I've had a few conversations over the last few weeks with people from past lives and various industries talking about what success looks like, and what the enemy of success is. There's an overwhelming consensus that the things that you don't know are what really get in the way. Ed Catmull talks about this a little in Creativity, Inc., where it's extra perilous in creative fields. In my line of work, it's often that experience isn't gained until you, uh, experience it. I've also seen it happen where sales people, company founders and others struggle because they don't know what they don't know, and aren't listening to the right people to tell them what they don't know.
I've made these mistakes before. In my current gig, I did the things that I always do, that have served me well, but did so without regard to the change in context. I found that what works in smaller groups does not work in larger groups. People told me it wasn't going to work, but I didn't listen. The macro changes really made a lot of sense, and still do, but drilling down to the implementation level, the changes did not. I was half-wrong, but it didn't feel good to be half-right either.
This is one of the reasons that I value self-awareness as one of the most important qualities among leaders and people I consider successful. It's a hard thing to practice because no one really feels comfortable with getting it wrong. You would also think that giving yourself a pass for the things you don't know would go a long way, but it often doesn't.
When I was about to graduate from college, I was fairly convinced, as a matter of fact, that I would pursue a career in radio, and eventually, buy a few stations in rural areas and live a fairly modest lifestyle with a mini-empire of broadcast licenses. This path was borne partially out of arrogance, sure, but it was with zero expectation that the Internet was going to fundamentally change how we listen to music. I mean, I listen to music in my car now from individual audio files coming from a streaming service over a cellular telephone connection built into the car! Not only did I not see the Internet coming in that way, but I didn't see ubiquitous connectivity as a thing. It will be coming from low-orbit satellites before you know it.
On the plus side, once you have a little bit of that experience, it can go a long way. A few years after college, I abandoned the broadcast world for the Internet that was taking over everything, and that experience helped me see a more obvious future. When I was working for Penton Media, I was telling the publishers in my group that the printed vendor guides, and eventually their magazines, were going to go away as they knew them. People were still working with dial-up Internet connections then, but I said, just you wait, it will be everywhere eventually. I mean, we had Palm Pilots then, which weren't connected, but it was an obvious future. The publishers weren't having it, because, "But you need a computer to look up the directory," and, "No one wants to read things on a screen." You know how that turned out, but Penton eventually fired almost everyone and was delisted from the NYSE.
In my own career progression, it's funny how some of the things you get by way of experience are things you don't apply directly. My last few gigs, especially when consulting, included red flags that I saw early on, and I eventually ended up issuing "I told you so's" (tactfully, of course). In those cases, you have to let the people you work with come to those conclusions themselves, which is still not super fun.
This idea that what you don't know you don't know is frightening. Seriously, who wants to engage in risk if it's the things that you don't see coming that could bring you down? Maybe the real trick is getting just slightly ahead of the scary things before you get blindsided.