Time Spent Guessing
A hidden cost that we rarely discuss
This is the first of five articles in a series called “The Hidden Tax of Guessing Your Career.” We’re not just wasting time and talent, we are misallocating it at scale and it is time to put a better voice to this issue so we can find a better way to address it.
We tell people to follow their passion. Then we give them almost no real understanding of what that actually looks like in practice. So they guess. Our kids choose a major, a friend selects a training path, or we pursue a new career direction based on what we’ve heard, what sounds impressive, or what they/we think one is supposed to do. Sometimes it is driven by family expectations. Sometimes it is driven by money. Sometimes it is the absence of better information. And far too often, it is simply the pursuit of fantasy. I have called this pursuing a romantic ideal or understanding of what something is.
No matter what it is, at the heart of it is a guess.
And then they commit years of their life to this guess. Not learning a trade in a real environment nor building momentum through doing. Merely, committing to an idea of a career without ever really seeing it up close. What does a junior lawyer actually do on a daily basis? Not in the courtroom, but at a desk at 9:30 at night. What does a first-year consultant actually spend their time doing? What does it feel like to be in the middle of a long shift as a firefighter when it is quiet, repetitive, and physically demanding? We rarely show this part. We show the outcomes. We show the titles. We show the highlights.
So people optimize for something that is not real. Then, eventually, they run into reality. Sometimes that happens during training. Sometimes it happens after years of education. Sometimes it happens after they have already entered the workforce. And when that happens, the realization is simple but expensive. “This is not what I thought it would be.” At that point, the cost is already there.
Years spent moving in a direction that may not fit. Years that could have been used to build skill, income, and momentum somewhere else. This is the first hidden cost; the time spent guessing instead of experiencing. And it does not just stay with the individual, it carries forward into everything that comes next.



This is likely one of the most insightful articles you'll see here. We really do NOT talk about this, or switching costs, or the underlying background economics of our decisions as a whole, and we should. Craig makes excellent points here, and for those of you with high-school kids especially, it's worth a read.