Maybe this is weird but then again I've never claimed to not be weird.
I'm an "IT Guy". In the course of my job I often encounter technical issues ranging from the simple & mundane to the rare & cryptic. There are easy ones; A well-written, verbose error on a popular piece of software. If the solution is not obvious from the error, a quick trip to the vendors website or support pages should do the trick. The more difficult issues arise on custom-built, abandoned, or obscure software where the error message is something like "Unknown Error 1". And some of the trickiest are when I'm developing custom applications of my own.
I've developed a pretty reliable troubleshooting escalation list that has been handy.
Read the error - As mentioned earlier, sometimes error messages give you everything you need to solve the problem. A file permission is wrong. A configuration setting is missing, etc. Take action based on the error and try again.
Experience - How well do you know the app? Have you encountered similar problems in the same application? In other applications? This can be a good place to start.
Internal SMEs - Sometimes the fastest answer comes from the people that know best. If you have in-person access to a Subject Matter Expert don't waste time searching. While you might find a resolution online, the subject matter expert can teach you why something was broken enhancing your understanding and increasing your self-sufficiency.
Search - Obviously the Internet is a tremendous resource. Remember that error message above? The reason it sucks is because the error code was 1. If the error was something like "1326" you'd be a lot more likely to find useful information with a web search. The more detail you have the better off you are. Stay active in the vendors forums and support pages to reduce your time-to-resolution.
Collaborate - If you can't find the answer, engage a co-worker, contact, Linked-In friend, etc. Even if that person is not an SME (see above), it really is true that "two heads are better than one". Working through an issue together and with a fresh set of eyes can help you pick up on things you missed before.
Trouble Ticket - If you must... open a trouble ticket with the vendor. The ranking of this option on the scale actually varies drastically depending on the package you're supporting and the vendor. Some vendors have top-notch support that can answer even complex questions quickly. Many, however, do not and will simply open a work order, give you the number, and hopefully you'll hear back from someone in a week or so. If the vendor is good use them by all means. In that case they're effectively the SMEs from above.
That all seems rational and not-at-all wierd. It's the last item on my list that seems a bit strange... at least to me.
Note to Self - When all else fails, I write an email... to myself. I work through as much detail as I can think of even the seemingly trivial bits. I write it as if I'm asking a friend for help. A friend that knows only the basics of the application or issue and would appreciate knowing the specifics and the steps I've taken so far and the results they produced. I find that similar to collaborating, this can refresh my perspective on the issue and take me down new paths of resolution that I may have been overlooking due to blind familiarity.
Believe it or not, this last method has saved me more than once. In fact just recently and that's when I wondered if anyone else does this?
How about you? What creative troubleshooting steps do you employ?