Episode 275: Winning with Discipline, Confidence, Mental Toughness, and Self Initiative

Episode Summary

To get where we want to be and doing what we love to do, most of us try to figure out what we need to do to reach our goal, and it makes sense; it seems fair to assume that there must be an action plan to follow. The truth is instead of asking ourselves what we need to do, we should ask ourselves who do we need to be, then become that individual. After we achieve that, the actions that will take us to the place we want will flow naturally.  


Steve Shallenberger: Welcome to all of our Becoming Your Best podcast listeners, wherever you might be in the world. And we are privileged and honored to have you listening in today. This is Steve Shallenberger, your host, and we have a remarkable guest with us today. In just five years, he went from his high school team’s bench to a nine-year professional basketball career. And at the same time, he built a content publishing empire. Welcome, Dre Baldwin.

Dre Baldwin: Steve, thank you for having me here. I’m excited to be here.

Steve Shallenberger: We’re excited. This is going to be fun with our listeners today, they’re going to love you. And this will be a great interview, I can just say in advance. And before we get started today, I’d like to tell you a little bit more about Dre. He has been blogging since 2005 and publishing videos to YouTube starting in 2006. Dre has published over 8,000 videos, with his content being viewed by over 73 million times. And Dre’s daily Work On Your Game podcast has over 3 million listeners. He has given four TEDx talks and authored 27 books. Way to go, Dre.

Dre Baldwin: Thank you.

Steve Shallenberger: You have been busy. 

Dre Baldwin: That’s true. Very busy. 

Steve Shallenberger: Well, before we launch in – we’ve got so much to talk about today – we’d love to hear about your background, turning points in your life, where did you grow up and how did you end up to where you got? You’ve been doing some cool things.

Dre Baldwin: Sure. So, my background, I come from the city of Philadelphia, now I reside in Miami, Florida. I was always into sports, Steve. I played all the usual kid sports growing up – at least coming from the city – we played driveway football, kickball, backyard adjustable court basketball, and things like that. The first team sport that I played was football, but I didn’t get to play football seriously because I never got the equipment. When the football coaches said, “Bring your equipment.”, my family couldn’t afford the equipment, so I never really got to play football. And then I moved on to baseball, played that for a couple of years, but was never super passionate about baseball, was just an athlete, so I played it, but I knew I didn’t really have the talent for that. So, I then eventually moved on to basketball by the age of 14, which was actually pretty late for anyone who’s trying to do something in basketball playing in college, let alone in the pros. I didn’t make my high school team until I was a senior, sat on the bench that one year, averaged two points per game which, for people who don’t know basketball two points are not enough in basketball – maybe hockey or soccer but in basketball that wasn’t much. Then I walked on in college, knew I was going to college either way, but walked on to play sports in college and ended up playing at the division three level, which is the third tier of college sports. And I didn’t set the world on fire there, but I did actually play a lot more than I played in high school. And when I graduated from college, I wanted to continue my career playing professionally. Now, I knew I probably wasn’t going to get an NBA shot coming straight out of college, so I knew my career would begin playing professional basketball overseas. 

Dre Baldwin: Now at this time, there wasn’t a lot of information on how to actually do that, and I didn’t have any prospects, meaning there were no teams who were calling me, trying to sign me. I didn’t have any agents who were offering me job opportunities or anything like that. I was basically going to have to make it happen on my own. And at the time, there wasn’t much info on the internet about it – even to this day is not a lot of info except info that I created. So, imagine what I had to work with because I was the one who created the information. So, I didn’t play basketball my first year out of college, I worked a couple of “regular gigs”, I worked at Footlocker as a manager, worked at a gym called Bally Total Fitness, selling memberships. And then the following year after graduation, I went to this event called an Exposure Camp, Steve. I would guess most of your audience does not know what that is. Now, an Exposure Camp is like a job fair, but it’s for athletes. So, you go there and there’s a bunch of jobs, work prospects like a job fair, and the people in the audience are the people with the jobs just like a job fair. The difference is we don’t just walk around handing out resumes, we actually bring our sneakers and we play basketball in front of these decision-makers, trying to get ourselves a job in pro basketball. I played pretty well at that Exposure Camp, I leveraged my performance there to sign with an agent. I had to find an agent, sell myself to an agent, an agent to represent me. That agent helped me get my career started playing overseas, we started a nearly decade-long career through eight different countries. Now at the same time, I took the footage from that Exposure Camp. That footage – now we’re talking 2005 – that footage was on this device called a VHS tape, you remember those?

Steve Shallenberger: Yep. The camera was as big as your chest.

Dre Baldwin: That’s right. You had to have strong shoulders to record VHS; nowadays you just need a hand, but back then you needed a good body. So, I took that VHS footage, and I got it put onto a data CD from an audiovisual store. I put the data CD in my computer and I uploaded that footage – just a highlight clip – to this brand new website I just heard about. They said you can put up videos as much as you want for free, it was called Now that is where I basically started a parallel career. Now this one I didn’t know would be a career till about four or five years later, but I was just putting random basketball videos up from maybe 2005 through maybe 2008, 2009 and I started to build a little bit of an audience there. Again, I didn’t know that will be a career until later. But this is how I started two careers at the exact same time.

Dre Baldwin: So, fast forward to today – I’m sure we’ll get to a lot of stuff in between – fast forward to today, I’m the CEO of my company called Work On Your Game Incorporated. And what we do here is we take the mental tools that get you to the top 1% of the sports world and we teach how those tools translate over into the business world and into everyday life. Because that’s what a lot of athletes who are watching the basketball videos once they found out a little bit about my story because I would reply to their comments and things like that, they were just asking “Dre, coming from that kind of background, how’d you even had an idea you could become pro? What was your mentality?” And I realized that that was the main thing that people wanted from me. And when I started talking about it, Steve, people who were not athletes started hearing it and saying, “Look, Dre, I’m not trying to learn how to play ball, but when you talk about that mental game stuff, everybody needs that. That’s not just a basketball thing, it’s not just a sports thing.” So, that’s how Work On Your Game became Work On Your Game to where I knew I could give this message not only to athletes but to anybody out there. And hey, here we are.

Steve Shallenberger: Okay, well, that is a great story. The vast majority of our listeners know about the spirit of Becoming Your Best, which comes from our book Becoming Your Best: The 12 Principles of Highly Successful Leaders. Well, I’ve got to say that I want to tell our listeners how we got introduced to Dre. It was through an email, but we have lots of emails regularly with requests for people to be on the Becoming Your Best podcast show. But Dre went a step way beyond that and that is he created a special customized video just for Steve and Rob. This is so creative. I knew right then, as soon as I saw it, that this was a man who had the spirit of Becoming Your Best. And it’s not just when he was younger, trying to improve himself, but he’s doing it right now. And when you’re becoming your best, it’s virtually impossible to not touch other lives. So, I’m just thinking, Dre that you did your first startup when you went to that camp. I mean, you had to package yourself and market yourself and figure out the whole thing, so we’ve got an entrepreneur on our hands here. 

Dre Baldwin: That’s correct. 

Steve Shallenberger: Yeah. 

Dre Baldwin: You’re right about that. 

Steve Shallenberger: Good job. Okay. Well, you’ve talked a little about Work On Your Game. So how can an everyday person use it?

Dre Baldwin: Wow. Well, Work On Your Game has four principles: discipline – showing up every day to do the work; confidence – putting yourself out there boldly and authentically; mental toughness – continuing to show up, doing the work, putting yourself out there even when a success you’ve expected to achieve is yet to be achieved; and personal initiative – making things happen instead of waiting for things to happen. Now, while I initially was using those tools, those attributes in the sports world, as I mentioned earlier, when people who were not athletes started coming across those messages, they said, “Man, this applies to anyone.” And nowadays as a full-time entrepreneur, this applies to everybody. To be an entrepreneur, to write a book, to sell a course, to be an influencer, of course, you have to show up all the time, you have to believe in yourself and your work, there will be setbacks, there will be challenges – all life is a series of challenges, especially in business – you’re going to have to deal with them mentally first, then tangibly, and you’ve got to be a self-starter. If you want to become somebody in this world, you can’t sit around and wait for the opportunity to find you. You’ve got to find it or even become the opportunity yourself. So, these principles apply in anything that you do, even if you never picked up a ball before in your life and you don’t plan to.

Steve Shallenberger: Okay, great. That is a great outline. So, discipline, confidence, mental toughness, and personal initiative. Man, those are big time. So, why is discipline such an important aspect of success?

Dre Baldwin: Discipline is the foundational tool of the Work On Your Game philosophy and of becoming good at anything because it’s that consistency. It is showing up every single day. It’s funny because I know you’re an author and people out there who sell courses and write books and things like that people always hype up the launches, right? I’m launching this book or I’m launching this course and they tell you so much around that day or that week or that 72 hours when the cart is open but nobody makes a big deal about all the other days after that. Because after the launch is over you still gotta keep showing up and doing the job. You sold the course now you’ve got to deliver the course. You sold the book, now people want to know “Okay what else you got? I already read the book.” The metaphor that I use, Steve, is a lot of people get so focused on the wedding but they don’t focus on the marriage. Now, the wedding is exciting but the marriage is really the thing that matters the most. So, the discipline is knowing that you have to show up every single day doing that work and that’s really what makes you a professional because the professional is a person who shows up and delivers even when they don’t quite feel like delivering. The amateur shows up when they’re motivated and inspired but a pro knows that they won’t always be motivated and inspired but they still have to show up and do that job. Number one because a man paid for it and number two because that’s the expectation when the word professional is next to your name, that you show up and do your job. And nobody knows how you’re feeling because your performance does not vary that much day by day over time.

Steve Shallenberger: Okay. So, drawing upon your basketball experience and also carrying this over into everyday life, what are some ways that people can really develop discipline? What are some things that help them be good at it?

Dre Baldwin: The number one thing people need for discipline is an anchor. Sometimes people ask “Well Dre, I want to be disciplined but how can I be disciplined if I don’t really…” Most people are not looking for discipline. So, how do you actually find something that is going to make you disciplined? You’ve got to have something in your life that may be either a direct thing or something tangential to it that you want or care about strongly enough that you’re willing to be disciplined in order to get there. For example, if a person wants to lose 30 pounds by the summer but they hate going to the gym, the question then becomes very simple. Which one is more important to you, your hate of the gym or your loss of that 30 pounds, so you can look good on a beach? One of them has to win. Whichever one wins is the one that you’re going to do. So, if your “hating the gym” wins you’re not going to lose that weight but if you want to look good on the beach matters enough you will move past or even despite your hate of going to the gym and doing burpees in a Bootcamp class, you will still go to the gym and do what you need to do because your desire for the outcome is more important than your dislike of the process. So, that’s the most important thing when it comes to discipline. 

Dre Baldwin: The second thing someone can do is create routines. Create routines and systems, so that you don’t have to remember to be disciplined. One of the biggest challenges people have with discipline and one of the biggest mistakes that lead to a lack of discipline is people not having any process or system for their discipline. So, for example, if you’re a person who – let’s just use the same one – you want to lose weight. You don’t want to go to the gym but you realize going to the gym is part of the process of losing weight so you can look better because that’s really what you want. One of the things that you can do, a simple system that you can put in place is laying out your gym clothes the night before, so when you wake up the clothes are already ready so you don’t have to make the decision to pull out gym clothes. You don’t have to use willpower to decide to put on your workout sneakers or to fish them out of the closet because they’re already next to your bed. The workout clothes are already there, you already have your keys ready, you already know exactly what you’re going to do in the gym. That is a system. When you have that system in place that replaces the willpower that you would otherwise need to use to push yourself to go do the thing. 

Dre Baldwin: And the third way that people can invoke discipline is to stop trying to force it. Our discipline does not work when it’s forced. It may work for a short period of time but you won’t be able to keep forcing discipline consistently over an extended period of time. So, make it easy on yourself by using the systems, by finding something that is an anchor that is stronger than your despite whatever you have an aversion to that is causing you to not be disciplined in the first place.

Steve Shallenberger: Okay. Well, that is really great advice for people, to have a purpose, a desire that drives them on that’s greater than the things that don’t. And have a system in place, a routine. Great. So, how does mental toughness – well let’s go back to the discipline – how does it create confidence? Because you mentioned that’s the second pillar there.

Dre Baldwin: Well, confidence is defined as your belief in the ability to do something and the way that you develop that belief is by actually doing it, by doing the work. When you show up every single day and you put that work in, first that is where you develop that confidence. And sometimes when I talk about confidence, the framework that I use is this for us, called the “Super You”. Which is you at your highest possible level of confidence and taking it even 20 levels higher than that. Sometimes people say, “Well, I want to make sure I keep my confidence under control. I want to make sure I’m being humble.” Well, understand being disciplined is the most humble thing you can do. Because when you’re disciplined, you’re showing up every single day working because who shows up every single day to work, who isn’t humble? Nobody. You have to have the humility to know that showing up every single day and doing the work is something that you still need to do, despite your success, despite how good you may be, or how much people tell you how great you are. And that’s where the confidence comes from: knowing that you’ve done the work, you have bought the confidence that allows you to go out there and perform and believe in yourself and present yourself and your work in such a way that other people want to buy into it. Confidence is not something that you get one time and it’s done. Confidence is like a membership – I mean, just extending this gym equation – confidence is like having a membership to the gym, you have to keep paying for it with your discipline.

Steve Shallenberger: Oh, man, I’ll tell you, this is inspiring stuff, Dre. Way to go. I mean, that’s good for anyone. You’re right. So, how does mental toughness contribute to being successful whether it’s sports or business or life in general? Because that’s really what you’re creating, and you’re down in the trenches now and I love the humility part, and then it does create confidence. And so, let’s hit the mental toughness part because you’re going to get beat up, right?

Dre Baldwin: Right. Well, Steve, no matter what you do, no matter how good you are, how disciplined, how hard you work, or how confident you are, you’re going to face setbacks in life. We know this is an inevitability because no human being is perfect. Life is just imperfect, all of us mere mortals, we’re going to make mistakes, and we can’t control circumstances, we can’t control the weather, and we can’t control other people. So, there will be challenges that you face in life, and that’s all life is, just a series of challenges and situations to be handled and dealt with. Mental toughness is the measure of how disciplined and how confident you allow yourself to remain even when the situation is not going as expected. Even when it was going as expected and all of a sudden is not, even when things were normal, but now they’re not normal anymore. And I think right now, in our world is perfect timing to even be talking about something like this because this has happened to people over the last year, plus. Your mental toughness is your willingness to deal with that stress. Because there will be all kinds of stress that happen in life – some of it is a good kind of stress that we like, some of it is a kind of stress that we don’t want. It’s your willingness and ability to handle it and not allow it to beat you down, but your ability to kind of work with it and still keep doing what you need to do. That’s really what mental toughness is about. Some people use the terms grit, perseverance, resilience – in this sense, they are all interchangeable.

Steve Shallenberger: Dre, what was one of the toughest challenges you’ve had in life? And how did you apply this mental toughness to get through it?

Dre Baldwin: The toughest challenge was probably right at that point when I started those parallel careers when I got out of college, and I had this idea. Now I have a college degree, most people look at someone with a college degree as a success. But I was looking towards playing pro basketball, my college degree really had nothing to do with my prospects as a basketball player. And I didn’t have any prospects to make it in pro ball. And here I am now an adult, out of school, what am I going to do? And that was the goal, yet I had no kind of strategy, plan, anything to go and make it happen. It was definitely an uphill battle. And even that whole first year out of college, I didn’t have anything going on as far as basketball went. I just had a job and I’m working, I’m a “regular guy”. And then to go and making that happen, first of all, I had to go to this event, I had to take initiative to go to this event the take my chances there with 200 other guys who were all trying to make themselves look good. Then I had to play well enough to get them to say good things about me, then I had to go sell myself to an agent to get an agent to represent me, then the agent had to sell me to a pro team to get them to give me a shot, then I had to get on the court with that team, and prove that I was actually worth the shot. So, there were so many roles at a dice that I had to take in that situation. And while now when I look back and tell the story, it sounds like this neat, perfect story, it was anything but neat and perfect when it was happening. And I was the only person on this planet probably at that time who knew me and knew what I had going on, who could see that it was going to become what it became. So, it took a high level of mental toughness because most people in those type of situations in life, they just give up, they just say “Forget it. Okay, I had my run.” Now I got to play in high school, I played in college and I did a good amount. Most people don’t even do that, so let me just let it go and go do something else in my life. But I just refused to see things that way and I chose to have a different view, a different vision for my life and I refused to allow the “reality” of the situation to stop me from continuing to pursue my vision. And that’s one of the main reasons why we’re here right now having this conversation.

Steve Shallenberger: I’m sure you had setbacks along the way.

Dre Baldwin: Absolutely. I had a ton of setbacks along the way.

Steve Shallenberger: Well, way to believe in yourself and push through it, bud. That’s really an inspiration. 

Dre Baldwin: Oh, thank you. 

Steve Shallenberger: Yeah, you bet. All right. Well, let’s talk about the personal initiative part. I mean, you definitely have been showing some personal initiative. And so, how big of a deal is personal initiative for one’s career and in business and life in general?

Dre Baldwin: Well, I mean, like you said, Steve, is the very reason we’re having this conversation. It was the personal initiative, the fact that I reached out to you the way I did. I don’t know where I first got the seed planted in my head, but when I got it planted in my head, I let it stay there and I let it germinate and grow, which was do something now and ask for forgiveness later. Ask for forgiveness rather than permission. I don’t know if that was the exact quote that I heard, but it was something along those lines of just go do things and then you figure it out along the way. Because the challenge for many people – and I’m sure you hear from people like this all the time yourself, Steve – is that they have these plans, and these ideas and visions of things that they want to do or want to have or want to be, but they want to get more information or they want to bounce their ideas off 30 different people before they do anything. And by the time they finally decide what to do, the opportunity is gone. So, might just taking all the money off the table because they take so long to think about and plan and contemplate what to do. The person who knew nothing had no plan, no thinking, they just started doing stuff, they had the advantage over you. Because first of all, they went first; secondly, 90% of what you’re going to learn about doing anything you learn once you start doing it. You don’t learn before you start doing it. And a lot of people really misconstrue that because most of the stuff that you think is the “right” plan before you begin isn’t even going to be accurate. By the time you start, it’ll be completely different and you learn that along the way. So, you start now and you fix it as you go. And that’s really what personal initiative is about, is being the person who’s willing to move, the person who’s willing to go, the person who’s not standing on the sidelines, waiting to see what everybody else says or what everybody else does. And the thing about initiative is nobody gives you initiative. You never hear the phrase, “Somebody gave me the initiative or gave me the lead”. You take the lead, you take initiative, you have to be the one who moves first. And when you move first, you are a leader and people will follow you because you had the courage to go first. You don’t have to be good, you don’t have to be right, you just have to be the one who moves.

Steve Shallenberger: Okay, nice. I appreciate your humility, as well, Dre. The next question has to do with that. So, what’s the most valuable thing people get from you? What would you say from what you’ve done and the experiences you’ve had, and you continue to have. What can others learn from you?

Dre Baldwin: The most valuable thing people want when they come to me, Steve, is they want to self-actualize. They want to become that version of themselves that they have been holding back from being. They want to be that version of themselves that maybe they’ve been afraid to be, that maybe the world has properly socialized them to not be and they fit themselves into a neat, perfect little box, maybe even become successful in that box, but they know that there’s more out there. So, when people come to me, they’re looking to get those core feelings. And when they get those core feelings of who they are being, then that bleeds into what they do, and then, of course, bleeds into the results that they have.

Steve Shallenberger: Yeah, it really is about digging deep and saying what does my best look like? And I’m going for it. 

Dre Baldwin: That’s right. 

Steve Shallenberger: Yeah, yeah. Good for you, bud. Okay, well, things always go so fast. Any final tips you’d like to leave with our listeners today? This has been fun. Wow, man, congratulations on all you’re doing.

Dre Baldwin: The final tip that I will leave with your listeners here today is that since so many of us in life focus so much on doing – especially if you’re listening to a show like this, I know you’re a person of action, who’s willing to go out and do the work – the challenge that many of us have with all that stuff we’re doing is that we never ask ourselves a key important question, which is “Who do I need to be? What type of person do I need to be in life? How do I need to see myself when I look in the mirror? What kind of energy do I need to have when I walk into a room? How do I want people to feel about me, my aura, just my energy when they come across me?” When you answer that question and you start actually becoming that individual, then the actions that you take will automatically flow from that being, and then those actions will start producing the kind of results that you want, at levels that you didn’t even think possible. But you had to start with who you are being, don’t start with what you’re doing. A lot of people spend their whole lives doing a whole lot of hard work, but because they’re not being their true or highest level version of themselves everything that they do still doesn’t produce the kind of results that it should. So, ask yourself the question “Who do I need to be?” Write down the answers, all in terms of being not actions but being, and then the actions will automatically fall from that. 

Steve Shallenberger: Yeah, that’s great advice. So, how can people find out about what you’re doing, Dre?

Dre Baldwin: Well, I’m doing a lot. The best way to find out about what I’m doing is I’ll give them one place to go and then they can spread out like spider legs from there. So, I have a book that I get people for free that if they just cover the shipping, they can get it. Can I share that, Steve?

Steve Shallenberger: Sure, please. I’d like you to.

Dre Baldwin: Okay, so that book is called The Mirror Of Motivation, and the subtitle is The Self-guide to Self-discipline. So, we talked about discipline here and the reason why I get his book away for free – and this is a physical book – is because discipline is the first principle to Work On Your Game philosophy and it’s something that most people don’t go looking around for. So, the best way to get people to get on discipline, Steve, is you’ve got to give it to them for free. So, when it comes to discipline, this book will help you look in the mirror and ask yourself the question, “Who do I need to be?” And it’s not going to be me hyping you up, or me telling you who you need to be as a person because that wouldn’t make any sense. It’s me giving you the frameworks for you to ask that question and answer it for yourself. So, when you answer that question, “Who do I need to be?”, the actions, the things you do will automatically flow from that ideal being, and then the results will flow from there. So, when it comes to the being, all you’re doing is assuming the position of that person. What does that person walk like? What do they talk like? How do they sound? How do they think about themselves? What is their energy? Then the actions come from that, then the results will come from that. You can get the book The Mirror Of Motivation for free by just going to So, just the title of the book, The book is a free physical book, all we ask that you help us out by covering shipping, and we will ship that to you wherever you are.

Steve Shallenberger: Okay, and I want to ask one other question. Are you too old or too young for these principles? 

Dre Baldwin: No, these principles are universal. They apply to everybody; everybody needs these no matter what you’re doing, no matter how old you are.

Steve Shallenberger: It’s been fun. Thank you, Dre, for being part of this show today. What a great and productive visit this has been. We wish you the best as you continue to bless people all over the world. And it’s been a delight to have you with us, Dre.

Dre Baldwin: Thank you for having me, Steven. It was an exciting conversation.

Steve Shallenberger: Yeah, it was very good. And to all of our listeners, wherever you might be, it’s been a privilege to have you with us today. We wish you the very best in all that you’re doing. Have a great day.

Steve Shallenberger

Founder, Becoming Your Best
CEO, executive, corporate trainer, and community leader.

Dre Baldwin

Owner, Work On Your Game Inc

Professional basketball player, author of 27 books, and motivational speaker

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