Hidden Gems: Meet James Whittaker of Win the Day

Today we’d like to introduce you to James Whittaker.

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I grew up in Brisbane, a beautiful city that encapsulates all the best things about Australia. In 2012, I felt the itch to live in a new city, so I moved to Boston, MA, about as far away from Brisbane as you can get. One year after that, I moved to Los Angeles.

I spent the first few years living in Marina del Rey running international businesses remotely. It was a great lifestyle, but everything changed in 2019 when my wife and I had our first child. We moved to family neighborhood Westchester, which is also when I launched the Win the Day podcast. Filmed out of The Network Studios in Culver City, a short drive from my home, the podcast has been one of the most rewarding ventures I’ve ever been involved in. It’s been the platform for conversations with some of LA’s best and brightest—everyone from Olympic gold medalists and special forces operators to business leaders and medical experts.

It also spawned Win the Day as the go-to solution for high-growth organizations wanting their teams to operate closer to their potential more often.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I don’t think there’s such thing as a smooth road in life—if you’re on one, it just means you haven’t been on it long enough!

The biggest struggle for me was the transition to parenthood in 2019. The modern world, especially schools and and organizations, is not setup to integrate with households that have two working parents. The result of this friction is overwhelm—and as a new parent I felt it big time. My wife and I both travel a lot for work, often have stacked days, and now with two kids it’s certainly been an adjustment.

This is a struggle felt by all households with two working parents who are trying to keep their marriage strong, careers flourishing, and health on track, while still being present with and good role models for their kids. When you’re in it, there’s very little room to breathe, and you feel like there’s no reprieve in sight.

At the time, I had also been coaching CEOs and founders, but observed there was only so far they could go if their teams were not along for the ride. I became obsessed with finding a solution to this critical problem of “overwhelm” that was destroying workplaces and homes everywhere. I realized the answer was right in front of me: Win the Day.

We’ve been impressed with Win the Day, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
After experiencing it firsthand, I launched Win the Day to solve the problem of “overwhelm” in high-growth organizations. In early pilot tests, I discovered that these teams were only operating at 55% of their potential, on average, and some much less. That underperformance was causing massive friction in the workplace, and contributing to the stress that those couples I mentioned earlier felt at home, too. It’s a lose-lose scenario, without any relief in sight.

The quote I kept thinking of was from Michelangelo: “I saw the angel in the marble and carved until I set him free.” Through a short individual assessment, I give someone a benchmark—the awareness of where they’re at now—with 1-on-1 support, to unleash what they’re capable of. This is done alongside the most practical, science-backed actions I’ve compiled—with support of Harvard psychologists, Navy SEALs, and renowned medical leaders—into a 30-day action plan, personalized for each individual.

When the data poured in for those participants in the Win the Day program, we could see significant measurable gains in productivity, leadership capabilities, and retention—but the biggest gains were observed in stress management and work-life integration. With clear data, my clients finally began to understand and reap the benefits of having happy, productive, and purpose-driven employees.

The actions that saved me at my lowest are now being used by leading organizations throughout the US. The biggest struggle has now become a win-win scenario.

Is there something surprising that you feel even people who know you might not know about?
Like most Australians, I’m an avid coffee drinker, and love that LA is becoming known as the coffee capital of the US. My happy place is Likeminded on Washington Boulevard, Venice. I’m there most days for a sauna, cold plunge, and coffee.

Contact Info:

• Website: https://winthe.day
• Instagram: https://www.instagram.com/jameswhitt
• Facebook: https://fb.com/jameswhitt
• LinkedIn: https://www.linkedin.com/in/jameswhittaker1
• Twitter: https://x.com/JWhittaker01
• Youtube: https://www.youtube.com/@JamesWhittaker1