I’ve been asked twice in the past hour what books I’d recommend someone take a look at if they have a learning stipend at their company – or if they just want to learn something new over the holidays. Here are my top 50 books – and a few other stipend ideas – sorted out by topic and (roughly) ranked in order of importance in my opinion.

NOTE: This will be a running list and I will add and subtract to it over time. I’m also at my mom’s for the holidays and not in front of my bookcase so I may have missed a few good ones. If you think I had an egregious miss, please let me know :).

Three Things You Can Do With A Stipend 

  • Buy a sales course: I’m preferential to John Barrows, though I’m sure there are many great options 
  • Subscribe to a Patreon Page: They are usually $10/month and very affordable. Kevin Dorsey, Scott Leese, and Dave Gerhardt are a few fan favorites 
  • Book – lots and lots of books, below. 

Classics For Success 

  • Think and Grow Rich by Napolean Hill
  • How To Win Friends and Influence People by Dale Carnegie 
  • Awaken The Giant Within by Tony Robbins 
  • The 7 Habits of Highly Effective People 
  • The War of Art by Steven Pressfield 
  • The Greatest Salesman in the World by Og Mandino 
  • The Magic of Thinking Big by David Schwartz


  • The Little Red Book of Selling by Jeffrey Gitomer
  • Fanatical Prospecting by Jeb Blount 
  • Influence by Robert Cialdini 
  • The 10X Rule by Grant Cardone 
  • Building A Storybrand by Donald Miller 
  • Addicted To The Process by Scott Leese 
  • Never Split The Difference by Chris Voss 
  • Sell It Like Serhant by Ryan Serhant

Mindset / Psychology / Philosophy 

  • Man’s Search for Meaning by Viktor Frankl
  • Mindset by Carol Dweck
  • The Obstacle is the Way by Ryan Holiday
  • The Four Agreements by Don Miguel Ruiz
  • On The Shortness of Life by Seneca 
  • Grit by Angela Duckworth 
  • Ego is the Enemy by Ryan Holiday 
  • The Power of Intention by Wayne Dyer
  • Relentless by Tim Grover 
  • Can’t Hurt Me by David Goggins

Career / Leadership 

  • The One Thing by Gary Keller
  • Extreme Ownership by Jocko Willink 
  • Start With Why by Simon Sinek 
  • John Wooden’s Blue Book 
  • The Score Takes Care of Itself by Bill Walsh
  • Give and Take by Adam Grant 
  • Tools of Titans by Tim Ferriss 
  • 4 Hour Workweek by Tim Ferriss 
  • Principles by Ray Dalio  
  • Linchpin by Seth Godin
  • The Dip by Seth Godin 
  • Leaders Eat Last by Simon Sinek 
  • Dare To Lead by Brene Brown 
  • Deep Work by Cal Newport 
  • Untamed by Glennon Doyle

Other Important Life Skills / Entrepreneur Stories 

  • Shoe Dog by Phil Knight 
  • Made in America by Sam Walton 
  • Atomic Habits by James Clear
  • I WIll Teach You To Be Rich by Ramit Sethi 
  • Zero To One by Peter Thiel 
  • On Writing by Stephen King 
  • The Hard Thing About Hard Things by Ben Horowitz
  • Living With A Seal by Jesse Itzler
  • Do The Work by Steven Pressfield 
  • Thinking In Bets by Annie Duke