This is part 2 in a series, Coming out as a Mac user.

As you embark on your new Mac lifestyle, you’ll be faced with choices that challenge you to think about who you really are, and what’s really important to you. Are you an iconoclast, a design freak, a fashionista who does everything with style and flair? Or are you a conciliator, a mediator, the kind to bring people together and bridge between worlds?

Choosing the right applications for your Mac often feels like a choice between these two different identities: the choice between a shiny, stylin’ Mac-specific app, and an often less-shiny, cross-platform-compatible alternative.

But you don’t have to choose between personal style and social substance. You can the coolest kid on the block and play well with others, as long as you’ve got your Mac kitted out with the right tools for every job. Here are my recommendations on the key software choices for every Mac user:

  1. safarifirefoxSafari or Firefox? Both. Use Firefox for any browsing you might to want to organize, track, or enter data into: there are more add-ons for Firefox, so things like adding bookmarks to delicious are much easier in Firefox. But with all those add-ons (and frankly, without ’em) Firefox is a memory-hogging beast: if your Mac slows down, or craps out, try quitting Firefox, and you’ll often find that your problems will clear right up. So Safari is my choice for any quick Google searches or browsing that I don’t plan on tracking, and in fact, if you specifically don’t want to track your surfing (for example, while enjoying the latest clothing-free video offerings) you can turn on “private browsing” and Safari will keep your session off-the-record. And do use delicious to store bookmarks, rather than storing them in your browser: that way they’ll be accessible from Safari, Firefox, and even from a PC if you need to use one.
  2. iWork or Microsoft Office? Ideally, both. iWork’s apps are great for specific things: Keynote makes super sexy presentations, Pages is great as a lightweight layout/desktop publishing app, and Numbers…well, I can’t imagine why I’d use this over Excel but I’m sure that someone will now tell me. But for day-to-day document creation, and especially, document sharing, you might as well stick with Word and Excel. You’re going to have lots of new stuff to learn on your Mac, so you might as well stick with these old workhorses and have your word processor and spreadsheet editor feel familiar. Plus, if you are doing any kind of collaboration with your friends from Before The Switch, those PC users are going to send you Office files that you’ll find easiest to work with in Office. Just to be sure to go with Office 2008 as opposed to an earlier version — it was a nice upgrade.
  3. MobileMe or Google Calendar? Both. MobileMe isn’t cheap — $109 per year — and lots of techies will point out that you can do just about everything it offers for free by using other services. Sure you can. But for $109, spare yourself the headache, and ensure your calendar, address book etc. are backed up and accessible via web browser (useful if you’re on another computer). If you’re an iPhone user, this is a must: MobileMe does an amazing, seamless, effortless job of keeping your iPhone and Mac synced in real-time, without any cables or manual backups. But MobileMe is very much a single-user tool: it doesn’t offer much in the way of collaboration for teams. So if you need to share calendars with your colleagues, use Google Apps, and use BusySync and MobileMe to keep your Google Calendar perpetually synced to your computer and your iPhone.
  4. Apple apps or Entourage? Apple apps. If you’ve been an Outlook user, it’ll seem natural to go with Entourage, Microsoft‘s Outlook knockoff for Mac users. RESIST! There are some things to like about Entourage, like the one-stop-shopping for calendar, contact and mail info, but that’s also what you need to be wary of: Entourage stores them all in one big database, so if one part goes down or gets corrupted (typically, your mail) then the whole thing is wrecked. That’s the stick….but there’s also a big carrot: the glory of Apple’s own free, built-in Mail, Address Book and iCal applications. These are so core to the Mac system that you’ll find benefits cropping up all over the place once you start using the native applications. Names typed in Address Book-enabled apps turn into easy links to that person’s contact info; your iPhone and your computer can stay constantly and effortlessly in sync thanks to MobileMe;  e-mailed invitations convert to calendar events (I know, just like Entourage), and there is full, seamless integration between contact info, emails and calendars.

    If you really really want that all-in-one feel for your mail, address book and calendar, you can use a wrap-’em-up application like CRM4Mac; and if you’ve already made the (wrong) decision, you can get help switching away from Entourage. A final tip: if you ever need more help or tips for the Apple personal info management apps, you’ll find that googling “Address Book” gets you exactly nowhere….or rather, everywhere, since you’ll be swamped with results. Google for “”, “” and “” to find resources specific to the Apple applications.

  5. Preview or Acrobat? Preview is all you need to view a PDF, and it also provides all the support you need to create PDFs of most documents (by choosing “Print” and then working from the PDF drop-down in the bottom left of your print dialog box). The only reason to use Adobe Acrobat is to create complex or advanced PDFs like forms that people can fill out within the PDF itself.
  6. Nambu or TweetDeck? If you’re a Twitter user, you’ll want a client to use on your Mac. People with multiple Twitter accounts will want to use Nambu, or possibly Seesmic Desktop (Nambu is prettier, but more crashy.) People with a single Twitter account can use TweetDeck, which is pretty and not crashy. Both Nambu and TweetDeck can be even more life-changingly awesome if you follow my recommendations for grouping your Twitter follows.
  7. VooDooPad or EverNote? Right now, you probably take notes in a variety of applications: Word, TextEdit, even — god forbid — paper. As a result, it’s a pain to find your notes, let alone have them all open when and where you need them. Please, please, please: switch to a dedicated note-taking program that keeps all your notes in one place and lets you organize them by keywords or categories. It will rock your world and change your life; just see my blog posts on VoodooPad and EverNote. Which brings me to my painful recommendation. VoodooPad represents everything I love about Mac applications and Mac developers: it’s pretty, it runs fast, it’s intuitive, it integrates with all the native Apple apps, and it has the most wonderfully responsive and helpful developer (I taxed Gus with many questions and suggestions, all addressed quickly and effectively). But VoodooPad is very much a local, single-user app; about a year ago, I switched to the cross-platform, web-enabled Evernote, which lets me access and edit my notes via web browser, too. Read my ecstatic reviews of both EverNote and VoodooPad to see which one is right for you.
  8. Dropbox-backupBackup or Dropbox? Definitely, absolutely, positively both. Backup is MobileMe’s service for backing up key files; it’s not big or fast enough to replace regular backups to a local drive (using Apple’s awesome Time Machine), but it’s the easiest way to automate regular backups of key files (like your Documents folder). Dropbox is your answer for sharing files with a team, or keeping your files accessible across computers; just install Dropbox on your Mac, and any file or folder you put there will be backed up to a web server. You can choose to share some or all of your Dropbox folders with colleagues, and you’ll probably want to spend the $99/year to get the large-scale capacity that allows you to store virtually all your files online. In fact, I’d recommend putting your Dropbox folder at the top level of your user directory (the folder that holds your documents, pictures, music folders etc.) and then stick all those folders inside DropBox so they stay synced and backed up.
  9. iChat or Skype? Again, both. I use iChat as my primary chat tool for working with our team (we connect via AIM accounts, but iChat also works with your MobileMe ID); it’s fast, it’s got a lovely interface, and it uses Bonjour, Apple’s local networking protocol, so I can stay connected to people in my office without being online with the whole world. But Skype is now the virtually universal platform for connecting via audio or video with clients and colleagues; I’m far more likely to schedule a Skype call than an iChat session, and when I’m on Skype for a call or meeting, I often use its chat function to share files or URLs while we talk.

I know, I know: I’ve promised to help you choose between software tools, but I’m mostly recommending that you choose “all of the above”. But that’s what’s beautiful about the Mac: the consistency of the user experience across applications makes it relatively easy and intuitive to use a new tool, so you might as well use the best tool for every job. In many cases, that means using one software tool when you’re flying solo (MobileMe, Keynote, Safari, Backup) and another tool when you want to tap the power of cross-platform collaboration through the social web (Google calendar, DropBox, Firefox, Skype).

What other software choices are you struggling with as a new Mac user? What software choices would experienced Mac users recommend? Let me know in comments below.