Is Direct-Enter-Enter cheating?

I do the same as the OP when leaving my home base. I'm under Class B to my west and Class C a few miles to my east. I set the course during runup, depart staying clear of the B and C, and once clear direct-direct. I'm always VFR.
 
IFR. Outside of class B airspace, you won't have a "cleared route" VFR.
In that case, I think the controller was just having a bad day, and accidentally treated you like an IFR. I have heard IFRs being chewed out on the radio for going direct to destination when they weren't actually cleared direct to destination, but that wouldn't apply to a VFR, because you're picking your own route anyway (except for vectors when you're in terminal airspace). Even if you'd filed a VFR flightplan, the controller wouldn't have had access to it.
 
Another reason not to go direct (sometimes) is when you're flying over sparsely-populated areas. For example, I'll gladly add 20 minutes to a trip to stay close to the Trans-Canada Highway north of Lake Huron and and Lake Superior, so that if anything goes wrong, I'm not 50+ miles from the nearest cabin. I've heard pilots doing the same flying over mountains (sometimes that highway is the only suitable forced-landing option within many miles).
 
In that case, I think the controller was just having a bad day, and accidentally treated you like an IFR. I have heard IFRs being chewed out on the radio for going direct to destination when they weren't actually cleared direct to destination, but that wouldn't apply to a VFR, because you're picking your own route anyway (except for vectors when you're in terminal airspace). Even if you'd filed a VFR flightplan, the controller wouldn't have had access to it.

It wasn't me, and the pilot was IFR.

It makes no difference what I put on a VFR flight plan route. You're not obliged to EVER follow it and it's not even really used even for search and rescue.
 
It wasn't me, and the pilot was IFR.
In that case, the controller was right and your friend was wrong: "resume own navigation" is not an IFR clearance direct to destination, just the end of vectors. As someone else mentioned, these days (with RNAV) they'll usually clear you direct to the next waypoint on your course; in the VOR days, you just had to reintercept the airway as best you could.
 
That’s interesting considering you said you don’t even have students plot from destination to first checkpoint.

Kind of two different scenarios, though.

The initial climb and maneuvering to get out of the pattern usually doesn't change the desired track by more than a degree or two on a flight of any real distance. So telling ATC 100 or 105 or 103 or 110 is all within a reasonable range of accuracy.

On a student XC to a point only 50 nm or so away, though, and generally using dead reckoning to navigate, the errors can add up, however.
 
Here's an example of that:

As far as what to do other than in the terrain avoidance scenario, it depends. If IFR, fly your clearance. "Cleared direct fix" means directly to that fix, not backtracking to find your original direct line to the fix. If VFR, fly what makes sense. Direct-enter-enter is handy if you are off course, but as mentioned above you need to correct for the wind so you don't keep going off course and and up homing to the destination. (Wind isn't the only way to get off course, of course.)

When I saw the thread title, I immediately thought of this tragic crash that took six lives, three of them children. Going direct from a location that has deviated from the original planned flight path when there is surrounding terrain can have serious consequences, and one should always consider the ramifications of doing so.
 
Depending on where you were vectored in relation to the original course, and your clearance, "activate leg" is another option.
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