Trying Gmail For A Week

Ever since I switched to the Mac, I’ve had N (where N is a suitably large number) tell me that I should switch to Gmail from Exchange.  I finally decided to try it for a week and see if it works for me.  Given my Mac experience – where I had to commit and really use it, I’ve decided to do the same on Gmail.

For now, I’m just going to use Gmail (instead of Google Apps) because I don’t want to go through the hell of switching the domain since I’ve got a bunch of other people (e.g. my family members) on it in a variety of configurations.  That’ll limit me a little as I won’t be able to use the Apps Marketplace, but the benefit is I’ll be able to mess around with a variety of other Gmail stuff.

If you’ve got Gmail addons, hints, tips, and trick, leave them for me here.  At the end of next week, I’ll either be switching to Gmail or heading back to Mac Mail against my Exchange server.

  • Joe

    I set Outlook so it doesn't automatically send things when I hit the send button on the message, it just queues things in the outbox. I use it as a fail-safe against accidentally sending things before they're ready to go. When I went to Gmail/Google Apps, I was always worried about hitting "send" instead of "save," and later found an app to help prevent this. In the add-ons, there's one that allows you to cancel a "send" and go back to message up to 10 seconds after you hit send. Love it.

  • Bill Rice

    Gotta dig into the labs features under settings.

    I love the multiple inbox feature. All my variety of work and personal emails flow into a centralized Gmail inbox and intelligently replies from the right email address (not forwarded) and also selects the right signature file.

    Takes a couple of minutes to set-up, but it is bliss after that. Works much like the All Inboxes on the iPhone.

    Another nice feature for large inbox processors–Send and Archive.

    Good luck! I think you will be a pleased convert.

  • Make sure to enable shortcuts save so much time. I love gmail for searching past emails and the speed.

    • +1. If you're really dedicated get the free stickers, which will make you look like a fool – albeit a dedicated one.

    • I echo these two recommendations – I you use keyboard shortcuts elsewhere – gotta enable them for Gmail.

      Also, I only tag a few specific topics in my email, the search is so good I can find anything.

  • Use Rapportive!

    • Rapportive is amazing. I love seeing people's recent tweets or a song they just listened to. It makes it much easier to make a personal connection with them.

    • Rick Gregory

      Totally agree. Rapportive is insanely cool.

      Brad – learn the mail specific search operators. Things like 'is:starred' etc. There are a couple of odd ones, for example is:unread will work, but is:unstarred will not (you need to do -is:starred). It might not matter for a week, but over time it's useful. If you end up using labels to tag things, you can do a search like 'label:foo' to return all things with the foo label.

    • I've had a mixed experience with rapportive, I like what it's suppose to do, but find it has about a 5% success rate with my contact list.

    • Rapportive with Chrome is very useful not only for business contacts, but also for personal contacts.

  • Note that you can use it just like you do exchange – with Apple Mail. You may want to turn off the "All Mail" folder over IMAP if you aren't ready to use the "Archive" feature yet.

    I use this setup because I found the Gmail web interface to be too slow. Apple Mail is much faster for me. I still like that I can go to the web interface anytime if I'm at a different computer or want to use Gmail search.

    I also check my mail using the Mail app on my iPhone, but have a bookmark on the screen to Gmail for doing mobile search.

    • Thanks – yeah – just set this up as a backup but I'm going to try really hard to live in Gmail.

    • dmlandry

      I'm with you on using Apple Mail. Light CPU load = longer battery life. Offline mail access without any hassle.

      Gmail interface has it's uses though. A tool like any other — right thing to use for the right situations.

  • Keyboard shortcuts make GMail awesome, in the browser. Make sure it's enabled in settings, then hit '?' to pull up the cheat-sheet.

  • hamerb

    the best way to enjoy the experience is to have all of your old emails forwarded to the gmail account and then bulk archive everything to get a clean inbox. This way you'll get a in-flight view of gmail where it really shines; and new emails will be automagically linked to existing conversations.

    When I switched years ago I imported a few years worth of emails from an exchange server and did not run into many issues.

  • Pmoehring

    Loads of the labs stuff is great (find it in the settings):
    – canned responses (one-click emails that you always repeat)
    – undo send (5-10 seconds time to undo)
    – Send and archive – make sure to use this and do an "archive all" first thing, it helps you keep an empty inbox
    – labels are great for sorting and GTD
    – automated filters that send alerts, signup mails, etc into labels are great
    – if you use [email protected], you can automate filters by incoming email address easily (as opposed to reverse filtering). These are great for newsletters, mailing lists, and the like.

    – batchblue as CRM/contact management
    – rapportive for contextual info on people mailing you (adds pics, recent twitter messages, etc.). Then again, you'll probably use Gist.

    Have fun and enjoy the switch, it's good stuff.

  • Weldon Dodd

    Try our rapportive ( with the web interface. I find this incredibly useful.

    I'll also second the suggestion for "send and archive" in Labs.

    Use IMAP for email on Mac Mail or iPhone (faster this way), but use the Google Sync (Active Sync) for Calendars and Contacts on iPhone. You can also setup iCal on your Mac to connect to Google calendar directly and Address Book can sync with Google Contacts.

    Save the gmail bookmarklet (in mobile Safari) to your homescreen on the iPhone. The web interface is really useful even if you have contacts, calendars, and email setup with the native iPhone apps.

    One of the biggest advantages for me is that the web interface on the iPhone allows for searching email, but it's done on the server (and Google happens to be quite good at search). I have 15 years of email archives in my Google Apps account (uploaded via IMAP in batches) and I can search all 2GB of email text lightning fast. It's amazing to me how much faster this is than searching local mail folders on my MacBook Pro.

  • betoiii

    Use keyboard shortcuts! Efficiency goes through the roof!

  • Too bad you're not using Google Apps, you could use our Kwaga for social info and automatic reminders.

  • Always archive, never delete.

    Take the 5 minutes to enable and learn the keyboard shortcuts.

    Don't get hung up on labels … search is amazing.


    • Rob

      this is really all you need to know about gmail. do these things and you'll be happier.

    • I totally agree and think that trusting search is the biggest thing. When you come from other systems you feel like you have to organize all of your emails. With Gmail, just archive and know that you can always find it again with a quick search if you need it.

    • I actually prefer to delete for certain things, especially marketing messages and machine-generated notifications. I've set up a custom shortcut key to do make it more intuitive for me.

      Try multiple inboxes in Google Labs. I use it get a birdseye view of Inbox, Later (things I will get to soon) and Waiting Fors (things I'm awaiting a response on).

      A hack for waiting fors is set up a filter on outbound messages that looks for something like "wf" at the bottom of the message and applies the Waiting For label. Then when I send an email to someone asking a question or scheduling an appointment or whatever I just put "wf" after my sig.

  • phil swenson

    or mailplane:

    best of desktop client + best of web interface

  • So much has been covered. I'll add to the chorus of those suggesting Rapportive. Take a close look at the gadgets; many of those features ought to be standard (and in time, they become incorporated.)

    My only organic suggestion is to use Mac Mail with your Gmail as an IMAP account. The process of "flagging" messages in mirrors "starring" in Gmail (a nice feature.) Consider that labels in the web interface become folders in the IMAP implementation. Depending on your experience with Outlook, you may or may not find this paradigm useful.

    I use about 200 or so rules in Gmail to filter emails to appropriate folders. Conveniently, in, you'll receive separate unread counts. You can also access "All Mail" in by going to [Gmail]. There's a gadget called "Advanced IMAP controls" that lets you show/hide folders in IMAP, so you could filter out noise in if you so choose.

    If you stick with the web interface, Gmail is very nicely AJAXed. Press "?" to see a screen-pop of shortcuts. They become second nature over time.

    Gmail has evolved greatly over the years. It becomes less responsive with large (> 2 GB) mailboxes, but Google is rapidly working on that.

  • It took me a while to get used to it but once I started moving between devices I found myself having to use both Mac Mail and Gmail. Eventually, I weened myself off of Mac Mail entirely now feel less dependent on location or my hardware to have access to my mail. Switching costs for hardware have also radically dropped if I ever decide to move to the latest whiz-bang hardware in the future. Unfortunately, my experiences w/Google Docs have not been as positive and their spreadsheet program is just too rudimentary (as far as I've been able to figure it out ;). The word processing doc has weird formatting compatibility issues w/Word docs that frustrate me. For Powerpoint though, I'm beginning to play w/SlideRocket and really like it. It's like a SaaS version of Keynote. Definitely check it out.

  • Paul

    If you can come to terms with the threading features and caveats, you will love Gmail. If you email to large interactive groups on a frequent basis, you may find yourself disliking the threading. I do love Gmail and the threading; but that fateful day when I cc:ed a group of 20 and they all replied at least twice was not a happy day.

  • reece

    i can’t believe there are ‘techies’ left who aren’t on gmail.

    Labs >

    Send & Archive

    Undo Send

    Keyboard Shortcuts

    and Rapportive is an awesome extension.

    • Ditto for Rapportive, very quick and ability to leave notes on profiles.

      Also, try out Boomerang for 'send later' functionality:


      Maps preview

      Mark as read button

      Multiple inboxes is a MUST (sort by to:, from: is:, etc)

      Just our of curiosity, why so late to adopt/try out Gmail?

  • phil swenson

    One thought on gmail. The power comes through when you (mostly) quit thinking about organizing your emails. The days of manually organizing your messages by dragging your messages to folders are over. You simply search for what you want. Learn the search interface

  • The big payoff comes when you move the domain over. This is especially true when you have family members etc. There will be pain from the initial move, but after that the overall pain level of hosting people on a family domain goes way down.

  • Excellent choice! It took me weeks to get comfortable with gmail, but now I can't live without it. Opening Outlook or LotusNotes makes me sick!

  • Setup up Mail App and use it as an IMAP client.

  • Hi Brad- I LOVE Gmail. And I was one of those who used MacMail when I first got my laptop. Gmail is so much better. Once you get used to it the whole organizing by conversation thread works great. I also loved it last week when I wrote an email that said "I've attached……" but when I hit send Gmail recognized that there wasn't actually a file attached and asked me about it! Genius!! Also been extremely happy with their spam filtering….much better than other services. (and no, I do not work for Google!) Have to say I also love my Mac and happy that you are too!

  • messel

    Primary stuff you'll care about:
    -rules are called filters
    -labels instead of folders (so messages can have multiple categories)
    -get Rapportive it's a great way to get instant information about folks who contact you.

    After you get it I'll send you an email asking if any startups in your portfolio or network are looking for a fanatically motivated web hacker. I found out I was laid off today from my part time day job as a defense contractor and have never felt more ready for a big shift.

  • Rahul Vohra

    Hey Brad, this is Rahul from Rapportive:

    I'll join in the chorus of our lovely users: try Rapportive out; we promise you'll fall in love with it 🙂

    As an investor, you'll _definitely_ want to add the CrunchBase Raplet. Imagine seeing a company's one-liner and recent news when they email you, or an investor's portfolio or recent funding events. For a screenshot of this, see:

    To add the CrunchBase Raplet, hit "Add or Remove Raplets" in the Rapportive menu at the top of Gmail and it should be obvious from there. Then just look at an email from an investor or entrepreneur. Joyous win.

    Rahul, CEO of Rapportive

  • Dave

    You love threaded email so will love Gmail. I struggle with it because I find I miss an email that is slotted into a thread during a discussion with a bunch of people but that is personal. Gmail is great. __1. Filters are huge. With auto-filters to add labels, it really saves a huge time suck from dragging and dropping emails to the right "folder" in other email clients. You can basically read everything on a certain topic and hit archive right away. I've found my label categories are able to be much broader than in Outlook folders because the Gmail search function is so good I just need labels to get me in the area code then search finds what I need rather than with Outlook where I need an endless array of sub-folders. __2. Send and archive is a genius, simple function particularly when paired with good filters. __3. Use Chrome. Amazingly fast on my computers, particualrly for Gmail. __4. Play with Labs. If you use it, turn on voice playing in email. There are a lot of great features in Labs depending on your taste.__5. You can drag attachments into Gmail, which is neat. I'm a little surprised they don't advertise it more because it is often easier than "attach" and digging through folder trees.

  • Dave

    LIkely obvious but remember to check your spam folder periodically. Gmail has by far the best spam filter I have seen, but it does pick up real emails periodically–particularly from list serves. With an auto-delete after 30 days, I have missed a few things every once in a while when I forget to check it.

  • Jud Valeski

    I resisted gmail for a long time. No folders!?! insane. weird "archive" notion!?! crazy. getting over lacking folders was hard… getting over archive vs. delete wasn't so bad. I ultimately bowed down to gmail for two reasons (and I can _never_ go back; similar to mac).

    1. keyboard driven navigation. mice suck and should die. gmail lets me ignore my mouse and instead drive email using vi shortcut keystrokes; bliss.
    2. search. UI metaphors for accessing data, other than search, suck and should die. search is it, and gmail gives me a google-powered backend search infrastructure to my mail.

    all my mail is "in the cloud" accessible through POP (yuck), IMAP (sometimes good), and a web browser (iphone, desktop or other). no more "ugh, my client is busy indexing mail *again*" or "ugh, my local mail db corrupted… time to rebuild." webmail wins.

    I now find local files through osx spotlight, and find mail/attachments/google docs, through google search text boxes.

    watching google (labs too) try and figure out the third-rail (mail + calendar) associations has been interesting, and for the most part it's "right." viewing calendars and sending invitations through the mail interface is going pretty well in gmail, but more importantly I can tell they're constantly working on it and will eventually get it right.

  • Too many to list, but here's a few:
    Check out the Google Labs. I have a dozen or so enabled. Little things like catching when you say the word attach and forgot to attach something are GREAT! Not to mention the Send and Archive Button.

    The way it handles multiple email addresses is awesome too (even across multiple domains). I handle all my dozen online profiles all through the one email which sends out from the other domains.

    The converting an email thread to a task or a calendar item is slick and convenient too.

    A lot of other things you'll just enjoy and don't even have to know are there.

  • Brad

    There’s a cool, but little known feature of DNS and Google Apps Email that might come in handy if you like what you see with Google Mail. You can leave where it is, but at it’s registrar, point the mail (using MX records) to Google Apps email. Then, in Google Apps Email you can set up lots of individual email accounts all hanging off (e.g. [email protected]). I guess if some of your family members are using for their own email, it will be a tricky switch. I have email accounts with two domains now over at Google Apps Email, and pull at them from iPhones, iPads and Macs, and I’m lovin’ life. Cheers, Joe Glynn

  • nicholasnapp

    Better GMail (avail. for Firefox & Chrome) adds a bunch of small but nice enhancements — row highlight on mouse-over, icon for attachment file type, also brings nested folders but you can enable that in Labs

    Docs PDF/PowerPoint Viewer (by Google) — automatically opens office/pdf files as temporary Google Docs files i.e. within a new browser tab

    Rapportive — yes, it really is handy, and I second the vote for Crunchbase plugin/raplet

    Send using Gmail — Make sure you get the "no button" version (don't need yet another icon in the toolbar). Ensures that clicking any mailto: link on a page opens Gmail, not a desktop mail app

    In labs, I'm using:

    Don't forget Bob & Wrong Bob
    Insert Images
    Mark Unread from here
    Navbar drag n drop
    Nested labels
    Signature tweaks
    Undo Send

  • Adam

    Create a filter with is:unread. This will catch ALL incoming mail. Have it labelled with @Unread, which will be the top label.

    Go through each email and create a filter for it, Misc, VC, etc. What's left in your inbox are emails you need to deal with immediately. Unread lets you see your entire world, and the individual labels let you see things by individual topic.

    Feel free to ask if you want a screenshot of my setup.

    • Thanks for the suggestion. I run inbox zero so I rarely have much in
      my inbox so I'm notnsure this onenis important to me.

  • pravesh

    I like the drag and drop feature of gmail.

  • top 3

    1) search – dont waste time filtering/labeling/sorting, etc
    2) short cut keys (remember to activate it & learn the most used ones)
    3) task bar

    One more (multiple inboxes) – cant leave this one out 🙂

  • Check out Google labs–the green beaker in the upper right. Lots of fun things to play with.

  • Mike Briggs

    I use thunderbird as my primary gmail client. My style is to browse through hundreds of emails every morning and it's much faster with thunderbird.

  • mtupper

    Good Call Brad!!!

    Looks like your massive following covered most of the good stuff. I don't know if I saw the Tasks mentioned, but I think you might like turning emails into tasks by going to More actions / Add to tasks. Thats another money feature.


  • dojo4

    Brad, you might like to try Mailplane for part of the week. It gives you that dedicated mail client feel, with Gmail inside.

  • joshkarp

    Brad, you might want to checkout a mail client called Postbox –

    It's built upon Thunderbird and has quite a few really cool features. You can do "quick view" on attachments where instead of downloading and/or opening the attachment, you simply hit the spacebar from within Postbox and get a preview of the attachment. It has tabs, saved searches, universal inbox, integrates with iCal, etc.


  • There is an interesting ecosystem of gmail hacks and tweaks.

    First, labels in Gmail are folders in Outlook, as you no doubt have discovered.
    Here's a nice walk-through with tips

    Since I'm a data guy, I like the idea that "all" of my email is there and searchable.

    One tip is to use filters for special recipients or topics to pre-assign filters to email so that it appears in your inbox with labels pre-assigned.

    One tip is that you can put more than one label on a message or from a person.
    This enables you to "bucket" it in several labels (folders if you will). A single search or click on that folder (er, label) on the left brings up said category and similar set of messages.

    In Labs (settings, Labs) I have a few faves:
    Add any Gadget by URL (for the geeks)
    Authentication Icon for Verified Senders (looks nice and assures me that it's not spam)
    Creat a document and related, customized keyboard shortcuts (to allow you to use your "old familiar" control-n (etc) keystrokes
    "Don't forget bob" and the related "got the wrong bob" has saved my rear several times
    Calendar is nice. If you're using an android or iPhone it has a very good sync experience
    "Insert Images" rocks. Gotta have it.
    "send and archive helps clean my inbox
    "undo send" is a nice little way to grab back that email if you forgot to say something (or said something you want to take back. Only suggestion would be to ask them to give me more than 15 seconds to say "d'oh!"
    Google maps previews are very helpful
    "Move Icon Column" helps me configure the inbox to look more like the way I look at Outlook
    "nested labels" is something I'm experimenting with… may make it more like Outlook's heirarchy. But that's moot to 20-somethings and younger. They're okay with the Gmail conversation threading, which I am still not totally comfortable with. It's an age thing and a mental change thing.
    Superstars is nice, but the search/sort feature is not yet there.
    Rules: I set up rules to assign labels. Labels are Gmail's answer to Outlook "folders." This takes a lot of getting used-to.

    MakeUseOf always has some cool new ideas.

    Too much signal-to-noise in these two, but there are some gems hidden here.
    I'd stay away from greasemonkey scripts and firefox extensions at first, as they can be a time sink when they don't behave as expected.

    Gmail Craze: 40 + Tools and Hacks for Gmail
    Mar 18, 2007 … All for Gmail: handy Firefox extensions, best Greasemonkey scripts, some desktop tools and lots of useful tips. Take this Gmail thingie to …

    Ultimate GMail Collection: over 80 Tools and Tips
    Jul 27, 2007 … It's been four months since our first Gmail Roundup. And Gmail being as popular as it is, it's time for a major update. So here you go, …

    Good luck and have fun.

    The most dramatic adjustment I think will be the sift from Outlook-style folder icons to the "label" look, which I think you can easily fix with the custom labels and add-ins.

    The other big difference which I'm still not totally accustomed-to, is this message threading. It can be a big pain. The way I fix this these days is to "edit subject" which effectively starts a new "thread." At some point they'll have a Labs fix to go back to date heirarchy. But for now I'd stick with a slight tweak on the Subject, and that will "fix" the issue of messages being buried in threads.


    Matt Weeks

  • I love my gmail and also forward my business email to my business gmail .my server for my business is and then all data is everywhere and Gmail igoogle front page has all my favorite news and blogs to greet me as my home page. Fondly, Cheray

  • Owen

    I switched to Gmail from Outlook for both work and personal 2 years ago. I liked Outlook with all the nifty features. But Gmail has made me realize the value of simplicity and good design, and I am more productive because I'm not futzing around with so many superfluous features. It's also free which is nice.

  • Brad, I took the exact opposite approach and literally, this week. I switched from GMail to Thunderbird on a recommendation by a co-worker. He felt it was a better interface when using multiple e-mail accounts. I am a student, have a job, help a non-profit and have a personal e-mail. So, I want to organize my e-mail in one interface, although separated and organized.

    I am (was?) a GMail loyalist and have all 4 accounts set up for it, but I would like to be convinced by Tbird. After preliminary usage, Thunderbird seems to do a better job of organizing the 4 accounts and e-mails, mostly because I can open many windows. I don't want to open a ton of chrome tabs when I have to look at 3 e-mails, two inboxes and still want to browse. W/Tbid, everything is self-contained in an application.

    Also, I figure the macbook pro (as opposed to say a netbook) is powerful enough to support 3rd party app's like Thunderbird, so why not clear up space in my browser. As a gmail user, I know all of the keyboard shortcuts and love em. So I need Tbird to do the same for my switch to stick. However, I am getting used to the shortcuts, which helps. Also, I have yet to run into problems with Tbird search, in fact, the results layout is actually quite nice.

    I'll keep you posted? Anyone, is there anything I am missing as to why this switch might come back to haunt me?

    • if only my CRM had a a gmail (or apps) add-on. That's the only reason I use Outlook now.

  • To solve the domain problem, you might want to look into getting your domain registrar to help you with re-configuring your DNS and mail forwarding as follows. You can forward individual email addresses to different locations.

    e.g., at i forward [email protected] to [email protected]; drop the wildcard emails completely, send [email protected] to my [email protected] account, etc.

    My point is, with a DNS black-belt helping (GoDaddy has a bunch of them) you could move your account to Gmail, while picking off certain family members addresses, to stay right where they are.

    Glad you decided to try GMail, it is pulling so many great replies from GMail black-belts!

    I think we GMail converts should lobby Brad to try GMail for a MONTH, versus a WEEK – like he did with the Mac. The hop to GMail is a pretty big one, i don't think one week is long enough. And Brad, look at all the support your'e getting here!

  • As one of the "N", welcome!

    My tips are 100k foot level. Forget about folders, nested folders, etc. because search just works. I label for convenience but because the filters work like a dream, you can add multiple labels to a message. Easy. Use one inbox, not several. Use "canned responses", not signatures.

    Most of all, keep it very simple. Because search is so good and you can archive messages without deleting them from your inbox, it's a new paradigm so re-training your brain is the biggest challenge. Don't worry so much about the coolness or not of the add-ons, because the Google add-on ecosystem is always going to be better long-term than any pure software product.

  • Neil Heuer

    I never understood why gmail doesn't let you do partial word searches?! If you are searching for a phone number and searched for 239 and in your email it says 239-555-1212 it will not find the result?

    +1 for Mailplane on the mac. Works real well and when firefox craps out on you you can still read your email!

    Also check this out:

    Makes your interface much more productive giving you various filtering capabilities. Very sharp.

  • Gmail rocks. Every start-up I talk to uses Google Apps and it's also the mostly used app among OneLogin's customers. You might want to check out OneLogin, which can give you and your family/organization secure one-click to all your web apps.

    If you are using Google Apps Premium Edition, you can even use SAML to provide super elegant single sign-on for the entire organization, but we also support the free Google Apps.


  • Becky Smith

    I like being able to make sub folders in labels. EX: I have a label for Personal Stuff. Under that I wanted Recipes. This is what to put into the label field Personal Stuff/Recipes

  • Michael

    enable keyboard shortcuts!

  • Michael

    I also found this Chrome/Firefox addon for Gmail yesterday.
    It adds an extra search layer to Gmail. Ps. I love Gmail!!

  • I love the ability to place single emails under multiple labels – like tags. In fact, my filing system is more tag based rather than folder/subfolder based. Even then, someone earlier said don't get hung up on the labels because search is so powerful. They are right – I search many times a day before I even think on clicking on a label!