There's an employment section of Less Wrong Community How-Tos and Recommendations that includes ideas like doing a working holiday in Australia.

I'll give you one example, and maybe you'll be able to find something similar appropriate for him.

Social dance instructor. It's all sorts of good things that a tech degree is very far from, and would pay dividends for the rest of his life. It's social, it's expressive, it's physical. There's also the "cohort of youngins working for nothing" effect.

I would think this generalizes somewhat to various kinds of fitness instruction.

I've always thought that car salesman would make for very good experience. Negotiating and persuading are useful skills to have.

But that's the angle I'd suggest - find a "something different" job that leaves you with skills that will be personally useful long after the year is done.

Another angle to look at - doing a few different things for the year.

I would recommend spending that year outside of the United States.

AFAIK the satisfice for money, optimize for interestingness tends to be something more for already highly experienced people. For young people most jobs tend to be optimize for experience, satisfice for money and hardly any fun, or have a fun startup and optimize for fun, but not a living salary.

Modestly but regularly paying jobs with high fun level for beginners... perhaps he should avoid for-profit businesses for now, as they expect beginners to do sucky jobs in return for experience, and focus on academia, public sector or NGO's. Somewhere abroad perhaps. Teaching abroad perhaps? Some kind of an NGO sending CS/Math people to teach or tutor bright kids in third-world countries?

Let's focus on one criteria: if it is one year, it cannot be something that takes half a year to learn. He must work from what he already knows and that is probably academic stuff, not job experience, hence it should be probably teaching or academic research. Teaching is likelier and probably abroad as he can contribute more that way and find it more interesting.

Spend a lot of time around someone that he admires, who may not be in his field of study, and who may live in a different part of the world. Figure out how to observe them at work, or be their assistant, or something like that.

It may be more important to find the person or people to learn from than the specific activity.

My suggestion would be for your brother to pursue education in an area that is important, yet less familiar to him. Depending on what he chooses can help dictate the where he lives and how he could fund it.

Ex. I recently took 5 months in between jobs that were largely managerial and qualitative in nature to participate in a full-time code school program. Besides the practical use of learning to code, the greatest benefit to me was in the way it pushed me to be more structured with my thinking and explicit in my instructions to others. As your brother is a CS/Math major, I would think something along the lines of philosophy and history might be interesting topics to explore. Below are some examples.

What to study: History/Philosophy Focus: Modern Philosophy and the making of the modern world Where to live: Paris, London, Berlin - Bonus points if you live with a local host family What to read: Hobbes, Rousseau, Locke et al. What to do: Learn the basics of another language, travel, experience the culture, and connect it to your readings and apply your new found appreciation for history and philosophy to your work. It will help you frame your arguments. How to fund: English and Math tutoring

What to study: History/Philosophy Focus: Ancient Philosophy and Alternative Economics Where to live: China What to read: The 5 classics, the 4 books, History of China Podcast (its excellent), Poetry, Communist/Maoist lit. etc. What to do: travel, learn about Chinese culture and basic Mandarin (Peking Uni in Beijing offers courses in culture and language at a fairly cheap rate) How to fund: English and Math tutoring will work most anywhere, but China has more options for Americans in terms of paid gigs. He would be a hot commodity in China.

Bonus Points: Focus on physical fitness and developing a routine to manage physical health (prep for life at a desk)

Your sibling may or may not be interested in participating in Google Summer of Code, though the pay may be too little and I've heard (but not confirmed) that only around 10% of all applicants are taken.