I've been trying to be a bit more bold lately.
When I first started mucking around on Ubuntu, I managed to bust my installation a few times. I became quite proficient at re-installing and having two hard drives installed, I was always running two copies of Ubuntu so that I could always have one that was functioning. I soon learnt the usefulness of having my /home on a seperate partition, so that my user settings survived the process and also I became proficient at transferring my downloaded .deb files in my /var/cache/apt/archives over to my new install, so that I could avoid downloading them all again (I'm on a dialup connection so this is painful). I started hanging out in the #ubuntu channel on IRC, and was soon taken under the wing by one of the regulars there who was more proficient at linux than I was, and instructed in the methods of 'how to do thing without breaking your box'. Since then I have been fairly careful with what I have installed on my system. I would always favour installation of software from the ubuntu repositories over trying to install the latest versions from source, and never leaving non-ubuntu sources sitting in my sources.list after I had acquired whatever particular package I was after. Lately I have begun to be a bit more bold in my software experimentation. I was searching for some type of wiki style system that I could use locally, to store all the links and references I use when helping people on the ubuntu forums. It was becoming tiresome to hunt them down each time I needed to recommend a link. I searched high and low through sourceforge and freshmeat and came across a couple of candidates. Tomboy looked pretty good and so did Zim. I quickly found that tomboy was in the standard repositories so that was on my system in no time at all and was really great. At the same time I tried to install Zim, which is written in Perl, and was having a particularly hard time of it, with it constantly spitting out errors about Perl modules being not installed. Initially I was doing something totally noobish and trying to run the ./configure command without first giving it executable permissions. This was followed by the installer constantly complaining that it could not 'make' the install, despite the fact that I had installed build-essential. Digging around a bit I finally found a Perl config file somewhere that seemed to be telling Perl where to look for different applications, and the pointer for 'make' had not been set. I edited that manually and got further along in the process. I persevered with it finally working out how to get the Perl modules downloaded and installed, but there was a few that refused to install no matter what I tried. In particular some Gtk::TrayIcon or whatever it is called, simply refused to download and install. I decided I would give the 'make install' a go regardless and see what happened. I've learnt to use 'checkinstall now rather than 'make install', as this will add an entry in synaptic so I can easily uninstall afterwards. So I ran checkinstall, and to my surprise it ran without error. I type 'zim' in console and a pretty little interface pops up and seems to be functional! So I'm now happily building my own little desktop wiki to reference all those helpful links and guides that others like to know about when they have issues with Ubuntu. It was an interesting little adventure anyway and I feel far more confident now about taking on my next non-standard installation of software on Ubuntu. :D