Dre Baldwin of ‘Work On Your Game’: Rising Through Resilience; Five Things You Can Do To Become More Resilient

Fotis Georgiadis
Sep 24, 2020 · 10 min read

Challenge yourself. You can’t build resilience by only doing things that you know you can do! Challenge yourself by aiming to do hard things, with “hard” being defined as something you haven’t done and are not sure you can do.

In this interview series, we are exploring the subject of resilience among successful business leaders. Resilience is one characteristic that many successful leaders share in common, and in many cases it is the most important trait necessary to survive and thrive in today’s complex market.

I had the pleasure of interviewing Dre “DreAllDay” Baldwin.

In just 5 years, Dre Baldwin went from the end of his high school team’s bench, to the first contract of a 9-year professional basketball career.

While playing professional basketball, Dre pioneered new genres of personal branding and entrepreneurship via an ever-growing content publishing empire.

Dre started blogging in 2005 and began publishing videos to YouTube in 2006. He has published over 7,000 videos to 134,000+ subscribers, his content being viewed over 73 million times to date.

Dre’s daily Work On Your Game Podcast MasterClass has over 1,500 episodes and more than 3 million downloads.

Dre has given 4 TED Talks on Discipline, Confidence, Mental Toughness & Personal Initiative and has authored 27 books. He has appeared in national campaigns with Nike, Finish Line, Wendy’s, Gatorade, Buick, Wilson Sports, STASH Investments and DIME magazine.

A Philadelphia native and Penn State alum, Dre lives in Miami.

Thank you so much for joining us! Our readers would love to get to know you a bit better. Can you tell us a bit about your backstory?

Happy to be here!

Sure. I am originally from Philadelphia, PA, and was always into sports. After brief tries at football (where I couldn’t afford playing equipment) and baseball (where I had no talent), I decided to try basketball. After years of trial and error, while slowly improving, I made my high school team on my final try senior year and walked on to play college ball at the NCAA Division 3 level.

From there, I hustled my way into professional basketball, starting a 9-year overseas career. At the same time that my pro basketball career began in 2005, I published my first video to a new site that allowed anyone to upload unlimited video: YouTube. Unbeknownst to me, I had started another career online that would run parallel to my basketball career.

Today, I am a full-time CEO of my company Work On Your Game, where we teach the Mental Game tools necessary to succeed in sports and how these tools apply to business and life.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

In basketball: Talent and skill surely matter, but there are more talented/skilled players than there are job opportunities in the pro basketball world. Many of the players who “make it” are not only talented, but are in the right place at the right time and get seen by the right people. That kind of “luck” can be manufactured when you know how to market and promote yourself!

In entrepreneurship: There are many people with value to share with the world, but can’t — because no one knows who they are! And, while getting known is important, there’s also the matter of being known to the RIGHT people — those who have both the need and the resources to get what you’re offering.

Marketing is the key skill that allowed my pro basketball career to happen, and targeting is my key skill as an entrepreneur.

What do you think makes your company stand out? Can you share a story?

What makes Work On Your Game Inc. stand out is that we take the “Mental Game” tools necessary for succeeding in professional sports and share how these frameworks work in business and life.

Additionally, people know the key thing they’re going to get from me: the unvarnished, never-sugar coated TRUTH. And, while you may not always agree with my point of view or angle, you will always understand where I’m coming from and why, since I will always support my arguments with solid reasoning.

I know these things because I talk to my audience & clients! Every year or two, I get on one-on-one calls with my clients and customers and interview them, asking what it is they get from us that they don’t get anywhere else. What I’ve shared with you is what they share with us.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I would give credit to my parents, who set the example for me.

My mother was big on having her children be educated and literate; my older sister and I were reading and writing before starting school. This is a big part of why I’m an author today. Mom was also a strict disciplinarian who made sure we understood the importance of getting things done.

My father’s example was of someone waking up early and going to work every day, often on public transportation, to take care of his family. I bring this discipline and mental toughness to my work today as an adult.

The most important aspect of these traits that I saw modeled by my parents is that neither of them ever lectured us about what they were doing. It was all by example. As I grew into an adult and got to think about it, I could see that I was modeling what I’d seen them do; my business is built on these principles!

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Resilience is defined as “the capacity to recover quickly from difficulties.” I group the term along with “grit,” “perseverance,” and the third principle of the Work On Your Game philosophy, which we call “Mental Toughness.” We define it as your ability to remain disciplined and confident even when things aren’t going as expected and success is slow to arrive on the scene, despite your best efforts.

Key characteristics of resilient people:

  • Disciplined: The only way to “keep going” through setbacks is to continue showing up and doing your job. Many people fall off of their discipline when results are slow to show.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

There are many people whom we all know of whose stories are decorated with the many times they’ve been knocked down and come back. You’ve probably heard of all of them. So, I’ll answer that I think of myself!

I choose myself because one of the principle tenets of my business and philosophy is resilience. The way I’ve faced setbacks, regrouped and come back to be even better is the same way that I teach my clients and students to do. We, as they say, practice what we preach.

I stress discipline, confidence, personal accountability and focus — the attributes you just asked about — to my audience literally every day. If anyone is qualified to be mntioned as a picture of resilience, I am. Why wait for someone else to point me out?

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

That would be in playing professional basketball.

Someone has to make it there, of course, but players with my background — started “late” at age 14; didn’t make the high school varsity until senior year; walked on at a D3 college — don’t even think about making it, let alone do we actually make it happen. I had many people tell me, both maliciously and in the “trying to help you” type of way, that basketball would not be my future. Luckily, I had the requisite resilience to listen to myself more than I listened to anyone else.

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

I got recruited to a school after my freshman year of college. After playing one season for the coach who recruited me, he was replaced with a new coach who wanted to bring in many of his own players for his program. I became a casualty of those sweeping changes and didn’t play on the team for my last year and a half of college.

At a D3 school already, it looked like my basketball career was pretty much over, and for most players in that situation, 99% of them, it would be. But I had different plans and a different vision for my life.

I continued training even while going to school and not being on the team. Being that I came from a small school that never produced a professional basketball player, I focused on getting myself seen and known in the pro basketball world after college. I attended an exposure camp, which is basically a job fair for athletes, a year after finishing school and impressed enough there to get my career started shortly after.

This was both my biggest setback and one of my greatest accomplishments all in one story.

Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

I think I’ve always had a certain energy within me that drives me to fight back against unwanted circumstances and turn things my way. That alone isn’t enough to make it happen, though!

The mental game tools that I teach people now are the same tools I was forced to develop to make myself into a “somebody” in both the sport and the business worlds.

For me, the time in my youth that most sticks out is in continuing to try out for the varsity basketball team in high school (there were no freshman or junior varsity teams at my school at the time). Most boys my age would try out once or twice, and if they hadn’t made it by then, they took it as a sign that they should give up on basketball. While many of them were smart to find something else to do — basketball was not their thing — I can’t help but to think that some of them threw their potential in the trash can by giving up so easily.

The habit of easily quitting shows itself in many areas of life.

Resilience is like a muscle that can be strengthened. In your opinion, what are 5 steps that someone can take to become more resilient? Please share a story or an example for each.

  1. Challenge yourself. You can’t build resilience by only doing things that you know you can do! Challenge yourself by aiming to do hard things, with “hard” being defined as something you haven’t done and are not sure you can do.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

That would be the movement we have now: Work On Your Game! Without even explaining it, anyone who hears it understands what it means and knows how it applies to them. Everyone has a “game” that has room for improvement.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them :-)

I would want to sit down with a person who’s in a similar line of work to what I do, but is doing things better or different from me. That’s the kind of person I can learn from!

How can our readers follow you on social media?

I’m on every platform and publish daily; my most active app right now is Instagram @DreBaldwin.

This was very inspiring. Thank you so much for joining us!

Thanks for having me!

Authority Magazine

In-depth Interviews with Authorities in Pop Culture, Business, Tech, Wellness, & Social Impact

Authority Magazine

In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

Fotis Georgiadis

Written by

Passionate about bringing emerging technologies to the market

Authority Magazine

In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.