Sometimes it's because we went through the trouble of making the mistake for you.
I got my start with an old CB radio, a shortwave radio my grandfather gave me, and a scanner. I had some truly awful antennas early on, but I made do.
Problem is, now I have the money, I don't have time. I've got a lot of cool toys tools at work to play with. I suspect when I retire, I'll get more involved in the hobby again. Right now, it's sort of limited by time.