Two Different Places and Rambling

I heard from one of my old bosses this morning, who has finally (after over a year) secured a position in Seattle.

It's always nice to hear from old co-workers, especially when they've secured new employment. You of course ask a bit about the new company, are they moving and selling/renting their house, how things are going in general, etc. - and then follow up with a short update of your own. You make the generic comments about "Hope to see you again" - although in this case, I actually do go to Seattle from time to time and have a chance of running into him again.

Contrast this with a random thought yesterday: on a whim, I went to look up someone I knew while doing business at The Firm. Turns out she has done well for herself; so well, in fact, that she has moved to the next level of licensing and could potentially go out on her own if she so desires. She has done very well for herself since she entered the industry 8 years ago.

I bring these two up in juxtapose as I consider my own career path 20 years later. I've changed careers 4 times and moved around a great deal, but I continue to hold the title and responsibility I hold the same as I have for 8 years. Have I truly advanced in this field? Have I truly moved forward? Or do I just do the same thing at different places? Could that be part of my dissatisfaction?

The reality is that for what I do now, there is no real end game. The only path is up, with decreasing positions and similar responsibilities. Is that what I want? Is the fact that more of the same is not that attractive driving me to this contradiction of seeking that which I subconsciously don't want to seek?