Depending on the app doing the counting, those refer to the number of people I’ve collected as contacts over the past six or so years of my digital life. The number varies — actually, much more than I expected — but, regardless, it’s high enough that I’ve decided to seek outside help in keeping them straight.

As the number of social networking options grows — along with the number of contacts we amass through each of them — several apps have popped up claiming to bring the address book up to speed with the rest of our digitally-connected lives. Until now, I’ve resisted them, intrigued by their promises, but mostly skeptical that they could actually do too much to help.

But, one of my New Year’s resolutions is to be a better correspondent with family and friends — including pals from years gone by whom I only see on Facebook, LinkedIn and Twitter.  So, I’m finally giving a few of these address-books-on-steroids a try. Here are some notes on what I’ve learned so far.

Addappt

One of the newer apps out there, Addappt’s big pitch is that it automagically keeps the contacts in your iPhone’s address book up to date. In theory, it’s one of those concepts so useful and seemingly so simple, you wonder why your iPhone doesn’t do it yet. But in practice, it’s a little too clunky to be convenient – for the moment, at least.

Because the app is so new (it just launched a month ago on iOS), users need to request an invite code to access the app. Once the app is running on your phone, it syncs with the contacts in your address book. But in order for the auto-updating to happen, each contact needs to download the app and then approve you as a contact. The company emphasizes that greater privacy is the upside of this trade-off – but it still feels like it takes too many steps to reap the big benefits.  It also doesn’t integrate with other social networks, so you don’t get access to your global roster of contacts.

Still, it’s a nicely designed app that breathes a bit more life into the standard address book — it pulls in photos of contacts when available and, for other contacts on Addappt, it tells you their local time zone so you know when (not) to call. And, it’s young: as it develops, it could smooth some its kinks out.

Brewster

Brewster, which launched on iOS in August, really tries to be more of a people and relationship manager than just a digital address book. And though it has a few bugs, it does a pretty decent job. It aggregates your contacts from across all your social networks and then applies some big-data algorithms to help you make sense of it all. According to this app, I have 6,174 contacts (which I think is closest to the real number as it seems to de-dupe better than others, although it was still missing a few). But it organizes them by college, previous employers, industry, location and most mutual connections.

One of my favorite features is the “updates” tab, which highlights people celebrating a birthday, changing jobs or with whom you’re losing touch. It’s like a streamlined Facebook or LinkedIn newsfeed that provides light reminders for getting back in touch or reaching out. Its search function is also one of the strongest I tested. You can search for any keyword — from online media to sushi to Bon Jovi — to find people who might be most interested in a new job opportunity to grabbing last minute dinner to going to a concert.

But, it’s not without bugs either. Its interface emphasizes photos, so if you don’t have rich relationships with contacts, you might see a lot of grey silhouettes. And all that data crunching takes time – running searches felt longer relative to other apps. Also, even though you can manually edit profiles, be prepared for unexpected mash-ups of your contacts, like this one to the right of my colleagues Tom (the one in the photograph), Matthew (the one called out by name) and Ernie (the one who belongs to the bio).

Cobook

One of the simpler apps I tried, Cobook is like the iPhone’s address book with just a little bit more pizzazz. The iOS app combines contacts from your address book and social networks but doesn’t try to do anything fancy with the data (like Brewster). For each contact, you get a minimalist profile with clickable tabs that take you to their Facebook, LinkedIn or Twitter pages (although it does show recent tweets within the app). Even though it’s more basic than Brewster and Smartr (see below), there’s still something nice about the simplicity and it’s not as image-focused as Brewster, so you can view more contacts at once. It also makes sharing contacts with others and copying data to your iPhone’s address book easier than a few other apps — both functions can be done in just about one click.

Contacts+

I haven’t tried this one firsthand as it’s only available for Android devices, but as most of the others are iOS-only, I didn’t want to leave Contacts+ out. The app, which last month raised $1 million in seed funding, also aggregates contacts from across different social networks, but makes a point of letting people post and communicate from within the app. Like Brewster and Smartr, it prioritizes people according to how frequently you communicate with them. It also lets people choose between a grid view (that displays contacts’ photos) and a list view of their names — (an option I wouldn’t mind having on Brewster). It has a 4.5-star rating in the Google Play store and has been downloaded more than one million times, but to get its full functionality, users on both the sending and receiving ends of a message need to download the app.

Smartr

Launched by email manager Xobni, Smartr seemed to offer the best balance of speed, search functionality, insights and design. It aggregates contacts from across all social networks, email accounts and your address book. The privacy conscious might not be thrilled by the level of detail it pulls in, but it includes some fun features, like the email history for each of your contacts, including a graph of your communication and the subject of your very first note.

Like Brewster, it prioritizes contacts by the frequency of communication and generates a list of mutual contacts, which I actually found easier to search (as it wasn’t image-based) and more complete (as it seems to do a deeper dive into your email). Similar to Brewster’s “updates” tab, Smartr’s opening screen rotates through various tweets and images from contacts. But I had a mixed reaction to it. I liked the lightweight updates and reminders for getting in touch with friends, but found the content to be dated and random. Instead of surfacing the most recent content, it surfaced tweets that were days old and it seemed to get stuck on just a few contacts instead of casting a wide net. Also, even though the company says it makes a point of de-duping, it clearly doesn’t de-dupe enough. According to the app, I have north of 9,000 contacts, but I spotted multiple entries (in some cases 5) for the same person.

Image by Milos Luzanin via Shutterstock.

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Various apps like Bump and CardMunch are available for certain platforms, but for many the answer is still cutting and pasting information out of email signatures into various digital address books and updating it manually when friends or colleagues send out the, ‘hey, I got a new number!’ email. ContactMonkey aims to offer a better way.

The Toronto, Canada-based company was started by Scott Pielsticker last year after he returned from a trade show with hundreds of business cards and faced the time consuming task of updating his address book. His solution was ContactMonkey, a sort of cloud-based online business card (here’s Pielsticker’s as an example) you complete with your details and then share with contacts as a URL or QR code. Associates can then easily download all your details to any of 19 kinds of address book with the option to receive a notification whenever your details are updated.

The service is free to individuals, while companies are charged $3 per user per month for “white label” ContactMonkey pages, which feature a firm’s branding. Users can also receive notifications detailing exactly who has downloaded their details, a feature that seems likely to appeal to anyone interested in lead generation. So far 10,000 people are using the service, with particular interest from sales-focused professional services firms like lawyers and real estate agents. The company also just received $800,000 in seed funding from Plazacorp Ventures and angel investors, which it intends to use to ramp up its sales operation.

“The basic idea is very, very simple,” says Pielsticker, boiling down his product to its essence. “Most business people have an email signature and the premise behind that is we want people to be able to communicate with us. ContactMonkey makes it easy for them to actually grab those details. I don’t care if you’re using Outlook, a Blackberry or an iPhone. I want you to have my details irrespective of what device you’re using.”

While many digital natives may be content to search their email for a contact’s details and experience no difficulty keeping in touch with their networks, ContactMonkey seems like a painless, platform-agnostic solution for those who are frustrated by incomplete and out-of-date address books. If that’s you or your clients, check out the service.

Are you frustrated with keeping your address book up to date or are you pretty content an ad hoc system? 

Image courtesy of ContactMonkey.

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1. Take a picture of your products and serial numbers

Whether you want to inventory your items or need a handy reference when there’s a problem, taking a picture of the product as well as its serial number means you won’t be in the awkward position of trying to talk on the phone while on the floor with a flashlight trying to read those teeny tiny numbers.

Plus, if you should have a theft or disaster, having a visual record of your items makes it easier for your insurance company to settle your claim.

2. Schedule your items with insurance

Speaking of insurance, I suggest contacting your homeowners, renters, or business insurance provider to see about separate insurance for your most expensive technology items. While insurance providers and policies vary, typically scheduling an item provides it extra protection and covers it separate from your regular deductible. If your computer is scheduled, many times it will even cover data recovery should your computer be dropped or damaged.

3. Track key information in your Address Book and iCal

If only you’d contacted tech support before the warranty expired, the broken gadget would have been repaired at no charge! There’s an easy way to make sure you have all your info on hand when you need it.

As you take pictures of your items in step 1, put the serial number and warranty expiration date in your Address Book along with tech support’s phone number (create custom fields for Serial Number and Tech Support if you wish). Attach the picture of the item to the address book entry.

Then put the warranty expiration in your iCal Now you’ve got all the info you need in one place and won’t miss that warranty expiration date.

A bonus outcome of this tip is that if you are at the electronics store and you have questions about compatibility or which model you own, the information will be handy so long as you sync your address book info manually or through iCloud.

While these tips won’t prevent problems from occurring, they’ll help protect you from further cost and inconvenience when they do.

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The program has three major components: Calendar Cleaner, Contacts Cleaner and Sync Tune-Up. If you want just one of the components, you can purchase the first two separately at the Mac App Store. However it’s likely you’ll need all three so I recommend the buying the full package.

Contacts Cleaner looks for issues that could cause errors such as invalid characters, malformed phone numbers as well as duplicate information. What I like about this program is that it not only finds the errors, but tells you why it thinks they represent a problem. For example, I’d often put “husband and wife” in the First Name field, but Contacts Cleaner warns me “This contact has a space in the first name. In some cases these names can become transposed after syncing with Google.” Sure enough when I went into Google, I noticed that problem.

Calendar Cleaner does similar checks for errors that can occur with your various sync destinations. My calendar was fraught with malformed recurring events that wouldn’t sync, and a pass by Calendar Cleaner fixed those in no time.

Both programs give you the option of opening the item within Address Book or iCal in order to make sure you know what kind of change is being made before you authorize it. Apple’s Address Book application looks for merged items itself, but doesn’t give you options to control what is merged. iCal users have no built-in options to search for duplicates and merge events.

Finally, Sync Tune-Up (only available as part of the bundle) gives you a front end for more fine-grained control over fixing your sync-related issues, such as de-registering individual devices and software, or the “nuclear” option which rebuilds the entire sync database. If your sync is taking extra long or you’ve made a bunch of changes with your devices or accounts, a nice reset can do you a world of good. A good indication of problems can be found by looking at your console logs and looking for mentions of the “truth” and too much vacuuming.

The more you sync, the more likely it is that problems will occur. To prevent or repair these problems, Spanning Tools is a great option.

Disclosure: Spanning Tools provided a copy of the software for review purposes.

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Apple Address Book and MobileMe Contacts

Apple’s Address Book application on Mac OS X Snow Leopard has the ability to print directly to address labels.  First create a new group called “Holiday Cards 2010″ in Apple’s Address Book.  Add the contacts you wish to send a card to this season to this new group.  Once this task is complete, simply select the group and perform the following steps:

1. Select File>Print from the Address Book Menu
2. Click the icon next to your Printer choice that looks like an upside-down triangle
3. From the Style drop down menu, choose Mailing Labels
4. Under the Layout tab, set the Page to Avery Standard and 8160 (or whatever type of mailing label you have)

Now you’re all set to print.  I would also recommend saving the results as a PDF file, and printing from there.  That way you’ll always have a record of whom you already mailed cards to this holiday season. If you want to change the font or add an image to the address labels, from that same print dialog box where you choose which type of label you’re using, simply toggle over from Layout to the Label tab and make any changes you want.

Avery Designer Pro and Google Contacts

Just as with the Apple Address Book solution above, the first thing to do when you’re dealing with your Google-stored addresses is to create a new group called “Holiday Cards 2010″ in Google’s Contacts.  Add your chosen contacts to the group. Now we’ll export the group to a local file on your Mac, and use Avery’s Designer Pro for Mac application to actually print the labels. Once you’ve installed Avery’s software, perform the following steps:

1. Export the contact group in Google Contacts as a “Google CSV” file (google.csv)
2. Launch Avery Designer Pro and choose 8160 – Easy Peel Mailing Labels (or whatever type of mailing label you have) from the list of all Avery Products
3. Click on the Use Blank button in the bottom right hand corner of Avery Designer Pro
4. From the toolbar located on the top left, click on the Text Box button to add a text box to the label
5. Now click on the Mail Merge button located just below the toolbar, this will prompt you to load the exported CSV file (google.csv)
6. Select the exported CSV file from the file system, and insert the columns you want to show up on the label

Now you can print from Avery Designer Pro’s File menu.  I would again recommend saving the results as a PDF file, and printing from there.

This technique is a little more flexible considering you have the option to choose one of Avery’s design styles. It’s also a little more powerful since you are actually designing the address labels in a designer that even supports layers, and of course a little more complex, as you need to export data and install and use a third-party application.

You can also mix and match the above two solutions, as you could certainly export your Google Contacts as a vCard and import them into Apple’s Address Book. The Avery Designer Pro application can also import Apple Address Book Contacts.  Either way, hopefully you find printing mailing labels on a Mac one of the easier one of the easier things to cross of your list this holiday.

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This is especially important if you, like many people, store information like credit card numbers and passwords in the address book. Ideally this private information is stored in a separate app on your iPhone such as one of these Weldon reviewed. However, not everyone is going to do that, and I have a possible compromise for those who want to store sensitive information in their address book.

The basic technique is to hide the sensitive data in plain sight, as part of what looks like just another ordinary contact. While it sure makes life easier to store your American Express card number under “American Express,” it also makes it easier for a criminal. If you absolutely need to store a credit card number, don’t be so obvious about it!

For credit cards, I suggest filing under a false name that only you know such as “Dave AX Smith.” Then use your own scheme of hiding the number as a combination of the street address and phone number, possibly across multiple contacts. I’m not going to tell you my exact strategy for storing this information, but it’s something I know and use for multiple credit cards. In this example, it’s an American express card with a number of 123456789012345 with an expiration of 09/12.

Here’s the way the card looks. It would be very unlikely someone browsing the address book could figure out it is a credit card.

A variation of this scheme can be used for passwords to websites or other sensitive information. If you think your address book is private, it’s time to get over that fallacy and take steps to protect the data within. While you may not choose my exact method, please be aware of the risks your address book is subject to and come up with some way of obscuring the data. If you don’t want to use a separate app for storing sensitive information, that’s fine, but I’d suggest you consider this middle ground.

When signing up for a Silentale account, you are presented with a wizard that helps connect your email and social network accounts, including Facebook, Twitter, LinkedIn, Google Contacts, Highrise, Gmail, Google Apps Mail, IMAP/POP3 email, AOL Mail, Hotmail/Live Mail, and Yahoo! Mail. You can connect to many of these services via OAuth or Facebook Connect, although you have to give Silentale your Google Apps and Gmail passwords, which may make some people uncomfortable.

Once connected, it may take a while for your contacts and message history to be imported, but then, Silentale lets you view and search for information in an elegant and easy-to-navigate interface with only three tabs — Messages, Contacts, and Connectors (which is what Silentale calls the external accounts you have given it).

The Messages screen is laid out in a Twitter-style timeline, and Contacts are presented in a multi-column screen that includes tools to merge contacts and edit names and pictures, but nothing else. The screen is headed with a field for searching messages and contacts. As I write this, contact searches are working, but message searches seem to fail. Silentale does offer a nicely laid out support function where one can report bugs.

Silentale also has an API, and is encouraging development of third-party applications. Android and iPhone apps are on the way, and there are add-ons for Outlook and Firefox available now. When you go to a friend’s profile in a site like Facebook in Firefox, the add-on displays a contact’s details, as well as recent messages you’ve exchanged with them.

Silentale is currently in public beta, and the service is offering free unlimited accounts until May 31. After that, it will offer several pricing levels, plus free accounts for connecting five services or less.

Silentale’s biggest strength is its simple, responsive and attractive interface. While it doesn’t have some of the features that Gist does, its search functions and ability to archive messages make it worth a close look.

Let us know what you think of Silentale below.

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Simply put, Contacts (installed as a Firefox add-on) makes your browser “aware” of contact lists and address books you’re using elsewhere on the web, but rather than simply providing a view of these aggregated contacts, the add-on integrates them into form elements, so that names and addresses are auto-completed as you type.

Installing Contacts requires a browser restart, after which this add-on is available from Firefox’s Tools menu. Firstly, you need to link your contacts to Firefox:

Currently, Contacts enables you to synchronize with Mac OS X’s address book, Gmail contacts and Twitter. An additional feature scans through imported contacts, adding Gravatar avatars for each entry where available. Notably, creating these hooks to other services is a simple one-click process; presumably because authentication details already reside in Firefox’s cookies.

I’d actually forgotten I’d installed Contacts a few days ago, until today I was signing up for MixCloud — a web radio service. As I was completing the signup form, Firefox handily auto-completed my email address alongside a thumbnail of my avatar!

Contacts works well and includes APIs to extend the importing and permissions features, though auto-completion is currently limited to email addresses only.

Despite growing competition from Opera, Safari and Chrome — and perhaps even IE9 — Contacts underlines Mozilla’s commitment to utility, openness and innovation; the add-on certainly feels like something others will emulate and adopt as standard browser behavior.

Have you tried Contacts? How is it working for you so far?

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Apple’s original implementation of “smart” file management isn’t just limited to the Finder, and in fact, you’ve probably seen it more often in other applications like Address Book and Mail.

Here are some ideas of how you can harness the power of these two applications using the same idea as Smart Folders.

Smart Groups

Address Book provides support for smart groups which allow for dynamic content, just like a smart folder. As new content is added that meet your guidelines, the group will automatically update.

Creating a Smart Group is as simple as going to File and selecting “New Smart Group…” or by clicking the plus icon (+) in the lower left corner of the Address Book window. Then give your group a name and set of criteria. As you add your second criterion, you’ll have the choice for your group to consist of any of your rules or all of your rules.

Here’s some ideas for useful smart groups.

Upcoming Birthdays

Interested in who might have a birthday this month? Set the birthday criterion to include entries that occur within the next month. (This will include all birthdays within a month of the current date or when you click to view the group.)

Missing Email Addresses

To see a list of people who you do not have an email address for, set the email criterion to include entries that are not set.

My Coworkers

Most companies offer their employees an email address that uses the corporate domain. If you created a smart group for “email” that contains “yourdomain.com” then you will have a group that is always updated with all of your coworkers. An extra bonus, these Smart Groups also show up and autocomplete in Mail.

Or Anything You Want

Since the Address Book allows for a “notes” section on each card, you can use this region to “tag” cards and then use a smart group to show results based on that information. (You could also repurpose one of the other standard fields for this use.) For example, throwing the word “family” into the appropriate contacts’ card would allow for you to create a smart group that just showed your family members.

Currently, Smart Groups cannot be synced to iPods or iPhones. While they also cannot be synced through MobileMe to me.com or Windows computers, they can still sync through MobileMe to other Macs.

Smart Mailboxes

Mail has its own flavor of smart file management too with the implementation of smart mailboxes. To create one, use the Mailbox menu or the plus (+) icon in the lower left of the message viewer and select “New Smart Mailbox.”

Give your smart mailbox a name and choose the appropriate criteria for your mailbox. With the ability to create criteria based on recipient, subject, mailbox, date, message, attachment and more, you can create some pretty powerful mailboxes to help organize your workflow. Here’s a few suggestions.

Recently Viewed

Most people process tons of email on a daily basis and frequently people have multiple email addresses for different purposes. With all of these messages, is there an easy way to find that email you were looking at last night?

Sure! Create a new smart mailbox and select “date last viewed” and choose “is in the last” and specify a number of days.

Recently Sent

If I wanted to quickly find an email that I had sent recently, I could create a Smart Group that showed me messages in the mailbox “Sent” that were “date received” in the past 2 days. Also make sure you tick the “Include messages from Sent” checkbox.

Emails from My Family

Remember the family smart group we made in our Address Book earlier? We can create a smart mailbox to show us all the messages from those family members.

Select “Sender is Member of Group” and then choose the appropriate group from the drop down menu.

Similar to Smart Groups, Smart Mailboxes do not sync to iPods or iPhones nor to me.com or Windows computers through MobileMe. They will only sync via MobileMe to other Macs.

Do you use Smart Groups or Smart Mailboxes? Have any tips you’d like to share? Share them in the comments.

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There are comprehensive third party desktop syncing programs available such as Missing Sync, but realize that with a “Google-based” phone, over-the-air syncing is automatic and built in. When you purchase your Android-based phone, you’ll link it with your Google account (a free Google account is required to use the phone’s over-the-air syncing). Your phone will generally auto-sync with your Google account allowing you to possibly ditch your MobileMe subscription. The task then is to get your Mac to sync with the Google account.

1) Foreplay

While using a Droid isn’t as easy as using an iPhone, it’s not that much harder. Here’s a tip, do NOT allow your mobile phone company to import your contacts from your old phone. This has caused problems with synchronization for some. It’s best to start with a clean list of contacts in your Google account. If you haven’t synced your previous phone with your Mac, go ahead and do it before switching phones. If you can’t, you might consider typing the phone numbers into your Mac Address Book beforehand.

2) Safe Syncing

Syncing is only one step above the SCSI voodoo of previous generations. It’s always best to start with a core data set and push it to other devices. Trying to merge two data sets can result in duplication and corruption.

If your Google account already has contacts, export them from Google as a vCard file and import them into your Mac Address Book.
Once imported, delete the contacts from Google so the initial sync pushes all your Mac info into Gmail. As always, it’s a good idea to back up your data before any sync endeavor. From the Mac Address Book, go to the File menu, then choose Export, and then Address Book Archive.

For your calendar, the safe sync concept is similar but you actually want to start with a populated Google calendar and a clear iCal. From experience, if you push too much into Google at once, it can choke. If you already have a Google calendar, back it up by clicking “Settings” under the “My calendars” Then choose “Export Calendars”.

They’ll download as a zip file that you can double click and get the individual .ICS files. Similarly, backup your iCal by visiting the File Menu and choose “Backup iCal.”

Syncing can be buggy under the best of circumstances, which is why I recommend backups throughout the whole process.

Now that both your Google Calendar and your iCal calender are backed up, you’ll then want to export your existing iCal calendars and import then into your Google calendar. This isn’t the same as backing them up. Click on a calendar, and then go to the File menu and choose “Export This” which will create individual .iCal files for each calender you use. Note that Google doesn’t like To Dos so go ahead and remove those beforehand.

Now that you have your individual iCals exported, go to that same Settings tab in Google under “My Calendars” and now import your individual iCals into your existing calendars. Note: it won’t give you an option to create a new calendar from the import, so have your Google calendars ready beforehand. Finally, delete your iCal calendars (remember to back up first) so your iCal is clear of info and all your data is now on Google’s servers.

3) Getting Your Sync On

If you skipped step two, proceed at your own risk. You have been warned.

If you have Snow Leopard, Google contact syncing is built-in: go to the Address Book Preferences and check “Synchronize with Google”. Put in your Google name and password and let the syncing begin! For Leopard users, you’ll need to own an iPhone or iPod touch to enable syncing or use third party apps like Gsync.

To sync calendars, you’ll need to be running Leopard or Snow Leopard. Go to your iCal application and then go to Preferences and then Accounts. Click the + icon and put whatever you want for description. For username put your name@gmail.com and your password for Gmail. Then under the disclosure triangle for Server Options, put https://www.google.com/calendar/dav/(followed by your googlemail address) and then user. So for example, https://www.google.com/calendar/dav/myname@gmail.com/user would be what you enter. Your calendars will now start downloading from the cloud. Alternatively, you can use BusySync and avoid these hassles.

For photos, iTunes-like picture sync isn’t available, but you can mount your Droid like any other mass-storage device and have it recognized. You’ll need to enable USB mounting first. Go to the menu at the top of your phone and then click USB Connection to mount the SD card. To move music and other multimedia files easily I recommend DoubleTwist.

Having used a Droid for a while I’m pretty darn impressed and you gotta love the advertising. If Mac syncing is holding you back from buying one, you just removed one reason not to switch!

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