Required Reading and Degrees of Uncertainty
your Saturday roundup
Professionally, I focus on creating social benefit startups. In my Saturday morning emails I share what I’m learning and thinking. Topics range from better living and parenting to business and philosophy.
Choosing College. There’s broad agreement that basic education is a good investment for both individuals and society. For a time, college was a strong personal investment, even if we could doubt its shared value. Growing evidence suggests that recently college doesn’t always deliver an economic return. Even if you believe in the non-financial benefits of higher education, it’s important to understand its economic return. Be clear about what you’re seeking: status, knowledge, skills, accountability, power, camaraderie, connections, or wealth. Also assess your likelihood of finishing. A partial degree, with the costs, lost income, and negative signal, can become a burden—unless you're dropping out to become a (successful) founder. If what you want is a shared coming-of-age experience there are other options. Here are a few key points on the economics of college from the *Gap Letter*:
For the past few years, new college grads have experienced higher unemployment than the overall workforce for the first time since 1990.
52% of new and recent college graduates are underemployed.
Before AI, nearly 40% of good “entry-level” jobs were demanding at least 3 years work experience.
AI is prompting large employers of college grads to rethink and reduce entry-level hiring.
Douglas Webber, an economist at the Federal Reserve, calculates that if the total cost of college is $50,000 per year or more, the odds of coming out ahead today are no better than a coin flip.
College is worth it more often than not, but there are key exceptions. ROI for the median bachelor’s degree is $160,000, but that median belies a wide range of outcomes for individual programs. Bachelor’s degrees in engineering, computer science, nursing, and economics tend to have a payoff of $500,000 or more. Other majors, including fine arts, education, English, and psychology, usually have a smaller payoff — or none at all.
“Required Reading” for Our Kids: I’ve started assembling a “required reading” list for our kids—not school curriculum, but the kind of books that address broader questions. No book has all the answers. I hope these will prompt important conversations. What would make your list?
What Matters Most: A long advice letter from a father to a son heading off to college. I don’t agree with every word but it covers the right topics. Going through a chapter at a time with our oldest turned into a series of good conversations.
How to Get Rich: While not literally a book, it should be. A distilled philosophy of wealth and guidebook to obtain it. The core message: wealth creation is a skill, not a scam, and flows best when you solve valuable problems for the world. First trade time for money, then decouple the two—via assets, leverage, others labor, code, or creativity. It reframes wealth as permission to live freely, not just to accumulate.
The Happiness Hypothesis: A blend of ancient wisdom and modern psychology. Haidt takes old ideas and runs them through what we know for scientific studies. The understanding of the divided self and the centrality of relationships may be obvious but also important.
And maybe Selfish Reasons to Have More Kids (I want grandkids too!) and 15 Commitments of Conscious Leadership (as an intro to broader self-mastery topics).
AI Life Advice. Maybe our kids don’t want our advice or our static books. They’ll turn to AI instead. In many cases, they already are. Should we try to stop them? Or guide them? What kind of advice will AI give? Are some topics like building a workout plan or designing a meal safe, while others like choosing a life partner feel too personal or important to outsource? Or, as Harari suggests, might AI eventually be better at the big decisions, too? It’s remarkable how many of us already turn to AI for therapy, companionship, daily choices, even purpose. That shift only strengthens my conviction that critical thinking and epistemology—how we know what we know—are essential.
Until next time,
Miles