Cal Newport (personal website, Wikipedia page) is a moderately well-known author of four books as well as a computer science researcher. I have read two of his four books: How To Become a Straight-A Student The Unconventional Strategies Real College Students Use to Score High While Studying Less and How to Be a High School Superstar: A Revolutionary Plan to Get into College by Standing Out (Without Burning Out). I'm particularly interested in his book on becoming a high school superstar. My interest arises as part of trying to figure out how people can better use their extracurricular activities to have more fun, learn more, and create more value for the world. As Jonah recently pointed out, choosing high school extracurricular activities could in principle have huge social value in addition to the private benefits. And as far as I know, Cal Newport is the only person who has given systematic advice on high school extracurriculars to a broad audience. He's been referenced many times on Less Wrong.

In this post, I'll briefly discuss his suggestions in the latter book and some of my broad philosophical disagreements. I'm eager to know about the experiences of people who've tried to implement Newport's advice (particularly that pertaining to extracurriculars, but also any of his other advice). First impressions of people who click through the links and read about Newport right now would also be appreciated. I intend to write on some of these issues in more detail in the coming days, though those later posts of mine will not be focused solely on what Newport has to say.

You might also be interested in the comments on this Facebook post of mine discussing Newport's ideas.

A quick summary of Newport's views

Newport's book advises high school students to pick an extracurricular activity and shine at it to the level that it impresses admissions officers (and others). He offers a three-step plan for highschoolers:

1. The Law of Underscheduling: Pack your schedule with free time. Use this free time to explore: In particular, avoid getting being involved in too many activities, whether academic or extracurricular. Use your free time to read and learn about a wide range of stuff.
2. The Law of Focus: Master one serious interest. Don't waste time on unrelated activities: Newport cites the superstar effect and the Matthew effect to bolster his case for focusing on one activity after you've explored a reasonable amount.
3. The Law of Innovation: Pursue accomplishments that are hard to explain, not hard to do: Newport talked of a "failed-simulation effect" where things seem impressive if the people who hear about them can't easily imagine a standard path to them. He then offers some more guidelines both on how to innovate and on how to make one's innovation seem impressive.

Newport is targeting high school students who want to get into their dream college. He's trying to get them to stop doing boring, depressing activities and instead do fun, creative, and useful stuff that both improves their short-run life (by making them more relaxed and less stressed) and impresses admissions officers.

Broad areas of agreement

1. I think Newport is right to suggest that it doesn't make sense to devote too much energy to boring schoolwork or extracurriculars that one is doing just because one is "supposed" to do them. I think he's right that his approach is both less stressful and less wasteful of human resources and effort. And it is more likely, in expectation, to build human capital and produce direct value for society.
2. Newport is correct to emphasize the link between free time and being able to explore stuff, and his advice on how to explore can be quite helpful to high school students.
3. Newport's ideas for how to focus on a particular interest, and how to rack up accomplishments in a particular area, seem broadly sound.
4. When it comes to figuring out what impresses college admissions officers, Newport seems like he knows what he's talking about, although some of his examples make less sense than he thinks they do.

Broad philosophical differences

Before getting into the nuts and bolts of what I think Newport gets right and wrong, I want to talk of some broad differences between Newport (as he presents himself) and me. A few things I find somewhat jarring in Newport's writing:

1. Newport seems very concerned with signaling quality to colleges. This is fine: that's what his target audience cares most about, and if getting into a good college is important, then signaling quality to college can be quite important. What I find somewhat offputting is that he often confuses the signaling with the value of the activity itself, or at any rate fails to question whether some of the things he believes to be optimal from the signaling viewpoint could be counterproductive from the perspective of value creation (either personal or social). For instance, consider his observation of the existence of the failed-simulation effect. This points in favor both of picking things that are harder for other people to "see through" (rather than things that are straightforward but hard) and also in favor of making what you did seem more undoable than it actually is. I see these as downsides of the failed-simulation effect, and sources of genuine conflict between choosing what creates the most value (personal or social) and what impresses others. Newport seems to sidestep such dilemmas.
2. Newport doesn't adequately address the zero-sum context in which he is giving his advice. Top colleges have a limited number of places for students. If everybody successfully implemented Newport's advice, only a small fraction of them would be able to go to a top college. Note that I don't think Newport views his advice as zero-sum, and even if what I wrote above is correct, his advice could still be positive-sum in that it shifts people away from competing on stressful dimensions to doing activities that offer them more fun and learning and create more value. But again, the fact that he doesn't really address this issue head-on is a disappointment.
3. Newport seems to oversystematize in ways that don't feel right to me. Even though I agree with aspects of the broad direction he is pushing people in, I feel he's seeing too many patterns that may not exist.
4. In general, I feel that Newport doesn't go far enough. He operates within the standard set of constraints without questioning the logic of the enterprise or giving people a better understanding of the incentives of different actors in the system. He also doesn't provide adequate guidance on the self-calibration problem, and doesn't adequately encourage people to figure out how to calibrate their learning better in the context of the extracurricular activity where they cannot rely on standard measures such as grades to track their progress.

I'm curious to know what readers' main areas of disagreement with Newport are, and/or whether my listed areas of disagreement make sense to readers.

Cross-posted to Quora and the Cognito Mentoring blog.