The 5 Books I Reread Every Year (or How to Read Less)

The 5 Books I Reread Every Year (or How to Read Less)

5 best books of all time to reread

“The difference between who you are now and who you are five years from now, comes down to the people you meet and the books you read.”

~Anonymous [Tweet this Quote]

The Link Between Reading and Success

It’s no secret that when I get into things I tend to obsess.

In the past few years I’ve read hundreds of books. No joke – I keep track of every title during my weekly planning process.

I owe much of who I am to the things I’ve read.

Just about the only benefit of my absolutely miserable first (and only) ‘job’ after moving back from Spain was that I had a 45-minute train commute every morning and night. That travel time became sacred. And that was when I became absolutely obsessed with reading.

So much so that I took a few speed-reading classes and I even became the head San Francisco instructor for one of them.

Side note: The Iris Organization gives fantastic intensive weekend speed-reading courses all around the country if interested. I’m still close with the founder, Paul, and he’s offering you guys $50 off if you use the promo code “liveyourlegend” – btw, I don’t get any compensation for you using it. I just think it will help a lot. My reading speed went up by over 3x after their two-day class. 

And come to think of it, reading is where this site first originated. I read a book, Internet Riches, that talked of how ‘easy’ it was to create a website without knowing code. So, as a test, I tried it out…

I created a blog to post book reviews and recommendations of the most influential books. That site started out as Reading For Your Success and later turned into Live Your Legend. And here we are!

My life would be a fraction of what it’s become if books hadn’t been a part of it.

The 80/20 of reading – How to Read Less

The funny thing is that of the hundreds upon hundreds of books I’ve read, there are still only a few that have provided the majority of the benefit. The 80/20 rule never fails.

And as you may have seen, one of my New Years resolutions was to reread more books.

Those of you who have read a book more than once, know that it’s an entirely new experience. We are so focused on checking boxes, that we forget that the point of reading books is not to finish them and move on to the next. The value does not lie it how many titles you can say you’ve ‘read’. The value comes from digesting, learning and acting upon the new ideas. That takes time. And it takes swallowing our pride and obsession with making visible ‘progress’ (at least it did for me).

Read more of what you know has already changed your life and you can bet it’s time well spent.

So I’d like to share with you the five books that have made the biggest difference in my life and career. These are the ones I reread every year without fail. I also included a few more below the list that deserve a mention.

The 5 Books I Reread Every Year:

1. How to Win Friends and Influence People by Dale Carnegie

how to win friends and influence people

If the human race was only allowed one book, this would be it. Hands down. Nothing has been more impactful for my business or personal life. Eight years ago a good friend of mine in Sevilla told me he read it every quarter. Who reads anything every three months?? I picked up a copy the next day. It’s been my bible ever since.

The simplicity and practicality of the advice is bar none. You can read a chapter on the bus to work and literally put it to use the moment you step off. Lessons include: giving people a reputation to live up to, the value of one’s name, how to give a real compliment, how to give honest criticism and…wait for it…smiling. This is the foundation for EVERYTHING. And the most incredible part – it was written in 1936 and is still as relevant as ever. Very few books can own the claim of being even more useful nearly 100 years after publishing. Over 15 million copies sold too.

Oh yeah, and to this day Warren Buffett says the most valuable diploma ever received, and still framed on the center of his office wall, is his diploma from a Dale Carnegie course.

“Remember that a person’s name is to that person the sweetest and most important sound in any language.”
– Dale Carnegie, [Tweet this Quote]

2. The Alchemist by Paulo Coelho

the alchemist

Over 22 million copies sold in over 67 languages has this book in the running for the best-selling book in history. In some odd ways it’s almost like the 4-Hour Work Week in fiction form, although I read The Alchemist long before. The message is pure and brilliant. The story of a Spanish boy who opts to say no to societal norms and pursue the road less traveled, or as Paulo Coelho calls it, one’s Personal Legend – your life’s destiny.

In fact, last year I was rereading this book (for the fifth time I believe) as I was fly fishing my way through Patagonia with my dad. And through its message came the inspiration for Live Your Legend. We launched the new brand a couple months later. The message forever keeps me on a path true to what matters. Very very fast read too.

“There is only one thing that makes a dream impossible to achieve: the fear of failure.”

-Paulo Coelho [Tweet this quote]

3. Influence: The Psychology of Persuasion by Robert Cialdini

Influence the psychology of persuasion

Charlie Munger, the 88-year old billionaire partner of Warren Buffett, consistently labels this his #1 book. For those of who have any idea how many books Munger plows through in a week, you will appreciate such a claim. It’s also a NY best-seller of over 2m copies and Fortune Magazine 75 Smartest Business Books.

In writing the book, Cialdini spent three years going “undercover” applying for jobs and training at used car dealerships, fund-raising organizations and telemarketing firms to observe real-life situations of persuasion. He also reviews many of the most important theories and experiments in social psychology. It covers decades of research and provides simple ways to apply the techniques in dozens of everyday situations.

You ever wondered why people from Greenpeace stand out in the cold asking for signatures, why Starbucks gives out free samples or even why you’re more likely to follow a man in a suit as he jaywalks than you are a man in shorts and a tee-shirt? A lot of things you never thought twice about, start to make sense pretty fast. Combine the lessons here with How to Win Friends and watch out.

Here’s an interview I did with the author: 4 Ways to Be a More Effective Influencer, and a review I did of the book.

“Our best evidence of what people truly feel and believe comes less from their words than from their deeds.”

– Robert Cialdini [Tweet this Quote]

4. The 4-Hour Work Week by Timothy Ferriss


I know everyone talks about this one. And by now it may be a bit of a broken record, but there’s a reason it’s been a non-stop best seller since it hit the shelves in 2007. Very few books (if any) have had such a streak. Live Your Legend would not exist if it wasn’t for this book. Nor would my lifestyle or approach to the world.

There are two reasons I read it every year. One, because the message is so important to keep front of mind: that we ought to value our life not based on the zero’s in our bank account but on the time we have to spend doing the things we truly enjoy. And two, because the step by step tools for testing an idea, starting an online business, testing it and scaling it, are priceless. And every year as I learn more about business and grow Live Your Legend, topics in the book become even more relevant. Oh yeah, and there is no way I would have a five-person team out in India doing top-notch work for an amazing price, if this book didn’t encourage the experiment 4 years ago.

More than anything, Tim’s message taught me not to settle for anything less than what absolutely mattered to me, instead of simply doing what everyone else said. And it gave me the wherewithal to know the difference. The case studies and success stories in the new version are priceless too.

“The commonsense rules of the “real world” are a fragile collection of socially reinforced illusions.”

– Timothy Ferriss [Tweet this Quote]

5. Never Eat Alone by Keith Ferrazzi

never eat alone

The title says it all. And to be honest, if you only followed those three words, this book would change your life. And it no doubt has mine. It’s an invaluable tool not only in teaching the importance of human interaction and relationships in every walk of life (especially business), but also the step by step tools to create your connections.

I’m paying special attention as I reread this and How to Win Friends these next couple weeks as I develop the content for the How to Connect with Anyone course I’ve started to work on (more on that soon!). I remember that within months of first reading this and the 4-Hour Work Week, I had made personal connections with Warren Buffet, Jessica Biel and Tim Ferriss. I don’t think that was coincidence. After some personal time with Keith, I can say that he’s also a genuinely good person who cares about helping people. Also a NY best-seller and a foundational book in many ways.

“Be interesting! Your responsibility is to be someone worth talking to, and even better, worth talking about.”

-Keith Ferrazzi [Tweet this Quote]

The people you meet and the books you read…

Over a lifetime, those two things make up much of who you become.

Did you happen to notice any similarities with the 5 titles above?

Over half of my top books directly deal with meeting and connect with people.

That’s not a conincidence. When I’m not out making friends and meeting passionate people to help and inspire me to change the world, I’m often at home reading or writing about it.

Nothing else really matters. It all comes down to the people.

That’s why this How to Connect with Anyone course is so important to me.

So those five books are seriously all you need.

Read them once. Then read them again. Then a few more times.

Or take a few seconds now to think about what your top rereads are. Put one next on your list (and tell us the name in the comments below!)

Remember, there is no race to read and do as much as possible.

We read so that we can be better for it.

Watch what happens when you start to focus on what you already know works like magic.

To reading less and learning more…


What’s your favorite reread? Share with us in the comments!

And if you want to reread it a little faster, check out: 7 Quick Steps to Finishing a Non-Fiction Book in Half the Time While Retaining Twice as Much

P.S. The above list was pretty obvious for me to put together but there were some other books I’d love to include. The below are some of the best of all time, I just don’t necessarily think they need to be reread every year (although it certainly wouldn’t hurt…)

The rest of my most influential books:

Start with Why by Simon Sinek – People don’t buy what you do, they buy why you do it. My most powerful business lesson of 2011.

What Color is Your Parachute by Richard Bolles – 41 years in print as a best-seller and over 10m copies sold. Hands down the best job search book of all time. My passion for helping people find their path came from a sushi dinner I had with Richard, his son and my dad nearly 10 years ago. Live Your Legend came from his work. I was actually just at his birthday party last weekend and he said they’re working on a web app of the book too. I can’t wait to see that!

Inbound Marketing by Dharmesh Shah and Brian Halligan – This is the book that finally convinced me to take my blog seriously and turn it into a business. Best book on the subject I’ve seen. Very easy to follow steps after each chapter.

The Essays of Warren Buffett by Warren Buffett – The only book he’s ever written. Best single business book of all time as far as I’m concerned. It’s a compilation of 30 or so years of his annual letters divided into various subject on business, philanthropy, investing and life.

Unlimited Power by Tony Robbins – Most powerful overall book on personal psychology, human change, energy and vitality I’ve seen. This is what opened my world up to the personal development space.

In Defense of Food by Michael Pollan – I’ve read dozens upon dozens of books on health, fitness and nutrition. Hands-down the most easy to understand and follow. If you don’t want to read the whole thing, just remember the tag line: Eat Food, Not Too Much, Mostly Plants. Perfect, simple advice. Very fast read too.

Born to Run by Christopher McDougall – Most inspirational book I’ve read on the power of the human body and your mind’s influence on what’s possible. Reading this got me to run a barefoot ultra-marathon in a matter of months. Incredible story-telling too.

Let My People Go Surfing by Yvon Chouinard – The founder of Patagonia shares the most refreshing approach to business I’ve seen. Spoken from a guy who truly puts passion and love for people and experiences far ahead of money.

The Ultimate Gift by Jim Stovall – I think this is the only book that’s made me cry. I dive into it around the holidays each year. About a 2-hour read and the perfect reminder that the stuff we worry about so often, really doesn’t matter a bit. I absolutely love this message (and story).

That should keep you busy for a while…