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:

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 to level-up in your relationships, in your health, in your business, so the world knows how serious you are about what it is you want. Because, 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 favorite 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, I’ve got a special giveaway just for you. 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 with me? 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. 

We'll go through:

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.

🎞️ For the video interview, click here.


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).

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:

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.

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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).

Your time is limited, so don’t waste it living someone else’s life.”

Steve Jobs

Our guest today changed the world by bringing together fun, family, and friendship, in a product that has become a true household name. 

In 1985, Rob Angel was in his mid-twenties and working in Seattle as a waiter, earning $2/hour plus tips. With no business experience, plan, or money, Rob created the phenomenally successful and iconic board game Pictionary®. 

Remember, this was pre-internet, so Rob had to harness his intuition, resourcefulness, and work ethic, because he didn’t even know what steps to take, let alone how to take them. After assembling the first 1,000 games by hand in his tiny apartment, Rob met the existing gaming conglomerates head-on and turned Pictionary into a global powerhouse. 

Within four years, and with only two employees, Pictionary became the biggest selling board game in the world

For the next 15 years, Rob shepherded Pictionary to worldwide sales of more than 38 million games in over 60 countries and 45 languages. It had also appeared in blockbuster films like When Harry Met Sally and TV shows like Friends, not to mention the countless licensing deals with brands such as The Simpsons and Austin Powers

In 2001, Rob said goodbye to his baby, selling the phenomenally successful Pictionary to toy giant Mattel. 

Since then, in addition to spending time with his family, Rob has kept busy as an investor, philanthropist, and mentor to aspiring entrepreneurs.

Recently, Rob released Game Changer, which is a Wall Street Journal bestselling book that reveals the dizzying highs and crushing lows of his Pictionary adventure. And if you want a roadmap to success on your own terms, I can’t recommend it highly enough.

In this interview, we’ll go through:

As we get started, remember that the right bit of inspiration can completely transform someone’s life, so if there’s someone who needs to hear this episode, share it with them right now. 

Let’s WIN THE DAY with Rob Angel.

🎞️ For the video interview, click here.


Resources / links mentioned:

📙 Game Changer by Rob Angel.

📝 Rob Angel on Facebook.

📷 Rob Angel on Instagram.

⚡ Rob Angel website.

🎙️ Have a podcast of your own and want to learn how to monetize it? Join us at We Are Podcast, the world's #1 live and interactive event for podcasters. For 35% off ANY ticket, use promo code: WINTHEDAY

Your time is limited, so don’t waste it living someone else’s life.”

Steve Jobs

Our guest today changed the world by bringing together fun, family, and friendship, in a product that has become a true household name. 

In 1985, Rob Angel was in his mid-twenties and working in Seattle as a waiter, earning $2/hour plus tips. With no business experience, plan, or money, Rob created the phenomenally successful and iconic board game Pictionary®. 

Remember, this was pre-internet, so Rob had to harness his intuition, resourcefulness, and work ethic, because he didn’t even know what steps to take, let alone how to take them. After assembling the first 1,000 games by hand in his tiny apartment, Rob met the existing gaming conglomerates head-on and turned Pictionary into a global powerhouse. 

Within four years, and with only two employees, Pictionary became the biggest selling board game in the world

For the next 15 years, Rob shepherded Pictionary to worldwide sales of more than 38 million games in over 60 countries and 45 languages. It had also appeared in blockbuster films like When Harry Met Sally and TV shows like Friends, not to mention the countless licensing deals with brands such as The Simpsons and Austin Powers

In 2001, Rob said goodbye to his baby, selling the phenomenally successful Pictionary to toy giant Mattel. 

Since then, in addition to spending time with his family, Rob has kept busy as an investor, philanthropist, and mentor to aspiring entrepreneurs.

Recently, Rob released Game Changer, which is a Wall Street Journal bestselling book that reveals the dizzying highs and crushing lows of his Pictionary adventure. And if you want a roadmap to success on your own terms, I can’t recommend it highly enough.


Check out the YouTube or podcast version where Rob Angel does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more. 🚀


In this interview, we’ll go through:

Let’s WIN THE DAY with Rob Angel.

James Whittaker:
Rob, great to see you my friend. For the one person out there who doesn't know what Pictionary is, can you give a quick overview of the game and take us into the aha moment when you first created it?

Rob Angel:
Thanks for having me. Pictionary is a super simple game. It's drawing pictures to your teammates and having them guess the word. That's it. If you do enough words, guess enough words, you win the game. So it's super easy concept to understand, which I think is one of the main benefits and reason it was successful. And it started just as a hobby, just as an idea.

I graduated from college, Western Washington University in Bellingham, and I moved in with three buddies. I was a typical 22 year old, with no real prospects. I didn't know what I wanted to be when I grew up, and certainly didn't have a plan. But I always knew I was going to be an entrepreneur or do my own thing. And, as a result, I was going to be open, present, and aware. Basically, that just means when the opportunity came to me, I'd be ready for it.

One night my roommate says, "Hey, you want to play this new game I learned in college? It's like Charades on paper." .

Now I didn't know my life was about to change. It was like, okay, let's play. It was a typical night. And we got a dictionary and just started sketching words out of the dictionary. And then we did it the next night, and the next night, and the next night. It was like, "Holy crap." And this is 1982, so there were no distractions. There was no YouTube or video games. And I just thought, "This would make a great board game. I've got to do something with this."

This would make a great board game. I've got to do something with this.

It wasn't an aha moment, but it was an "I've got to share this with the world" moment. And that was just my original intention. It wasn't, "I'm going to make a business and make a million dollars." It wasn't, "I'm going to be rich." It was, how do I share this fun with the world? And that's what kind of got me started thinking about it.

You've had so many amazing memories from playing board games with friends, family, and even with complete strangers, which you detail in your incredible book, Game Changer. What is the inherent power of a board game?

Escape. It's like going to a movie, playing a game, or watching TV. It's escapism. So, for those moments you're playing the game and you're playing Pictionary, really nothing else exists. You're in the moment, you're in the present. When you're watching a movie, it's the same thing. And I think that's one of the super powers of games is that, and I've discovered with Pictionary in the long run is that people just were in that second and were able to communicate and have fun in collaboration.

And I kind of look at like a rock concert, like you're in that moment. You may not remember the words, but you remember the emotion.

What I love about your journey is that you were always so open to whatever the universe was going to throw at you.

So you had this thing that you were passionate about, but people get passionate about a whole bunch of different things. How do you take something from passion to business? And when do you know that it's a good fit?

Generally, you don't. I think following your passion doesn't always work. I think it's misnomer, follow your passion, and whoever they are that tell you to follow your passion, they don't tell you how to find that passion. They just assume you'll stumble into it. But I think you have to ask yourself three questions:

1) Are you in love with this idea? So I loved Pictionary. I wasn't thinking in the future, "Is it going to be a great business? Am I going to make money?" It was like, "I love this idea!" So do you love the idea?

2) Two, do a little research. Nowadays you can see if somebody else has done it. It doesn't mean you can't, but I play-tested the game, and people liked it, so I knew I wasn't the only potential customer for it.

3) Finally, are you willing to do the work? People sometimes forget that there's actual jobs to do and partners to find. So you have to be willing to do the work and make the sacrifices. And if you're willing to do those things and verbalize them, you have something at least to get started.

Yeah, a big part of it is motivating yourself to do the grunt work and doing those reps that others don't want to do.

They don't tell you that in entrepreneurial school. And it's kind of boring sometimes on your own. I didn't have a lot of people saying, "Rob, you can't do it" so there wasn't this motivation for people to show them wrong, but it was like I had to do it. I had to be there by myself many, many days. And that was enough motivation to see it through. But you got to motivate yourself somehow.

Within four years, Pictionary, your creation, had become the biggest selling board game in the world, which probably feels a little bit surreal for you to even hear today! Once you recognized that this fun game of yours had significant commercial appeal, how did you know what to do next?

I had no idea! But I think when I came up with it and I saw the idea, the opportunity, I think I did what a lot of people do. I procrastinated, I did nothing, because I wasn't ready and had all this self-doubt of how I could even get started. Because it was such a freaking mystery on what to do. I was a waiter — I knew nothing about business plans, marketing plans, or anything like that.

So I just bummed around for three years, basically. But I couldn't stop thinking about the idea. It never left my consciousness, and I kind of liken it to when you're in the shower and you have this amazing ideas when you're washing your hair, but by the time you're out of the shower, drying your hair, you forgot. But that wasn't me. I couldn't get rid of it. My brain was just overtaken. So I was waiting for the opportunity or the lightning bolt.

I was a waiter — I knew nothing about business plans, marketing plans, or anything like that.

And I was looking at Trivial Pursuit and I knew that the words, by the way, were the things that people would buy. You have to sell something. So I was selling convenience in a package, but the words, that was the linchpin. And so I see Trivial Pursuit and I look at the card and then I turn it over for the answer and I go, "Holy shit." I put the words on cards. It was literally that the problem I'm solving was how to put words into the game. I literally said F it, then I went in the backyard, opened up a dictionary, and started the word list.

And I wrote down the first word: "Aardvark." That was it. I got started. And that was the beginning of Pictionary.

There's a quote I want to mention to you from your book, where you said: "Working with limited resources fostered our creativity and innovation."

And that stood out to me because I heard Steve Wozniak, the Apple co-founder, say something similar about what made Apple so successful early on when they were trying to compete with all the big dogs.

I think it's really important for people to understand that that scarcity of resources can foster imagination and innovation and actually be a really good thing. Can you share more about that and what that looked like in a practical sense in your journey?

When you have too much information, you're not creative, so I looked at the not knowing and the unknown as a positive. I love not knowing what was going to happen next! I love not knowing how to market. So I had to figure it out as I went along. Just manufacturing the board game. There's no manufacturers that we knew of that could manufacture the game. So limited resources. We couldn't find somebody or more importantly, we couldn't pay anybody.

So we had to manufacturer the first 1,000 games by hand, nine different companies, in my apartment by hand. When it came to marketing, our marketing budget was zero. Zero. We had no money, so we had to be creative. At some point, you have to trust your instinct. You just got to go for it. And that's what we did day after day. It was a blast.

You had to use some guerrilla marketing strategies to get the word out there when you have a marketing budget of literally zero!

They say, break the rules. Well, I forgot to ask what the rules were! So I just kind of made my own. Every day was an adventure for my partners and I. Literally I was like Prairie dog. Every day, wake up and I go, "Okay, what are we going to do today? What are we going to sell? How are we going to market? I don't know. Let's just try something." I absolutely love those early days when the not knowing. That was the best part.

One big theme I felt from your book Game Changer was that you never left the key to your happiness in someone else's pocket. You hit the pavement, you closed the deals yourself, you ensured quality control, you kept the team tight and committed. How important was doing the reps yourself and the quality control attitude that you maintained for the scale of what Pictionary became?

Without it, we wouldn't have scaled. So, the scaling part is a whole different ball of wax. But in the beginning, having only two partners, the three of us, we had to control everything. The last thing we needed was one of those 1,000 games to go somewhere that we didn't know what was going to happen. Maybe it would go in somebody's warehouse and never see the light of day. We needed those games out in public — it was sampling.

All we were doing was test marketing those games to see how the public would react. My philosophy was, if I couldn't drive the games and deliver them myself, we didn't take the order. That way, we could demonstrate, promote, and market the books. We had to make noise in a small geographic area, because the technology that exists today didn't exist back then.

Today, influencers can blast things out and see what lands. But I literally had to control, physically control, where those went and that's why we made noise. That's why people paid attention. It was easier to go to the Seattle newspaper (which is the city where we launched) and say, "Hey, I'm a local guy. Do you want to do an article?" It wasn't going to happen in Chicago. So keeping it local and keeping tight control over everything was key to our success.

In the digital age, people want a magic bullet to success. They think all of these sales are going to happen automatically, and in doing so they really underestimate that the key is to get out there and do that legwork yourself to put the product in the hands of as many people as possible.

And I think that's one of the big problems, if you will, with Kickstarter, is exactly that reason. People have an idea. And I love the fact that people get their products made. But people don't realize there's work to be done in just making and getting your friends to buy in. And now you've got 1,000 games and you need to market those.

And the other thing that people kind of forget is that it needs to be a good product. This is that passion thing. I play-tested Pictionary because I thought it was fun, but what if it was just because of the beer we were drinking? We drank a lot of beer back there, let's be honest! And so maybe it was just the beer.

You've got to remember there's a business there. And that's that sacrifice part. I hear stories all the time that the manufacturing on Kickstarter took too long or cost too much, then the people couldn't even afford to ship the game. So you got to make sure you're paying attention.

I always ask people, what's your motivation? What's your intention?

For me, my intention of Pictionary was to share it with the world. That was my intention. What is your intention? If it's to make money at a game without knowing your product, I wouldn't do it because there's not a lot of money. If it's to create a job for yourself, which is also fine, maybe, but you got to make sure you market. And if it's just to say you did it, just check to see if it's worth your time. Is your energy really served by doing that?

And it's a hard call, man. This is not like, "Well, Rob, I really like this product." Well, then do it. Really understand why you're doing it and say it out loud. I think this is the one thing that people neglect. Say "This is a good idea!" out loud and see how you feel. See how it resonates. And if it does, go for it.

There's a mantra you repeated along your journey: "We take care of Pictionary and Pictionary will take care of us." Can you take us into what that means specifically and how it aided your decision-making along the way?

It goes back to, again, the same thing is the intention. As long as we are true to that game, our baby, we treated it like a baby. It wasn't a game. The first time I looked at it, it was like, "Oh, you're so sweet." I'm holding it in my arms. And I'm like, seriously, that first game that came off the production line. I'm going to do my best not to get choked up now after 35 years, it was a huge deal, with a huge emotional attachment.

But our mission was to keep the game the way it was because we knew what people enjoyed. We thought of what was best for our consumer. Not what's best for us, not the money. We thought about what was best for our consumer. That game was perfect the way it was. So when people wanted to change the packaging, which becomes a big issue later we can talk about, we said no.

We thought of what was best for our consumer. Not what's best for us, not the money.

But when somebody wanted to change out some of the graphics, somebody wanted to maybe do something else, we've always said no. Or it was a marketing idea that didn't meet the family values of Pictionary. So we never went for the money, so it kept Pictionary or your product or whatever you're trying to sell to what really its core was. And if it's going to be successful, then it will be successful, but don't fuck with it. And that's what we did.

We turned down so many deals and so much money over the years because it didn't serve the product, which in turn served us. It was selfish. Let's be honest — we wanted to make it successful so we'd be successful.

Yeah, you had that long-term success that would be impossible to understand for someone who doesn't know the DNA of the brand or product. You certainly wouldn't want someone to make decisions on the future of the product without properly understanding it.

Yeah, what you just said, long-term versus short-term, that was huge. If we were in it for the money short-term, I wouldn't be sitting here. Pictionary would have died out years ago, but I saw the golden goose. I saw what it could do and I wasn't going to give that up.

People have exits now and they're serial entrepreneurs. I love that by the way, but that's not me. Man, I was selling millions. I've got a golden goose. Why would I give that up?

With Pictionary, I was making money and I was having fun, so for literally 20 years of my life, I nurtured that thing.

Sharon Lechter [5x NY Times bestselling author and co-founder of Rich Dad Poor Dad brand / series] mentioned to me once that her favorite money was royalty / licensing money because it arrives while you sleep. There was a point in your life where some of the biggest companies in the world were knocking down your door and throwing money at you to basically license their products. After earning licensing money for many years, you ended up selling Pictionary for a substantial sum.

So what I wanted to ask you was what's better money — licensing money or selling the company money!?

I've never been asked that question! The answer is, we made a lot more money on the licensing than we did selling. And it was a big number when we sold, it's in the public record. So the money was great and it's mailbox money. However, we worked our asses off for those extra 17 years.

We were at a point where we had done all these things in Seattle, became very successful, sold 8,600 games, which doesn't seem like a lot, but it was huge for an independent company and we couldn't scale. So we had to figure out how to get on a national audience, and we just didn't have the financing. Typical start up. So licensing became our option, which is where basically somebody would do the manufacturing and distribution for us and give us a royalty. It sounded perfect to us!

So we had a meeting with a high profile brand and the deal didn't work out. But I learned a huge lesson. One of the most valuable lessons I ever learned was: it's not what you make, it's what you keep. And that was the beauty of licensing. When I started, when we got into it, I was going to have employees. I was going to have offices, be Rob Angel, Mr. Pictionary. No. We decided to license so we could keep more money. We had two employees, Mile and Brat.

Then the biggest game company in the world comes to us with a deal and we're talking it all through. And they promised us all these things, and packaging as we talked about earlier and whatnot. The deal comes, contract comes. I'm 26 years old. I'm making $500 a month and have a 10 year old beat-up car. Contract comes. First thing in the contract was a royalty rate.

One of the most valuable lessons I ever learned was: it's not what you make, it's what you keep.

Now again, money, that was the biggest royalty rate they'd ever given an independent game company ever. Ever. It was about $5 million to me over time. And I'm like, as I go to Costco, I was thinking of buying things I never even knew I needed, as you're going through the isles. I'm buying cars. I've got a second home. I'm in the Bahamas. I'm on a beach. This is awesome. This is going to work out great.

Then the marketing spend was there, but the last thing they didn't put in because we couldn't find it was that they wouldn't touch the surface packaging without our approval. Now on the surface, it's more than just packaging. They weren't men of their word. They told us they would put it in the contract because it was very important to us. So here I am, pen in hand and I'm thinking, "Sign the contract. You're ready."

But integrity is more important to me than the money. It really is. So I knew that if I couldn't trust them, I couldn't do business with them. So we said, "No" and we didn't have a Plan B. I was willing to go back to waiting tables rather than give up my principles. It sounds romantic, but I was dead serious. It was that important to do business with people we trust.

However, because of that everybody now knew we were in play. And a joint venture formed with all the guys who manufactured Trivial Pursuit and they gave us more money as well as all the guarantees we wanted, and we never looked back. It was a much better deal for us and they had integrity. The Universe was speaking and doing its magic.

With your business partners specifically, what did you do to maintain the integrity of that relationship to keep it together over the long term?

Well, I knew they had integrity, but it was never put to the test. In the beginning, we had some manufacturing problems and we were supposed to sort the first 500, assuming 1,000 games had 500 cards each, that's half a million game cards. Long story short, the printer couldn't sort them for us, and we'd already sent out the invitations for the launch. We're under the gun, we've got eight days. And so I threw a tantrum.

Okay. I admit this. It's the only time where I took it personally. I learned in business, don't take things personally. It wasn't like the printer was sitting in his office going, "How can I screw with Rob today? How can I make his day miserable?" No. It just happened. The facts don't change. But this terrible thing happens, so my partners and I did it by hand, and it was a terrible job, but it bonded us.

We got to communicate, we knew we could count on each other, and that set us up for those challenges. If things never go bad, you probably goofed up somewhere because something's going to go wrong. And because it did, it cemented our relationship, our friendship, and our business. So it turned into a very big positive.

Yeah, it's like how you respond to adversity when it inevitably strikes is what separates the real achievers.

And it's going to strike, so it's how you respond to it. I hate to be cliché. Every book you read and every social media post says, "It's how you respond." Well, it's true!

On the road to success, don't take things personal. Instead, think "How do we fix this?"

The mental health aspect of entrepreneurship is something that you and I are both passionate about spreading awareness of. You experienced self-doubt, negative self-talk, imposter syndrome, depression, all of those things and more along the journey. Is there a particularly dark day that stands out on the entrepreneurial journey for you? And if so, what did you do to get back on track mentally?

Yes. I'm glad you brought it up because it's a little secret they don't tell you in entrepreneurial school. 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 burnout. It was complete and total anxiety. I wasn't comfortable with myself. My authentic self had left and I was so off balanced. I was so out of alignment. And back then, we're talking early '90s before. Now we all know I was moody. 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. And 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.

Make sure you take an hour for yourself every day. Whether it's meditation, watching television, working out, or whatever it might be, but 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.

People almost drive themselves crazy trying to figure out what their passion is. Even I get asked that question constantly, almost every week, about "How do I find my passion?" Yet, no one talks about how do you find passion and inner peace at the same time.

When people are starting out, what is the role of passion and how can they harness inner peace so they can have that at the same time? Or is there just no real balance in the short-term if you're doing something like launching a product that could potentially change the world?

That's a long question to answer. I think you'll know. It's following your intuition. If you're off balance, you'll know, try to figure out how to get to center. If an idea that you have for a business, if it's not resonating, don't push it through, just pay attention to your gut, pay attention to what your brain and your heart. More importantly, I take that back, pay attention what your heart is saying, because your brain is going to override.

Human nature, physicality says, "Let me analyze this. Let me figure this out." But if this isn't working and it's not, "Am I in love" and all these things, you have to pay attention to your emotions and your feelings. And it's never going to end by the way, this whole conversation I've been doing it my whole life. With the spiritual journey, you're never done.

With the spiritual journey, you're never done.

You just can make accommodations as you go along, and do whatever works for you. That makes it all worthwhile. One of the things I say is nibble at the edges. For Pictionary, I waited for three years. Unless you try a lot of things, you're not going to know.

So nibble at the edges; you don't have to go all in right away. I play-tested a few times. I still really wasn't sure if I wanted to go all in with Pictionary, but the more I started doing it, the more confident I became. But I was doing other things as well. So nibble at the edges of a lot of different projects and ideas. When one comes to the forefront, then you go all in.

How did you reach the decision to sell Pictionary?

It was time. After 20 years with the product, our international license was becoming available and I'd had a family by then and I was just ready for a new adventure. I was ready to start something new and we'd made a lot of money, but we'd had a lot of fun doing it. It was just time.

How do you feel about digital games? Is that the type of thing that you would have gone down if you were launching Pictionary in 2021?

My guess is because now the culture is video games, I probably would have looked at that. I still am too, by the way, I'm not done creating. I love creating. So I'm not done, but it's a medium of the day. And the board game is what people played in 1985. And that's why it was the top of mind. That's why I went that direction.

There's an Albert Einstein quote I heard recently, I'd love to get your perspective on it: "A calm and modest life brings more happiness than the pursuit of success combined with constant restlessness." How do you feel about that quote in terms of the whole mental health journey?

Yeah. It resonates. Completely. It's the being in lack, the restless of "I need more, I need to compete, I need to do what they're doing." Man, that's just human nature. But the awareness of it, of your triggers, of the problem, of the situation, that's the start. If you just keep going without stopping and reflecting, that's where the trouble starts. At least it did for me.

I just kept going and going and pushing and pushing. The restlessness comes from lack. The restless comes from outside influences and outside sources. For the last seven or eight years, I've gone on a spiritual journey. I hate the term, by the way. I hate the term "spiritual journey." It just conjures up all this, "I'm going to go find myself." No, but for me, it's a journey to self. I needed to be more heart-centered. And so this quote totally resonates because when I am heart-centered and it's a constant battle, if you will, it's a constant pursuit.

If you just keep going without stopping and reflecting, that's where the trouble starts.

I'm never quite there and that's okay. I like the journey. I like the trying. But once you're more happy, confident, secure in even small amounts, you'll be less restless, you'll be more confident, and you'll be more successful. That's the nature of what we're trying to get here to. And whatever success looks like, it doesn't have to be money. It doesn't have to be a game. The success could be joy. It could be a non-profit, giving back. It doesn't matter. It's not my job to tell you, but just articulate success, go inward, and you'll get there faster.

What I love so much about the things you've shared today is that it's looking after yourself first should be the number one priority. It's almost like before you focus on anything else, you need to make sure you're right internally, and have that intent for everything that you want to do, supported by daily practices to look after yourself. With that, you'll be in a lot more alignment for everything else you do.

And I got to say one other thing about that. When you don't do your daily practices, give yourself permission to say it's okay. Because I beat myself up all the time over what I'm not doing. "Oh crap. I missed my meditation today. Oh crap. I missed it for two days. Now, I'm going out." I'm all angst-driven. No, not anymore. It's like, "Okay. I missed it. I'll do it tomorrow."

Give yourself permission to not be perfect. Give yourself permission to say it's okay. And you'll get it tomorrow.

Stop beating yourself up, and that's a lesson I tell myself every day. That's not conjecture, that's not out of a book. That's something I constantly, constantly preach to myself.

Yeah. It's easy for us to be compassionate to other people but it's often very hard for us to have self-compassion.

Yeah. Be compassionate.

This spiritual journey that you've been on for the last seven or eight years, what are some highlights or lessons? I know you've been to Burning Man. Is there any stuff that you want to reveal for the first time today or what things come to mind!?

Wow. Yeah, no. I'm enjoying the journey. I've done some Ayahuasca. That was an interesting experience.

Where did you do it?

I did it in Peru. That was amazing. That was one of those skeptical things, because I'd heard about it but wasn't sure. Finally, I was called, if you will — again with that woo-hoo stuff. I got to tell you, in the eight years before II started this spiritual journey, I had a friend who kept telling me "You've got to surrender, be present, and hold space." And I was like, "Come on. This is ridiculous!" Well, finally I bought it. So, I'm doing that. So yeah, I'm trying to go on all the rides. I'm trying all new things just to see what works and what doesn't. Ayahuasca worked pretty well for me.

For entrepreneurs in particular, it's certainly becoming more and more popular. A lot of people I know are even doing Ayahuasca here in the US without having to go to South America or Central America. For those who don't know anything about it, what does it involve and how was your experience specifically?

Well, first thing I'll say, it's NOT for everybody. Don't try this at home. I am not the expert. I'm looking right into camera when I say this! This is not my job and I'm not promoting anything. That enough disclaimers!?

Oh my goodness.

No, it was a way for me to find out more of my triggers, to find out what made me tick, even though I'm doing all this spiritual work — here we go again with that term — which includes coaches and therapists, all these. So it just was a way to get more clear, if you will. And it's not for everybody, so if you're not called, it's a no-no. I'm going to keep qualifying that. But it was just another tool that I found really resourceful for me.

What about people who are in a negative mindset or brain fog — are there any tools you can share with people to help them shift their energy?

Yeah, so I'm a big fan of touchstones. And for me, that's something physical to remind me of something I'm doing or want to remember. What I do is if I've had a great conversation or I've had a great idea or something magical has happened, I'll pick up a stone or something small and to remember to hold it, and this is what you should do, or this is what I recommend.

If there's something you want to remember, and it could be as simple as something I've said today that's resonated or you've had an idea and you want to remember it, or there's some emotions, usually an emotion, I pick something up, I put it in my hand. So if you're sitting at home right now, do this. Pick something up. I put it in my hand, I hold it. And this is kind of a Joe Dispenza thing that I've kind of alliterated on.

And I hold my hand and I close my eyes. I think about what's in my hand, and I think what it represents, and then I attach this emotion to it. I just don't remember what it is. I remember how I feel. It's how you feel. That's the important thing. And so when I let go, it's right there in the palm of my hand and I put it on my desk and I've got these stones all over my house. I've got hundreds of these things.

I just don't remember what it is. I remember how I feel.

So next time, whatever you just held in your hand and you look at it, remember the emotion you felt with it. And that's the memory, that's the touchstone and do it time and time again if it resonates with you. It's just a remembrance of an emotion. And for me personally, I've found it super, super powerful because I forget visions. I forget things that I see. I forget the specific conversation. But when I've had this amazing heartfelt conversation with somebody, I know how it felt. I know the emotion, I remember the words and these touchstones remind me. And it's something I practice, I preach. I really think if you give it a try, it will work for you too.

So they bring you back into that feeling when you were there experiencing it?

That's exactly what it is. It's all about the feeling. So it's like Pictionary, going back to that. You don't remember the words of Pictionary. You may remember one or two of the sketches, but you remember how you felt, you remember the emotion, you remember who you were playing with. You remember the joy. That's what these touchstones are to me.

I'll just quickly say, it started when my father passed and his favorite color was yellow and I'm going through, and I'm sad, and I'm walking past a junk shop. And there were all these yellow stones, I'm crying. Dad was speaking to me, hello dad. He was there and I bought a bunch of these things and I gave one to everybody at the funeral. Everyone at the funeral. And to this day, I carry them with me in my travel bag. He's always with me. So they're powerful.

I love that. Thank you for sharing. It's really interesting. And I know there's a lot of people struggling right now, particularly with what's happened with COVID the last year and a half. Using something like touchstones seems to be a great way to help shift that energy and focus on the bigger picture when you don't feel like it.

Absolutely.

In Game Changer, you mentioned that your intent with Pictionary was to create a game that was so entertaining, so fun, and so engaging. What experiences in your life today give you those same feelings?

Exploring. Yeah. I'm totally in exploration mode again. Well, the book for a while, writing a book was an interesting process. Oh my gosh. Just remembering everything was crazy to go through it and the stories and calling the people who were involved. They remembered things differently than me. That was interesting as well, but it's my book! So whatever's in there is how I remember it.

So right now, I'm exploring and I'm looking at turning the book into a docu-series, that's kind of keeping my attention these days and just trying new things. I still love travel, meeting new people, new experiences that way. That's really one of my joy is that new experience, new people, new events.

How do you balance the hunger for future achievements with all the amazing things you've done with retaining happiness in the present?

It's hard. It's hard. I'd love to say I'm perfect. And, "Oh my gosh, look at me, my life's perfect." No. I was going to say it's a daily struggle, but it's not a daily struggle. Struggle is not the right word. It's a daily pursuit. It's my daily pursuit. My girlfriend calls it the daily pursuit of not stressing. So the more stressed I am, the less creative I am. So that's my daily pursuit.

If things stress me, I try desperately to not be there, to not go in that direction. And it's a hard balance, but I really like the trying now. This journey that I'm on, the tools I've learned have really given me almost a hope for the future. My future is not so bad. My present is not so bad, but it's a daily pursuit.

It's hard, isn't it? You can feel parts of your brain want you to push, push, push, but if you succumbed to that all the time you'd be massively out of sync with your daily practices. Before you know it, something has happened, and you're saying to yourself, "Wow, how did I get here again?" So being true to those daily practices seems to be incredibly important, I've found.

100%. And for the record, I don't have a lot of daily practices. I know you're supposed to meditate every day and you're supposed to wake up at the same time. I do my best. And when I do it, I feel great. When I don't, it's okay.

A big part of what you're doing now is helping aspiring entrepreneurs find their aardvark and get their business off the ground. Is there a specific blueprint that you'd like to take them through or are there certain questions that you like to ask them to make sure that they're clear on their idea or to help figure out if their idea actually has legs? What do you mainly focus on when you're working with aspiring entrepreneurs?

It goes back to what I said earlier: what is your intention? And it doesn't have to be just a game or anything else. Why do you want to do this? Because to be honest, just because you want to be an entrepreneur doesn't mean you should be an entrepreneur. Some people are just always meant to be working for somebody else and they work well in that environment. And that's okay. I'm not saying one's better than the other. It doesn't matter.

I talked to a CEO of a large corporation recently. I don't want to mention his name, but it was someone whose name you would recognize. And I said, "Are you an entrepreneur or worker bee?" And he goes, without hesitation, "I'm a worker bee. I don't have a creative bone in my body, but I can make things happen. I can hire the right talent."

Just because you want to be an entrepreneur doesn't mean you should be an entrepreneur.

So it's not an either or.

And I ask them, why do you want to be an entrepreneur? Check in with yourself, articulate that. And as I said earlier, are you willing to do the work? And most of the time, the answer is yes. And great. And then we just start diving into it, fleshing out the idea, coming up with different ways to look at their idea and helping them that way.

Yeah, for those who want to be entrepreneurs for the first time, not properly recognizing the complexity that can bring into your life, especially if you're not in a position financially, to be able to have that. It's like imagine having something occupying your mind seven days a week that's taking you away from your kids and your friends, all of those different things. It's tough.

You and I had such a great conversation at dinner the other night, particularly about parenting. What do you do specifically on the parenting side to make sure that you maintain a good relationship with your kids and support them in their journeys?

I make sure they're heard and I make sure they feel loved. And what I was doing without knowing is I was making them a part of the journey because I didn't know what I was doing. They don't give you a manual!

It sounds very much like when you started Pictionary!

Exactly. But parenting is a tough job. And so just keep the lines of communication open. This is another one of those do as I say, not as I do. You've got to be the parent, not their friend. A lot of times I was their friend, and it backfired. But I've an amazing relationship with my kids. And it's really my legacy. Pictionary, the book for me, great. But everything is my relationship with my children.

And when they call and we talk all the time, that's what brings me joy. I just had a conversation with let's say one of my children about something that's been bothering them for years. But I wasn't hearing what was bothering them, and I kept answering the same way. So finally, with my own found knowledge, I thought "What am I missing?" So I went at it a different way and it just opened up the flood gates in a really positive way of conversation.

So just don't be afraid to have a conversation at any age with your kids. And it just pays dividends, I'll tell you.

Really powerful stuff. Was there anything specifically that you learned on your business journey with Pictionary that helped shaped the way that you parent? Obviously you had the freedom to spend with them, which I think is great.

I'm thinking that one through. The first thing that came to mind was being adaptable. So for Pictionary, considering we didn't know what we're doing half the time, which was fun, we had to be profoundly flexible in everything we did. Now they call it adapting and pivoting. You just have to be flexible because we didn't know what we're doing.

And if something didn't work, we'd have to immediately change directions. And that's just true in business all the time. That's not a new concept, but we were willing to make the change. And so with my kids, now that I'm being asked the question, thank you, you had to be profoundly flexible because they're changing every fricking day, hormones kick in and then they get a girlfriend or a boyfriend. All these things are going crazy. So I don't know what I'm doing half the time.

You just have to be flexible with how they're growing and hopefully you're growing at the same time.


Check out the YouTube or podcast version where Rob Angel does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more. 🚀


Final question: what's one thing you do to win the day?

I give myself grace to not be perfect. When I start going crazy with my inner dialogue, I give myself grace, I take a breath, I chill, and then I can move forward.


Resources / links mentioned:

📙 Game Changer by Rob Angel:

📝 Rob Angel on Facebook.

📷 Rob Angel on Instagram.

⚡ Rob Angel website.

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