Not everything works with everything else.

Your expectations have changed so quickly that you might not have noticed. It wasn’t long ago that most people used a single PC at a single location and were content to leave the data on that computer behind when they left that desk. When you closed Outlook on the office computer, you didn’t expect to open up the same mailbox at home. If you had files to work on at home, you’d burn them to a CD or copy them to a USB drive or email them to your home email address. You might have gotten a notebook if you expected to be mobile but the data on it was still mostly separate from your other computers and devices.

It’s been eight years or so since that began to change – when Small Business Server 2003 brought easy remote access to office computers, for example. But the big change in attitude started with the iPhone and grew exponentially with the explosion of iPads and Android phones and tablets, mostly in the last couple of years.

It now seems natural to expect that your mail, contacts, calendars, tasks, files, photos, and music will be available on all the devices you own. You don’t care how that’s accomplished.

  • You want your company mailbox on phones by Apple, Google, Microsoft and Blackberry, maybe all four.
  • You want your Apple iPad to display your Google calendar and your Yahoo mail and the POP3 mail in Outlook.
  • You want to work on your company files on your home computer and then open the edited copies on the office computer in the morning.
  • You want to walk into the living room and see your photos.
  • You want to pull out your phone and play your music.

A thousand – nay, ten thousand things are being designed to help accomplish all those things and all the other variations on them, leading to a landscape that is as confusing as anything the industry has seen in 20 years. Because the reality is that for many reasons, you’re asking for things that the devices or programs were not designed to do. In some cases you’re looking for devices to cooperate with each other even though they were designed by companies that are fierce antagonists. Between Windows computers, Apple mobile devices, Google online services, local copies of Outlook, and the occasional Blackberry – the combinations are endless.

Not all of them work.

The overall lesson is that you have to remember two things:

  • When you choose a program, a service, or a device, you are locking yourself into a relationship that will affect other things you want to use. Plan ahead! Be knowledgeable about what will work for you, or ask for help.
  • Not everything will work. If you buy a device and then call me after it’s in your hands to set it up, it may not go as smoothly as if you called me ahead of time.

I can give you random examples of things that just don’t work.

MUSIC Apple today will announce its new cloud music service. A modest subscription fee will give you access to your music library from anywhere. If you use iTunes, it will likely be very appealing – unless you have an Android phone. We won’t know if that’s supported until about noon on Monday. It probably won’t be. On the other hand, Amazon and Google both introduced their own cloud music services recently. Neither of them run on iPads or iPhones.

FILES We are in the early years of developing services to sync files from device to device or provide easy access to files stored in the cloud. Today’s New York Times article briefly describes the efforts by the big players – Dropbox, Microsoft Skydrive, and Google Docs, plus the next tier of smaller companies like,,, 4Shared and SpiderOak. It’s also a likely direction for Apple iCloud and Amazon Cloud Drive. Some companies will change direction or fold up, some services will not work smoothly, some will not work on some device that you buy.

MAIL You’d be amazed at the number of ways your mail, contacts and calendar might be stored. There are online services – Google Gmail, Hotmail, Yahoo mail. There are POP3 mailboxes stored in individual copies of Outlook or viewed through an ISP’s webmail. There are Exchange mailboxes run onsite by a business or hosted in the cloud.

You want that information on your new iPhone or iPad or Android phone or notebook computer or Blackberry tablet, and you don’t much care how it gets there, right? It might not be possible.

People are being driven to do extraordinary things that make me shiver. Let’s store our calendar in Google calendar, use an app to sync it to Outlook, then have iTunes sync Outlook to the iPad! There are a thousand variations, each with individual points of failure that might work, or that might bring heartache or lost data or duplication.

Microsoft’s ActiveSync has become the de facto standard for syncing certain kinds of data across all platforms. That’s what Google uses to sync its services with Android devices, and that’s the mechanism used by hosted Exchange mailboxes to sync with all platforms – Apple iPhones/iPads, Android phones/tablets, and Windows phones/computers.  It syncs calendar/contacts/mail over the air flawlessly. (Not tasks, oddly enough.)

The problem is, it only works with a custom domain (“”) or a Gmail address, not a POP3 address from an ISP (“” or “”).

Your choices online and your trips into Best Buy or Verizon or AT&T deserve some thought. You may not realize it but you may already have made choices that determine what will or won’t work for you. If you’re in the Apple ecosystem, stay there – don’t look at the Android phones. If you bought an Android phone, the iPad might or might not do everything you hope. If you work in an office with Windows computers, buying a Mac to work from home will have some very rough edges.

It’s the Wild West. It reminds me of the early days of personal computer hardware when each purchase was a gamble on getting something that would run.

Keep talking to your friendly consultant. It will save money and aggravation in the long run.

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