What software would you buy first?

Ben Brooks over at The Brooks Review asked the following question:

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).

It’s an interesting question, so I thought I’d give it a go. I went through my Applications folder and this is what I came up with:

I’m not counting the software that comes bundled with the Mac, like Mail, iCal, the iLife suite, etc., as I never bought it independently. I also didn’t count any free/open source apps, so the list only shows the order in which I’d buy them if I could only afford one at a time.

This little exercise made me realise how little additional software I use. It really is amazing what the Mac comes with out of the box. I also realised how many great free apps I use. Kudos to the developers of the following:

UPDATE (21/10/2011): A few apps have changed since I wrote this. Mostly due to Mac OS X Lion. I'll leave the above as is for historical purposes, but I wanted to give an update on what's changed:

  1. I'm no longer using Blogo as my blogging client. It doesn't support Lion (as of this writing) and it seemed to be abandoned. The last blog post on their site says they're working on a new version, but it's not a priority. I'm now using MarsEdit and absolutely love it.
  2. I'm no longer using Paperless. After installing Lion I decided to keep all my receipts in Together. I created a special folder for them. The only downside is that Paperless can count totals on several receipts, which is handy. But I found I rarely used it as I only referred back to them at tax time and did that with my accountant anyway.
  3. I'm no longer using Notebook. I may come back to it again as it's a wonderful app, but I don't have the need for it at the moment.
  4. I added Byword as a TextEditor replacement. It's a beautiful app that handles Markdown exceptionally well. I reviewed Byword here.
  5. I added Day One. It's a journalling app that has an iPhone/iPad version and they all sync via Dropbox. And it looks beautiful.

Those last 2 I'd add towards the top of the list, Byword after Aperture (it's that good) and Day One after Carbon Copy Cloner.


  1. I have a paid 50MB Dropbox account. And yes, the link is a referral. ?
  2. Can be used for free, but you should make a donation. ?
  3. I’d probably buy Yojimbo instead of Together since it has an iPad version. The reason I bought Together is because it doesn’t use a proprietary database to store files. They’re just in folders. ?
  4. I haven’t upgraded in ages and don’t have any plans to. Aperture and a few plugins do most of what I need. I’m thinking of giving Acorn and Pixelmator a try though as they seem to do most of what I use Photoshop for. ?
  5. Couldn’t live without nvALT. Currently playing with a few iOS apps to replace Simplenote. ?
  6. A few examples of what HyperDither does in my photography blog. ?