12 Lessons to Win the Day with James Whittaker

June 8, 2021
James Whittaker

Check out this episode on the Win the Day Podcast

Each day, if you do not make the decision to win, you have automatically made the decision to lose.”

James Whittaker

Welcome to Win the Day and today is a special one – this is Episode 50!

Before we dive into all the good stuff for today, I just want to say an enormous THANK YOU for listening to this podcast, watching it on YouTube, and sharing it with friends. Your support means the world to me, and we’ve got some seriously kickass episodes coming up! So if you haven’t already, hit subscribe on YouTube or follow on Spotify. Together, let’s bring more and more positive energy into the world.

Because this show is about growth. It’s about recognizing that, while we might’ve faced adversity, challenges – even serious trauma – in our past, all that matters is what we decide to do from here. That’s why to truly win the day, we must begin every morning with an acknowledgement that the day – THIS day – is there to be won.

When I’m bringing these guests on the show – who are some of the most accomplished individuals on the planet – I’m trying to hone in on what they’ve done different:

  • What do they action or discard from their life;
  • How do they respond to failure; and
  • How do they create such impactful relationships.

With that information, I can learn, you can learn, and together we can inspire others through our example. That’s growth. Every day, we get better and better, so we can make the world – and everyone in it – a better place.

But this show is nothing without ACTION, so make sure with every episode you think about what 2-3 things you’re going to do as a result of what you’ve learned. As Napoleon Hill said, “Action is the real measure of intelligence.”

Today, in honor of our 50th episode, I’m going to share with you my 12 most memorable takeaways from the guests’ we’ve had on the show. These are the value bombs that have stood out to me the most, and I know will be enormously impactful for you too.

And because of this milestone, we've got a special giveaway! Make sure you check out the podcast or YouTube version of this episode for more info on that.

The quote for this episode is one I put up at every speech:

“Each day, if you do not make the decision to win, you have automatically made the decision to lose.”

If you can figure that quote out, and turn that into a habit, the rest is easy.

In fact, I started saying “Win the day” because I wanted something more succinct from that sentence that I could use for my podcast. And the rest is history! Here we are, 50 episodes in, and you and I are still making the decision to win because the alternative, which is slowly losing every day, eroding our progress, and sabotaging our dreams, is not something we can tolerate. We’ve got ONE life to live and we’re going to unlock every little particle of potential inside us so our time on the earth is well spent.

So are you ready to win? I hope so! And if there’s a friend or loved one who wants to join us, share this episode with them right now.

In honor of our 50th episode, here are the 12 best tips to win the day, every day. Welcome to the Win the Day All-Star Edition. 

NOTE: This episode contains exclusive clips from special guests who have come on the show. For the best experience, we recommend checking out either the podcast or YouTube version of this episode.

1. The best way to show you’re grateful for something is to take care of it.

I’ve noticed that the word “gratitude” has become hijacked lately, a little bit like the “self-love” movement. People talk a big gratitude game and post their fancy snaps on Instagram, but what Gabby Reece shared during Episode 43 of the show is that the best way to show you’re grateful for something is to actually take care of it.

That means, behind closed doors, when the phone’s away, you’re looking after the things you’re grateful for – whether that’s your physical health, your mental health, or the most important people in your life.

Here’s what Gabby shared:

“I don't need to lose my health to covet it.

The other thing I'm doing is I'm practicing. When people talk about gratitude, the best way I can show that, "Hey, I'm really grateful for my health," is to take care of it. That's ultimately what I'm doing.

The other side of that is it's a level of sanity. I am a better functioning organism if I can also take care of the physical avatar to the best of my ability. It's a law of the universe. It's the truth, and so I don't need to keep relearning that lesson. I know what the lesson is, and I'm just ahead with it.”

So if, like me, you’ve been bitten by the gratitude bug, that’s awesome! Just make sure you’re doing the reps behind the scenes. Those daily reps add up to massive results over time.

2. Actively pursue calm so you can thrive in chaos.

If there’s one thing the covid pandemic has emphasized in bold, italic, and underline, it’s that the world is shifting faster than ever before – but, most importantly, it’s going to keep getting faster and faster, as George Chanos reminded us in Episode 27.

When the covid pandemic started, there was an entrepreneur in Australia who saw it coming months ahead of time, and that was Kerwin Rae.

In Episode 31 Kerwin came on the show to reveal those insights with us, but what I found most impactful was his emphasis on pursuing calm at all costs. As the world is getting faster, more chaotic, more transactional, more automated, and more digital, we’re faced with sensory stimulation like we’ve never even imagined – and that’s an absolute recipe for disaster where our mental health is concerned.

Yet, Kerwin reminds us that we need to shift away from passive sensory overload, and instead shift to more proactively putting ourselves in situations that get us out of our comfort zone in a good way. And if we can do that regularly, and train ourselves to be effective and calm in complete chaos, we will not only be extremely well positioned to benefit from the rapidly changing world but we'll also insulate ourselves from failure that could be completely demobilizing for most people.

Here’s what Kerwin said:

“The more you can regulate stress in a healthy way, at levels that other people can't, the more you’ll enable yourself to go further than anyone else can.

That’s the beautiful thing about being human. We all have this capability to grow. We all have this capability to change and transform.

The only difference between someone who plays here and someone who plays here is their ability to expose themselves to information, in some cases, stress, at a level that they can regulate in a healthy way. That's why not everyone's going to be able to build a multi-billion-dollar company because not everyone could cope with the mental stress of even considering working with those denominations and those values.

And that's why you'll always find where your limit is, and wherever that limit is you'll be constrained by some level of fear that triggers a level of stress.”

3. Tie your financial goals to your definite major purpose.

Most people recognize the importance of proper goal-setting in achieving what they want. (And to start practicing what I believe is the most effective goal-setting system available, download my Success Plan. Free instant download; no opt-in required). But when it comes to your financial goals, the secret sauce is how you tie them into your definite major purpose.

Your definite major purpose is the core goal you have that most of your other sub-goals stem from.

Anyone can put “$1 million” on a goal sheet, but tying it into your definite major purpose, backing it by emotion, and then outlining the steps you need to take to get there and how that will impact the world is going to make it 100x more likely for you to achieve that goal.

In Episode 38, personal finance expert Adam Carroll shared this with us:

“My parents were very positive-minded and they talked about opportunity a lot. My dad was big into Deepak Chopra back in the day. And he would tell me growing up that I was a wizard, and I didn't really understand what he was telling me at the time. I had visions of Harry Potter-esque kind of wizards.

But what he was telling me, I believe, is that I could create whatever environment I wanted to create; that I had the ability to manifest my own desires. And so when I read Think and Grow Rich the first time – which you are obviously well-versed in – I realized how important the messages of definiteness of purpose, and of focus and attention, were. I have a saying up on my door up here and it says “The definiteness of purpose for acquiring wealth is necessary for its acquisition.”

And I kept reading that over and over and over again. Think and Grow Rich was one of the first books that got me on the path. Then I went down this unbelievable rabbit hole of finding all of the quantum physics and law of attraction books that were out there. I realized that we are all constantly, consciously or unconsciously, creating our own environment.”

So powerful.

Remember, Adam is the guy whose TED Talk on playing Monopoly with real money has 6+ million views. So if you’ve got big financial goals – and you should because the more resources you have at your disposal the more you can contribute to the causes you care about the most – you need to tie it into a higher purpose or mission that you have for your life.

4. Your past isn’t your future.

If we’ve been brought up in an environment that doesn’t reward creativity, growth or love, we might feel that we’re doomed to continue that cycle. Or worse, we might never recognize that a problem even exists because it seems “normal” to us.

But in Episode 37, Dr Sonja Stribling – who’s one of the toughest and most resilient people I’ve ever met – stated:

“When you hear me say that 'If you didn't come from a wealthy family, let a wealthy family come from you,' it empowers you to realize that just because you came from nothing doesn't mean your family has to carry on that tradition. It means you get to create whatever lifestyle you want. That's just been my mantra. I don't want my children to suffer the way I did or the way my mother did.

And it's not just about the money. Being rich is more about teaching different ways that your children don't have to always go get a 9:00am to 5:00pm job and always have to go to school because school is not for everyone. There are other means to create wealth. You just need to know where to find those ideas and the strategies and the tips and tools to do so.”

While, at times, you might feel that your future is pre-destined because of the circumstances where you grew up, it’s never too late to be what you want to be, lead by example, and inspire future generations to take ownership of their lives. And while the goal of flipping the script of generational poverty in your family and turning it to generational wealth might be great financially, never forget that it’s the lessons, the relationships, and the attitude to handling adversity that are the most important things.

5. There is no excuse for you to remain mediocre.

This might seem harsh, but I’ve interviewed enough people now who have overcome the most horrific circumstances imaginable and gone on to incredible success. To see firsthand what they’ve been able to do with their lives but, more importantly, how grateful they are for that adversity, has been the biggest blessing I've had on this journey. In some of their deepest pain, they were able to use those experiences as fuel to live a life of compassion, meaning, and impact.

Some of those people are Janine Shepherd, who I mentioned in chapter one of Think and Grow Rich: The Legacy. Her story as a walking paraplegic is extraordinary. Remember, she had qualified for the Olympic Games, only to have her athletic dreams and physical being completely destroyed through no fault of her own.

There’s Jim Stovall who, at 18, went totally and permanently blind, before going on to write 30 bestselling books and become the founder of the Narrative Television Network – while blind. Todd Love, who became a triple amputee at 18 years old after being blown up by an IED in Afghanistan; Todd views the explosion as a “gift” and has since completed the Spartan Race on numerous occasions to inspire others.

Or Sonja Stribling, who we just mentioned in the last tip, who was born into a family as the youngest of 12 children, to parents who only had a second-grade education. At age 15, she gave birth to her first child. And just two years later, at 17 years old, she was raped and left for dead in a field. Sonja is now an internationally regarded female empowerment coach who helps millions of people around the world.

There are too many examples of this.

Make no mistake, how you respond to adversity when it INEVITABLY strikes is what separates ordinary people from extraordinary achievers.

And in Episode 30, #1 NY Times bestselling author Keith Ferrazzi shared a very succinct approach for those who want to become extraordinary:

“There is no excuse for you to remain mediocre. If you want to be extraordinary, you chart your path. If you hold onto your individual title, you'll never have enough resources under your control to really break through. You need to go to Peter Diamandis, you need to go to Jim Kwik, you need to get James Whittaker who knows everything about podcasts to teach you about podcasts, right?

You need to expand your view of team. If you don't redefine your view of team, you will remain mediocre with mediocre resources.”

So think about what you can do to turn your individual mission into a shared mission.

There is no excuse for you to remain mediocre. If you want to be extraordinary, you chart your path and build the team to get you there. That’s it. It’s so empowering.

Rather than dwell on our misfortune, or people who’ve wronged us, or whatever it might be, we instead need to channel that energy into constructive means so we can create the very circumstances we want.

That all starts with a recognition that a better life awaits (irrespective of what has happened to us in the past), followed by a focus on detailed plans to make it happen, then a commitment to seeing it through with the right people around us.

6. Regardless of what happened yesterday, wake up ready to win today.

Like most of these tips, the real growth comes when you can turn them into a habit – that way, when the voice of doubt kicks in, it’s quickly overridden by habit and you do what needs to be done.

One of the best habits to have is waking up and recognizing today as a clean slate, which means you leave any drama, frustration, or stress in the past where it belongs. And you wake up excited for another opportunity to do exactly what you want to do.

In Episode 42, ultra athlete Marcus Smith, who was almost killed after being hit by a vehicle while cycling, shared this:

“We ALL have tough days. We ALL get overwhelmed and we have to be honest with ourselves on that. But I think what the difference is from what you said and from what I see in my life is that no matter how bad today is I'll wake up tomorrow and it's a new day, and I'm ready to dominate and you're ready to win the day.

If I can just encourage people that every time you go to bed, when you get up the next day, you've been just gifted this unique opportunity to do amazing things. You've got a fresh mind. And if you start the day with this great positive mindset that you're going to have an awesome life, you can just rinse and repeat that. It's beautiful.”

And there’s a level of peace that you can see in these people. They’re at peace with themselves and what has happened to them, and they’re even at peace with the people who were responsible for their most brutal pain.

But more than peace, they also know exactly who they are, what they’re capable of, and how they will inch closer toward their mission.

7. Always take time for yourself.

There’s been many moments in my life – too many to name – where I’ve reached a pretty dark place and felt overwhelmed and frustrated, and the negative self-talk got noisier and noisier.

Inevitably, in every one of those instances, it was because I either did not know about the daily rituals for success, or I had become so overwhelmed with work that I neglected those daily rituals of success.

If we fall out of alignment, that’s when those dark feelings emerge, and it’s a horrible feeling to find yourself in a situation where you’re saying, “How did I get here AGAIN?”

It can be a difficult road to come back from.

In Episode 48, Rob Angel – who was the creator of the world’s bestselling board game, Pictionary – mentioned how he had to take a leave of absence from his own business because he was totally out of alignment:

“As entrepreneurs, they say you've got to push hard and make sure you're working 24/7, and you've got to push, push, push. Well, that's what I wound up doing. And about 5-6 years in, I changed my mission from giving Pictionary to the world and people having fun, to how do I make more money and push this game.

It wasn't just burnout. It was complete and total anxiety. I wasn't comfortable with myself. My authentic self had left and I was so off balance. I was so out of alignment. But I didn't know how to deal with it. So for a couple of years, I was getting in fights with my partners over nothing.

And I wouldn't show up for work periodically and it just became untenable. So I took a leave of absence. That's all I could do. I had to remove myself and recalibrate and took about six months. I came back to the business and the partners accepted me and took up the slack. But you don't have to do that. You can pre-warn.

Make sure you take an hour for yourself every day. Whether it's meditation, watching television, working out, or whatever it might be, where you don't think about your business. Because guess what? If you're not there for 20 minutes, it's going to be there when you get back. It's not like it'll fail if you take time for yourself.

I do believe in meditation. But if that just sounds so woo-hoo and off the wall, take a walk, anything, but you've got to take care of yourself mentally, spiritually, and physically to be more productive and make more money and be more successful. You have to.”

So make sure you stay in alignment. And the best way to do to that is: to always have an idea of what success looks like to you in ALL areas; and, second, make sure your own cup is full at all times, because the more you have the more you have to give.

8. Give yourself time to heal and re-align.

A surprising theme I noted from most of the people who’ve come on the show is that a deliberate break has been the springboard to their greatest achievement. In Episode 26, Australian entrepreneur Michael Fox (founder of Fable Food Co) shared how he raised more than US $30 million for an exciting business venture that was backed by some of the most established retailers and venture capital firms in the world.

But after losing everything – his business, the $30 million in investor money, 10 years of his life, and even his marriage – Michael took six months off in Europe where he allowed his intellectual curiosity to go where it wanted to go.

In that moment of massive internal transition, which didn’t have any boundaries or time constraints around it (like he’d had with the rigorous demands of running his own business), Michael became drawn to one particular topic, which became the foundation of his new mission: to end industrial agriculture.

Michael went all-in on that mission, and in a few short years has created a high-end meat alternative that uses mushrooms, which is now available in more than 1,000 supermarkets and has partnered with people like acclaimed chef Heston Blumenthal.

Here’s what Michael had to say:

“My wife and I, with our one-and-a-half-year-old, went to Denmark. For me, it was a great period to have a reset – I didn't have any pressure to find a job or figure out what I was going to do next. I just knew, okay, there's six months, I can focus on being a dad and do whatever I feel like doing.

I ended up reading a lot of books. And because I've been vegetarian for four and a half years, I just ended up reading more about industrial animal agriculture. There were other areas that I was really passionate about and started exploring too, like community living and some different areas like that. But I just ended up reading all these different areas that I was passionate about.

Then towards the end of the six months, I started thinking, “Well, there's two or three areas I'm deeply passionate about, is there a business model or something that I could do?” Well, actually, I didn't even want to start a new business. I was thinking that maybe I could work for someone else in in the meat alternative space because it’s a space that's been growing really quickly.

That six months allowed me to explore whatever I wanted to, wherever my intellectual curiosity took me. That really helped me narrow in on what my passion was and what industry I might like to enter. We added lifestyle decisions around that, and got to work."

So if you’ve gone through a very difficult period, make sure you take a defined period of time – without any boundaries, constraints, or pressure – to allow your intellectual curiosity to go wherever it wants to go. You’ll likely find answers to what you want with much more clarity than you’ve experienced ever before, which could be the perfect springboard to your next chapter.

9. The most important opinion is how you feel about yourself.

All those who do great things have one fundamental attribute: unwavering self-belief. In a world, where haters come with the territory, and everything we see comes with a like, share, and comment button, it’s more important than ever to recognize that there’s only ONE opinion that really matters and it’s how you feel about yourself.

In Episode 32, a truly unique guy, Coss Marte, came on the show to share his story. Coss was brought up in very difficult circumstances, before finding massive success on the wrong side of the law. As one of New York’s most prominent drug dealers, Coss was earning more than $5 million a year at 21 years old and needed eight mobile phones just to store the sheer number of customer contacts. Eventually, he was sentenced to a lengthy prison sentence, but was able to use his time inside to start a new career as a fitness entrepreneur.

There was one quote that stood out to me during our conversation: “My mentality was nothing is going to stop me.” Even in a prison cell, Coss was going to turn his dream into a reality, and I would never bet against someone with that level of faith in themselves.

Here’s how Coss describes what happened next:

“I started realizing that I was affecting not only the thousands of people that I sold drugs to, but I started thinking about their families. I started thinking about my family. I started thinking about this web of destruction that I'd created, and I felt so much regret. I said, “I want to give back in some sort of way.”

I came up with the idea of ConBody in that cell. Then, I lost 70 pounds in six months, while helping 20 other inmates lose more than 1,000 pounds combined. So, I started this whole workout program in the prison yard. I knew then that it’s what I wanted to do when I came home: a prison-style bootcamp. In my cell, I wrote a mini-business plan and a 90-day workout plan.

I said to myself that I would do what I wrote, and I did.

About a year later, I came home and put it into action. I started training classes in the park, then rented out studios, then eventually opened up my own studio. It escalated to building an online workout platform where I now train thousands of people all over the world. Today, we've trained more than 50,000 people. But the most beautiful thing is that we've hired over 40 people coming out of the prison system, and none of them have come back into the system.”

So next time you’re faced with an opinion about what you’re not capable of, whether it’s from a family member, a friend, or a total stranger, remember that those comments are based on THEIR limitations. The most important opinion is how you feel about yourself, so take action on your dreams and what you know you're capable of.

10. Create imagined memories to manifest your ideal outcomes.

That might sound a little woo-woo, but what Emily Fletcher shared in Episode 29 blew me away. Emily is the world’s leader in meditation for high performance, and one of the most valuable takeaways I got from her episode was that the mind doesn’t know the difference between imagined memories we create for the future and actual memories from our past.

So if we’re serious about creating a life we love, a powerful method is to consciously remind ourselves of the outcomes we want and have the discipline to do it every day. We literally visualize an important moment – whether it’s a client meeting, a keynote presentation, a guest appearance on a podcast – and play out the entire event in our most optimal state.

That way, when it happens in real time, we’ve already trained our subconscious to deliver at the highest possible level and made sure we’re perfectly prepared for that opportunity.

Emily uses a combination of meditation and manifestation to reduce the impact of previous trauma while empowering us to get the absolute best result from important events we have coming up in the future:

“Mindfulness is really good at dealing with your stress in the now. And then the manifesting piece is all about dealing with your dreams for the future. So it sounds a little hippy-dippy. It sounds a little woo-woo. Maybe not to you or your audience!

But I would define manifesting as consciously creating a life you love. It is reminding yourself of your dreams. And what I've found is that the combination – and this might really be the thing that keeps you committed to meditation – the combination of meditation and manifesting is so much more powerful than either one alone. Because you could meditate all day, but if you're not clear about what it is that you want it's very hard for nature to give you the thing.

And conversely, you could manifest all day, lining your walls with vision boards, but if you're not meditating and your nervous system is riddled with stress and trauma, and limiting beliefs that you can't even see, then again it's going to be a lot harder for you to achieve your dreams. But when you do them together, you get rid of the stress in your body, you peel away these subconscious limiting beliefs, and you remind yourself of your dreams every day, twice a day, and things start to show up a lot more quickly.”

It’s one hell of a bio-hack, yet so few people do it. If now is the time to massively level-up with what you’re doing, create imagined memories for future events to manifest your ideal outcomes.

11. Help the people who want the help, not the people who need the help.

This has been a lesson I learned the hard way. Naively, I thought I could help everyone, and you might have felt – or still feel – the same way. But if we try to lift people up who don’t even want to be lifted, not only are we NOT going to be able to lift them up but they’ll likely end up pulling us down to their level.

But in Episode 33, mindset expert John Assaraf mentioned:

“On many occasions I’ve worked harder at helping somebody achieve their goal than they have. But that brings me back to a couple of things that I've discovered over the years. First and foremost, help the people who want the help, not the people who need the help.

Number two, don't be in the convincing business, because if you've got to convince somebody, then they're not sold on themselves doing it.

Number three, every person I work with I ask the question, “Are you interested or are you committed?” And if they tell me they're committed, and they're willing to do whatever it takes, and be radically honest with themselves, and radically honest with what they do, or don't do, then I'm willing to help you.

But anybody else, I have no interest in helping. I don't want to spend my time trying to talk somebody into what they should be doing.”

Powerful, right!? And I’ll never forget it. John shared a TON of gold in that episode.

12. Action is everything.

There’s a quote we mentioned at the start of this episode from Napoleon Hill: “Action is the real measure of intelligence.” Hill also mentioned “It doesn’t matter what you know; it matters what you DO with what you know.”

And when Brandon T. Adams came on the show in Episode 35, he said this:

“Action is what gets results. The number one thing holding people back is they think about something and they strategize all day. At the end of the day, an idea is shit unless you actually take action towards it, and that's what I learned in Think and Grow Rich. You've got to take daily action, even if it's one thing you do every day, every single day, just one thing you accomplish. It'll build up, it's the compound effect. It'll slowly build up over time, and eventually, get you your bigger opportunity.

If you take action, get outside your comfort zone, and become comfortable being uncomfortable, you will find opportunity. And then follow up on the opportunity; don't just get it and then let it go. You have to follow up and keep taking action, every single day.”

And that’s success in a nutshell. Eventually, you have to get your hands dirty. You’ve got to get out of your comfort zone. You’ve got to take action. So a question I want you to ask yourself right now is:

Who do I need to become to succeed in this rapidly changing world?

There might be skills you need to get, relationships you have to establish, limiting beliefs you need to overcome. The world is changing faster than ever, so it’s more important than ever to make sure you’re clear on who you need to become so you can figure out what action you need to take.


I hope you’ve enjoyed those 12 tips to win the day every day! If you wanted to dive into those in more detail, you can check out the full episodes, available in video on YouTube and in audio on Apple Podcasts, Spotify, Google, Amazon, and everywhere you listen to podcasts.

What was your favorite tip? Let me know in either the comments on the YouTube video or in a review on Apple Podcasts. We’ll then pick out THREE lucky people to receive a signed copy of Think and Grow Rich: The Legacy delivered to wherever you are in the world for free.

Is there someone in your life who needs some help winning the day? Share this episode with them now. They’ll thank you for it later, I promise.

To finish, I want to leave you with the quote for today’s episode:

“Each day if you do not make the decision to win you have automatically made the decision to lose.”

Imprint that on your mind so nothing can knock you off course ever again.

That’s all, folks! Remember, to get out there and win the day. And think about how strong you'll be when we hit 100 episodes 😉

Onwards and upwards always,
James Whittaker

Resources / links mentioned:

Success Plan.

🎥 YouTube version of this episode.

Episodes mentioned:

Win the Day with Gabby Reece (Ep 43).

Win the Day with John Assaraf (Ep 33).

Win the Day with Rob Angel (Ep 48).

Win the Day with Keith Ferrazzi (Ep 30).

Win the Day with Kerwin Rae (Ep 31).

Win the Day with Emily Fletcher (Ep 29).

Win the Day with Coss Marte (Ep 32).

Win the Day with Dr Sonja Stribling (Ep 37).

Win the Day with Brandon T. Adams (Ep 35).

Win the Day with Adam Carroll (Ep 38).

Win the Day with Michael Fox (Ep 26).

Win the Day with Marcus Smith (Ep 42).

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