Offer Yourself Up to the Big Cheese

If you’re going to be an assistant, try to assist the most important person in the company that you can. Alternatively, you can assist a high-up-ish person in the area that you’re most interested in, but try not to go down much further than that. This way, you’ll have built-in mentors where it counts, even if they’re not able to throw their weight around as effectively as CEOs. It’s like working on an assembly line that produces stuffed dogs: You can share the workbench with the guy who sews on the button noses. Or you can assist the foreman, the one who supervises the fashioning together of all the doggie parts—someone who really knows, and really cares, about what goes on in multiple areas of the factory.

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The truth is, there’s nothing more demoralizing or uninspiring than doing menial tasks in a vacuum. Like making 500 copies of a document without understanding why everyone on the third floor needs to read it for the company to move forward. It’s too abstract for you to feel invested enough to really hustle. A good boss, on the other hand, gives you the big picture: “We’re trying to sell more Christmas scarves this year,” or “Our mission is to make trucker hats cool again,” or whatever the case may be. A boss like this will confer a sense of context and, therefore, legitimacy to whatever it is that you’re doing.

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Another benefit of working for the big cheese is that they know more than you do. They simply do; that’s why they are too busy and too important to un-jam the fax machine. If you pay attention to them, you will learn some of what they know, which will eventually help you become more like them. You’re learning, by example, what you might be doing in 15 years if you stayed on this course — something you could never learn in school or from a website. You’re also learning what kind of degrees and credentials people at the top have (and what it takes to get there). In addition, you’re becoming privy to all kinds of industry culture and inside scoop. You’re getting firsthand answers to questions like, “Is this world a nice environment, or is it catty and competitive?” and, “Do I even care?” After all, the pursuit of this kind of experience and know-how is the reason people take internships. If nothing else, this time you’re getting paid.