Awesome question. I also have two small boys and I think about these same things. I'm also hesitant about conventional education and sometimes wish that if I ha

Awesome question. I also have two small boys and I think about these same things. I'm also hesitant about conventional education and sometimes wish that if I had the financial means, I might like to home-school them (at least for some of their schooling years). Some random thoughts: * I think failure is glorified in a way that is not healthy, particularly in the startup field. Try to optimise for success https://signalvnoise.com/posts/1555-learning-from-failure-is-overrated https://signalvnoise.com/posts/1555-learning-from-failure-is... * Like you, I'd like to find the right/correct answer but lately it's the context that's more important. Helping my boys put this int practise would be valuable I think - more-so in human relationships than STEM pursuits. * If I can humble myself to learn how to learn about someone else's point of view, rather than attacking and trying to pull them around to my view, then I'll be setting a good example to my boys. I don't what them to think they have to agree or even tolerate other's points of view, but they should respect that someone else holds something different, even (especially) when they don't agree with it. * I'd also like them to build strong convictions to what they believe. I'd like them to use science and evidence to support things but at the same time, many things in life that are important, have to be taken on some measure of faith - I'd like my boys to have the resolve to choose a foundation they agree with and resist external influence if it's very important to them.