@Rilles It doesn't feel sufficient to provide 5, based on my assumption of what's really being asked. So here's a list of 21 books that have had the most profound impact on my once-self-described 'self-improvement journey' + my now 'spiritual journey'. Roughly in chronological order. Self-Improvement Journey (2014-2019) The Two-Week Lucid Dreamer by Derek Raltson A random e-book I found on the iBooks store one day when I was bored in bed and messing around with my phone. I had my first lucid dream within a few weeks. Even though it only lasted 5 seconds, it was a euphoric experience! And paved the way to further reading and my first entrance into the world of self-improvement. Predictably Irrational by Dan Ariely My first dive into understanding the behaviour of myself and others. Rich Dad Poor Dad by Robert Kiyosaki The first ember of realization that I could build a business as my wealth vehicle and free myself from the system to a certain degree. The 7 Habits of Highly Effective People by Stephen Covey Great classic self-help that has served me well in life and business. The Millionaire Fastlane The next level up from Rich Dad Poor Dad that really gets into the specifics of building that wealth vehicle. Has served me well. The Choose Yourself Guide to Wealthy by James Altucher I grew to love Altucher's absolute transparency about the terrible situations he's been in. Divorce. Losing his house. Failing at business multiple times. Being a geek. The Game by Neil Strauss Blew my world apart. Understanding social dynamics and female psychology. Wow. Ended up getting into the whole pick-up scene and learned alot, although that's well behind me now. The Story of the Human Body by Daniel Lieberman Sheesh. Blew up my world-view. Helped me understand more about my behaviour and the current situation of humans and society in the last 300 years. Made me question more about what I eat, why we wear shoes, the authenticity/lack-of-authenticity of doctors etc. Sex God Method by Daniel Love Title says it all. Evolutionary Psychology by David Buss Another reality-blower like The Story of the Human Body. Work The System by Sam Carpenter Has completely changed the way I do business. Has improved it. I don't work much these days and business still grows at a nice level. Systems for the win. The Rational Male by Rollo Tomassi Helped me come to terms of the realities of life. Has helped me become way more detached from outcomes than I once was. Especially in the domain of relationships with women. The Future Is Faster Than You Think by Peter Diamandis Crazy how things are converging so fast with technology. Potential to completely change what we typically value and how we typically conduct ourselves on the spiritual path. And it's closer than we think. Being Infinite by Martin Ball The first book that I can remember where I began to enter the 'spiritual side of self-improvement'. Watched Leo's interview with Martin Ball and also had a chat with Martin myself. Incredible stuff. Encouraged me to pursue psychedelics further. Spiritual Journey (2020) The Almanack of Naval Ravikant: A Guide to Wealth and Happiness Still self-improvementy but Ravikant is pretty woke. A great summation of 10's of books I've read earlier on in my life. But possibly better thanks to Ravikan's way of communicating. Out of Your Mind by Alan Watts A beautiful aid for helping me understand non-duality on a conceptual level. Love, Freedom, and Alonelness: The Koan of Relationships by Osho Absolutely ripped my life apart in the greatest way. Took me to the next level of consciousness. Osho speaks Truth like I've seen in no other to date. Had a library of 150,000 books and spent much of his childhood in silence. It's my understanding that he was fully enlightened. Autobiography of a Spiritually Incorrect Mystic by Osho Page turner. Gasping every second page. In my top 5, hands down. Letting Go by David Hawkins An incredibly useful tool that's helped me to gauge where I'm at on my spiritual journey. And where others are at so I know the greats are to study. The Bible by Who The Hell Knows For Sure I took Duncan Trussel's suggestion on his JRE episode and read the Book of John under the influence of LSD. Some of the bible verses are crazy when viewed in this manner. When you replace 'God' as in white-beared guy in the sky with 'God' as in pure consciousness, the Bible completely changes. One verse for example is, "Be still and know that I am God". The Gnostic Gospels There's a fantastic description of Non-Duality in one of the Gnostic Gospels that were left out of the mainstream Bible. I believe it was Jesus who put forward the description.