39 Things I’d Have Told Myself at College Graduation

Life since college has been great, but it definitely hasn’t been easy. Unsplash

My time in college was more than I could have ever wished for: I learned from sage advisors, made lifelong friends, studied and worked in developing countries, interned at startups, founded organizations, got cheated on and dumped, and took my fair share of derision for pursuing what was perceived by some to be an uncommon path.

I learned a lot from these experiences, so when I graduated from the University of Chicago five and a half years ago, I wrote a post called the 31 Things I’d Have Told Myself Before College. The post has since been shared thousands of times, and many students and young people have emailed me asking if I could write one about the things I’ve learned since graduating college.

Since college, I’ve had the chance to lead and grow Moneythink, serve as the youngest appointed advisor to former President Obama, serve as an entrepreneur-in-residence at the Department of Homeland Security, fall in love with my now-wife, become a diaper-changing ninja dad to two amazing boys, live in Europe, and get in the best shape of my life.

But life since college has also been challenging: my mentor passed away, my mom and a very close friend struggled with cancer, a cyberstalker hunted down and harassed our family, we fought to navigate both the US and EU immigration systems while keeping our businesses healthy, and we’ve almost gone broke in the process.

Here are the things I’d tell myself if I could go back to that day I graduated college and offer advice. Most of these points include references to books for further reading; think of this as a library rather than something you need to digest immediately. Pick one piece of advice and one book that resonates with you most now, order it on Amazon, and read it during your next vacation. Without further ado:

Work:

When you’re deciding what to do for work in your 20’s, first ask: “what am I optimizing for?” Unsplash

1. The most important skill you can learn is how to manage your own psychology. Learn to keep calm nerves, reduce exaggerative perceptions, see people and decisions objectively, keep your ego out of the picture, and step onto your own mental balcony to view yourself from outside yourself. At the same time, learn to accept fear, stress, and paranoia as accomplices—helpful instincts that can help you take pause, examine a situation more closely, prepare more thoroughly, and level up.

Read Ben Horowitz’s The Hard Thing About Hard Things, and Gavin de Becker’s The Gift of Fear.

2. When you’re deciding what to do for work in your 20’s, first ask: “what am I optimizing for?” It’s sometimes necessary to optimize for money when you have student debt or pressure from your parents to support yourself*; it’s tempting to optimize for status when you see all your friends taking jobs at big-name companies. But if you don’t have urgent financial issues, then understand that money and status are ephemeral: instead, optimize as much as possible for learning, meaningful relationships, and impact.

Read The Startup of You by Ben Casnocha and Reid Hoffman.

3. To optimize for learning, remember that your 20’s are your apprenticeship. Choose endeavors that will challenge you, expose you to as many sectors and tiers of the professional world as possible, give you the chance to develop domain expertise, and help you build some skills. Whenever possible, take opportunities that are higher risk, closer to the front lines of decision-making, and give you responsibility and exposure at the expense of pay or recognition.

Read Mastery by Robert Greene and Mastery by George Leonard (yes they’re both called Mastery).

4. To optimize for meaningful relationships, consider that your 20’s are a time when you have high mobility, few personal obligations, and unlimited curiosity. Focus on developing relationships with mentors from whom you can learn and peers with whom you can build and grow. In your work, first identify what you want to get better at, then seek out mentors to share their wisdom with you; make the most of their time by sending agendas beforehand, and show appreciation by thanking them afterward and keeping them posted on your progress and learning. Outside of daily work, attend as many conferences and summits as you can in the fields that interest you, and learn to start conversations with random strangers; organize dinner parties wherever you go; remember that the best way to be interesting is to be genuinely interested.

Read Never Eat Alone and Who’s Got Your Back? by Keith Ferrazzi.

5. To optimize for impact, consider that your ideals at the time of graduating from university are the least jaded, eroded, or corrupted that they’ll likely ever be. So if you feel any sense of moral obligation toward using your life for the betterment of humanity, then recognize that now—in your 20’s, not at the end of your career after you’ve maybe made millions—is the time to manifest those ideals. Perhaps your impact will be smaller than it could be later when you have more power or influence, but your experiences helping others will have an impact on you that will sophisticate your moral compass long before you hold power and influence, and ensure that as you grow into leadership positions of greater responsibility later, you always remember what matters.

Read The Road to Character by David Brooks, and How Will You Measure Your Life by Clayton Christensen.

6. Frame your career exploits in terms of territory, not hierarchy. Where can you develop unique expertise? Where can you deliver massive value? Where can you be respected as a peer contributor regardless of your age or seniority level? Then as much as possible strive to break out of, transcend, and shun environments where your success, mobility, influence, or respect is dependent on rank. Unless your dreams are in the military, a government agency, hospitals, or law firms, today’s reality is that you can excel much faster and add far greater value if you think in terms of territory instead of hierarchy.

Read The War of Art by Steven Pressfield.

7. Make your life about more than you: develop a platform to share your learning, relationships, and impact with others. This could mean founding a young professionals group locally or on social media. This could mean writing regular email updates to all the people in your life who’ve helped you, sharing what you’re learning. This could mean organizing for a social cause and giving others a chance to find meaning. When you stand for something more than yourself, other people begin to see interacting with you as a way of interacting with something that’s more than either of you. When done well, this builds trust and makes your network something that you can tap into far more readily when opportunities arise.

Read Platform by Michael Hyatt.

8. Understand the role of advice, and learn to develop principles and intuition. Asking others for advice can be a great way to learn and build relationships when you’re starting out. But after you’ve done it a few times you quickly learn that all advice is not made equal, and what’s often missing is context. As life goes on and your situations become more complex, it becomes harder to find prescriptions for success because no one understands as well as you do the application context, i.e. the real-life scenario in which the advice is supposed to get applied. So, what quickly becomes more important than asking for advice is the ability to reflect on your experiences—through journaling, meditation, and talking with trusted peers—to form principles and intuition. Over time, advice will become something used more to check your gut and expand your perspective rather than to prescribe action.

Read Principles by Ray Dalio and Meditations by Marcus Aurelius.

9. Tactics matter. Check with both parties first before making email introductions. Send agendas and meeting confirmations in advance. Research enough to at least show you did some. Follow up quickly over email from your phone, even if only to say youll follow up more thoroughly later. Write thoughtful hand-written thank you’s. No typo’s. If there’s a disagreement, pick up the phone or walk over in person and seek mutual understanding, then resolve it and move forward; don’t try to handle it over email. Don’t assume that these things don’t matter just because you don’t see your boss or colleagues doing them. These are secret habits that nobody is teaching millennials and you’ll differentiate yourself massively if you use them.

10. Don’t stake your self worth on external accolades. If you find yourself in a position where you’re winning awards like Forbes 30 under 30 or Crain’s 20 in their 20’s, keep your feet on the ground. The only thing that changes after such accolades is that it becomes slightly easier to get high-level meetings, and you meet some other interesting people who received the award. But you haven’t “made it”; you’re not a better person; you don’t feel any different on the other side. You still wake up the next day with fires to put out, all the unsexy work to keep doing behind the scenes, and all the normal reminders that you still have a lot to learn.

Read Ryan Holiday’s Ego Is the Enemy.

11. Play the long game. Our culture has wrongly glorified success at an early age. But there’s no 5 secrets to becoming a millionaire by 30, and you’re not going to build the next Facebook or Microsoft right out of the gate. Sorry if that’s news. A much healthier and realistic orientation for your ambition is to plan for a life of projects, relationships, and learning, and apply the exponential gains you see in each of those domains so that your achievements become more meaningful and sophisticated as you become wiser, more skilled, and more connected. As Gary Vaynerchuk says: macro patience, micro speed.

12. *If you do have a lot of student debt, pressure to support yourself, or financial family obligations, then that constraint is very real, and earning money is the most important thing to optimize for.  

Read I Will Teach You to Be Rich by Ramit Sethi.

Life:

Remind yourself that you chose your commitments. Unsplash

13. “Far and away, the best prize that life has to offer is work worth doing,” said Theodore Roosevelt. What he didn’t say is that if you’re living in a truly engaged way, all of life is work. Your job is work, your relationship is work, your friends and family are work, your self is work. Every part of your life should present challenges. If there’s a part of your life that never experiences challenges, then it’s not growing or evolving or developing: it’s dying.

Read Tiny Beautiful Things by Cheryl Strayed.

14. “For the first 30 years of your life, you make your habits. For the last 30 years of your life, your habits make you.” —Steve Jobs.

Ponder that for a second. We put ourselves in toxic environments and wonder decades later how we have become people that we no longer respect. We choose to work in settings where people cut corners and turn blind eyes, then we do it, too. We check social media 24/7 and compare our behind-the-scenes to others people’s highlight reels, but wonder why we feel lost and insecure. Use your 20’s to get your shit together before the stakes are higher.

Read James Clear’s articles on habit-building.

15. Your physicality is the foundation for everything else in your life, so invest in your body. A strong and healthy body and mind will improve your performance at work, make you more confident and attractive to mates, will reduce how often you’re sick, and will improve your quality of life on a deeply primal level. Learn how to move: join a CrossFit gym, a yoga studio, and an Aikido dojo, and don’t look at the price tags – They will always be cheaper than your hospital bills down the road. Learn how to eat: as a start, cut out grains, dairy, and anything in a package. Go get a food sensitivity test. Learn how to breathe: go find a Zen dojo and sit silently for an hour, then do it again every week for a few months. You don’t have to “become a CrossFitter” or a Yogi or “go Paleo” forever, but learning how to move and eat and breathe properly are fundamental skills that have been forgotten in modern living, which will serve you for the rest of your life with immeasurable ROI: as a business person, a partner, a parent, and as you’re learning to harmonize all of the above.

16. Sitting is the new smoking. At work and in life, opt for walking meetings, walking phone calls, standing desks. The benefits are countless, and the risks of sitting are even more countless.

17. Remember that the chances of you even existing are so infinitesimally small in the first place that you should probably do a cosmic gut-check and remind yourself how lucky you are to be alive for an instant on this tiny blue planet in a corner of the universe. Even if nothing else seems to be working out in your favor, be grateful for the chance you have to make meaning out of your brief time on earth.

18. Similarly, remind yourself that you chose your commitments. You made the choice to commit to this job and these projects and these meetings instead of taking other more lucrative opportunities. You made the choice to date this person and be in this relationship instead of continuing to date other people. You made the choice to help your parents this weekend instead of going to parties with friends. When commitments get real and the FOMO creeps in, victim narratives creep in, too. We easily forget that we chose these things. The way to prevent this from happening is to make the choice anew every single morning: it is my decision to live this way, and I choose this life with my deepest values. And I also have the power to choose something different if that is what is right.

Read The Subtle Art of Not Giving a F*ck by Mark Manson.

19. Just as much as growing is about learning and building new skills, it’s about letting go. Letting go of victim narratives, baggage, toxic relationships, self-imposed limitations, desires to impress others, and fear of the unknown. And just in case you were wondering, you have a lot more problems than you are aware of, and the things you think are problems—the things you hate about yourself—may actually not be that big of a deal. If there’s a time to get a therapist, it’s now. If there’s a time to stay in on Friday nights and journal about your values and who you want to be, it’s now. Shed the fictions that have been layered on top of your true self, and get in touch with yourself so you can explode from the center for the rest of your life.

Read Freedom from the Known by Krishnamurti.

20. “Pain + Reflection = Progress” —Ray Dalio.

It’s natural to shy away from pain, but pain is what sets you free…if you reflect on it. When things don’t go as planned, or when tragedy strikes, take the time to grieve or mourn, but ensure that part of the process is also a deep reflection on how you can grow from this experience.

Read Discipline Equals Freedom by Jocko Willink and Strain to Gain. And if you really need to unwind and zoom out, consider taking an Emotional Vacation.

21. Expect the unexpected, and learn the art of turning inconveniences into opportunities. If you’re moving fast enough your norm should be what most people would consider unpleasant: lots of failure, lots of botched plans, lots of work you don’t “feel” like doing, lots of complex decisions that end up hurting someone’s feelings, lots of hard conversations. But there’s power in changing your perception to first interpret all events as neutral occurrences before assigning value to them, then think “how can I make this work for me?” How can I be like a hydra, that benefits from what others would see as unfortunate? How can I be like a fire that grows when oxygen is blown on it? How can I be like a furnace that takes everything it is given as fuel? How can I cultivate a love of fate (Amor Fati)? How can I, as Nietzsche said, “not merely bear it, but…love it”?

Read The Obstacle Is the Way by Ryan Holiday, Antifragile by Nassim Nicholas Taleb, and The Black Swan by Nassim Nicholas Taleb.

22. Something that makes it easier to expect the unexpected is to build buffers in your life for when shit hits the fan. Save every penny you have while you and your family are healthy because you might need financial savings to get through an unexpected event. Invest in your friends, community, and reputation, because you never know when you’ll need a hug or a favor. Invest in your physical health by training and eating right because it might be the thing that gets you through a crisis when everything else in your life falls apart. And invest in your own psychology and spirituality through therapy, coaching, and personal development because your mental and emotional patterns are the ultimate determinant of what will get you through tough times. This might mean making efforts that don’t feel necessary or pleasant right now: going to a friend’s home to cook dinner when he’s sick or prepare interviews when she’s looking for new work; cultivating healthier eating habits when there are tasty donuts at work or waking up earlier to work out consistently when you don’t feel like it; saving money when you’d rather spend it. These are all investments that will buffer your fall and help you bounce back when you need it.

Read Man’s Search for Meaning by Viktor Frankl.

23. Abandon a compartmentalized view of life wherein each part of life is a distraction from the others, and embrace a view of life wherein each of life’s dimensions enhances the others. My sons inspire me with humor, curiosity, and playfulness. My wife inspires me with passion, authenticity, fire, and honesty. My work gives me a sense of contribution, legitimacy, legacy, and role modeling. My fitness and martial arts give me a sense of deep truth, confidence, humility, and centeredness. My self-worth is diversified across multiple dimensions, and each enhances the others. So push back against society’s tendency to force you to compartmentalize; the world needs more leaders who aren’t afraid to be human.

Read the Tao te Qing by Lao Tzu.

24. Morning routines and bedtime routines can be helpful, but developing dependencies on them can be more paralyzing than helpful. What’s more helpful is to develop the ability to achieve a peak state rapidly at any time, anywhere. To center yourself, to focus your attention, to invoke feelings that put you in “best self” mode. This is something you must find through trial and error, so play around with what works best for you—a hot drink, a little yoga, a quick workout, journaling, meditation—but the simpler and faster, the better.

25. Keep asking “why” and exposing yourself to perspectives other than your own. It’s much harder after college to continue thinking differently because you’re not given readings, you’re likely in an office all day, and you’re economically dependent on conforming.

26. One way to stay exposed to perspectives other than your own is to build local community. Be a neighbor, not a stranger. Take your headphones out, smile, and say hi. Knock on people’s doors to ask for cooking ingredients and bring cookies on holidays. Host local potlucks even if you disagree with some people’s perspectives. Engaging locally will break you out of your elitist little bubble and keep you exposed to and engaged with perspectives other than your own. Seek to understand and coexist; our world is becoming more polarized at the level of personal ideology and it’s draining us of our human cooperative potential. Fight for our collective humanity!

27. Just like in high school, the people in college who seemed “popular” and gave you a hard time will struggle to excel in the real world, and will come back to you asking favors, pretending they never treated you wrongly. Meet them with kindness, not spite or vengefulness—not because you care about them but because they are now a toxic distraction from your goals and the best way to change them is not to engage but to lead by example.

28. Especially since you are an urban white male in the US, you need to invest time and energy to understand your privilege. And not just so you don’t sound ignorant, but really because it’s the right thing to do. If you want to lead people in any significant way for the public good, you need to understand people with experiences other than your own. Educate yourself on the histories of oppressed peoples, and seek out thoughtful conversations with friends from minority groups. Out of respect, make it clear in those conversations that you don’t expect them to educate you, and that you recognize it’s not their responsibility to explain these things to you. It might be easy to go your whole life misunderstanding your fellow (wo)man because you’re afraid to misstep while navigating sensitive territory, but not participating in this dialogue would be a crime by omission. Inform yourself, engage on the topic of privilege with friends and family, and speak up whenever you see privilege being abused by anyone and everyone.

29. Until you find yourself in love, your three priorities are to hustle in your career, invest in friendships that have lifelong potential, and work your ass off on turning yourself into the best version of yourself. There’s really nothing else.

Love:

You have to learn to embrace creative compromises. Unsplash

Since so much of what we’ve learned we learned together, my wife and I co-authored this section. We brainstormed way more thoughts than can fit into a few bullets so just kept the actionable ones that we are certain made a huge impact on our lives and the lives of our friends; love is so much more than a few lessons learned.

30. Here’s the truth: If you hadn’t traveled and partied and fooled around a lot in high school and college, I’d tell you that now is the time to do that so you aren’t still wanting later.

31. Date lots of people if you can so that you wont have any unanswered questions when you finally settle with the right person. You have to learn that what you’re after is a lot more than a pretty face and a fit body; you’re looking for a soul. You have to learn that fights don’t always mean the relationship is over. You have to learn how to say sorry and hug it out. You have to learn how to swallow pride and realize that there is no winning or losing, and that the only real winning is the team victory when the relationship grows. You have to learn to embrace creative compromises, enjoy giving without expecting anything in return, and that succeeding in a relationship means mastering your partner’s love language, however long that takes.

32. Once you decide that you’re seeking a long-term partner and aren’t just dating to explore, then start filtering based on your non-negotiables. Non-negotiables are the values, beliefs, desires, and habits you want (or don’t want) to share with your partner and you need to start thinking about them now, not when you enter a relationship. Do you want kids? Do you want to live in foreign places? Do you want to buy a house next to your parents? Do you value alone time, or need a lot of time together every day? Do you love your work? What is essential for your long-term happiness? We tend to think that talking about these “elephants in the room” will kill a relationship early or at the very least kill sexual tension. But these conversations can also expand each partner’s perspective, open up new possibilities, and relieve fears. And if your partner clashes with your nonnegotiable or isn’t interested in working through these conversations, then maybe it’s a sign they’re not compatible…and that’s ok.

33. When you find something worth fighting for and you’re certain that both you and the other person want it, then hold on tight, do not let go, and do not let anything get in the way. Chase it down tenaciously and do whatever it takes to keep love alive. Do not hesitate and do not second-guess. Smash doubts with your heart’s fist. It is so easy to let excuses get in the way—career, distance, visas, finances—but nothing can stand in the way of real love and connection except a lack of tenacity. Not chasing love will leave you regretful. Die with no regrets.

34. Love is an act, not a feeling. Relationships take work, and they aren’t supposed to be easy. Crying and arguing and feeling ridiculous are part of making progress, working things out, and growing together. If you’re in a relationship you know is the real thing, don’t give up just because things seem hard.

35. You’re never prepared to fall in love, and you’re never ready to have kids. The only preparation you can have is a constant effort to develop a growth mindset; to adapt and learn and rise to the occasion. Over and over again, for the rest of your life.

36. Intimate Growth Together (IGT). Since you are striving to develop a growth mindset (rather than fixed mindset), it’s likely you’ll need to be with another growth mindset person to feel fulfilled. And oh, how fulfilling it is! To understand each others’ journeys, dreams, and struggles. To have each other to confide in. To come out on the other side of conflicts smiling, each a better human being. To form a joint life vision and family vision together and then execute on it joyfully, knowing that the process of learning and growing together is more important for the continuing future of this beautiful, rich, deep relationship than any immutable part of who you each are or where you each come from. As they say, “Happiness is the only thing that doubles, when you share it.”

37. Unpredictable circumstances can place relationships under stress, and sometimes it can seem insurmountable. Just as it is important to build a mental balcony of perspective for yourself when times are hard, so it is important to build a shared mental balcony, one that has two seats, one that holds space for you and your partner to ask each other and yourselves: “Would I still believe in you if xyz didn’t happen? If we weren’t romantic partners, would I (still) think highly of you? What makes you not just a suitable mate but an admirable human being?” Trust can wear down, but true belief in the other person rarely changes and it can become the stepping stone to restore trust in each other. You have to believe. In yourself. In the other person. In each other. And in your ability to conquer the world together. Everything else is a matter of putting in the work. Without belief, we can’t survive.

38.The strongest thing a man can do is cry” —Jay Z.

The act of weeping and bearing your naked emotions, of taking down your guard, is an act of bravery, courage, and strength. This ability to not just tell—but show—another person what is in your heart and soul, is one of a man’s ultimate superpowers. But society raises boys to think that crying is “girly” and that “girly” is a bad thing. We poison little boys with these thoughts and make them hide their weaknesses behind “manly” facades, so they never heal from the emotional injuries of their childhoods. The key to love is being willing to put your aching heart on the table with your partner’s and fully engage in the process of healing together.

Read Daring Greatly by Brené Brown, and watch The Mask You Live In on Netflix.

39. Our generation has been systematically trained and indoctrinated to defer the idea of finding a partner and raising a family until at least the age of 30, often 40, to instead focus on developing our careers. While it’s important to build career momentum and financial stability early, you don’t need 15 years of 90 hour workweeks before you’re ready to find a partner or have a baby. In fact, ignoring your eventual family aspirations for your entire 20’s is “a great way to have awful relationships for the rest of your life.” And if you’re lucky enough to find a partner you believe in, trust, and respect, then consider having kids early. Believe me, you’ll never look back.

Ted Gonder is an entrepreneur on a mission to even the odds for future generations. He serves as co-founding CEO of Moneythink, a nonprofit organization dedicated to building the financial capability of young adults through technology-enhanced mentorship, and until July 2015, he was a member of the U.S. President’s Advisory Council on Financial Capability for Young Americans. 

39 Things I’d Have Told Myself at College Graduation