I personally make a guess depending on certain games as to how long I've played them. I've definitely lost track of how long I've played certain games ( especially on console ) like Borderlands or Sonic Unleashed on xbox360. Especially since I never wrote any of that kinda stuff down in middle/high school because I didn't care how long I had been playing in total.
Though, I will say that I like and dislike how Steam tracks your progress in playing games. I was roughly 4-6 minutes off of playing for 2 hours in order to buy some game related account themes but now I'm 2.7 hours in accoring to them because I ended up leaving it on in the background. In the future, I'm not gonna remember I did that, so I'll assume I actually played all that time. There's no nuance in their monitoring. If the game runs, so does their meter of how long it's been on, regardless of you playing or not.
Though, I assume a good solution would be using any form of note taking program and jotting down your play times and dates and any other notes you want. Or using a spreadsheet with that same information. As long as you don't lose that/those file(s), depending on what solution(s) you choose to take, it should be fine as long as you actually remember to do it and aren't lazy about that, like I would be.