Here are some books that I would recommend that are enjoyable, informative, and that give insight.

Name Categories Description/Take Aways
The Tipping Point by Malcom Gladwell Psychology, People, Social, Behavior 80/20 rule, Power of Context, Broken Glass Theory
Steve Jobs by Walter Isaacson Biography, Entrepreneurship, Business A very good businessman who knew very little about computers but a lot about humans
The 7 Habits of Highly Effective People by Stephen Covey Personal Development, Management, Productivity Read once, take action, repeat. If you are starting something new (new school year, new job, new move) read this.
Smarter Faster Better: The Secrets of Being Productive in Life and Business by Charles Duhigg Productivity, Management, Behavior Enjoyable story telling. Each chapter is it's own point.
Shoe Dogs by Phil Knight Biography, Narrative/Memoir, Entrepreneurship The history of Nike. Oregen. Track. How to make something not appealing appealing.
My Experiments with Truth by Mahatma Gandhi Biography, Spiritual A man who's flaws and mistakes are out in the open for us to learn from. His journey of seeking truth in the world.
Flash Boys by Michael Lewis US Stock Market, Finance, High Frequency Trading The story of a trader, a programmer, and an industry. The story of IEX - getting back to the original purpose of a stock exchange
Algorithms to Live By by Brian Christian and Tom Griffiths Behavior, Data Analytics Using data to make decisions in life
Outliers by Malcolm Gladwell Behavior, Psychology, People What makes successful people successful? A lot of outside factors actually
When Breath Becomes Air by Paul Kalanithi Memoir How would you live if you knew you were going to die?
Ego is the enemy by Ryan Holiday Behavior, Psychology, Stoicism What the title says. Takes snippets of many people's lives
Scrum: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland Productivity, Management Scrum: How to produce efficiently and management a team