Ben Brooks asks:

if you had to start over, buying all of your apps from scratch, in what order would you buy them (the assumption being you couldn’t afford to re-buy them all at once, but over time you could afford them all). I have been thinking about this for a while now and I started with a list of all the apps I normally use that I would need to purchase. From there I started arranging them in order of what I would buy first.

I’m going through something vaguely similar now, because I have a new iMac. Rather than fire old data across, I’m thinking ‘what should I install first?’ and only having the most important applications on there.

But if it was a case of literally installing in order, how could that be achieved? I use SuperDuper! for back-ups, but could conceivably get by on Carbon Copy Cloner for a while first; I use Scrivener and WriteRoom for writing copy, but could use TextWrangler. In each of these cases (and more), I end up imagining using a sub-optimal solution, in order to create a linear list.

Entire world:

You’re overthinking this, you idiot.

Yes, fair enough, so here’s the stuff I absolutely would have to have installed, and that one has to pay for, in a vaguely linear order:

• SuperDuper! (incremental back-up/cloning)
• Scrivener (fantastic writing app)
• Acorn (image editor)
• SizeUp (window management)
• WriteRoom (full-screen text editor)
• On The Job (time tracker)
• Numbers (spreadsheet)
• Photoshop (image editor)
• Transmit (FTP client)
• BBEdit (text/code editor)
• Default Folder X (open/save dialog add-on)
• GarageBand (audio editor)
• Call Recorder for Skype (recorder, for use in interviews)
• iPhoto (photo catalogue)
• PhoneView (iOS device manager)
• iStat Menus (system monitor—I use it for the clock)

I do use other software, but those are the ones I’d really miss, roughly in the order that I’d miss them (or, rather, in the order that I depend on them).

UPDATE: A few people have asked where Dropbox is, which is fair enough. The above list concentrated on paid-for applications, which wasn’t clear. Free stuff I currently use daily includes Dropbox (online back-up/sync), Pastebot Sync (iOS-to-Mac copy/paste), Twitter, the Reeder for Mac beta, Carbon Copy Cloner (cloning, as a fail-safe in case SuperDuper! doesn’t work) and The Unarchiver. These, of course, could all be installed on day one.