In some ways this job is like a maze: where we wind up is rarely where we think we’re headed from the start. We also have limited information with which to navigate and, though there are methods and skills we develop to help us make the best decisions possible, sometimes the lack of information leaves us with nothing better than a gamble.
I’ve had several big successes in my career and honestly I’m less responsible for those successes than people would like to believe. Likewise, I’ve had some failures, and honestly I’m less responsible for those failures than it would seem to a casual observer. Certainly there are ways to measure CTO abilities and outcomes, but usually you have to dig in deeper than the resume bullet points or anecdotes that are often the only things communicated.
You can go through your maze and make all the best decisions and still hit a wall, or you can go through and make all the wrong decisions or act chaotically and get through in record time. Over a large enough sample size outcomes will normalize, but few of us do this long enough to get there, and usually early outcomes lead us into the mazes of our future.