Dropping Outlook for webmail? My 60 day experiment

December 19, 2007 by Phil Montero 

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.

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  1. william@andersonjr.com says:

    congrats on making this leap! the only time i’ve had an itch to get back to a desktop app is when i’m on a plane or somewhere that i’m not able to hop on an internet connection. but in today’s world, those places are very few and far between.

    i switched over using a combination of the apple iphone and google’s gmail/gcal/greader/blogger, etc. it’s been great.

    any update on how your experiment is panning out?

  2. David Worden says:

    I really had no choice in the matter. I moved from Austin, TX and having Roadrunner cable out to the country using only satellite internet as my link to the outside world. Hughes net webmail is not the best in the world, but is usable. I find the freedom to grab my mail wherever as a new luxury. Recently I had to attend a funeral 200 miles away and was able to get my email on my laptop using the free hotel internet connection. It was great knowing that my contacts were still there and a reply to previous email sent arrived on webmail while I was at the hotel. —- David

  3. Phil Montero says:

    Thanks for the comments so far.

    William – I just posted an update on my progress with moving to webmail (and other online apps). Check it out at http://www.theanywhereoffice.com/digital-lifestyle/tools-and-technology/dropping-outlook-for-webmail-an-update-on-my-adventures-in-cloud-computing.htm

    David – I agree totally about the freedom to grab your mail wherever you are is a new found joy. I used to do this by either bringing my laptop with me or using GoToMyPC from a computer with internet access to get into my laptop remotely and access Outlook that way – but having all my mail available from Gmail and being able to jump into it quickly on any computer (or from my phone) is a truly wonderful. Especially – as you mentioned – having a single collection of all sent email, replies, and other messages and contacts.

  4. Gbenga Adeoye says:

    In my own case my laptop was stolen.I really want the freedom but now I cant access all my mails that must have gone into my outlook.

    I need to be delivered from this addiction.
    How can I get out of my attachment to Outlook?

    Guide me on how to still access my outlook e mails now that I dont have my laptop.

    • Phil Montero says:

      Gbenda – sorry to hear about your laptop being stolen. I guess the first question I would have is were you running Outlook standalone (where all the mail lived only on your laptop) or were you connected to an Exchange email server (often used in a corporate environment) where your mail might still live on the server. If the mail only lived on your Outlook and you don’t have a backup copy then it appears unfortunately the old mail would be lost. If you do have a backup or the mail lives on a server somewhere then there are ways to import that mail into Gmail.

      This is what I did as my mail was all located in Outlook in standalone fashion on my laptop. I was able to connect to my new Gmail account using Outlook and move copies of all my important mail up to the Gmail servers by copying them over to the new folder that lived on Gmail. I found this article that walks you through some of the steps. If you are using a Google Apps account (like I am) rather than a standard Gmail account it appears they have a tool for that called the Google Email Uploader.

      I hope your email is recoverable and you are able to break free from Outlook and move your mail to the cloud. I think you will find it a freeing experience and it will save you from just the type of problem you are dealing with now which is typical of what happens when you can only access your email from one computer or location. Best of luck with the shift! – Phil

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  1. [...] was almost a year ago when I posted about my 60 day experiment to stop using Outlook as my primary email program and contact manager and instead move to a web-based email system. [...]



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