50 Lessons I’ve Learned Over the Last Six Years

These are some things I’ve learned, or at the very least thought about, over the last few years. Hopefully some of these ideas are useful to you as well.

Beware of assuming tasks will be simple. They rarely are, even when they should be.
There are no shortcuts to deeply understanding things. It’s incremental. It doesn’t happen overnight (or in a few nights) and there’s no point in pretending otherwise.
“This meeting could have been an email” is a lie, because nobody reads emails.
If you ever find yourself being too confused to ask questions, that may indicate that there is a bare minimum of prerequisite knowledge being presumed, and that you don’t have it. It might be worth figuring out where those gaps are and filling them in, because everything will make so much more sense afterwards. (Or possibly, in hindsight.)
When someone gives you advice, what they’re really doing is mapping their life experiences and knowledge to what they know about you and trying to come up with an insight that will resonate, or at the very least, help. Lots of people are bad at this, so not all advice is created equal. For example, taking time management advice from someone whose brain works very differently from yours is almost certainly a bad idea, and taking career advice from someone with completely opposite career goals from yours is usually also a bad idea. The flipside of this is that following advice from someone whose brain works very similar to yours can be a good idea even if the advice sounds insane on the surface.
Grades are pretty meaningless as a marker of competence. To a certain extent, so are degrees.
A new mentoring relationship doesn’t really become useful until after the first 4-6 months, because that’s how long it takes to build trust (at minimum). It’s not that the first few months won’t be useful at all – if you think they’re completely useless, that opinion is unlikely to change significantly, and you should find a different person to mentor you – but you probably won’t be able to go very deep at the start because you’ll still be building context and vibe-checking each other.
A lot of people seem to think that “networking” is all about meeting people in positions higher than you who can eventually get you a job, and while that isn’t technically wrong, the more useful (and frankly, more natural) view of networking is going out of your way to build relationships with people you work with and with peers at your level because there’s a good chance you’ll cross paths again in the future, and at that point, it will help you to have a prior relationship with them. The world is small.
There is nothing wrong with having a “boring life.” Sometimes, having an eventful life just means that a lot of bad stuff happens to you. And while the story of a tumultuous life is maybe more interesting to tell, it is very, very unpleasant to live through.
The way you get to do really cool (sometimes, even once-in-a-lifetime) stuff is by engaging with things you find interesting, trying things, and putting yourself out there even if it seems pointless or out of your reach. If you do this enough times, you will eventually get to do something cool. What will not help you do cool things is wallowing in your jealousy of other people. (Seriously, putting yourself out there is the gift that keeps on giving. It is very hard for people to tell you about opportunities or offer them to you if you have no track record and they don’t know that you exist. There’s a subset of cool stuff that you can’t just sign up for.)
The fastest way to improve is to be around people who will hold you to a higher standard than you hold yourself. The corollary of this is that dropping your standards when surrounded with people who hold lower standards than you is the first step towards stagnating (or worse, deskilling).
If you really want to tell how good you are at something, evaluate how well you do it when you’re at your worst, not how well you do it at your best. Can you do it in a crisis? Can you do it under pressure? How much of that skillset is automatic for you?
Aimlessly messing around doesn’t get you good at anything nearly as fast or as well as deliberate practice does, but it’s more fun, it’s more low pressure, and it does get you somewhere if you stick at it long enough. So maybe it’s okay not to look down on yourself for choosing to do so.
Talk to people. Reach out to people, even when the anxiety makes writing a short message take 30 minutes longer than it should. It’s always worth it, but only in hindsight.
What stops you from learning things is fear. What helps you drive the fear away is diving into something in a small way on a regular basis, because eventually you start making bigger steps without even noticing.
Not understanding something does not mean you should fear it. It means you should ask a ton of questions.
Popular doesn’t mean bad, and clichés are cliché for a reason.
The things you will regret later won’t be the things you tried and failed at, but the things you wanted to try and could have tried but didn’t. Future you won’t give a shit about how scared you were.
You can be the fullest version of yourself, or you can conform to other people’s expectations of you, but you cannot do both.
The problem with workplaces is that they have to function for the average employee the organization is able to attract, which is not always the same as being maximally effective or efficient in the theoretical sense. Sometimes decisions that seem insane to you are actually necessary for everyone else.
If you hate your roommate, get noise cancelling headphones.
BACK UP YOUR FILES!!!
Ambition needs an outlet. If you’re a naturally ambitious person, burying your internal drive will only work for so long. There’s only so much time you can spend pretending you’re happy with settling for average before your brain starts to go insane.
Sometimes working on projects is a lot easier when no one knows they exist. It’s a lot more difficult to work that way, and it makes promoting your work a lot more difficult but at least then there are no expectations.
If you’re going to work on a personal project, especially a project that will take up a significant time investment, make sure it’s something that matters to you. No one will care about your project more than you. Your project should, first and foremost, be something that enriches your life. (That being said, others liking your work is the absolute coolest feeling.)
When you’ve spent your entire life defining yourself as one thing and that identity is suddenly ripped away from you, that can be awkward and disorienting for a while. But that’s okay – you can always re-invent yourself.
Getting to know your professors is incredibly useful. If a prof actually knows who you are, they’re more likely to recommend you for stuff, take an interest in how you’re doing, offer life advice, etc. Also profs are typically people who know a lot of interesting things and have worked on interesting projects or in interesting places and picking their brains can just be fun.
The main difference between writing for yourself and writing for other people is that when you write for other people, you need to make sure that all of the context that mostly existed in your head for the first draft actually makes it on the page somehow. Sometimes you write something so incredibly specific to you that no one else can parse it and therefore no one else cares.
Universities low-key do not care about doing what is best for students (and also give really bad co-op advice).
You do not have to have the same priorities as other people! The problem with comparing yourself to other people is sometimes they have completely different priorities, goals and backgrounds, and comparison implies an equivalence between your situations that is not actually there.
American portion sizes really are that big; it is not just a stereotype.
Auditing classes is possibly one of the most underrated academic experiences available to students – it’s great because you get to learn something for fun from (hopefully) an expert without the added pressure of needing to stress over fully understanding anything. Being able to have a productive relationship with some aspect of formal education without the added pressure of *academic stress* is very new and feels a little bit strange, but in a refreshing way.
If you are overwhelmed because you are unqualified to do something, finding someone with actual qualifications to do it for you should not be viewed as a failure.
A huge part of working anywhere is understanding the workplace culture and politics and figuring out how to navigate them. Sometimes, not being able to navigate the politics means you won’t be able to actually do your job, no matter how competent you think you are technically.
Effective teaching doesn’t scale super well – the smaller the class, the better it usually is. Things start to get dramatically worse at around the point where there are too many students to fit in a classroom (as opposed to a lecture hall).
It seems like different people have a different amount of “bandwidth” for how many people they can actively keep in contact with at any given time, and also a different amount of “range” in terms of diversity of people they interact with. People who seem to always know what’s going on, or be aware of things you aren’t aware of, or know a concerning amount of people probably have a higher bandwidth and/or range for social interaction than you.
Nothing is inherently unlearnable. Just because something seems completely impossible to you now doesn’t mean it will seem impossible to you even four months from now, and you can learn a shocking amount in a year.
It takes a specific kind of personality to become one of the best in the world at something, and while people who have pulled it off are fascinating to talk to, they do a lot of crazy things to get to the top, and you might not be willing to go down that path.
Education is just as much about passing down culture and perspective as it is about teaching actual content, and that’s sort of where online education (or even just bad education) falls short in general. A program that has no clear perspective and no culture will fail to deliver any sort of coherent experience to students. There are many perspectives that are equally valuable and may be of interest to different people, but there definitely should be a perspective.
It is okay to drop out of doing things. It is also okay to set boundaries. You do not need to do everything (or be able to do everything) in order to seem competent or successful. The voice that’s saying otherwise is called imposter syndrome.
Sometimes people just project confidence despite having no idea what they’re talking about, and once you catch them in the act of misrepresenting their knowledge it becomes a lot easier to ignore them.
People who say things like “sleep is for the weak” are a lot more interested in performing hyperproductivity than they are in actually being productive.
Geniuses and prodigies do exist, and there isn’t much you can do about it. Yes, every once in a while, you might meet someone and feel completely outclassed. But being a prodigy isn’t everything. It’s better to focus on trying to be the best possible version of yourself than it is to attempt to match someone else’s, because sometimes you just can’t.
A really good way to be memorable is to ask good questions at talks and during meetings. If you do this consistently enough, people will eventually know who you are. (This is whether you like it or not. I don’t always like it.)
The bar for competence in the workplace is, at times, terrifyingly low.
When giving presentations, scaffolding – creating a framework or context on which to attach new ideas – is really important because it gives your audience something familiar to latch onto. Being bombarded with 100% new content in a talk is not very conducive to retention or learning. Concrete examples are good, analogies are good, and trying to convey why your ideas should matter to your audience is key.
Academic papers are written for and meant to be read by experts. In practice, what that means is that if you’ve taken one graduate level course in an area, you might be able to stumble through a related paper with a lot of patience, some crying, deep confusion, and some additional research. If you don’t have graduate level coursework in the area (or equivalent knowledge), the paper will feel impossible and you will need to go acquire that knowledge on your own. Pro tip: you’re not really meant to read and understand papers from cover to cover, at least not on first read. No one actually does this.
Part of artistic maturity is getting to a point where you’re comfortable with and confident in your own approach, philosophy, and practice, and where you don’t feel attacked or somehow illegitimate if an established artist advocates for a way of doing things that is completely orthogonal to your own. Actually, I feel like this is part of maturity and confidence in general – it’s being comfortable with the choices you make, even if they’re somewhat outside of the norm, and being willing to stand by those choices.
It’s really important to do what you can to avoid deep burnout. I know people who push through it regularly, but I don’t know how they do it and there’s no way that can be healthy. Every time I burn out, it takes me weeks to get back to a level where I’m actually able to take on a reasonable amount of things.
Be careful not to spend 100% of your time on things that mainly matter to other people. Carve out some time to do things that are just for you as well.