James Whittaker headshot

To understand why James Whittaker is so passionate about helping people activate their winning life—and how he arrived at the notion of Win the Day—it helps to rewind to his past. 

His childhood was, in a word, idyllic: He grew up in Brisbane, Australia, with a great family, attending a good school. “I had everything that we define as being on that great path to success,” Whittaker says. 

And yet: All that perfection couldn’t combat an anxiety disorder, which he found debilitating. In response, as a young adult, Whittaker became deeply apathetic. “The only way that I could get through all of these things was if I decided not to care,” he remembers. Others around him were flourishing, yet he was struggling to show up to school and work. 

“I felt like a… human destined for the scrapheap.” 

Rock bottom came, and then, a turnaround. It’s this inflection point—when Whittaker went from apathy to declaring himself ready to engage—that influenced the trajectory of the rest of his life. And, it’s why he’s so passionate about helping others live up to their potential, in his speaking, through his coaching and programs and with his books and other writing. 

“What I’m obsessed with is how do we take ordinary people and make them extraordinary achievers,” he says. 

Here, a look at how Whittaker got to where he is, and why he believes so strongly in the Win the Day mentality. 

From Australia to America and onto a new path 

After his crisis point as a young adult, Whittaker became an eager consumer of self-help materials, from subscribing to SUCCESS magazine to reading classics like How to Win Friends and Influence People. “I wanted to learn from the best in the world through books about everything,” he recalls. 

Things in his life got better—a lot better. After establishing a successful corporate career in Australia, in 2012, he moved to Boston, where he got his MBA. It’s around this moment—inspired at least somewhat by the entrepreneurs he was encountering in Boston—when he struck out on his own as an entrepreneur with Win the Day.

The birth of Win the Day

Here’s how Whittaker’s signature idea of winning the day was born: He was working for the Napoleon Hill Foundation, writing the book Think and Grow Rich: The Legacy and producing a movie with the same title. An idea leaped out at him, which essentially was that if people don’t make the decision to win, they’ve automatically made the decision to lose. 

“But that’s a bit clunky to say,” Whittaker notes. 

He wanted to come up with his own pithier version, something people could use as a simple mantra to save themselves daily. 

“And that’s where ‘Win the Day’ came from,” he remembers. 

Win the Day is a podcast and a coaching program, but it’s more than that too. It’s a mentality. “The mission, to be very clear, is to help every person on the planet to activate their Winning Life,” Whittaker writes on his blog. 

James Whittaker’s WIN method explained

One of the main ideas Whittaker talks about as a speaker is how people can activate their winning life “through implementing what I call the ‘WIN’ method,” he says. That’s an acronym, with the letters standing for the following ideas: 

  • Wonder: People should be intensively curious about how great they can be in “this one extraordinary life you’ve been given,” Whittaker says. Their vision should be bigger than getting out of bed each day and trudging through their routine. “What I mean by wonder is: What is your purpose? And what are your goals to show that you’re living in alignment with that purpose?” Whittaker says. 
  • Intent: This, Whittaker says, is “your commitment to a course of actions every day.” Think of intent as being your habits, your friends, the culture (books, movies, podcasts, and so on) that you take in. 
  • Nurture: This “is really your approach to adversity,” Whittaker says. How do you respond when bad things happen? How willing are you to put yourself in stressful situations? 

Whittaker, who can remember clearly that time in his life when he was focusless and disengaged, believes there’s always an opportunity for anyone—at any age—to “get back on track and Win the Day.” 

So many people are struggling, and so many seek to get to the next level, he says. But this isn’t possible if they don’t have their life in order. “That’s why to me any business success and career success… starts with a very clear awareness and assessment of who you are and where you want to go as an individual,” Whittaker says. 

That’s the starting point. “And then we go from there to integrate that with how everything that you do in your life personally and professionally can create success for you and give you energy,” Whittaker says.  

A foundation that lends itself to the pursuit of success 

Whittaker’s background is ideally situated to grow his understanding of what entrepreneurs need and what defines success. Years in the corporate world, along with time spent as an entrepreneur himself, mean he sees what big companies and corporations need. 

Plus, there’s all those hours in conversation with great thinkers, experts and entrepreneurs. For the Win the Day podcast, he’s interviewed experts as diverse as Michael Breus (aka the “Sleep Doctor”) and Navy SEAL Andrew Sullivan. On any given day, he might speak to psychologists, leaders and executives and other people who spend their own time thinking deeply about what it means to flourish.  

These conversations have shown him that the recipe for success is a combination of resourcefulness (how you acquire what you want) and resilience (how you persist in the face of adversity). During Whittaker’s speaking events, he caters to the audience, but broad themes include leveraging relationships, scaling income (without scaling workload) and activating a winning life. 

Getting results quickly and efficiently, Whittaker believes, is a matter of manufacturing opportunity to create meaning and profitability in both your life and business. Success in both life and business are essential: “We don’t really want to have one without the other,” he says. 

As for him? He’s precisely where he wants to be. 

“For the rest of my life, all I’m focused on is Win the Day, and how can I become the best in the world? And how can I help as many people as possible with that? I’ll do that forever.” 

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Photo courtesy of James Whittaker.