A few months ago, I wrote about the general observation that scaling is always the problem in a wide variety of life and work endeavors. I still believe that, but the problem definition itself scales... it's not just one thing. Experience is a problem, too, and I don't think it's always valued the way that it should be.
I lived through (no, experienced) a period of time where we roundly rejected experienced people in business because they were too stuck on the old ways of doing things. This was the dotcom expansion. We were correct in that those people didn't have the experience to guide us through this Internet revolution, but we were also arrogant to believe that we had all of the answers. More specifically, we didn't have the experience to figure things out. No one did because we didn't really have a situation like that. No one did.
It didn't last, as the expansion was replaced by some painful contraction. We had to learn a lot of new things because we had no mentors, since they didn't really exist. We gained experience by doing since it was the only way to get there. By the end of the last decade, as people stopped chasing Internet unicorns as a business opportunity, realizing that there were enduring practices and principles that could help us build sustainable businesses, we started to learn from people who had the conventional experience that we rejected only a few years before.
This cycle demonstrated to me that experience is vitally important, and you can't really buy your way into it. You either have it or you don't, and if you don't, you need to get it. It comes by learning the hard way, or learning via mentors and people who already have that experience. The latter is far more efficient, obviously.
I was catching up with a friend recently, comparing our long-term experiences, and also how those compare to what others have. In our cases, we both had a series of jobs where we worked with really great people that taught us how to be professional software developers. We've rarely had to be the "smartest" people in the room, because someone else was always better. Even as we've reached more of a management stage of our respective careers, we rely heavily on people who are better at the things that we're not good at. It's how you hire.
The times in my career that I've struggled the most are the times I had to learn without reference or help. I had to invent things that frankly had already been invented, but you don't know that without people to tell you as much. I remember a consulting gig I had a dozen years ago or so, because I only had one other person on the project, and he was very junior. This was a great thing for him, because he got a ton from me, but I had to figure stuff out, which was not great for me. A few years later I learned a bunch of stuff from others that was like, "If only I had people to teach me this stuff back then." I'm sensitive to that these days, because there is a significant technical cost when you don't have mentored experience to build stuff up. The self-learned experience can be a liability to an extent.
Knowing whether or not you or your people have the more efficient experience is another one for the self-awareness bucket that I value.