I'm just a novice, or an "advanced beginner" at best. The first bourbon I had was I.W. Harper and I thought it was awful, more or less. Just based on that experience I was determined to find a better bourbon. I did a lot of research on the internet (I couldn't ask friends because almost no one knew anything about bourbon) to find something better.
I figured out I should try Blanton's. So I tried that and W.L. Weller Centennial and bought a whole lot of other bourbons either in bars or in liquor stores, in mini-bottles or pints whenever possible. (Including ryes and scotch and J.D....what the hell it's all whiskey, right?) I'm still buying and trying, probably always will be.
I appreciate all the advice about how to go about things systematically, but that isn't always possible. You're in a bar and you order something you've never tried before, and that's your experience of that particular whiskey. You form an opinion based on that experience. It's an entirely human thing to do.
The process of finding out what you like and don't like should be--or at least can be-- chaotic and random and haphazard. Systematic tasting may have its place but don't discount the beauty of random experimentation.
I do agree that it's good to use some lower-shelf stuff as a basis for comparison. I try to keep the I.W. Harper in my liquor cabinet even though I don't like it just so I can remind myself from time to time what drove me to seek out something better.