Book: The 4 Hour Workweek by Timothy Ferriss

The general idea of the book is protecting your time* - From meetings, overbearing bosses, and phone calls, something I can relate to.

I will be more receptive to you if you outline your ideas about the position in an e-mail rather than "hop on a call for a quick chat about this opportunity". I've taken to sending a link to this portfolio, a few relevant posts, and asking if this is in line with the position, and encouraging them to ask more questions.

I'm picking out the quotes that spoke to me. 

 "Risks weren't that scary once you took them."

It's true!

"It is far more lucrative and fun to leverage your strengths instead of attempting to fix all the chinks in your armor."

Struggling to drill down and use the Cybersecurity minor? Not for me. Security is to be respected and should be incorporated into new builds, and I will leave the CISSP to others and cheer them on.

 Learning, writing, and teaching? That's more my speed.

 "Most bosses are less than pleased if you spend one hour in the office each day..."

Because bosses and the entire workforce often operate by fear. 

Fear on the employee's side that you may become unemployed, so you play along.

Look for the company that lets you have a flexible working day where you become happy, relaxed, and civically engaged!

"Most people are fast to stop you before you get started but hesitant to get in the way if you're moving."

That's true!

"How has doing what you "should" resulted in subpar experiences or regret for not having done something else?"

I can tell you from experience; The "right" thing (college, certifications) have not helped me one iota. What society tells us is "right" is working for fewer and fewer people, and we should think more critically about following everything.

 Think about who benefits from us going to college initially; Between debt and underemployment - It's not us.

"Doing less meaningless work [...] This is hard for most to accept, because our culture tends to reward personal sacrifice instead of personal productivity."

See 'Most companies operate by fear' above.

The book surprisingly becomes outdated in ways it didn't anticipate; That you would have to wheedle your boss to support your remote work, as if they're the donkey and the carrot is more productivity. It still is a good framework on how to prompt for feedback and negotiate with people.

I'll leave you with my favorite quote - "Reality is negotiable."

*Also a lot of "taking advantage of the 'Global South'