31 Things I’d Have Told Myself Before College

It’s been almost a year since I graduated from college. I had an incredible four years at the University of Chicago, and learned more than I could have ever anticipated. Now that it’s in the past, I sometimes wonder: what do I wish I knew before entering college that I know now? Here’s the advice I’d have shared with my 18-year-old self:

  1. Master the art of asking great questions.
    Questions are the driving force of learning. The faster you can optimize your ability to learn, the faster you’ll get where you want to go.

  2. Outside of exams, forget about knowing the right answer—you’re wrong most of the time, anyway. What’s more important is knowing where and how to find the variety of answers that are most likely to be right.

  3. Talk 20% of the time; listen 80% of the time. One of the fastest ways to win someone’s favor is to give them permission to talk excessively about themself—you can do this by asking great questions. One of the fastest ways to lose someone’s favor is to talk excessively about yourself—strive for verbal staccato, and speak only when you believe it will contribute value.

  4. Understand that college is an imperfect friend filter. Just because the admissions process is selective does not mean that everyone you meet in college will be your friend. You must curate your own network; nobody is going to curate it for you. Recognize that you are the average of the five people you spend the most time around and that it’s up to you to be proactive about finding and building friendships and communities, inside and outside of school, while you’re a student.

  5. Quit early, quit often. The fastest way to “find your passion” is through the process of elimination. Try as many things as you can as early as possible. Internships, clubs, sports, social groups. Create criteria to determine what you value in each of those activities, then one by one quit those activities and hone in on the ones that fit you best. This seems obvious but the only way I’ve gotten to a place where I’m relatively comfortable with high commitment levels is through the process of elimination. To truly commit to something, you have to know that there aren’t that many other things which would be a better use of your time and energy.

  6. Find or create unconventional internship opportunities for yourself. Go beyond your college’s career services center to seize truly unique and interesting opportunities. Prioritize unpaid internships with greater opportunities for learning over paid internships with lesser opportunities for learning. View every experience as an investment in your future–not for the stamp it will put on your resume but for the things it will teach you about your purpose in the world. Read Recession Proof Graduate and Mastery.

  7. Learn to endure haters. Sometimes the process of joining and quitting works out smoothly–you join a club, enjoy it (or not), learn something (or not), stay a while (or not), then go on. Other times, particularly with activities that require higher buy-in and groups whose participants pride themselves on their unique, secretive, or exclusive identity (such as fraternities or sports teams), your act of quitting may result in hateful social backlash. Understand that others’ hateful comments are almost always an expression of the haters’ own insecurities, and usually have little to do with you. Winston Churchill said that if you don’t have enemies, you’re doing something wrong. Rather than taking haters’ comments personally, use them as validation that those people were never your friends in the first place, and that you’re probably doing something right.

  8. Engage with conflict. If you want to lead yourself and others, you’ll need to get comfortable making complex decisions that involve tough trade-offs (often offending people that you care about). Leadership is a contact sport. The trick is to be as fluid, harmonious, compassionate, empathetic, and loving as possible, especially with adversaries. Remember that you’re usually wrong, that political bickering is childish, and that picking your battles wisely will win you the war.

  9. Rethink the risks of standing out. Conformity offers emotional security, comfort, and “fun”–in most institutional settings, it’s “cool” to conform. It also tends to be “uncool” to stand out (until you’re successful). The short-term risks of standing out include short-term embarrassment, rejection, alienation, and failure. These things hurt, so our natural tendency is to avoid them. In avoiding these risks, we often undervalue the potential benefits of standing out: rapid learning, unique experiences, memorable stories, and meaningful self-discovery. Standing out seems riskier than conforming. But nobody ever talks about the risks of conforming: boredom (the worst of tortues), an uninteresting narrative (you’ll never land your dream job), regret (we don’t regret the things we do; we regret the things we don’t do), a long and frustrated journey through the rest of your life (stemming from a lack of self-awareness). The “road less traveled” is often also the path of least resistance because it’s not a rat race.

  10. Understand that college is a fundamentally risk-mitigating institution. Student status offers access to the most incredible resources on the planet: conversations with the world’s wisest people, access to incredible libraries, instant forgiveness of most mistakes. The only real risks in college are those relating to finances, family, and your long-term reputation. Everything else is just a perceived risk.

  11. The sooner you learn how to not take things personally, the better.

  12. There is a difference between taking offense and standing up for what you believe. The first is tied to your fragile ego. The second is grounded in your true self.

  13. Get into the habit of recording “fringe thoughts.” These are the thoughts that happen when you’re in the shower, on a morning jog, daydreaming, and drifting off to bed—they’re your moments of minor genius. Keep a notebook near you so that they don’t flit away never to be remembered again. Capture them, internalize them, and if they’re good, don’t be selfish: share them.

  14. Consider turning these “fringe thoughts” into some form of public writing to begin exposing yourself to public criticism. Start a blog, record your best thoughts on it, and share it with a few friends. If you state what you believe most deeply, then the comments will range from praise and agreement to criticism and disagreement. Don’t be surprised by the latter–criticism is a natural circumstance of living in line with your values. Nobody will remember later what a fool you seemed (because indeed, you might say some foolish things); rather, many will eventually confess that they admired your boldness and commitment to self-determination but were afraid to admit it at the time.

  15. Build a personal brand online. Purchase your personal domain name then link it to your blog and/or a portfolio page. If you link it to your blog, people who Google you (potential employers, usually) will learn how you think. If you link it to your personal portfolio page (super-resume), people who Google you will see that you take your work seriously. Either way, the bottom line is that you want to control what people see when they Google you. Owning your domain and projecting a positive identity will set you apart and make you remarkable to employers because so few students do it (most are just advised to drop their boring resume into a pile of thousands, never to be seen again). Use http://strikingly.com to make a beautiful personal portfolio of your college experiences quickly and easily.

  16. Learn about stoicism. Life is unpredictable: to win, you have to learn to thrive in the chaos. Having a philosophical system to support this helps tremendously.

  17. Read books that will change your life, especially the classics. For some of the denser material, finding the right translation can offset potential boredom. Think of the time you spend with ancient authors as time spent with the best mentors of all time: nowhere else can you find the same level of wisdom-density and intellectual return-on-investment. If you’re really not a natural reader (trust me, I wasn’t), try this set of techniques.

  18. Read the blogs of people who inspire you. They provide ongoing inspiration from living sources, and can sometimes even lead to new friendships. Derek Sivers, Tim Ferriss, Cal Newport, Chris Guillebeau, Seth Godin, Sebastian Marshall, Jason Shen, Ben Casnocha, Julien Smith, Ryan Holiday, Ramit Sethi, Brainpickings, Leangains, and Leo Babuta have all influenced my thinking.

  19. Tell your family how much you love them. If you’re moving away for college, you’ll feel pangs of homesickness and loneliness. In those moments, pull out a pen and paper and write the things you wish you had the courage to say to your family. Then put those writings in the mail and send them home. Always consider the possibility that everyone you love could die tomorrow; would they die knowing how you truly feel about them?

  20. Accept that death is a natural part of life, and think about it a lot. Think especially about what you would regret having not done if you died tomorrow. Do not defer your dreams.

  21. Even though your parents mean what’s best for you, they probably don’t know what’s best for you. As much as they love you, you must understand that they too are human: their desire for legacy and the pride they feel about the worldview they’ve developed can compromise the quality of their advice. To reduce your dependency on them and increase the control you have over your future, you must self-educate, take calculated risks, find means to separate yourself financially, and gently cut the cord.

  22. Be very selective with whose advice you listen to. A lot of older people love to give advice because it makes them feel important; be aware that everyone has their own projection bias and will rarely give advice that’s fitting for your personal goals or intentions. Only listen to advice from: a) people who’ve done what you want to do at the scale you want to do it [or who’ve built what you want to build at the scale you want to build it], b) slightly older and more accomplished peers who inspire you to be better, and c) your gut. And remember that the best mentors are the ones who ask you tough questions rather than telling you what you “should” do. If someone prescribes advice or uses the phrase “you should” before they express genuine interest in understanding who you are or what you care about, then they’re probably not someone you want as a mentor.

  23. Don’t complain. Everybody’s suffering, and most people are suffering much more than you are. Instead, when you find yourself feeling like complaining, pause and look inward to ask: “why do I feel this way? What can I do to change my circumstances?” If you can’t do anything to change your circumstances, then just smile and keep breathing and eventually things will work out; if you can do something to change your circumstances, then take action and stop waiting around.

  24. Play the student card. “Hi ______, My name is Zack and I’m a student at the University of Colorado…” works every time. People love to help students by giving time, advice, and resources. Use this while you still can.

  25. “Character cannot be developed in ease and quiet. Only through experience of trial and suffering can the soul be strengthened, vision cleared, ambition inspired, and success achieved.” - Helen Keller

  26. To this end, front-load discomfort. The more uncomfortable situations you opt into early in life (so long as you approach them with the intention of self-betterment and learning), the better you’ll know yourself, and the less likely you’ll be to experience a quarter-life or mid-life crisis later. Long-term regret is so much worse than short-term fear, failure, or rejection. Discomfort does not equate to unhappiness. Nothing worth doing is easy. One friend of mine calls this optimizing your “second derivative learning”: focus less on short-term cash, grades, and other “first derivative” achievements and more on the learning, character-building, and practice behind them. Another friend thinks of his life like a rocket ship, and the purpose of his college years was to fill the tank with as much high-octane fuel as possible by training his mind and body to endure the tests of higher-stress activities later in life. Laziness during youth is the biggest waste of all, since our college years are the ones during which our body can handle the greatest strain. “Fame is a vapor, popularity an accident, riches take wing, and only character endures.”

  27. Do things that make you speechless. If at any time you’re perfectly able to articulate your stage in life, then you’re not moving fast enough. “Fear is a compass pointing true north;” trust the compass. Constantly be making epic moves to surprise yourself and others. Be like the honey badger: shove your face into the beehive first, then find the larvae. Put yourself in situations where you’re in over your head, then look to the gods and your inner strength to force yourself to rise to the occasion.

  28. Keep your allies close. Build an inner-circle that you keep posted every couple of months through an e-newsletter. Fill these updates with personal and professional happenings, discoveries, and most importantly: challenges. Vulnerability is the best way to build trust with your inner circle of champions and evangelists. These people will appreciate your inclusion and respect your effort (even if you’re not a very good writer).

  29. Travel internationally. Ideally as a volunteer or an intern rather than through a formal “study abroad” program. It’ll be harder, you’ll be forced to engage with the culture more intensively, and you’ll have a grittier experience–it’ll shake you to your core and challenge your assumptions about why you exist. Plus, you might actually make money. Study abroad programs, by comparison, are likely to shelter and insulate you, drain your wallet, and short-change your potential.

  30. Leverage the resources that your college campus offers. One writer calls this “finding hidden education subsidies”. Most people go through college thinking that they’re paying for a diploma and some classes. Well, if you’re on campus anyway, you’d better milk it for all it’s worth. Seek out funds to support your travels, and travel as much as possible: to conferences, other cities, other countries, additional educational opportunities, and more. Tap into the alumni network and meet with alumni that have pursued careers that interest you. Go to events with interesting speakers and approach the speakers after the event; get their business card and set up a phone call with them afterward to get acquainted and ask their advice on things. Go to office hours (especially if you’re skipping a lot of classes) to build personal relationships with professors and maximize the personalized learning you receive (which is worth far more money than classes, which you could just watch online anyway).

  31. Spend a lot of time alone. It’s easy to get caught up in the social frivolities of college life, but it’s just as important to make friends with yourself as it is to make friends with others. Learn to meditate, pray, go for long jogs, write in a journal, or whatever else silences the noise and lets you renew. College is a four-year pass to set the direction of your life, so there is no single more important task you can do than to meditate on that question. Consider how you will measure your life, consider the type of person you want to become, and consider how you will remain the captain of your own soul as your ship leaves the shore.


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