On getting better and making progress

I recently met with an old coworker who is making some big life changes by moving to another country and team. It was great to catch up and share about some of the decisions we've both made in the last year to learn/experience new things, better support our families, etc.  As we were parting, she made the comment along the lines, "as long as we're getting better, that's what's important".  The "getting better" part has been bouncing around in my head, stirring up some thoughts.

When we say that we're "getting better", what do we mean?  Similarly, when does it really mean for someone to "make progress" or to be "progressive"?  I believe all of these phrases assume some sort of end state or goal.  When we say them, are we thinking about the end, or are we following a cultural current to make the same decisions as those who came before us?  For example, Patrick, who is 3 years older than me, was a level X in his company at my age, and now is a level Y, so that is what I'm shooting for too.  Or Bill and Mandy did Z by the time their first child was one year old, thus we should as well.

At some point (and ideally sooner than later), we need to ask ourselves what the objective is - what's the point of all our toiling and labor?  Unless we have clarity on this, we can't claim to be making progress.  C.S. Lewis takes this one step further by bringing up "right" and "wrong" in his discussion on progress:

We all want progress, but if you're on the wrong road, progress means doing an about-turn and walking back to the right road; in that case, the man who turns back soonest is the most progressive.

Are we willing to humbly explore with ourselves and others whether we're on the "right road"?  What is the right road, and how do we know if we're on it?  I by no means have all or many answers here, but let me know if it's a topic you want to dialog on.  I certainly welcome it as an invigorating and worthwhile discussion!