I realize that everyone's process is different, but I feel certain that every woodworker has certain waypoints on his or her journey. For beginners, it may be as simple as a straight cut with a circular saw. For seasoned veterans, perhaps the hand-cut full blind mitered dovetail.
For myself, I started in woodworking because I had an original idea for a coffee table, and was too frugal (i.e., cheap) to pay someone else to execute my design. Countless hours later, I had one hell of a sturdy coffee table. There came a tremendous satisfaction in finishing a project, even if it was nothing but a bunch of strips of plywood. That was Milestone #1: Completing the First Project.
Another milestone for me was my first decent set of hand-cut dovetails. It took 6 tries, and they still don't look 'good' but at least I didn't burn these. Oddly enough, to date I have not used a dovetail joint in a project I've built.
Some other milestones for me include first (good) M&T joint, first working jig, first improvement to existing machinery, first commission, first (good) panel glue-up, and first project SWMBO would allow me to leave in the house. I may be using the Milestone moniker a bit loosely, but you get the idea.
I hit another milestone today. It was this: "Dude, those are way nicer than what you see in the stores." That was my buddy, referring to a pair of end tables I made this weekend. Admittedly, he furniture shops at Big Lots, but the reverence was genuine.
Also, for some of y'all, there's got to be a point at which you don't reach many more real milestones. The learning curve has pretty well flattened out. I mean, is there ever a point at which woodworking becomes purely rote execution, or is there _always_ a challenge in it? For all the work I did on two end tables (and two accent tables last weekend), I figure I've got small tables down cold. At least, small tables with 2x2 legs and 4" aprons and dowel joints. :)
So what is the standard by which we measure our growth? First project? First dovetail? First commission? First cabinet? Or maybe Last cabinet, Mr. Watson? Anyway, I'm rambling a bit, and was curious.