
I don’t know you as well as I would like, but I do know one thing.
Being fired the moment Monday rolls around isn’t the worst thing that could happen to you career.
In fact, I have the full force of math behind me when I say that it might even put it on an upward trajectory when the dust settles.
Let me explain.
The vexing question of when to stop picking
By now, you must have encountered the secretary’s challenge, which asks you to imagine that you are recruiting an executive assistant with 100 candidates.
Being short on time and wanting to make a strong choice under uncertainty, you want to maximize your chances of choosing the best candidate without seeing them all.
How many people do you interview for this job?
Believe it or not, the answer is nowhere near 100.
Actually, it is 37.
Mathematicians who study optimal stopping have shown that when options are available in a row and you cannot go back to previous options, the best strategy is to spend about 37 percent of your first opportunity to observe without completing the observation (e.g., Ferguson, 1989). You use this stage to get a sense of the scope of what’s out there, and then you choose the next option that trumps everything you’ve seen so far. This approach maximizes the probability of obtaining the best overall selection.
It’s not a waste to pick up enough to read your environment and how you fit into it, as it’s a prerequisite to making the best decision you can.
Now think about how you got to where you are today.
Have you learned what 37 percent of your options are available to you?
Or did you take the first or third viable path, with early definition and quiet pressure to commit before you had enough information to know what you were doing?
Careers are less like careful optimization and more like early closure.
How to deal with inadequacy
Developmental psychologist Alison Gopnik described the difference between children and adults using a simple metaphor (Gopnik, Griffiths, & Lucas, 2015). Children act like lights, casting a wide light and exploring a wide range of possibilities. Adults act like flashlights, focusing on what is immediately relevant and filtering out the rest. In experiments, children consistently outperform adults in tasks that require discovering unusual patterns or hidden rules because they search more widely and remain open to alternatives.
This change comes at a high price. When we narrow too early, we stop seeing the full picture of the options available to us.
Arne Gullich and his colleagues show a similar pattern at the highest level of performance (Güllich et al, 2025). Among the tens of thousands of elite performers, the road to the top is rarely as straight a line as our professional advisors would have us think.
Early specialization is the exception, not the rule, when it comes to the greats. Many top performers delay commitment, move across domains, and build a broader base before committing. This longer selection period allows them to find a better match for their ability and field.
And so we’re stuck somewhere along trajectories that may have peaked years ago or still have room for growth, without a clear sense of what’s right.
The good news is that where things are today is more important than if we were to open the search.
That’s why it makes sense to take back control of the selection process and deliberately start exploring again, even if you feel stuck in your current role.
Two ways to restart the selection process
First, get your mind back into search mode by reading three books at once.
One should reinforce a strength you already have, challenge an obvious weakness, and the third should be completely random. By doing this, you reset the habit of broad scanning rather than narrow drilling and allow yourself to let go of what doesn’t serve you and put away the book that no longer holds you. attention.
Second, make your counterfactuals realistic.
Return to a critical decision point in your life and retrace the path you didn’t take. If you didn’t have your current job, what would you do instead? What was your backup plan if your first choice for college fell through? Most people can answer this quickly because the alternative was real at the time.
Now take the small paths to it. Read what you read, learn what you learn, talk to people in that space, and immerse yourself until the alternative stops feeling hypothetical and starts feeling viable again.
Grit has its place; When you’re on the right track, it helps you stay on track and makes sure you don’t stop prematurely.
But when you’re locked in too early, it becomes the glue that binds you to a version of your life chosen with very little information.
So don’t waste your grain on the wrong hill.
Broaden your search, improve your fit, and then try hard instead of climbing your own personal Mount Everest.




