Advice to Young People: Be More Ambitious

I wrote a somewhat-cathartic blog post over at the Praxis site yesterday about why young people should be more open and honest about their ambition.

I think young people who can otherwise be more ambitious like to hedge their ambition for a few reasons, none of them particularly good upon examination:

  1. If you don’t show your hand, nobody can know when you fail. This is probably the most common reason that high-achievers don’t broadcast bigger ambitions; they aren’t used to failure. They may have a goal to build a billion-dollar business or to publish a number of best-selling books someday, but if they announce that to people before it happens and then it never materializes, they end up looking like idiots.
    1. I don’t like this one because, although it makes the most sense to me, I think that downplaying your ambitions has an adverse psychological effect on yourself. As you continue to repeat that your ambitions aren’t as high or aren’t as big as you’d like, you will start aiming for those lower ambitions in time. If you contradict those lower ambitions in your thought and behavior, you still have to deal with the fact that you are actively contradicting yourself, which has confusing psychological effects.
    2. Even if you don’t hit those goals, ask yourself, “What’s the big deal?” Lots of people fail at the first few attempts at anything (failure is a necessary condition for learning quickly and effectively). Instead, ask yourself, “What’s the worst and best that could happen if I set my goals high?” and “What’s the worst and best that could happen if I set my goals low?”
      1. In the first case, the worst that could happen is that you swing for the fences and miss. You are allowed to take more than one swing, so you correct course and try again. If you swing for the fences and hit, you achieve something very few people ever achieve.
      2. In the second case, the worst that could happen is you swing and miss. The best that could happen is you swing and achieve something most other people achieve.
        1. The point of this analogy is that setting big goals is not a necessary and sufficient condition for success but it is a necessary condition. Nobody has ever accidentally become successful.
  2. Broadcasting ambitions before you have achieved anything else comes off as arrogant and cocky. Nobody wants to look like they think they can actually build that billion-dollar business (or whatever the goal is).
    1. The best way to think of this one is to ask yourself, “Do I really want the approbation of people who think that ambition is generally cocky?” We grow up being taught these stories of great men and women who moved mountains and achieved so much in their lifetimes and are then taught that it is haughty to want to model them. “Better lower your ambitions, kid, because life will beat you down.”
    2. At best, this is a cynical approach to the world. At worst, it crushes the human spirit. Even if the world can be harsh on people and even if everybody doesn’t achieve their goals, that doesn’t mean that once we fail to achieve those ambitions our lives are over and we are complete and total failures. People who are psychologically spritely know how to shift their goals at failures and take them as learning opportunities to move on to the next ambition.
  3. Big ambition implies the chances for big failure. Young people are insulated from and avoid failure for the first 16-22 years of their lives and want to avoid rejection when possible. Applying for that exclusive job or going for that big deal means that you could lose them. Nobody wants to experience that, so they hedge.
    1. Like 1 and 2, the question here needs to be asked as “compared to what?” Yes, losing that big deal does hurt, but the deal can never be had or lost in the first place if you don’t go for it.
    2. Failure is a natural part of learning and, while it should be minimized within reason, is a process through which you can learn, correct course, and move forward.
    3. Big failure is not debilitating. Even complete, total failure in the modern United States isn’t that bad. The bottom isn’t that far and you can always pick yourself back up and get moving again.

Cherishing the ambition you have as a young person is a powerful tool. It is the spark that sets apart all of the hard-working young people with whom I am excited about working. If you want to set yourself apart in the long run, don’t like that spark die out.

Advice to Young People: Be More Ambitious

Work Out Your Discipline Like a Muscle

A lot of the most successful people I know have habits that appear odd at first glance. They may eat an inordinate number of pistachios and eat no carbs (or, even odder, somehow eat only carbs and maintain great shape), they may wake up two hours before the sun comes up, they may consume only certain drinks, they may only use a certain type of pen, etc. These odd habits are not a function of their success — being successful probably didn’t make them odd — and they are not the cause of their success.

Instead, I think peculiar habits are a product (and at the same time, a creator, of) discipline.

The one common theme I have noticed among all of the successful people I know is that they are more disciplined than their less-successful peers. This may not be in every part of their lives — Marc Andreessen talks on the Tim Ferriss show about how he shows up to work at 9 and filled full of coffee for the rest of the day. But he is surely more disciplined when it comes to investing and to building a tech company than most people who try.

If you want to develop that sense of discipline that unites the successful, start small. Decide you’ll write once a day (recommendation from my friend Isaac), go to the gym once a day, wake up an hour earlier, or change your eating habits. You’ll find that as you do these little things more often, doing things that require more discipline become easier.

Send me comments and hatemail here.

Work Out Your Discipline Like a Muscle

Perks of Signing Up for My Email List

As you’ve probably noticed by now, there are multiple ways all over this site that you can sign up for my email list, like the bar at the top of the page and the email capture that may or may not have appeared when you opened this page.

I don’t do this to spam you or to sell you anything. I do this because I want to build a community of people who are interested in taking control of their lives and being in the pilot’s seat. The emails I send to the list are not formatted or sent out through a mass-emailer. I open up a new message in gmail and copy and paste all of your email addresses into BCC and start typing. This is a real, organic email from me.

Some of the perks of signing up:

  • Advance notice and sneak-peeks of new content I am releasing, like two forthcoming ebooks (hint, hint) and the foreword to the 2016 edition of John Taylor Gatto’s Dumbing Us Down.
  • Free content that you would otherwise have to buy from Amazon (hint, hint).
  • Advance notice of talks happening in your area.
  • Exclusive recaps of talks I am giving that week.
  • Exclusive deals and discounts on material and products from companies with whom I work.
  • Scholarship opportunities for Praxis.

I hope to add even more special content in the future. I promise not to spam you and won’t send emails just for the sake of sending them. If you like what I have to say and post here, why not sign up? You can always unsubscribe in the future.

Perks of Signing Up for My Email List

Get my Foreword to John Taylor Gatto’s Dumbing Us Down

I couldn’t be more excited to publicly announce that I had the honor of writing the foreword to the 25th Anniversary Edition of John Taylor Gatto’s Dumbing Us Down: The Hidden Curriculum of Compulsory SchoolingIf you’ve never read this book, place a pre-order for the new edition now.


If you have read the book, buy a few copies to give to friends and family. Give it to teachers, parents, and student you know. Gatto was New York state’s Teacher of the Year when he publicly resigned in disgust after decades of teaching. Convinced that school is not broken but systematically working towards the ends for which it was designed, he spent the rest of his career documenting his teaching career and writing a history of compulsory school.

You can get a copy of my foreword to the 25th Anniversary Edition direct to your inbox by signing up for my email list at the bar at the top of the screen or in the lower right-hand corner by Friday, October 14.

Get my Foreword to John Taylor Gatto’s Dumbing Us Down

New Recordings, Guest Appearance, and a Free eBook!

Here are a few updates from what I’ve been up to (or others have been up to relevant to me) in the past week.

I joined The School Sucks Project podcast today to talk credentialing, career success, schooling (and deschooling) and so much more. If you aren’t familiar with SSP and enjoy my writing on education, do check it out. It is a phenomenal project. You can listen here or on iTunes.

Tom Woods (whose show I joined this spring, here) put out a free eBook on education without the state. Yours truly is featured in one of the chapters. You can get it here.

I released a few more short recordings. If you enjoy these recordings, subscribe to my email list (above) and let me know. I may have a cool project coming down the pipeline…

On fulfillment and the difference between being reactive and proactive:

The truth about college earnings reports:



New Recordings, Guest Appearance, and a Free eBook!

DeSchoolhouse Rock! Politicians Are (Sort Of) Real People

Today’s recording focuses on politicians…sort of. It’s important to understand that they are people like you and I — they want to keep their jobs and they want to make money. They aren’t some kind of altruistic civically-minded Ubermenschen. No effective politician is. Once you understand this, you unlock a lot of possibilities for changing political outcomes without changing politicians.

Intro segment: Clint Webb for Senate, from Whitest Kids U Know

Send me feedback here.


DeSchoolhouse Rock! Politicians Are (Sort Of) Real People

The Truth About College Admissions

People like to paint college admissions as this process of being the objectively smartest or the objectively most virtuous when it is really like any other system out there, one driven by the interests of the decision makers.

I go into three areas of the college admissions process and explain how to understand them:

  1. Getting In
  2. Understanding Acceptance Rates (and Why Colleges That Want to Reject You Want You to Apply)
  3. Understanding Selection Bias

Feedback, comments, and hatemail can be sent to me here.


The Truth About College Admissions

You Don’t Hate Mondays or Capitalism – You Just Hate Your Job

Today’s audio blog is in reaction to a sentiment I’ve seen some friends share – “You don’t hate Mondays, you hate capitalism.”

My response is simple: you don’t hate either of these, you hate your job.

The good news is, you can change this. You can stop hating it or you can quit.

Here are some resources referenced in the conversation:

The Four Hour Workweek by Tim Ferriss

Udemy for learning new skills

Apple’s guide to Swift

Stoicism: books by Seneca

Stoicism: books by Epictetus

Deskboubnd: Standing Up to a Sitting World by Kelly Starrett

Thanks to Isaac Chapman for some feedback on audio quality. If you have feedback, leave a comment on Soundcloud or shoot me an email here.




You Don’t Hate Mondays or Capitalism – You Just Hate Your Job

Quick Thoughts on the Paradox of School & the Family

I was giving a talk at Floria Gulf Coast University the other night near Fort Myers when I noticed a flyer on the door of the lecture hall. The sign (I wish I had gotten a picture now) read: “PARENT FREE ZONE.”

I chuckled at first, thinking it was more of a tongue-in-cheek joke to new freshmen who were used to having their parents around. Then my stomach sank when I had the realization that it probably wasn’t a joke.

Continue reading “Quick Thoughts on the Paradox of School & the Family”

Quick Thoughts on the Paradox of School & the Family

A New Approach to Content (Audio)

The other morning, I opened up my blog to record some monologues of articles I have written. After a few attempts, I realized that they weren’t best-made for recording. Instead, I decided to do a personal monologue based on the articles. Instead of blogging for the day, I recorded audio.

Here’s yesterday’s, based on this piece:

And here is today’s, urging young people to not go back to school:


A New Approach to Content (Audio)

When Those You Respect Respect You

Thinking of success & excellence as being entirely independent of other people only makes sense in an atomistic world. In reality, those we respect and admire are mirrors for our own values and ability to strive towards excellence.

I consider myself successful in an endeavor when other people I respect begin to respect me in that domain. This is not a sufficient condition for success or excellence in a given domain but has proven to be a damn good indicator that I am making positive progress in my striving. For those that know me, this may come as a surprise given my philosophical foundations in individualism and virtue ethics. Eudaimonia is not based off of being popular — Aristotle himself argued against this in the Nicomachean Ethics on the basis that the life of popularity (“the political life”) is too contingent on having property and the support of others when compared to the life of the mind (“the contemplative life”).

Yet, success need not be defined in terms of others and their conceptions of ourselves and it need not be defined in everybody else’s conceptions of ourselves. Rather, by carefully selecting those whom we respect (and with whom we associate via friendship), we indirectly and inadvertently get a benchmark against which we can measure our own virtuous progress.

Continue reading “When Those You Respect Respect You”

When Those You Respect Respect You

Content Roundup and Updates on Forthcoming Work

I’ve been busy with work with the Praxis team the last few days and building out our improved education program for preparing apprentices for on-boarding at startups across the country.

The End of School is currently on sale for the lowest price that Amazon will allow it to be sold at and the reviews are starting to come in.

I plan to write more regularly in the next month, contributing to The Mission on Medium and have been republished a number of times over at My focus for the next few weeks will be on subjects related to education, finance (monetary policy), technology, and social change.

Recently featured on LinkedIn’s Editor’s Picks: The Student Debt Crisis Hurts Us All by Stifling Innovation and Growth

Recent podcast interview: Slayback to the Future with Isaac Morehouse

Upcoming Speaking Engagements:

  • July 16, 2016 — Pennsylvania DeMolay State Convention — Seven Springs, PA — Speaking on The End of School and how to approach career and education as a young person today.
  • July 20, 2016 — d10e — San Francisco, CA — Leading a panel on the future of work.
  • July 30, 2016 — Global Innovation — Mexico City, Mexico — Speaking on how to get stakeholders to buy into an idea.


Content Roundup and Updates on Forthcoming Work

On Resentment, Indignation, and the Emotional Case for Political Diminution

An understanding of the expectations of a given community helps inform where resentment and guilt ought to be targeted in times of crisis. This is hard when your community-of-reference is large.

In times of national crisis, emotions run high and influence policy debate at a disproportionate level to the norm. People who would otherwise consider themselves to be levelheaded, rational, and not influenced by their emotional feelings in matters of policy and reform are overtaken by rhetoric that plays on resentment, guilt, and indignation.

This certainly pollutes a lot of discussions, especially those in which the cost of broadcasting your opinion is essentially zero (e.g., on twitter of Facebook). It makes it feel like that the quality of debate has gone downhill and that we are marching towards a national Zeitgeist of immature pandering and childish accusations (although this is inaccurate). A few days after the crisis or tragedy, there’s usually a reactionary wave of people telling everybody else how valuable it is to be levelheaded and not allow ourselves to make rash decisions fueled by emotions.

The pendulum swings back and forth between these two camps — one fueled by righteous indignation and the other by cool rationality (or the desire to appear as such) — until the next crisis or tragedy changes the locus of attention to a new pet issue. It’s not uncommon to feel pigeonholed into one camp or another, forced to choose between appearing insensitive to watershed moments or looking like you can’t step back and stoically address serious issues.

What if both camps are wrong?

Continue reading “On Resentment, Indignation, and the Emotional Case for Political Diminution”

On Resentment, Indignation, and the Emotional Case for Political Diminution

On Fetishizing Failure & the Rise of Failure Porn

“Ten things I learned from failing.”

“How to Fail Forward.”

“What Failure Taught Me About My Relationship”

“How I Launched My New Venture and Failed and Am A Better Person Because of It.”

I don’t know if these are actually titles of pieces talking about failing and overcoming it but they easily could be. These could be articles in your very stream here on Medium when you click back to the home page. They infect our social media feeds and signal to us the bright side — even the joy — of failure.

The rise of social media and open blogging platforms like WordPress and Medium make these possible. Before these platforms, you wouldn’t hear about other people’s failures as much because media outlets figured people would rather spend time reading about the successful, the beautiful, the sexy, the rich, and the powerful. Who wants to read about a guy who’s coffee business failed? Who wants to read about the girl whose marriage fell apart? Who wants to spend time hearing about failure?

Turns out a lot of people do.

The Bright Side: Failure Isn’t That Bad

There’s a virtue to the proliferation of this genre — it teaches us that failure really isn’t that bad. After 12–16 years of school teaching us that failure must be avoided at all costs and that failure at a given venture = failure of the individual in question, articles recounting stories of failing and turning out okay are a welcome reprieve.

Turns out, life is full of failure. Lots of people we think of as successful have failed in previous ventures and may even be failures in other areas of their lives.

Before the mass-popularization of pieces that highlight the failure of common people, the closest equivalent you could find would be articles talking about how many times famous people failed before hitting it big. These are obviously intended to inspire. “If Richard Branson can fail this many times over, you can too!”

The primal risk-aversion internalized by the fear of failure is, ironically, the dangerous part. What started as an evolutionary mechanism to keep our simple monkey brains from falling off a cliff or signaling to the tribe that we are incompetent and should be left behind in times of emergency has made people weak and flaccid. It’s led to several generations of people — especially since the relative wealth boom of the Industrial Revolution — who are more interested in safety and risk-reduction than they are in trying new, interesting things that may bring with them the chance of failure.

Instead of pushing the envelope to do everything from finish audacious building ventures ahead of schedule to traversing the solar system, from launching a multi-million dollar venture to launching an etsy business, a lot of people would rather settle for a paycheck.

The three most harmful addictions are heroin, carbohydrates, and a monthly salary.” — Nassim Nicholas Taleb

So these feel-good articles and blog pieces about how you can recover from failure have a huge bright side — they assure us that if you do give into that temptation to try something different and scary, chances are, you’ll turn out okay. The bottom in the United States really isn’t that low (especially when compared to anywhere else for the rest of human history) and it is rare that somebody stays at the bottom.

The Dark Side: The Rise of Failure Porn and Losing the Nuance

Still, I can’t help but feel a little uncomfortable when we see these articles shared around on Facebook or twitter. Their intention is presumably good, but the fact that entire genre has popped up from this little thesis is disturbing. At its most insidious, we’ve seen the development of the genre offailure porn — a genre people enjoy to make themselves feel better about their own failures, oftentimes rooted in Schadenfreude.

If we sit back and bask in others’ failures so much that we begin to fetishize failure, the element of failure that our monkey brains understood and understood well starts to die off.

The biggest danger here is losing sight of the fact that failure sucks and it should be avoided as much as possible. Failing sets us back from the progress we could have made in other areas — opportunity cost is felt most when risky ventures fail — and can be psychologically jarring. We see articles and stories about people recovering from failure so easily that it seems less-necessary to avoid.

Levi Morehouse, CEO and founder of Ceterus, put it well in a discussion on this topic:

Failing is not the end, but it it awful. Choose the right wall, climb it well, push through challenges, and succeeding is better than starting a wall and quitting and trying a new one repeatedly until hopefully succeeding.

Avoid it but do not fear it. Falling happens to everyone, those who avoid it but do not fear it are best positioned for ultimate success. Failing is giving up on a goal, avoid this at all costs.Failing does not happen to everyone. It is not the end but it is worse than falling.

We lose an important nuance of failure when we indulge in these articles — fear of failure should not keep you from trying something, but failure should still be avoided as much as reasonably possible.

Understand that failure isn’t really that bad (especially today, for what most people are trying), but also know that failure is rooted in the decision to give up.

Don’t let the fetishization of failure make you give up before you otherwise would. If you’re going to fetishize anything, fetishize success so that more people strive towards that.

Kudos to Levi Morehouse for discussing this topic with me on multiple occasions and being a breath of fresh air on this topic.

Continue reading “On Fetishizing Failure & the Rise of Failure Porn”

On Fetishizing Failure & the Rise of Failure Porn

Four Ways to Think About Changing the World

I recently finished the phenomenal series of essays by Venkatesh Rao, Breaking Smart, focused on how software is eating the world and the implications from this. It’s easily the best thing I have read this year so far. This turned me on to a little compilation of essays by Rao called Be Slightly Evil  (Taylor Pearson has a good little chunk of excerpts here), which focuses mostly on how to navigate organizations and present yourself in workplace conflict.

In BSE, Rao presents a dichotomy for how people view whether or not people can change. He lines up idealists and tragedians. Idealism is a common theme in American culture (especially politics), he says, and is defined by the belief that people can change. The American Dream and the rise of Self-Help are testaments to this. The idea of changing towards an end — like what you may see in an inspirational instagram post — is the theme here. Self-betterment, personal development, and the study of getting an individual from the place where they currently are — imperfect — towards a more perfect end (Rao notes that this phrase appears in the founding documents of the United States) are mindsets in the idealists world.

Continue reading “Four Ways to Think About Changing the World”

Four Ways to Think About Changing the World