"I filed direct" - Everyone. Everywhere. All the time.
Generating an IFR flight plan is part art and part logic. It is highly dependent on your geographical area (mountainous, coastal, etc.), and how far you are willing to travel to fly pre-checked routes vs. "direct". Here is what I teach my students.
I recommend pilots plan their route on SkyVector.com. It's so simple, so quick to use, and is extremely user-friendly (trust me, I have a PhD in this stuff) for planning purposes. My favorite feature is the quick picture-in-picture view of approach plates. It's free, it's easy, and it's solid.
My flight plans are based on the following factors:
1. Altitude
I almost exclusively fly airways. As long as it doesn't add an absurd amount of distance. The reason I do this is that airways often guarantee lower altitudes compared to the off route obstruction clearance altitude (OROCA). Airways are "cut-outs" in the terrain that allow you to fly without worrying (too much) about obstacles. So if you can, fly airways!
2. Navigation Redundancy
I trust my GPS. And trust GPS integrity way more than VOR integrity. I experienced an unplanned VOR outage at least twice in the local area. Nevertheless, I like to fly Victor airways because they offer me both GPS and VOR navigation. Two is better than one.
3. Loss of Communication
When you lose communications in IMC, you need to follow specific guidelines to fly laterally (AVEF) and vertically (MEA). Remember the acronmys, right?
For lateral navigation, fly these in order:
Assigned
Vectored
Expected
Filed
For vertical navigation, fly the highest of these, for the longest time possible:
Minimum Enroute Altitude (MEA)
Expected
Assigned
After you squawk 7600, ATC starts scrambling trying to figure out what your plan is and how you will land. That is the "E" in the acronyms. But that may involve hypotheticals. In terms of lateral navigation, you situation will most probably come own to "FILED". If you filed direct, with no granularity, you are not helping yourself or ATC very much.
When I file a flight plan, I ALWAYS file to an Initial Approach Fix (IAF). This covers your basis all the way to (4) - filed. By filing to an IAF, ATC can always expect me to fly the approach that begins with that fix.
4. Direction of Travel
Many ATC systems pick up your first route waypoint as the direction of travel. For example, check out this short flight plan out of Savannah, GA:
Notice how to join V37, I filed KSAV to SAV. Although that is necessary to fly a VOR-only aircraft, SAV is actually to the North of KSAV, and my route is southbound. The ATC computers will interpret that as a northbound departure, because that is the first waypoint on your route. Is that a biggie? No. But, you can expect a weirder clearance from ATC. They would for example give you "radar vectors" to some fix on V37 and then "as filed". So if you expect a fast "cleared to destination as filed", you may not get that unless you account for this. I like to help ATC when I can, so I apply this little piece of information.
5. Preferred Routes
When possible, it's always good to fly preferred ATC routes. To search for these - the easy way, click on this FAA link. Here is an example from KLAX to KVNY:
6. Alternate Location
If I need an alternate per IFR, I chose an airport on my planned route. This way I can fly over it and visually see what the weather looks like. It may of course change by the time I need to fly back, but it's nevertheless an extra variable that can aid decision making.
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