Success Decoded: James Whittaker’s Personal Journey to Win the Day

UPDATED: August 31, 2023
PUBLISHED: August 22, 2023
James Whittaker, entrepreneur, author, and creator of Win the Day

Why does a sense of purpose so often elude us? With the advantages of instant communication and the world’s knowledge at our fingertips, motivated people may struggle to obtain personal achievement and find meaning. According to bestselling author James Whittaker, discovering our own path to success requires a change in mindset. He has strategically mapped this approach, and he calls it Win the Day.

“By default, we often lose the day,” Whittaker explains from his Los Angeles residence. “Our modern comforts make it too easy to become distracted, procrastinate and sit there scrolling through our phone.”

Today, Whittaker has appeared in global media including The Today Show and The Sydney Morning Herald, and his Win the Day podcast has drawn more than 30 million views. Money Magazine named his personal finance book, The Beginner’s Guide to Wealth, “Book of the Month,” and his second title, Think and Grow Rich: The Legacy, has been translated into six languages.

How Whittaker developed Win the Day

But Whittaker wasn’t always a top financial speaker. By high school, he had developed debilitating anxiety so strong, he often felt the urge to flee the classroom. With no understanding of psychology or mindset to guide him, he managed by simply deciding not to care. But that coping mechanism brought its own challenges.

“When you don’t care about what you’re doing, you’re not motivated to understand the rules of the game,” Whittaker says. “You’re not motivated to put the work in relative to your peers, to get a great result, which is going to open up other opportunities.”

This malaise brought health issues with it. He says he ate poorly and went out drinking too much. His mental condition and social situation declined until one day, at age 23, he hit rock bottom. He says he had become disgusted with himself, something he describes as a “powerful motivator.”

“It was at that moment I swore never to be a victim again.”

He put his full effort into shifting to a growth mindset, developing resilience and working toward peak performance. That included building and rebuilding his relationships, working out and hiring a sports dietician to improve his health.

By age 28, he managed 30 financial advisers with $2 billion under management. Still, with his newfound sense of growth and purpose, he knew he had more to offer. He left the corporate world and traveled to Shanghai and Boston to earn his MBA. Beyond classes, the experience exposed him to other cultures—and entrepreneurship. 

“For the first time I saw people my age and younger who were raising money, pitching ideas and changing the world through their companies,” Whittaker recalls. “And that was a really big lesson for me that if they can do it, then I can do it, too.”

Guiding others to Win the Day

A financial background, exposure to entrepreneurship and his own journey provided Whittaker with the formula for helping others. He developed the Win the Day approach to help others find their own purpose. But it’s an approach that takes work. In fact, Whittaker advises that becoming the best version of yourself requires a commitment to positive daily practices.

“Many people are just stuck following the same routine that isn’t giving them great results,” Whittaker explains. “And for those who are trying to break through, the only way they’re doing that is by running harder on the treadmill. What they really need is to get clear on who they are and where they want to go. It’s the most fundamental first step.”

The Win the Day method helps you discover who you are and what you want from life. From there, Whittaker addresses pain points and guides you to find your purpose and realize your dreams. He attacks self-defeating narratives while teaching strategies to steer adversity into motivation. 

Whittaker further introduces motivated professionals to top thinkers and doers, and he helps students learn the skills required to build lasting relationships.

“We need relationships in our lives to achieve our goals,” Whittaker advises. “That comes to pass by turning yourself into someone of increasing value, and by giving without the expectation of anything in return. That’s how you create, maintain and leverage high-power relationships.”

Intentional living requires commitment.

While Whittaker’s Win the Day method improves lives, it’s intended for those who are dedicated to making a change. He provides the tips and strategies necessary, but only those professionals who are dedicated see improvement.

“There is a much better life for you. You can get good results really fast,” Whittaker says. “But that only works if you turn up and you make the decision to win. Without that, you’ve automatically made the decision to lose.”

As another step in helping others build more purposeful lives, Whittaker has developed the Win the Day Accelerator. Presented by SUCCESS, the eight-part program is designed to help you activate that winning life—once and for all. The program will give you clarity on your goals and purpose, practical strategies to overcome challenges, expert guidance and more. 

“We’re going to activate your winning life,” Whittaker says of this project. “We’re going to identify what opportunities and experiences you need to have the impact that you want from your one extraordinary life and to become your best self.”

Do you want to unlock your full potential? Enroll in the Win the Day Accelerator today and get ready to transform your mindset, gain clarity and bring meaning, growth and happiness to every single day. 

Bryan Lindenberger

Bryan enjoys the digital space where arts and technology meet. As a writer, he has worked in education, health and wellbeing, and manufacturing. He also assists smaller businesses in web development including accessibility and content development. In his free time, he hikes trails in central Florida.