1. The degrading job.
Whether you are slinging burgers, managing a cash register, or making lattés for a never-ending stream of office workers who don’t care how early it is, they’re going to yell their order at you and you have to go through it. You have to work at the kind of job that teaches you just how deeply ingrained the concept of social castes is in some people. You have to depend on tips, or the whims of customers, and take all the wrath that should rightfully be directed at your manager (who is somehow never there).
What you learn: What it feels like to be the nobody that everyone takes out their irrational rage on, and how good it feels when someone finally treats you like a human being in that position. (And this will ensure that you will never be that mean customer yourself, because you will know how it felt on the other side.)
2. The awesome job (where no one works).
It’s often a food service job, but it could very easily be retail. Either way, you have an awesome crew of people you love hanging out with, performing practical jokes with, and coming up with hilarious ways to pass your shifts. And the direct result of this is that absolutely no work gets done, and you’re constantly in the process of getting yelled at/on the verge of getting fired for gross insubordination.
What you learn: The workplace is the kind of place where you should have some fun, but nowhere near a lot of fun. It’s probably best to work with people that you can pleasantly tolerate, instead of people you immediately want to become best friends with.
3. The assistant-to-the-assistant job.
It’s important to have that internship position where you are getting the coffee for the person who gets the coffee. It’s important to know what it feels like to be surrounded by power, and influence, and the kinds of things you want to be doing someday — and be completely removed from all of the action and the fun stuff. At the end of the day, the ladder that needs to be climbed to get your way out of the deadly internship cycle is one that is a long one, and has to be started from the very bottom (unless your dad is friends with someone, but let’s not even go there).
What you learn: How these people treat the person who is lowest on the food chain, and whether or not it’s the kind of place you want to be investing your career prospects in if you manage to climb your way up.
4. The “attempt at artistry” job.
At some point you pick up a snapback, learn a couple of deep house songs, and are like “Maybe I should be a DJ?” and actually pursue this for a few weeks. You have to do this, even if it’s clearly unlikely that you will ever achieve real success, because you’ll always kick yourself if you didn’t at least give it a shot.
What you learn: These kinds of hobbies are best pursued in the off-hours of a steady job, and not as a full-time grind kind of thing right off the bat, because the opportunities for it to go incredibly, painfully wrong are much too high, and it’s always important to have money to buy food on a regular basis.
5. The devil-manager job.
The hatred that a low-level employee has for a power-drunken manager is a hatred that has no parallel in modern literature. It’s a roiling, deafening kind of hatred that obscures any kind of perspective you might have otherwise had about the job. And despite the kinds of trials and tribulations it will cause you, it is imperative that you get to know what it means to have that kind of supervisor. Because one day (with any luck), you will be a supervisor, and will have underlings beneath you who are forced to defer, despite the respect they may or may not have for you.
What you learn: What a terrible manager looks like, how they function, what people say about them behind their back, and how not to be one.
6. The “finally, professional!” job.
That moment when you first sink into your fancy, lumbar-supporting chair, look at your own computer and desk, and appreciate the fact that you are working in a “professional” setting after all of that struggling and serving coffees and folding t-shirts, is a great one. But it also can have its downsides, and can easily demonstrate that having the glorified “office” job is not at all a guarantee of professional bliss, and might end up just as unfulfilling or limiting as any other service-based job. (It also might not leave you the time to break out your snapback and practice your DJ-ing skills.)
What you learn: That an office job may very well not be the end of your career pathway, and that there is nothing wrong with that. (Or that it could be what you want, but that there is no reason to judge people who haven’t taken the same path as you.)
7. The job where you want to stay.
Whether it’s a restaurant you love, a small business you can believe in, or an office that has the perfect work-life balance, the best job you’ll have in your 20s is the one where you actually want to stay. Despite the tendency we have to want to move to the next big thing, and to keep it moving, there is something really nice about the feeling of, “Hey, I actually want to start constructing a career here and plan out my future with this job as a component.” It’s a little unfamiliar, and a little scary, but one of the best feelings that a working girl (or guy) can ever have.
What you learn: Settling can be awesome! 
