Going Google (apps), Part 1: Move your mail

Woody Leonhard

Are you getting tired of struggling with Microsoft’s increasingly complex, sometimes arcane, and always expensive versions of Office?

This article, the first in a series, will show you how easy it is to move from bloated and pricey desktop programs to fast, free — though somewhat less capable — Google apps.

Small-biz/family computing is changing — rapidly

My decision to take a detailed look at Google apps was prompted by purely practical needs: finding a simpler and less costly computing system for a family business.

My wife runs a fairly typical small business — a bakery with four locations and 40 or so employees. The bakery’s data needs aren’t particularly demanding: daily sales reports, petty cash, inventory reports, etc. from the shops. It also needs relatively simple accounting: accounts payable, receivables, bank reconciliations, and payroll. Then there’s the usual business email and letters. The bakery’s accountant does all the heavy lifting — taxes, government reporting, and the like.

In many respects, the business is no different from millions of small businesses and innumerable small organizations such as charities, social groups, and clubs. For that matter, individuals (like me!) handle comparable tasks every day: keeping track of investments, budgeting, writing and filing letters — all the stuff Word, Excel, and Outlook have helped us get done for decades.

Unfortunately, Microsoft Office has become too bloated and expensive for the bakery — and many other small businesses — and that’s making alternatives more attractive.

In the March 14 Top Story, Fred Langa talked about two free Office replacements — LibreOffice and Open Office — that provide many of the same features as Microsoft Office. Although they lack some of Office’s capabilities, they’re fabulously priced: they’re free!

I’ve tried LibreOffice. In my estimation, it can be a fine replacement for Microsoft Office, if your needs aren’t extensive or complicated. LibreOffice is, however, PC-bound. It doesn’t fit well into the new world of Internet and mobile computing. Mobile devices — iPads, iPhones, Galaxies, Nexuseseses, etc. — are ubiquitous, and businesses are keenly interested in exploiting their capabilities. And they can so do at virtually no cost beyond hardware.

Whether for a business, organization, or even a family, effective computing no longer requires a full computer to do tasks that are relatively simple. A bakery employee, for example, no longer needs to boot her laptop just to update a simple sales report. She can now do it from her phone. When she needs to check her son’s homework assignment, she does so on an iPad or similar tablet.

Much of mobile computing requires storing your data in the cloud — and feeling confident it’s sufficiently secure. My take on online data storage? If you’re holding state secrets or you’re worried about an intelligence agency such as the NSA snooping in your files, don’t store your data online unless it’s highly encrypted — which brings up other issues. In the real world of small businesses (and families), effectively sharing some data is more important than keeping it all under strict, local lock and key.

All of which brings us back to Google Apps, which are free for personal use but fee-based for business uses. Google Apps for Business (site) costs just U.S. $50 per person per year. It offers all sorts of online tools — centralized email, basic accounting, etc. — that organizations need in order to keep running.

Putting your email back into the cloud

As I stated at the top, this series is about moving from Office to Google apps. I’ll start with email, because it’s the application most of us use every day, yet it’s also the app that’s easiest to switch — more so than word processing, spreadsheets, and, most certainly, accounting.

I’ve been using Outlook since its inception in Office 97. The times I’ve sworn at it are too numerous to recount. Because I don’t want the overhead or expense of running Exchange Server, all my mail is stored in a collection of huge .pst files.

Except — well, some of those files don’t work anymore. For whatever reason, the .psts get gummed up, and running all the diagnostic software in the world won’t bring them back. I’ve found myself diving for backup copies of Outlook files on a monotonously regular basis — and sometimes the backups won’t work.

Outlook itself can be a snarly program. It freezes on me from time to time — and I’m talking about Outlook 2013, not one of the older versions that are even more prone to freezes. Sometimes it crashes and swallows whatever I’ve been typing. But I’ve continued to use Outlook, convinced it was the only email program capable of handling the huge volume of mail I manage every day.

It turns out I was wrong. The only insurmountable obstacles keeping me strapped to Outlook were fear and inertia.

Many PC users — especially business users — worry about getting work done with a Web-based email app. What if the Internet connection goes down? That was a completely valid concern a few years ago. Internet connections were often undependable. Today, however, most business-grade Web connections are quite reliable, and there are often backup connections (such as our smartphones) available.

For the rare times you’re without an Internet connection, a Google Chrome add-in — Gmail Offline (site) — lets you read and respond to mail. (For me, responding to messages without a connection to the Web is like tying one hand behind my back.)

So I made the switch to Gmail and have no regrets. Why not Hotmail/Outlook.com? Microsoft’s Web-based product is similar to Gmail in many ways. But there are also some key differences.

In particular, consider how Gmail automatically groups incoming mail into two bunches — one high-priority, the other low-priority — based on the way you’ve treated similar mail in the past. Gmail is also more adept at synching calendars and contact lists across Apple and Android devices. (And, yes, I’ve seen the Scroogled ads: pot calling the kettle black, IMHO.) Feel free to try both mail services and use the one you prefer.

Move an existing email account to Gmail

It’s surprising how few people know they can use Gmail (or Hotmail) with an existing email address. You don’t have to convert your current address to @gmail.com or @hotmail.com. In my case, I moved woody (at) askwoody (dot com) from my own email servers to Gmail — and nobody knew, not a soul.

Now that my mail is on Gmail, I can easily check for new messages on my Galaxy Note or iPad. The Gmail apps (calendaring and contacts came along with mail) for Apple and Android work quite well. Moreover, I no longer have to worry about backing up .pst files or putting up with Outlook’s weird ways of handling IMAP. Nor do I have to fret over program hangs. Instead of storing every bloody bit of incoming mail in .pst files, I archive selectively.

And searches? Oh my! Where Outlook might take about three minutes to search its Sent Files folder, Gmail takes seconds.

If your current email provider supports POP3 (and it probably does), all you need is your email user name, password, and POP server address (your mail provider should have it). Here are the details for moving all your mail to Gmail:

Step 1. If you don’t have a Gmail account already, go to the Gmail site, click the big red Create an Account box (upper-right corner), and follow the instructions.

Step 2. Sign in to Gmail. Now click the Gear icon (right side, above your messages) and choose Settings. Select the Accounts and Import tab. Next to Check Mail from Other Accounts (Using POP3), click the Add a POP3 mail account you own link.

Step 3. In the dialog box that pops up, type the email address you want to use with Gmail and click Next Step. Enter your username and password plus the details for your mail provider’s server. I typically check the Leave a copy of retrieved message on the server box; it gives me an emergency out, should something go bump in the night. I also check the Always use a secure connection (SSL) when retrieving mail box.

For Label incoming messages, pick an address from the drop-down list or create a new one. I don’t automatically Archive incoming messages. When you’re done, click Add Account; Gmail then starts sucking up all the mail it can find. If you’ve set up Outlook to leave copies of mail on the server, importing can take hours.

Step 4. While Gmail copies your mail over to its servers, you get a dialog box that asks whether you want to be able to send mail using your original email address (e.g. woody [at] askwoody [dot com]). Click Yes, then Next Step. You’ll see another dialog box that confirms details about your previous user name. Click Next Step again.

Gmail will ask whether you want to send outbound mail through Gmail or through your original email provider. Having been bitten by ISPs that block port 25 (for more, see my Aug. 27, 2009, Woody’s Windows column), I always opt to send via Google; as long as I have an Internet connection, my mail always goes out. Click Next Step.

Step 5. Gmail next asks you to verify the email address you’ll be using from now on (either your old address or a new address). Click Send Verification and then check your old (Outlook) inbox. You’ll get an email with a verification code. Type the code into the next Gmail dialog box and click Verify. And you’re done!

Step 6. Consider carefully whether you want to automatically export all your contacts from Outlook into the Google Contacts list. If you do, follow the steps on the Export Outlook Contacts to Google Gmail page for creating a CSV file and importing it into Google Contacts.

If you’re feeling particularly brave, you can set up Outlook and Google Contacts to sync automatically (more info). But if you’re giving up on Outlook, why bother? A slipstick.com page gives detailed instructions for synching Outlook and Gmail via IMAP.

Step 7. If you want to copy your Sent Mail from Outlook to Gmail, it can be done by jumping through a few IMAP hoops. A How-To Geek story has a step-by-step explanation for setting up IMAP synching between Gmail and Outlook 2007. The steps also work for Outlook 2010 and 2013.

Once you have the two mail systems communicating via IMAP, copy the messages in your Outlook Sent Items folder into the new IMAP Save folder. Next, copy any messages in your Outlook inbox to the new IMAP Inbox folder. Wait a few minutes — or an hour or more — and they’ll appear inside Gmail. From there, you can move them all to your Gmail Archive — or anywhere else you like. Don’t be too surprised if some of your messages disappear; Gmail’s junk filter works much better than Outlook’s.

I still find myself going back to Outlook from time to time, typically to retrieve a deleted message that’s available only on the Outlook side of the fence. But overall, my trips to Outlook are blissfully rare.

Once your email is in Gmail, take a minute to download the Gmail apps for your iPhone, iPad, Android phone, or Android tablet. You don’t need to do a thing: mail you send on your phone appears on your PCl; mail you receive on your iPad is on your Galaxy or your Mac; and so on. For someone accustomed to lugging around a big laptop with a huge .pst file just to run Outlook, it’s like a breath of fresh air. Welcome to the 21st century — no Exchange Server required!

In my next column, I’ll show you how to take all those old Excel spreadsheets you have lying around, stick them into Google Drive, and share them with whomever.

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All Windows Secrets articles posted on 2013-04-18:

Woody Leonhard

About Woody Leonhard

Woody Leonhard is a Windows Secrets senior editor and a senior contributing editor at InfoWorld. His latest book, the comprehensive 1,080-page Windows 8 All-In-One For Dummies, delves into all the Win8 nooks and crannies. His many writings tell it like it is — whether Microsoft likes it or not.