That doesn't happen. There's a trip energy graph which shows your projected remaining charge when you reach your destination, and compares it with the actual usage. Energy use is strongly dependent on speed, so if you find yourself using more than projected, you can slow down a bit (5MPH is generally plenty) and get back on track. If you use more than expected you can see this happening with plenty of time to spare and take appropriate actions without any worries.
One of the nice things about an electric car is that the measure of remaining capacity is really accurate. In a typical gas car, anything below ~50 miles of range is basically a crapshoot. In an electric car, if it says you can make it 5 more miles, that might actually be 4, or 6, but it won't be zero.
I don't know what happened with the author, but given the total lack of discussion of the trip energy use graph in the article, I suspect he was not using all the tools available to him and misinterpreted something. That's not to make excuses for Tesla; they seriously need to improve their trip planner to stop being so stupid. However, if you take five minutes to familiarize yourself with the car and the tools it provides you, then there is no worry about the battery suddenly jumping to -22% and leaving you stranded. It's certainly not an "inevitable occasion."