to Gmail?

I’ve been using Yahoo! Mail for five years or so. Like many of you, I’ve invested a lot into that email address. Switching from an older account that was deluged by spam, friends found it painful to keep track of which email address was my active one. Many kept sending messages to the old account. Others always prefaced their emails with, “Which email address do you check? xxx or yyy?”, even after I’ve given them an answer like ten hundred thousand times. Ugh!

I’m also a power user of Yahoo!’s (YHOO) personal information management tools, such as Yahoo! Address Book and Yahoo! Calendar. They provide me with a way to carry my contact list and schedule anywhere I go, even if my mobile phone dies on me. Both are also tightly integrated with Yahoo! Mail. So switching from Yahoo! Mail isn’t just a matter of adopting Gmail, I’d also have to adopt Google’s (GOOG) Contact list (embedded within Gmail) and Google Calendar.

Quite a few hurdles. Is the switch worth it? Well, Google’s products are, admittedly, pretty damn cool. I’ve been using Google Docs, Google Reader, and other products fairly extensively. As they integrate them all into a tighter suite, their collective benefit increases for me. So what’s stopping me from switching? Let’s address each issue and see if any solutions exist.

Issue #1: Reminding Friends of My New Email Address

Sending a mass email to my friends is easy enough. Reminding those few friends who forget that I have a new email address is tougher. How can I make sure all of those dumb-dumb heads start using my new email address?

Potential Solution? Yup!

Yes, an easy solution exists! After emailing everyone, I can get Gmail to automatically receive all new emails. This can be done in one of two ways. Option one is setting up Gmail’s POP Mail Fetcher. Not all email services offer POP access, but Yahoo! Mail does if you purchase their premium plan (which I did). This tool will basically fetch all new emails from Yahoo! Mail and place them in my new Gmail account.

Option two is setting up automatic forwarding from my old email account. Most email services offer this, as does Yahoo! Mail. This does what you’d expect – it automatically forwards all new emails to my new email address. I haven’t tried this yet to know if changes the “from” field to my old address, however. Anyone know if it does?

Issue #2: Moving All Old Emails to New Email Account

This one’s a toughie. I have years and years of archived emails that I refer to often. It’s valuable data, not just for nostalgic reasons, but for business and reference purposes too. If I ever lost all of that data, I’d curl into a ball and cry. I’m also meticulous about organizing my old emails into their appropriate folders. If I had to tag all of my old emails in Gmail manually, I’d curl into a ball and, well, maybe not cry, but at least sniffle. Is there a way to migrate all of my old emails within their current folder structure, while retaining their “to”, “from” and “date” fields? (e.g. mass-forwarding them all is not an acceptable option.)

Potential Solution? Not Really

Well, howdy doody, a solution exists! Almost. For $9.95 per email account, YippieMove will automatically move all of my old emails to Gmail while retaining the emails’ integrity (e.g. “to”, “from”, and “date” fields) – I think. Their site doesn’t state this explicitly, though they claim that “with YippieMove, the emails will look the same on the destination as it did on the source.” There is one known flaw in the process currently: Gmail lists emails by the date at which they appeared within Gmail, not their actual delivery date. Weird. There’s also a more significant barrier for me… they don’t support Yahoo! Mail as of this post. Major bummer!

So I’m left without a realistic and acceptable solution to this issue for now.

Issue #3: Importing Yahoo! Address Book to Gmail Contacts

My Yahoo! Address Book is my little black book, my Rolodex, my birthdays list, my way of finding my friends’ contact info, everything. Without it, I’d have no way of contacting my friends, since it’s been decades since I’ve memorized a phone number. Keeping the integrity of all this data in Gmail’s Contact list is very important. Can I export my Yahoo! Address Book and import it into Gmail’s Contact list easily?

Potential Solution? Not Really

Almost, but not really. Exporting from Yahoo! Address Book is easy enough. I can get a CSV file formatted for Microsoft (MSFT) Outlook, Mozilla Thunderbird, Palm Desktop, and in a generic Yahoo! CSV format. But when I try importing this into Gmail, it picks up every field except addresses. Gmail expects addresses to come within a single “address” field, whereas every other application I’ve seen separates an address into “street”, “state”, “city”, etc. I haven’t been able to find a way to easily map the separate address fields into one either. Ugh.

Anyone want to write a quick script for concatenating multiple rows into one? Otherwise, I don’t believe a realistic and acceptable solution exists right now.

Issue #4: Importing Yahoo! Calendar to Google Calendar

I put my whole life onto Yahoo! Calendar. Well, not my whole life, but lots of important reminders, meetings, dinners, and other general events. Told you I’m a power user. There have been times where I’ve forgotten a lunch because I didn’t have it on my calendar. (Sorry!) In this multi-task-heavy world of mine, a calendar is a crucial tool in helping to organize and even prioritize all the things I need to do. Can I export my Yahoo! Calendar and import it into Google Calendar list easily?

Potential Solution? Yup!

Whew, the answer here is yes. All I need to do is export my Yahoo! Calendar into a CSV file (with the same format options as Yahoo! Address Book) and import it into Google Calendar. I’ve done this already as a proof of concept and originally ran into a snag – I received a constant “Google Calendar is temporarily unavailable” message for three straight weeks. That’s a heck of a long time for being “temporarily” unavailable. But then one day, my schedule appeared in Google Calendar. I’m not sure what happened, but it was finally a successful import. Whew.

Issue #5: Having the Ability to Use Disposable Email Addresses

Spam hasn’t been an issue for me on Yahoo! Mail (knock on wood). One reason is that I protect my email address vigorously. Another is that I use Yahoo! Mail’s AddressGuard feature a lot, which allows me to create an unlimited number of disposable email addresses to protect me against spam. This is such an important feature that I purchased a Yahoo! Mail Premium account just to have it. Does Gmail have disposable email addresses too?

Potential Solution? Not Really

Sort of. Technically Gmail does have disposable email addresses, but they aren’t as powerful as Yahoo! Mail’s. With Yahoo! Mail, I can create a new base ID before attaching a disposable suffix. For example, if my email address is “mike@yahoo.com”, I can create a new base ID of “mikesmail”. Then I can attach a disposable suffix of “-amazon” for all my Amazon.com purchases. This makes my full disposable email address: “mikesmail-amazon@yahoo.com”. There’s no way a spammer can guess that my actual email address is “mike@yahoo.com” from that. Gmail’s disposable email address method simply attaches a disposable suffix to my real email address. So “mike@gmail.com” becomes “mike+amazon@gmail.com”. I’ll give you a cookie if you can guess what my real email address from that disposable one. C’mon, what kind of spam protection is that?

Sadly, I don’t find this a realistic and acceptable solution right now.

Issue #6: Syncing Google Information with Mobile Phone

I currently have a BlackBerry and access my contact list and schedule frequently. While I use my online contact list and schedule as the master copies, being able to easily sync the two is critical. Being able to access my email is pretty high on the list too. Can Gmail, Gmail’s Contact list, and Google Calendar sync well with the BlackBerry?

Potential Solution? Not Really

Hmmm, there appear to be solutions, though some think it’s a horrible experience. BlackBerry’s native email reader seems to have problems pulling from Gmail’s POP settings. An alternative is to download the Gmail mobile client, though that app isn’t as quick as the native reader. Syncing Google Calendar is easier though. I can download Google Sync to my mobile phone and sync it easily. Sadly, this is not the case for Gmail’s Contact list and BlackBerry’s Address Book. There’s no way to sync those two currently. Ironically, one solution offered by a user on Google Groups is to auto-forward my email to Yahoo! Mail, since Yahoo offers easy syncing with the BlackBerry.

I wonder if the iPhone has any syncing problems with Google’s services. Oh, maybe so. Rats. Again, the lack of a realistic solution is unacceptable.

Conclusion

That’s two out of six possible points that Google’s personal information management tools have scored. Unfortunately for me, that means I can’t realistically and reliably switch over to Gmail, Gmail’s Contact list, and Google Calendar yet. Perhaps someday, Google will improve these tools. But until then, the barriers to entry are just too high. As much as I love their tools, the cons outweigh the benefits. Sorry Google.