Thus far, orbital skydiving has been the province of Star Trek and Starship Troopers, but new technological advances that deal with the heat of reentry could make orbital skydiving the next extreme sport.
One of the current barriers to orbital skydiving is protecting the diver from the extreme heat of reentering the Earth's atmosphere. But NASA may have developed a solution in the form of the Inflatable Re-entry Vehicle Experiment. The IRVE is vacuum-packaged around a cylinder of gas, so it can be quickly inflated and deployed upon reentry. In NASA's test, the IRVE successfully resisted the heat of reentry at subsonic speeds.
NASA is developing the shield in hopes of using it in a future Mars mission, but it may have applications right here on Earth. The company Orbital Outfitters is exploring technologies that would make regular orbital dives feasible. Their plan is to bust Colonel Joe Kittinger's record 102,800 ft jump and to make a habit of it, allowing wealthy thrill-seekers to plummet to Earth from space. You will still, of course, have to check your fall plan to ensure there are no giant drills in your trajectory.