One week on Gmail has me pining for Outlook

I love Microsoft Outlook. I know a lot of people hate it, but I'm inclined to believe that they don't use Outlook well enough. I've been using it as my primary email program since the 1990s, and there's not a lot I can complain about. But I quit it at the beginning of this week. It's working well in some ways, but in others I have some buyer's remorse.

There's a long story behind how I got to this point, but the bottom line is that my email domain is on Google Apps and I have an Android phone. By switching to using Gmail, Google Calendar and the other Google Apps. I gain a lot in terms of mobility. All of my data is in the same cloud. I can move from one computer to another, and everything I read on one looks read on the other.

I was doing some of this with Outlook using Google Apps Premier's Outlook synch. It works pretty well for what it's supposed to do, but it has limits and they were cramping my style.

The biggest problem is that I used Outlook as my RSS reader. I get a lot of snickers for this, but it's really an outstanding reader. Feeds and messages act like first-class peers of email folders and messages. But the storage is local; if I went to Outlook on another system my feeds weren't synched. This sucked considerably.

Switching over to all Google apps was easy: the email, contacts and calendar data were in there already. I exported an OPML file from Outlook and read it into Google Reader.

One (work) week later, here's my status:

Google Reader. Overall, it's a clear improvement. There is one thing I can't figure out how to do: Is it possible to read messages from a feed that has already been read, i.e. history? I don't see it. In Outlook they get stored in the .PST, so they're handy, and you can use autoarchive on the feed folders. Editor's note: Yes, click "view all items" in any feed.

Google Calendar. It's adequate, but barely. Google Calendar is almost Mickey Mouse compared to Outlook/Exchange. What I miss the most is the flexibility of pop-up alerts in Outlook and the better snooze options. I'll put up with it all, because it's good enough.

Gmail. Of course, it's the most important part of this switch. Where do I begin to lament? Gmail is limited by the browser interface in many ways, one of which is keyboard shortcuts. There are a lot of keyboard shortcuts available in Gmail, but they're weird and hard to remember. There's much less drag and drop available; I actually use it. I'll get over that.

I understand that labels have advantages over conventional folders, but they don't justify their unconventionality. I find these differences make filters harder to work with. Here's one Outlook feature I miss badly: You can set it so that when you reply to a message in a folder, a copy of your response is in the folder (as opposed to Sent Items). This makes the folder hold a more complete history of the conversation. I don't see a way to fake this with Gmail filters. Maybe the replies are there in the conversation view, but that's too hard to navigate.

I'm not going back, at least not soon. I've traded off the quality of my software experience for mobility. Whether that proves to be a good choice is too soon to tell.

Larry Seltzer is a freelance writer and consultant, dealing mostly with security matters. He has written recently for Infoworld, eWEEK, Dr. Dobb's Journal, and is a Contributing Editor at PC Magazine and author of their Security Watch blog. He has also written for Symantec Authentication (formerly VeriSign) and Lumension's Intelligent Whitelisting site.