Dropping Outlook for webmail? My 60 day experiment

Let me start by saying that for as long as I can remember I have been a devout Microsoft Outlook user. I lived, breathed, and worked in Outlook all day long using it not only for email – but also for organizing my contacts, calendar, tasks, and notes. About 6 months ago I upgraded to Office 2007 and really like the new version of Outlook – however I have been giving a lot of thought lately to just how mobile my email is (and can be).

This prompted me to start thinking about making the switch to using webmail. By moving away from Outlook to a web based email system I always have access to all my mail from any web browser. At a client site – no problem just jump on the web and I’m able to send, receive or access all of may mail. Visiting friends and family . . . I don’t even need my laptop with me as long as I can use their computer to get on the web.

But me leave the comforts of Outlook? Just the thought of it made me quiver . . . so I decided to conduct a 60 day experiment to see if I could leave my trusty Outlook behind and free myself to truly work the web!

I evaluated the big boys of webmail – Yahoo, Windows Live (formerly Hotmail), and Google’s Gmail. After a painstaking analysis of their various features and options and a few short tests I have decided to go with Yahoo Mail for my experiment. There are a lot of reasons why which I will explain in future posts – but one of the reasons is their new interface which makes the experience of working with it very similar to working with Outlook or any other desktop email program. Also it was important for me to be able to send mail from a number of different email addresses seamlessly so I could consolidate my mail into one program like I did with Outlook. While the other claim to do this they have some shortcomings in this area that Yahoo did not have (as long as I subscribe to their Yahoo! Mail Plus service for $20 a year).

I also like the fact that I can free myself from having to use a smartphone (like my current Treo 650) to access my email being that almost all phones have internet access and Yahoo provides a very usable wap (phone based) interface to access and work with your email. I’m planning on getting a new phone soon and wanted to move to something a bit simpler (my Treo tends to crash a lot and in the end I realized I want my phone to be mostly just that . . . a phone and not try to do everything). I spend enough time troubleshooting my computer – I don’t want to troubleshoot my phone too!

I decided now would be a good time for the test as I will be traveling a lot for the holidays so it would give me a good chance to really put it through it’s paces. So about 3 weeks ago I made the switch (gulp). I have a copy of all my email forwarding to my Yahoo Plus account (while leaving a copy on the mail server that I still have been downloading into Outlook once a week in case after the 60 days I decide to scrap my webmail experiment).

At first my mouse kept hovering over the Outlook icon on my taskbar every time I went to check or send an email but soon I overcame that and a strange feeling has overtaken me. Let’s call it a lightness of being . . . I feel less tied down not having to live in Outlook anymore. Instead of running into my home office to check my email I just use my phone’s web access to log into yahoo and view messages. And guess what? When I delete a message on my phone it’s gone the next time I access Yahoo’s webmail from my laptop. I also have to admit my laptop has been a lot snappier now that I don’t have a big resource hogging program like Outlook running all the time. Most of the time I am just working in my browser (which I always have open anyway).

I’m not fully convinced I am leaving Outlook yet – but so far I am really enjoying the experience! The next week or so when I am visiting family for the holidays will be much more telling. What about my calendar, tasks, and notes you ask? I’ll save that for another post in a few weeks. At that point I’ll share more details about my experience and what tools I am trying in replace of Outlook there – yes they are also web-based!

So what do you think? Are you an Outlook addict? Have any of you made the switch? Post a comment and let me know your thoughts and experiences.