Could be worn shift forks, weak drum stopper detent spring, worn drum, worn gears or a combo of a bunch of worn parts.
Also, my (350) did this when I shifted without the clutch. I shift with the clutch and make sure to roll back the rpm's and it stopped doing it. So make sure you make some gentle shifts and that might stop it.
Some have also said that heavier oil can cause jumping out of gear.
And yes, you could break something. Imagine running at WOT and the tranny jumping out of gear. Either the pistons will start punching the valves or the transmission may decide to jump back in a gear... instantly. These transmissions are strong, but can't take too much of that before the s'plode

Matt.