Graduate Unschool Progress Report: Week of 8/1/2016

CourseWhat Was my Goal?What I did...What did I learn?How Can I Improve my Approach?Potential Next Steps...
SWEWork for 30 minutes √Decided on objectives & course materialsWhat I'll be doing and whyAttempt an MIT problem and read/experiment with the 'Learning on Steroids' online course (LoS)Start LoS. Attempt a problem from MIT's 6.0042j course
VSK8Spend 30 minutes skating vert √Learned to skate my new vert board. Attempted to skate transition again. Filmed my starting point bs airVert skills atrophy quicklyHave a plan so I don't get confused or discouraged when I get to the skateparkStructure the learning approach using Tim Ferriss' 'How to 10x Your Results, One Tiny Tweak at a Time' podcast.
SOLOWork for 30 minutes √Decided on mini-courses and objectives. Clarified the learning method.Action is the underlying learning method. What I'll be doing and the underlying method. A course a week is not a goal, action matters.Compile all actionable tips into a journal. Cross them off as I complete themSynthesize 'I Will Teach You to be Rich' (IWT) into an actionable list
APPDWork for 30 minutes XNothingForce myself to start and complete the smallest possible section of the app course I'm takingGet 1% further in my online app developer course
OverallSpend 30 minutes a day XPublished 'Unquitting Unschool'. Made structural changesThe hardest part is getting started. Once I start the 30 minutes flies by, but now my willpower is mostly exhausted with starting.Make a progress report format (this). Keep a general Graduate Unschool journal. Update progress report fields every time I workSpend 30 minutes a day of focused on Graduate Unschool (GU) everyday

Notes: I feel like I didn’t make as much progress as I would have liked, but I made more progress than last week, and I identified a few changes I can make to improve next week. I understand this is not impressive, but right now it’s about sticking to my plans and moving forward, not impressing anyone.

The peak of the highest backside air I could land. The starting point for the vert skateboarding course.

The peak of the highest backside air I could land. My starting point for the vert skateboarding course.

Unquitting (Graduate) Unschool

This is a follow-up to my first post on this blog, the announcement of my Graduate Unschool project. I am writing this not with the excitement, enthusiasm, and optimism that shines through my original post, but instead with a lump in my throat, a knot in my stomach, and a deep sense of shame and embarrassment. I’ve tried to write other articles for the past few months, but I always felt somewhat dishonest for not addressing what’s going on with the largest and most ambitious project I’ve ever attempted (the sole thing I intended to base this website around) especially because it went so differently than I originally planned or expected. This is the article not the article I wanted to write. This is article I needed to write.

First, a little background on what I attempted. A year ago I decided that instead of attending graduate school I would create my own graduate school, make the courses up, hold myself accountable, and be extremely transparent about the process. I always seek to take on more and more, and after feeling bored and unchallenged at the end of my college experience, I decide to make this the most intense and difficult endeavor I’ve ever attempted. I designed five different courses, each with a unique and extremely difficult end goal, and each paired with a different learning method. The purpose of the project was to simultaneously learn about the topics I was most interested in, and to test and develop new learning methods, making the focus of the project primarily on learning how to learn. Below I have listed the course topics, goals, and learning methods, as well as where I currently stand with them.

Course Topic

Learning Method

End Goal

Current Standing

Software Engineering

Recursive Learning/ Deliberate Practice

Complete 9 MIT CS Courses, 150 Programming Puzzles from CtCI, and develop 2 board game AI Systems

Completed 2/9 MIT Courses, 2/10 problem sets on 6.0042j, 4/7 problem sets on 6.006, and <10 CtCI puzzles. No progress on board game AI.

Vert Skateboarding


Land a 1-2 foot high Caballerial on a ramp taller than 12 feet

Landed a 1 ft backside early grab in an 8 foot bowl

Solopreneurship (Solo-Entrepreneurship)

One Course of Action each Week

Complete 26 “homework assignments” based on self-improvement media. Create 26 actionable one pagers

4/26 one pagers (~15%)

App Development


Build an iPhone app and distribute it through the AppStore

Very Little Progress

Secret Course (Social Skills)

1% Improvement a Day

Improve my social skills by 515%


I gave myself a hard deadline of six months for the project, and intentionally chose goals and benchmarks that I believed would be completely impossible to accomplish in that time frame. I chose to do this because I saw getting close to perfect scores on tests and in college classes as a sign that I wasn’t pushing myself enough, that what I was attempting was too easy for me. Success to me has never been defined by how well I’ve performed, but instead whether or not I tried my absolute best, gave everything I had, and put my whole heart into it. Graduate Unschool was set up so that I could leave everything on the table and still potentially come up short.

Here’s what ended up actually happening. I was misled by my passion to start early. I became achievement focused instead of process focused and funneled my energy towards accomplishing the end goals instead of learning as much as possible. I stopped living in the present; I moved from wanting “to do” to wanting to “have done” my tasks (I didn’t want to sit down and do another MIT problem set, but I wanted to have completed the software engineering degree). I never expected anyone to follow, care about, or even read my progress and articles, (before announcing Graduate Unschool I’d spent almost a year blogging, and had never had more than three people read a single article), but when I realized that more people than I regularly have social contact with were keeping up with the project, I felt a pressure to perform. A pressure to not fail. Instead of trying my best simply to move forward everyday, I took my impossible goals seriously. I worked myself to complete frustration and exhaustion for a few weeks, then burned out. I felt guilty about my failure. I avoided the project. I made unsuccessful plans to catch up in secret, and I found myself with a guilt driven avoidance of the topics and learning methods I’d originally wanted to focus my life around.

Looking back it’s easy for me to speculate as to why this went so wildly different than I planned: I never even explored the learning methods because I was so caught up in accomplishing things, I was neither public nor transparent about any of it, but I’m ready to move forward and learn from this failed learning project.

I’ve given this a lot of thought and the truth is, I still care, I still want to learn, and I think I have partially purified my intentions. I’m going to take what I’ve learned from this past year and use it to approach the project in a healthier, more adaptive way. Instead of having harsh deadlines to fall behind and beat myself up about, I’m implementing the most powerful learning method I encountered during the project, consistently improving 1% a day, across the project as a whole. This keeps me grounded, it’s achievable without being easy, and moves me forward fast (at an exponential growth rate) without becoming overwhelming. I’m going to shift the focus off of myself and the end goals, and refocus it on learning about the learning process, and what new insights I gain as I progress through the project each week. This means I will no longer have to toil, writing a giant self indulgent article about my emotional state every time I give a Graduate Unschool update. Instead I will be posting weekly progress reports, regardless of how much progress I end up making that week, so that I can actually be public and transparent without becoming ego-protectant and narcissistic, as I’m afraid I became last time. Finally, there will be structural changes made to every course and the project in general, but these changes will be adaptive. They will happen as I move through the courses and learn more. I’d rather start moving in the right direction today than wait until I devise the perfect plan to start.

There was so much about college that I loved. The moments where I finally figured something out and dropped whatever I was doing to test it. The long hours of complete engagement in the problem solving process. The days where I unexpectedly acquired a new skill. The idea that there was always something left to learn. Graduating college was the truly disappointing part, but I think it’s because I was in it for the journey, not the destination. When I arrived I wondered why did I do all this work? Was this a giant waste of time? Did I even want this? I think I finally understand the answers to these questions. I did the work because I enjoyed doing the work. Time that you spend engaged and working on yourself is never a waste, even if it doesn’t turn out the way you expect it to. No, I never wanted to arrive anywhere, I was just enjoying the journey.

My learning journey will never end, and Graduate Unschool should be about making the journey as enjoyable and engaging as possible. I need to love what I’m doing everyday and not want it to end because even when I reach my foolishly intense end goals I don’t want to stop learning. This time I never want to arrive. I want to spend the rest of my life as a student. I want to hold true to the tagline of this website, learning full time, but I want to make it clear that the goal is to learn, not to learn full time for a couple of years then retire. I want to learn how to learn so that I can learn more. This is my manifesto for a lower pressure, healthier approach to my creative projects and my life in general. Consistency over intensity. Purpose over passion. Iteration over perfection. Humility over ego. Honesty over silence. Doing over being. Wanting over needing. Working over talking. Giving over expecting. The present over the future. Loving over infatuation. Unquitting unschool.

"When we lose we have a choice: Are we going to make this a lose-lose situation for ourselves.... Or will it be a lose ... and then win?" - Ryan Holiday

“When we lose we have a choice: Are we going to make this a lose-lose situation for ourselves…. Or will it be a lose … and then win?” – Ryan Holiday

Paleomodern Polymaths 25: Zoë Mattioli, How to Travel the World at 23, Meditation, Self-Experimentation

On this episode Zoë and I talk about: how to overcome the obstacles preventing you from going on your dream trip now (without needing to borrow money or get a crazy job), how to look inward, how to ground yourself in uncomfortable situations, how to cope with feeling like you don’t have a best friend, creating groups for growth and change, and what her hopes and dreams are for the future.

Selected Links for the Episode:

Selected Quotes from the Episode:

I love a good model face

Paleomodern Polymaths 24: Danielle Dallas Roosa, Creating a Show, Social Media Anxiety, Finding Your Authentic Self

On this episode I talk with Danielle Dallas Roosa about: the GoFundMe campaign for her new show Missing the Mark and what led her to make it now, how you can be more of your authentic self, and how social media has turned much of our lives into a performance. Hopefully Danielle’s story will motivate you to recognize your power and to start building your dreams today!


  • Intro
  • What is Missing the Mark/what led you to make it?
  • What does Danielle struggle with now?
  • What potentially misguided actions has Danielle taken to project a public image?/How did she bounce back from it
  • Danielle’s recommendations for people who are getting caught up trying to please others instead of being their authentic selves* (my favorite segment)
  • Why is it important that Danielle make her own show now
  • Danielle’s Thesis: Life as a Performance
  • How to relieve yourself from social(/social media) anxiety
  • The importance of being in a creative environment
  • What advice would Danielle give herself the day she graduated college?/Closing advice

Selected Links for the Episode:

Selected Quotes from the Episode:

  • “If you’re feeling lost, and you feel like this isn’t me, then what is you?…. Whatever that is, just start doing it.”-Danielle Dallas Roosa

Paleomodern Polymaths 23: Ryan’s Message to his Ex, Guiding Principals, NLP, Realizing You’re Awake

On this shorter episode Ryan and I catch up and share the ideas we’ve been tossing around in our heads recently. This one is jam-packed with actionable advice including: the guiding principles we use to improve and simplify our lives, how to be more authentically yourself, how to make progress towards the things that are important to you, and the importance of actually working hard at something. We let things get juicy as Ryan publicly reveals what he’s been wanting to say to his ex-girlfriend, we share stories of how we’ve gone overboard on certain things that have been detrimental to our lives and we recognize that our insecurities often reinforce our bad behavior. There’s more in here too, if you want to hear something in particular, just check out the chapter markers below. Thanks for listening.


  • Intro [0:00]
  • Being Yourself/Not Conforming [5:30]
  • The Guiding Principles we base our lives on [12:00]
  • Meta-Principles [15:30]
  • Realizing We’re Awake [17:15]
  • Stories of Ruts We’ve Gotten Stuck in/Going Overboard [20:30]
  • Why It’s Important to Have Principles [23:40]
  • How to use NLP to Improve Your Life [25:40]
  • How Insecurities Reinforce Bad Behavior [30:15]
  • I ask Ryan If you could speak directly to your ex-girlfriend, what would you say to her? and why is it important that he tell her this? [33:30]
  • The importance of Male Role Models in our Lives [40:00]
  • What is the Guiding Principle in my Life right now? [49:00]
  • What is Ryan actually working at really hard right now? [51:30]
  • We Give Closing Advice for Ourselves [1:03:10]

Selected Links for the Episode:

Selected Quotes from the Episode:

  • “If I’m not being weird then I feel like I’m just borrowing ideas from other people and repeating them and I don’t like that”
  • “How many times a day do you realize you’re awake?”
  • “Look at yourself from a third party perspective and think what decision should I be making?“-Ryan
  • “You were an important part of my life, it sucks being shut down by someone who I truly cared about. It feels like losing a best friend.”
  • “I spent a fourth of college being with this person and now that it’s over. It’s like all those memories I have, I’m having to delete out of my system.”-Ryan
  • “You can only put yourself out there so many times before you get exhausted with it… Why am I spending this energy on this person who clearly doesn’t want me around.”
Ryan, trying to break his streak at Lightning in a Bottle

Ryan, trying to break his streak at Lightning in a Bottle

Paleomodern Polymaths 22: Ian Borukhovich, How to Learn Anything, Information Consumption, Making and Sticking to Goals

Ian Borukhovich: B.S. physics, Ph.D biochemistry, lead of a data science team, musician, hand-balancer, + practitioner of other random skills

I finally had the opportunity to make a podcast episode focused around my favorite topic, learning how to learn. On this episode I had a conversation with Ian Borukhovich about: making fun goals that you can actually follow through on, learning via experimentation, how to continuously improve at anything, going deeper into the skills you’re interested in, and other learning/skill development related topics. Ian is one very few people I’ve met in real life that I feel comfortable describing as an actual polymath, and I’m sure with his relentless self-experimentation and evolving learning methodology he’ll only become more interesting as time passes.

My only advice around this episode is to try out some of his ideas/suggestions. I’ve been playing around with a few of them over the past few weeks they’ve been working well for me.


  • SkillSilo Ad [0:00]
  • Intro [1:22]
  • How I met Ian [7:00]
  • Information Consumption [10:30]
  • Goal Setting [20:15]
  • How to Continuously Improve at Anything [28:00]
  • How to Respond to Unsolicited Advice [38:00]
  • Going Deeper into Skills/Learning via Experimentation [41:00]
  • Creativity/Consistency/Play and Learning [1:05:00]
  • The Importance of Imperfection and Feedback [1:21:00]
  • Why you Need to be Socially Skilled to be Smart/Developing Social Skills [1:30:00]
  • Actionable Advice for Improving Social Skills [1:43:00]

Selected Links for the Episode:

Selected Quotes from the Episode:

  • “I always had this fantasy since I was young about being a self-made genius, and you were the first person I’d met that was really into that too.”
  • “All of this is a bit inhuman. To have stimulus that you’re constantly digesting, that you’re converting.” -Ian
  • “It’s not so important that I achieve exactly that goal, but spending time towards it is certainly valuable, and I appreciate that value so I’m going to pursue some piece of that goal, at least for some time.” -Ian
Ian, on goal setting

Ian, on goal setting

Sponsored Links:

Film Notes: Everybody Wants Some

(This post is inspired, in part, by Soraya Simi’s Film School Blog. She writes much smarter articles about filmmaking than I do.)

I initially thought (from the first few scenes) that Everybody Wants Some would be another typical 70s college movie from the dialogue, themes, forced unfunny jokes, and awkward lack of genuine connection between the characters. When characters in the cracked a one-liner, very few people in the audience laughed. However, there were genuinely hilarious moments not only in, but throughout the entire film, and once I realized that the movie knew how to be funny when it wanted to, I understood that the unfunny, awkward forced jokes were intentional, and there was more to the movie than what I naively assumed.

Everybody Wants Some is set in the magical week between when Jake (the protagonist) moves into his college town, and the first day of class. Much like the reality of the scenario, the moments bleed together, and the scenes don’t feel as though they have distinct endings and beginnings. The strong current of new information, exciting stimuli, friend-group dynamics, and seemingly urgent events always pulled me through these moments in my life, and the movie does the same. I was kept so ‘in the moment’ with the story that I often forgot what the main character’s motivation was, how we got there, or what I was supposed to be worrying about. Instead, my mind was fully captivated from the details of the scene around me. I spent my time reading the body language of the girls the main character danced and flirted with, studying the patterns of the different members of the friend group so that I could get to know them better, and trying to understand the relationships between the older members of the team. This to me is the mark of an excellent film, when you forget that you’re watching a movie because you are so captivated by the moments around you. The only elements that pulled me back to reality were the incredibly uncanny moments that were so familiar that I asked myself haven’t I been here before?  Didn’t I know someone exactly like that?  Didn’t I had this exact same conversation in college? The detailed realism is what makes this highly atypical college movie so fascinating. It isn’t mundane, and it isn’t fantastical. It’s the perfect balance of relatable and introspective that also managed to occasionally bring me to the edge of my seat.

The best way I can describe this movie in in the following statement. It is a genuine simulation of what it actually feels like to be a part of a group of male friends. This is something I would have not appreciated, understood or enjoyed until recently. Growing up, I did have a strong tribe of male friends (I usually had female friends outnumber male), excluding ages 12-14 and 15-18 (and now). Connecting with males was always confusing to me.  In college (and before) I felt like I never knew how to get past even the most basic social hurdles, like: how to tell if a guy enjoys my company, thinks I’m interesting, wants to hang out with me, when is the appropriate time is to suggest getting together outside of our location based friendship (which I was naturally very good at, but found myself completely incapable of stepping up the intimacy or intensity of our friendship), or even what we would do if I did manage to get them to spend time with me. I simply never figured it out, and slowly my male friends left my life. I stopped hanging out with Ryan. I didn’t hang out with my male roommates when I lived with them despite often wanting to. I just didn’t think I was interesting enough for people to want to be around.


This is the way things were before I noticed a giant hole in my life, which I now recognize as a lack of intimacy and social connection, or sense of belonging. The secret course was my (successful) attempt to put an end to the largest source of anxiety, anguish, and emptiness in my life. I spent a dedicated six months putting myself in social situations that made me feel physically uncomfortable, everyday, and slowly at first then all of a sudden I saw my life completely change. I went from having no friends, to having multiple strong tribes of friends. I went from having nobody to share anything below surface level feelings with, to the point where I was losing days to deep, engaging conversations on a regular basis, with: people I’d just met, people I’ve loved for years, and people I’d long desired to connect with, but felt unable to. I went from not knowing what to do around others, to being able to read and give off subtle social cues, and without feeling any sense of “control” over my social interactions, I knew how to get to a place where I felt comfortable. I learned: how to recognize when I wasn’t going to mesh well with someone, how to pull the interesting stories out of anyone who is open enough, how to share my downfalls instead of my triumphs to feel heard and seen as a person instead of a machine who pumps out accomplishments, how to directly talk about the things that make me anxious, and how to enjoy riding the wave of uncertainty and discomfort (enjoying the eustressful intensity) and seek non-deterministic situations where I’m stretched beyond my comfort-zone because that’s how I know I’m trying something new and I will most likely learn something about myself. I learned how to uncover the things that make other people so interesting and hear stories that people had never shared with anyone before, and sometimes had never fully thought through themselves. I learned how to relax, and see all social situations as play, where experimentation and off-beat provocative actions and statements make everything more fun.

Then, I moved to Dallas, where there was already an incredible group in place that I found myself lucky enough to be included in. Every person in the group is such a unique character, and I love diving deeper with all of them because I realize how complex they all are as people and how much I can learn from every one of them. Instead of expressing all my feelings about being a part of a tightly integrated friend group, I’m going to talk about how, in this context, Everybody Wants Some felt like it hit me at the perfect time.

The main character, Jake, is plain looking and quiet, and we see the entire movie through his real-time experiences. Through this we occasionally gain small degrees of self-awareness, not through hearing the thoughts, flashbacks, or fly-on-the-wall scenes featuring others, but purely via observation, because that is how we experience life. This makes easy to relate to the main character causing you to feel as though his newfound friends (the baseball team) are analogous to the people in your life. At first I saw them as one-dimensional foil characters, and the one dimensionality of the characters was bizarre, just the way it can be when you’re meeting a set of characters in your own life. There is an obvious trait that you seem to quickly pick up in everyone, and you seek observations that match that pattern (to prove yourself right) because humans are hard-wired to oversimplify and to recognize patterns, even when they are nonexistent. Later, as you see the people in different contexts, different locations (which the movie is great at pulling you through), different situations, and different emotional states, you realize that these people are as multifaceted and difficult to understand as it is to understand ourselves in our own heads.

The movie couldn’t have chosen a better climax than the scene where Jake spends the entire night, talking with the auburn-haired girl, completely lost in conversation, submitting to their desires and fully experiencing the present together. I remember every night I stayed up talking passionately and deeply with someone, and these often end up being the ‘peaks’ and formative moments of my life. Not the triumphs, but the moments when the world disappears and you only see the person in front of you. When you are only in the present moment and nowhere else. When you’re not worried about what this is, what this will be, what this has been, or where this is going, but simply enjoying that it is. My social goals can be simplified into: trying to enjoy and cultivate (but not put pressure on, control, or expect) perfect moments in my personal relationships, like what was portrayed at the end of the movie, or what I’ve described above. I’ve had an comparatively high density of those moments in magical pre-college week every semester, and while these moments can only ever sneak up on you, I’ve been lucky enough to have a few recently since I moved to Dallas. The old me would wish that I could have more, but the newer, more appreciative, present minded me only hopes to remember to not kill these moments when they start, but to instead submit to the moment, and follow my feelings.

If this movie served a purpose for me, it reminded me to allow myself to fully experience the world around me, and that the best scenes in my own life cannot be created or controlled, only enjoyed. Everybody Wants Some is a fun journey that is embedded with the virtues of patience, understanding, vulnerability, and non-judgement. Whether or not you choose to watch it, recognize that practicing these traits can make you feel much more like a character in the social scenes that play out in front of us everyday, and much less of an audience member.

The words in this article are mine, but the images were borrowed from the film. Go watch it.

Heuristic – Given a Set of Decisions, I will Choose the Decision that Leads to a Better Story

Heuristic – Given a Set of decisions, I will choose the decision that leads to a better story

(from Wikipedia: Heuristics can be mental shortcuts that ease the cognitive load of making a decision.)

Growing up I always wanted to be a writer and after reading The Four Hour Work Week and hearing Ryan Holiday’s repeated message that, “if… you want to be a writer…. Go do interesting things,”,  I began to understand that the best way to tell an interesting story is to live one.  Diving deeper into this idea, I started realizing that I value having a life worth writing about more than I value writing itself.  I’ve always been fascinated by storytelling, and have loved telling my stories in ways that I find interesting, compelling, or demonstrative.  As I experienced moments that I knew would become some of my best stories, I realized these were often the most memorable and fulfilling moments of my life.  Since then, I’ve used this as a metric to measure the overall quality of my live over a given period.  The metric works as follows;  The quality of my life over a given period is proportional to the mass density of the stories from that period of my life, where the mass density is found by weighting each story by it’s intensity then summing over the weighed stories and dividing by the length of the time period.  Since realizing this, I began using the heuristic above as a means to improve the quality of my life.

With any rule there arises questions about where it holds true and how it can be applied.  I think it’s best to answer these questions with a series of anecdotes from my personal life, in which I’ve stuck strong to the heuristic.

In practice, how can this be applied?  One of the most memorable experiences in my life was crashing an Up with People reunion when I was 20, and it all started with my response to a question.  I was swimming at a resort with my best friend when an attractive woman in her mid 20s approached me and asked if I wanted to come back to her room for drinks.  Although: I was already having a nice night, I was not planning on drinking, I was intimidated by the offer, and I had other potential obligations (I needed to wake up early ect…) I showed no ambivalence and said yes immediately, so that I could follow the story.  While there we played a game of truth or dare with the group of (all 5-25 years older than me) people in her room where I continuously reminded myself of my rule.  If I made a fool of myself it would certainly make a more interesting story than if I said no when asked to step outside my comfort zone.  I recognized: 1. If I own my actions I have nothing to be embarrassed of and 2. It was a relatively low stakes environment, I was a complete outsider and this would be my story to tell (or not tell) as I pleased.  I closely adhered to the heuristic and what followed was a two night cathartic experience which has permanently molded me as an individual, and created one of my better stories and best memories.

How does it work?  Recognize choices when they are presented to you, then think, if I were were viewing this as a scene in a movie, and the protagonist were given these choices, which option would I be secretly wishing they’d take?.  I find I’m more inclined to make provocative or risky decisions when I am able to view the situation from an outside perspective.

In 'Fight Club' the (unnamed) main character is so bored with his life he invents a new person so that he can hear an interesting story. After my first experience reunion crashing I realized that by stepping outside yourself for a second you gain a sense of objectivity about your current situation.

In ‘Fight Club’ the (unnamed) main character is so bored with his life he invents a new person so that he can hear an interesting story. After my first experience reunion crashing I realized that by stepping outside yourself for a second you gain a sense of objectivity about your current situation.

Does this heuristic break down at a point where situations can become too risky or dangerous?  No.  I have plenty of stories that are too high stakes to write about this publicly (that I love to tell in person ;)), so instead I’ll tell the story of how I made an important decision after months of anguish.  After my freshman year of college I was equally split deciding between 3 of the most difficult and time intensive majors in my school: Astronomy, Physics, and Mathematics.  I entered college so far behind in math and science that it would be a feat of it own to finish any one of these majors individually.  Plenty of my peers were combining two of them, and I wanted to do the same, but I was having trouble choosing my two favorites.  At this point in my life it was very important to me that I earn a high GPA and participate in plenty of research so that I would be in good standing when I applied for graduate schools.  After a year the paths started to trifurcate from each other and a decision had to be made.  I reached out to the smartest person I knew, a true polymath, who agreed to help me.  He told me that if I was interested in all three I should complete all three degrees.  When I explained that I was worried that taking more classes would hurt my GPA he told me to just get A’s in every class, that way I would never need to worry about my GPA.  When I said I had a four year scholarship and no interest in staying longer, he told me to complete all the courses in four years.  When I told him I was uncertain if anyone had completed the specific triple major in four years, he told me to be the first.  When I asked him what to do if I felt like I was in over my head or if I couldn’t handle it he told me to wait until I proved that I was overwhelmed (e.g. Seeing a significant drop in performance) and that I could revalue my situation at that point.  It never happened, but knowing I could revise my decision in the future gave the confidence to move forward and recognize that I was in control.  When I look back at my academic experience, I find myself feeling the strongest sense of pride around how different (and therefore interesting) my path was, and caring much less about the details of my performance.  Instead of being one of the many hundreds of graduating math majors, or one of the six Astronomy/Physics double majors, I found myself in a category of one with a combination that only I completed.

Lives that spiral out of control end up being more mundane we tend to naively predict.  I rarely hear the word fascinating used to describe the life of an active drug addict.  The self destructive stories and patterns we create for ourselves are usually obnoxiously repetitive.  When following the heuristic you will start the learn the dose dependence of high-risk behavior.  Should I have canceled the rest of my day when I was fifteen to get an energy healing from the girl who lived on her own?  Yes.  Should I have continued my pattern of breaking my foot every four months doing gymnastics moves that were far beyond my level?  Probably not.  Should I have remained deeply embedded in my high eccentric additions?  No.

What if you aren’t intrinsically an interesting person?  Then follow the heuristic to become one.  I rarely went to college parties because I often found myself, getting bored, and feeling like a boring person.  When people found out I didn’t drink or ‘party’ they would often ask me “well then what do you do for fun?”, as if those are the only available nighttime activities for an 18-22 year old.  I turned away from the obvious answer, and was forced to learn to find my own fun and to create my own stories.  I taught myself to skateboard.  I snuck into the pools at fancy resorts after hours (which led to the first anecdote).  I explored the unseen sides of my city.  I found vantage points and places to resonate with almost any mood, I rode ice blocks down what seemed like vertical golf course hills.  I went places I shouldn’t have gone to with people I should not have been with.  I freed myself to follow the energy of the people I met, which allowed me to spend full, uninterrupted nights talking and exploring with with someone the instant they stood out to me.  Once I’d fallen deeper in love with my city and further explored my surroundings I was able to return to the parties with an understanding of how to turn them into an enjoyable experience for me and for others.  As I explained to a friend I met at a party the day after I graduated, I come to parties to leave the party.  I’m here to find someone else to explore with, to show my favorite parts of the city to and learn a new perspective from, a practice that has served me well.

You are the author of the story of your life, so make it an interesting one.

Paleomodern Polymaths 21: Amelia Hollow, How to Get Unstuck, Becoming a Creative, Stories about My Depression, Why I’m Sober

On this episode I have a conversation with Amelia about where we are in our lives, roughly one year (~1.5 for her) out of college, still figuring out what we’re trying to accomplish, and how to move forward in this unique phase.  We talk about the expectations we had for our lives a year ago, what we’re working towards, how we feel stuck, how get ‘unstuck’, and how to actually work on the fulfilling things we love.  Amelia digs deep into me and I share the stories of how I struggled with and overcame multiple bouts of depression, and for the first time, I publicly talk about why I’m sober.  We ground things at the end by touching on what we dislike about ourselves, and what we find interesting about each other.

Out of all the podcasts I’ve been a part of, this experience has been the most motivating for me.  I can already see my life changing as a result of this conversation, and it only happened a few days ago.  Being around Amelia has been incredibly positive for me, and I hope some of our positivity is shared in this episode.


  • Intro [0:00]
  • Background on Amelia/not belonging in corporate America [10:25]
  • Where does Amelia belong/how to find your career passions [18:40]
  • The unique phase Amelia’s life is in right now [27:40]
  • What Amelia is struggling with now [30:30]
  • The story of how I started the podcast [33:00]
  • How our mindsets have shifted since graduating college [59:15]
  • How to get unstuck/become a creative [1:14:30]
  • What Amelia would do if she could do anything [1:30:20]
  • My story of experiencing and overcoming multiple periods of depression [1:58:00]
  • Why I’m sober [2:22:00]
  • “What about ourselves are we the most critical of, or do we like the least?” [2:28:15]
  • Why we find each other so interesting [2:44:00]
  • Outro [2:51:00]

Selected Links for the Episode:

Selected Quotes from the Episode:

  • “I always thought that there was something about me that people didn’t like and this was this emptiness inside that I felt.  There must be some reason why my parents won’t ask me questions, ever.  That they don’t show interest in my life.  And there must be a reason, it must be the same reason, why people don’t show interest in me, and I can’t seem to make friends, and why all of my girlfriends have been mean to me.”

  • “I would get myself into social situations everyday that would make my skin crawl”

  • “The output scares me.  It’s intimidating to put something out there that you made, and that has your name on it.” -Amelia

  • “Is this really a passion? Is this really what I would be doing, because, if it was, wouldn’t I be doing it?” -Amelia

  • “If I don’t do this now, when am I going to do it?” -Amelia

  • “I saw that there was the easy way, and the easy way was fragile and that it could fall apart at any minute and that I actually got fulfillment from pursuing these goals, whether or not they were delusional.  Willpower and discipline is a practice… and you get better at it through time.  I did it at first because I thought that I had to, and I still think that.  I still think if I don’t build this structure in my life, I’m going to go crazy.”

  • “I was doing stupid unfulfilling things and I got lost.  Then at one point I woke up and said holy shit what’s wrong with me, why haven’t I gotten out of bed, why do I feel like crying all the time, but I can’t.”

  • “I was one of the best rowers on my team because I learned how to say yeah you fucking can do this, don’t listen to your body that’s screaming at you to stop.”

  • “Thats where I get worried that I’ll get lost in my head…  [T]rying to figure out what part of that is me and what part is how I think I should be, for myself or for other people… I wish it were a little easier to be authentically who I am” -Amelia

Amelia Hollow

Paleomodern Polymaths 20: Robin Doner, Finding Yourself, Advice for your 20s, Being Trapped in Freedom

On this episode Ryan sits down with his uncle Robin, whom he truly admires.  He gives a grounded perspective on the limiting nature of too much freedom, life in your 20s, and how to overcome the emotional issues that hold us back.  He then shares with Ryan his incredibly ernest advice on: how to move forward in life, the importance of hard work, what you need to be happy, and how we can avoid the mistakes he made growing up.  This is a great episode for anyone who feels like they are in a exploratory phase of life (like I am), and all the credit for this one goes to Ryan Doner.  Thank you brotha 😉


  • Intro [0:00]
  • Intro song [2:10]
  • Ryan explains what Paleomodern Polymaths is to his non-millennial uncle [3:10]
  • The History of Robin Doner [4:30]
  • What Robin did in his 20s (working in Antarctica)/how he recognized the underlying emotional issues holding him back [7:00]
  • Robin’s perspective on the struggle to find direction in your early/mid 20s [13:40]
  • Robin’s exciting non-traditional work/feeling trapped by travel [17:40]
  • How you can explore yourself in the details of a continuous everyday life [22:10]
  • How childhood trauma (divorce/loss of a father) affected the Doners’ behavioral patterns [25:50]
  • The differences in exploring life/careers in your 20’s vs 40’s [31:55]
  • The struggle to move forward in life/how to move forward [35:00]
  • How to create external means to motivate yourself [41:10]
  • “What advice would Robin give his 23 year old self” [44:20]
  • How your potential is wasted if you aren’t working hard [49:10]
  • The stresses/limiting nature of freedom [53:10]
  • The list things you need to be happy in life/practical self improvement [1:01:40]
  • Finding meaning in life/reconnecting with yourself [1:11:10]

Selected Links for the Episode:

Selected Quotes from the Episode:

  • “If you spend too much by yourself, out in the woods, or alone, a lot of your thoughts easily become magnified, or your feelings.  You don’t have another person to help you balance those thoughts out, or to round them out.  Things can easily become overwhelming because they keep coming back up, and there’s no one else to just interact with, and shift your mind away from things” -Robin
  •  “If people see who I really am, they’re not gonna want to be around me.” -Robin
  •  “If you quit trying on that aspect, to see something new in life, you sort of, in some internal way, shut down and die.  You stop trying.” -Robin
  •  “If you get comfortable in a situation where there are no stakes, you lose any struggle and it totally crushes you when you experience a small setback.” -Ryan
  •  “It’s really easy to go exploring for years and never get anywhere.  I’m a prime candidate for that.” -Robin
  •  “I think we’re relatively gifted and I don’t know how much of a gift that is if you aren’t willing to just dive in and work hard at something.  Damn the consequences just go fucking do it and work hard at it.” -Robin
  • *”You’re an amazing, awesome person. You just have to believe that for yourself. And that’s the person you need to put forward in interacting with other people. And that person, if you always have him at the forefront, you won’t end up going through the same struggles that I’ve gone through. You won’t be running from yourself. So who you are…and I see who you are…put that person forward. That’s the person you want to go out and meet people with. You have the tendency to settle back in a little bit…be a little introspective…hide a little bit. Bring who you are out, and know that that person is someone who the world wants to see and be with. I tell my wife the same thing. I tell her, “when you’re being you, I love you. Who you are is the most beautiful, amazing person. That’s who I met, thats who I fell in love with. When you’re free to be you. So when you want the daily challenge, the real one, it’s to be you.” -Robin.  *Ryan’s favorite quote


Cover art