The Ultimate Holiday Gift Guide for 2020

December 8, 2020
James Whittaker

Check out this episode on the Win the Day Podcast

“When things change inside you, things change around you.”


Welcome to my third annual holiday gift guide! Each year, I outline the items that have made the biggest impact in my life throughout the year, and I know they’ll do the same for you.

Before we begin, this holiday season – rather than squandering money on gifts with little long-term value – consider giving something practical, like a life-changing book that gets the recipient excited about taking ownership of their future.

Aside from allowing us to delve into the minds of the most inspiring and innovative people who ever lived, books are a great gift because they sit there staring back at us: providing gentle prompts, imaginative thought, and unprecedented motivation when we need it most. In fact, many of the people I interviewed for Think and Grow Rich: The Legacy noted that, in times of distress, just staring at the cover of Napoleon Hill’s original classic made them feel better about themselves.

Audiobooks have again been a huge focus for me this year because you can listen with an increasing playback speed and also listen while you’re doing something else, such as cooking dinner or exercising, and it can even be used socially if, for example, you're driving and want to enjoy the book with someone else. Your mind gets amazingly good at an increased playback speed and now I listen to most books at about 1.5x, and you can simply rewind 15 or 30 seconds if there’s a point you missed or want to reinforce (which I do regularly).

For people who struggle with traditional books, I highly recommend audiobooks, although if you’re looking at a gift for someone other than yourself, perhaps a hardcover book is better.

Anytime I find a book that really speaks to me, I am sure to grab a copy of the hardcover version too so I can use as a quick reference point whenever I need it. And the #1 book I’ve read this year is actually an audiobook, as you’ll see below.

Filling your mind with the knowledge you need is the best way to transcend your circumstances so you can achieve whatever you want in life, regardless of what’s happened in your past. Every book I have read has changed my life in one way or another, so that hunger for learning should hopefully be a priority for you too.

Without further ado, here are the books that I think would make the best gifts this holiday season, for you, a friend or a loved one. They’re mentioned by category, rather than in any ranking order, so just pick whichever ones intrigue you the most.

Note: If you're new to the Win the Day show, welcome! You can subscribe to the podcast or on YouTube.

Best to future-proof your life:

Millennial Samurai by George Chanos

Many of you first came across George in Episode 27 of the Win the Day show where he spoke about the technological tsunami that’s sweeping the earth. That push to automation has only increased during the covid era, and this book contains hundreds of practical tips that you can use to prepare yourself for a world so different that even futurists have a hard time predicting it. George does an excellent job at communicating what some of those breakthroughs are likely to be in this easy to read book.

George has had an extraordinary career as Attorney General of Nevada, chairman of restaurant chain Capriotti’s, and even argued successfully in front of the United States Supreme Court. His book Millennial Samurai contains insights into artificial intelligence and so many other things that will rapidly transform the world in the next 30 years, and gives you a detailed plan to ensure you’re able to massively leverage the future rather than be made redundant by it.

George is an incredibly insightful bloke and if you want to future-proof your life, or be one of the leaders in the future, Millennial Samurai is the book for you.

Best for young people:

The Road to Success by Brandon T. Adams and Samantha Rossin

Brandon and Sam released this book in conjunction with their TV show Success In Your City to detail their journey all over the US to find out the true meaning of “success”. Together, they interviewed some incredible people who have defied the odds and created a life more meaningful than they ever imagined. Both the TV show and the book also include their wedding in Nashville, which was an amazing time, and – fun fact – I was actually the marriage officiant.

But the two themes of the book I enjoyed the most are:

  • First, the focus on the unrelenting work required to make something of yourself. Brandon and Sam have both been through so much, and to be taken into those moments is something special; and
  • Second, how raw this book is. Nothing about the journey is sugar-coated – not the imminent threat of bankruptcy, or their relationship teetering on the edge, or their struggles to even keep the project alive. They each even go into earlier memories from their own journeys that are so powerful to acknowledge them here wouldn’t do them justice.

If you want the perfect gift for a young adult with big dreams and looking to pursue a career as an entrepreneur, The Road to Success is highly recommended.

Best for parenting:

Blue Sky Kingdom by Bruce Kirkby

I just finished this book last week and it’s incredible. It reads like fiction. It’s a firsthand account of Bruce Kirkby, an engineering physicist by trade who quit his high-paying 9-5 job so he could spend his days in the great outdoors as a rafting guide. One day, after seeing how addicted he was to his iPhone, Bruce and his wife Christine decided to spend six months living in a Buddhist Monastery in the Himalayas so they could disconnect from modern life and reconnect with their two young children.

An extremely funny turn of events led to our mutual friend Wes Dening, who is a very successful TV producer in Los Angeles, coaxing Bruce into the idea of filming a TV show that documented their experience, which turned into a journey from Canada to Korea, India, Tibet, and many other places (including Mt Everest) with Bruce, Christine and their two young boys – on one condition: they wouldn’t use an airplane the entire time. That journey became the TV show My Big Crazy Family Adventure, which was a top-rated show on the Travel Channel.

Bruce is such a wonderful guy and his insights about what it means to reconnect with being human are a must read for all of us in this era of being increasingly distracted and glued to our phones that really don’t serve us like we think they do. Bruce also delves into the challenges of having a son on the autism spectrum, while balancing the rigors of modern life, and the stress of a 6-month backpacking trip through Asia with a film crew documenting your every move.

The language in the book is so creative and I can’t recommend it highly enough.

Best for personal growth:

Andrew Carnegie’s Mental Dynamite by Napoleon Hill and James Whittaker

This book was released just three months ago and has been getting rave reviews. It’s based on the initial conversation between Napoleon Hill and Andrew Carnegie. Hill, at the time, was a young reporter tasked with interviewing Carnegie who was (and still is!) one of the most successful people who ever lived, both in wealth accumulation and philanthropy.

In fact, before he died, Carnegie gave away almost his entire fortune so it could help make the world a better place. An example of that is the more than 7,000 public libraries that have been created from his gifts.

This book will show you how to master self-discipline, how to learn from defeat, and how to create relationships that give your life meaning, impact, and financial freedom. I’m so grateful that I was asked to help with this project, and you’ll see examples of the world’s leading individuals and companies who personify these lessons so you can have both the inspiration and the blueprint to achieve whatever you want in life – and make the world a better place along the way.

Andrew Carnegie’s Mental Dynamite is in thousands of bookstores in pretty much every country, so grab a copy today.

Best for gratitude:

The 5 Minute Journal by Intelligent Change

Next on our list is the best book for gratitude, and this is the only book that has made the list three years running! If you follow me on Instagram, you’ve probably seen how frequently I post these as daily stories. A huge percentage of CEOs have spoken about the importance of journaling for mental well-being; yet staring at a blank page each day can be daunting. The 5 Minute Journal provides a useful structure to start and finish the day in the right mindset.

On this show, we talk constantly about winning the day. The best way to win the day is to know what actions you’re going to take on a given day and how they relate to your long-term mission, and this book gives you a forum to be able to do just that.

To me, it’s been truly life-changing and it’s the book I gift the most. If you want an introduction to gratitude, this is where to start.

Best for relationships:

Leading Without Authority by Keith Ferrazzi

In August, I was extremely grateful to have Keith Ferrazzi on the Win the Day show. Keith is undoubtedly the global leader in relationships and networking. His latest book Leading Without Authority contains a blueprint to getting other people excited in your mission, so it becomes a shared mission – giving you a far greater probability of making an impact and having a lot of fun along the way.

What I love most about this book is how tactical it gets in the second half. In a covid world, this is essential reading, since Keith is also one of the world’s foremost experts in remote work, where he contributes to Harvard Business Review, Forbes, and The Wall Street Journal.

One of my proudest moments this year is having the opportunity to connect with Keith, and any of his work will change your life like it did for me. You can also check out his #1 NY Times bestselling book Never Eat Alone, which is still a monster hit today.

Best for empowerment:

Dare to Lead by Brene Brown

It’s hard to think about 'empowerment' without mentioning Brené Brown. Brené's work on the power of vulnerability has created a huge following, and her latest book Dare to Lead contains a lot of practical strategies to tap into your vulnerability and use it to strengthen, rather than weaken, your life. Like Keith, Brené is focused on real relationships with massive long term benefits, rather than transactional encounters that seek to benefit one person over another.

The book also delves into why values are so important and gives you a step by step guide to creating a compass that will point you in the right direction, no matter what crossroad you come across in life.

One big takeaway for me was that vulnerability without courage doesn’t exist. If you have that voice in your ear that says you’re not enough, but Dare to Lead give you the empowerment you need so you can start to make your mark on the world.

Best for entrepreneurs:

The Pumpkin Plan by Mike Michalowicz

My favorite book this year – I know you’ve been waiting for this one – is my recommendation for the best book for entrepreneurs, and it’s The Pumpkin Plan by Mike Michalowicz. We’ve actually got an interview with Mike scheduled for early next year, and he’s going to drop some incredible knowledge bombs.

To be clear, The Pumpkin Plan is the best audiobook I’ve ever heard – Mike has this incredible energy, and if you’re an entrepreneur or professional feeling constantly burnt out and that there aren’t enough hours in the day, this book will show you how to free up your time to focus on what matters most, while at the same time making a huge impact with your business.

Mike has written 7x bestselling books, and in The Pumpkin Plan he gives you a framework to turn your business from just another offering to being irresistibly magnetic. One of the biggest takeaways for me was the quote “Your first success is being happy”. As an entrepreneur, we constantly attach our happiness to tomorrow – or another date in the future – when what we should be doing is implementing a plan that gives us happiness and freedom in the present.

Mike is a great dude and you’re going to love this book if you’re an entrepreneur. Check out The Pumpkin Plan – I highly recommend the audiobook – and definitely keep an eye out for his episode on Win the Day coming in January 2021.

Best Gift (or Accompaniment) for Everyone:

The final recommendation on this list, which is the best gift (or gift accompaniment) for everyone, is a letter or card – handwritten if your legibility allows – to acknowledge the recipient for all the loving and selfless actions they have taken to brighten your world and illuminate your spirit. Expressing our gratitude to one another in the long form written medium has become a lost art, but that just means your opportunity to make an impression will be even more powerful.

You've heard me say many times before that the best way to get is to give first. This holiday season, give someone a piece of your heart, and watch the way your life changes as a result.

I proudly recommend all these books and know they would be a welcome gift in any stocking. This year give your friends and loved ones the inspiration and ability to help themselves.

As we approach the end of 2020, I wanted to thank each and every one of you for your continued support. This will be the last episode for the year, and we’ll be back stronger than ever in the second week of January with incredible guests. And their mission? To help you win the day, every day.

If you haven't checked out our YouTube channel, click here and get access to exclusive content and other videos to help you blast through whatever obstacles you're facing.

Have a wonderful holiday season with your loved ones and get excited for an incredible 2021.

Remember, to get out there and win the day. Until next year, onwards and upwards always.

Happy holidays,
James Whittaker

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