One good idea can take you pretty far

I get a fair amount of inbound from college students or early/mid twenty-somethings of the “how do I get into venture/startups?” variety. Usually my kneejerk response is to be careful what you wish for, and that you probably don’t yet realize that this job is a bad fit for nearly everyone with a well-adjusted personality. But I digress.

More practically and less cynically, it does sometimes put me in the position of having to think through what kind of advice might actually be useful to an ambitious and enterprising twenty-something. What kind of things do I frequently see 25-year-olds get wrong in the workplace? Where did I personally err, and what would I go back and change if I could?

If I could give one broadly applicable piece of advice, it would be this: Do not feel like you have to know everything about everything, or like you are supposed to appear like you have knowledge, opinions, or answers about everything and anything. In fact, don’t become convinced that “developing” in your career means having lots and lots of ideas or angles or secret wisdom or “theses”. You don’t have to know it all, and you don’t have to do it all. You just need to be on the lookout for the occasional very, very good idea.

This is not an argument against having broad interests or reading widely. Or having a multi-disciplinary approach, or just being curious and hungry for knowledge in general. All of that is wonderful and very human.

What I am saying is that many young professionals think that “success” means “appearing credible”, and appearing credible means having all the answers, knowing all the things that you’re supposed to by a certain age. This leads to an ambient, throbbing anxiety that not having clever takes or opinions or answers to anything that might come up during work hours makes you a fraud. 

What I wish I could convey to these folks is that it’s totally okay to be dumb, moronic, or uninformed about most things as long as you are occasionally brilliant about something important and big. That you can actually gain more respect in the workplace by being spiky than by being well-rounded. That if you start to think that everything is important (or worth knowing, or worth doing, or worth having an opinion on) you’ll never quite be able to tell what really is.

I’ve been a venture capital investor for over 8 years at this point (11 years total in the software industry). And I can honestly say, with a straight face, that I’ve had no more than 4 or 5 original and valuable insights (we call these “investment theses” in the biz) in that entire ~decade. I mean, I’ve had lots of other ideas, but only a handful have the combination of importance/scale, actionability (we can execute an investment that takes advantage of it), non-consensus-ness, and asymmetry to actually be worth betting the farm on. My entire investing record is a consequence of a few individual thoughts that grew into big ideas that became very important to me.

This is pretty counter-intuitive to how we model behavior in school. Business school especially (and consulting, and Fortune 500 jobs) teaches you to be well-rounded. Polished. Inoffensive. Eager. Thorough. Curious and questioning, but only about some things. This is somewhat analogous to the idea of being “big company”. Big company-ness is just what happens when being well-rounded gets expanded large across a whole population of people. Everyone CYAs, knowledge is power, 40 slide decks with 8 point Arial font text (with no main point to make), everyone talks talks talks because everything is important to know, everyone networks networks networks because everyone is important to know. It’s no wonder these folks have such a hard time adjusting into startups, where the name of the game is picking 1-2 objectives and ruthlessly ignoring 95% of other stuff that comes in the door.

Here’s two phrases I almost never hear from college students: “I don’t know” and “I don’t care”. Obviously I am not saying that they should act like flippant, jaded dicks. But I think that in a (business) world where everyone is in such a rush to be as broad and agreeable as possible, it’s healthy to have an appreciation that saying “yes” to the most exciting areas of inquiry means saying “no” to lots of stuff that you feel “meh” about. In some ways, it’s not just healthy, it’s brave.

I guess what I’m saying is… relax? Classwork starts out with an unread textbook and ends with a test, but most careers aren’t like that, there’s no bonus points for being thorough. If you wake up worried that you need to learn everything about everything as soon as possible, you’ll never get out of bed in the morning. But if you take the attitude of “I’m just going to try and discard all sorts of things until I find the right hill to climb that works for me”, work life can actually be a lot of fun.