Now that I have college-aged kids, I’ve been thinking more than usual about life paths.
Mainly I’ve been considering the daunting transition most of us make from the realm of school to the realm of work.
A good education is a wonderful thing. But the mechanisms inherent in the education system are poor preparation for the environment most young people move into after graduation.
I’m thinking specifically of a certain type of student who is driven and bright and conscientious. They are accustomed to succeeding through hard academic work - but that kind of work doesn’t map well onto what the private sector requires.
These high achievers distinguished themselves in school by succeeding within a set of well-defined parameters. Their exams and papers were graded with numbers and letters. On the majority of these, there was a right answer or a wrong answer. They listened to their professors explain a particular domain, whether physics or art history, and then showed their grasp of the topic.
The end result was a series of grades on paper that could be averaged into a GPA and ranked against peers.
Students who excel within this system are rightly proud of what they have accomplished. But ironically, that very success can set them up for a tough transition into the working world.
Here are the specific ways I see the world of work differing from the world of school, and why that matters for both new employees and the people hiring them.
In school, there is usually a “correct” answer.
At work, there rarely is.
This makes working sharply different from school. Unlike those right or wrong answers in school, the young employee faces an environment of great ambiguity. They will have certain responsibilities and goals in their job, but they won’t get a syllabus or a predictable grade every few months. Their success will be much more “Choose Your Own Adventure” than they are probably used to.
Even in well-defined roles, underlying questions always lurk in the background: Would a different way of doing this be better? Should I even be spending time on this in the first place?
Consider something like launching a new product feature. You could launch it quickly to beat a competitor to market, but it might have bugs. Or you could delay the launch to polish it, but lose the advantage of speed. Or you could launch a scaled-back version that splits the difference. None of these is the “right” answer. Each has pros and cons. You won’t find out if you were right for months or years, and maybe never at all. You are choosing between options that all have merit and all have drawbacks. You’re making trade-offs.
This is true across almost every domain of work. How much should we spend on this marketing campaign? Should we hire for this role now or wait for a better candidate? Should we enter this new market or focus on our core business?
These questions have no answer key in the back of the book.
School punishes failure.
Work requires it.
School encourages the student to learn material and then demonstrate their mastery with as much accuracy as possible. Work requires the employee to experiment and iterate to find the best solution - and that’s going to entail a lot of failure.
It would make no sense to mess up the midterms to do better on the final exam, but that is in many cases how achievement at work comes about. The new employee will need to learn an iterative process that academia doesn’t teach well:
Well, that didn’t work. That’s OK. Here’s what I learned, so let’s try this next.
At work, learning often resembles a series of errors. That will be uncomfortable for most A-students.
Your professors gave grades.
Your boss operates on perceptions.
Professors determine grades in school, of course, but in most cases they had to defend the grades they gave from an objective standpoint. There was that strong sense of “correct” or “not correct.”
Once the young person starts their first job, that changes.
It matters less that they are doing a good job and more that their boss THINKS they are doing a good job. They may still get something resembling a grade in the form of an annual performance review, but there’s a thick layer of managerial subjectivity between their work and that review. They will need to be savvy about what their boss values. They will need to make the case, over and over, that they are doing a good job. They can’t rely on the boss to see their brilliance and automatically give them an A.
School rewards independent study.
Work is a team sport.
Generally, academia encourages working independently. The primary goal in undergrad is the enrichment of one’s own brain. That is a wonderful thing.
But in the world of work, the young person needs to do much more collaboration than the occasional dreaded “group project” (the one where there was always that annoying slacker). At work, it’s mostly one big group project. The new worker needs to understand the complex, idiosyncratic humans on their team and how to deal with their personalities (including their manager). That will affect their career a great deal more than interpersonal factors affected their grades.
School will expel you for plagiarism.
Work needs you to steal good ideas.
There’s no greater academic sin than stealing someone else’s answers or copying their work. But in the private sector, stealing is required. A talented employee must determine what the best ideas and approaches are, adopt them, and adapt them to their own uses (within legal and ethical limits, of course).
If they sit alone and try to reinvent the wheel each time, they won’t get far.
Half the work is identifying who those smart people are and which of their ideas to adopt/pilfer/steal, but the new employee will do need to do it.

The world of work rarely gives the employee a clear rubric or a final grade like the student gets.
Employers and managers who are looking to capitalize on newly graduated talent would be wise to understand this dynamic. If you do, you can better help great students become great employees who get to contribute their best every day.




“School punishes failure.
Work requires it.” Oof! This is so powerful and so very true!
So much truth n this and yet the irony is employers are often equally blinded by a fixation that exam grades or the brand of a school college or university is a hallmark and assurance of quality. We are both critical of the system and yet perpetuate and reward it