I’ve been cutting my own hair for several years. I use a clipper on the sides and back, and scissors for the top and front, which I like a little longer than my clipper guards will permit.
Once you get good at it, it doesn’t take much longer than a typical shave-brush-and-floss session, although this will depend on your hairstyle.
I started out with trial-and-error, and my approach was simply to pick up some hair between my fingers and cut it shorter. You’ve probably seen your barber do this. The important thing is to be conservative… “measure twice, cut once” as the carpenters say.
Just watch yourself carefully in the mirror, and be sure to re-comb your hair often, to see what it would look like if you stopped there. If one area looks a little bushy, cut off some more. Wetting your hair makes it easier to handle, but gives a less-accurate picture of how it will look when dry. You get used to judging the difference.
With practice, your ability to judge where and how much to cut will improve, but it’s largely a matter of learning by doing.
(It was for me, anyway… a pro barber might have a more systematic training method.)
I can’t see the back, but that’s never been much of a problem. I can reach back there and feel it, and that’s always worked out just fine. The barber who used to cut my hair has complimented me on the quality of my results, so I think I’m doing pretty well.
Again, the important thing to remember is that this is more of an art than a science… you have to practice and learn from experience how to interpret what you’re seeing and how best to cut it.
If you’re a really busy guy, or naturally impatient, or can’t risk screwing up, then you probably shouldn’t try to learn this, but with practice, you’ll get to the point that you can confidently cut your hair the night before a job interview. I did, and I got the job!