Develop an “until” mindset. Due to a coaching change and me getting lost in the shuffle, I didn’t even play my last year and a half of college basketball. I didn’t sign my first professional contract till nearly three years after my last college basketball game! During that time period, my mindset was always focused on making it happen in professional basketball — I was going to keep working on it and looking for ways to make it happen UNTIL I figured it out. Many people stumble with perseverance because they will only keep trying “IF” things work out. When you change that “if” to “until,” you’ll keep going for as long as it takes.

As a part of my series about “Grit: The Most Overlooked Ingredient of Success” I had the pleasure of interviewing Dre Baldwin.

Dre Baldwin went from his high school bench to a 9-year professional basketball career in just 5 years.

Dre has published over 15,000 pieces of content online. His daily Work On Your Game Podcast has over 3 million listeners.

Dre has given 4 TED Talks and authored 27 books.

Free Book (just cover shipping):

Thank you so much for doing this with us! Can you tell us a story about what events have drawn you to this specific career path

I’m honored to be here.

I’ve always been into sports since I was a kid, and that led to a career in professional sports. I started publishing content online at the same time as my pro career was starting, and that’s where many people came to know me from.

Through my online content, people started asking me about my mental approach to sports. The answers I shared were the foundation for the brand, philosophy and business I now have, called “Work On Your Game,” that has since expanded far past sports.

Can you share your story about “Grit and Success”? First can you tell us a story about the hard times that you faced when you first started your journey?

Am I limited to only one? Ha…

When I wanted to play professional basketball coming out of college, where I had played at the division 3 level, I had no prospects. No professional teams, agents, managers, or scouts were interested in me. I didn’t have a super strong resume coming out of my small college, thus no one was checking for me. I had to hustle and create the energy and attention around my name in order for me to even begin my professional sports career.

I was able to do that, and had to continually do it throughout my 9 year career to keep my career going. Through that process, I learned the value of selling myself, making connections, and keeping my name top of mind with people who had the power to help move my career and business forward.

As a consultant, I was also unknown when I first began. To get my name known, I did a whole lot of unpaid work to get myself seen, heard, and known.

An important point that readers should pick up from this: I was also good at what I was doing! When people did see and hear me, they could see the value in what I brought to the table. Just putting out the energy and doing all the work is not necessarily the key to creating the success: you have to actually be able to deliver when you’re doing your work. This, I knew from my background in professional sports.

Where did you get the drive to continue even though things were so hard?

I’ve always been a competitor!

Coming from the Sports World, you have no choice but to compete in order to win; In sports, there’s always a winner and a loser. In business, theoretically, everyone can win in some way. In sports, there is always a clear winner and a clear loser. So you have to have and be willing to execute a sharp killer Instinct in order to succeed in sports.

I bring that same mentality to the business world.

And it wasn’t so much that I was competing against an individual person or entity; I was competing against any circumstances and situations that were not to my liking. My competition was the fact that I didn’t have the results that I wanted, and that became my drive. It was about changing the circumstances; that’s what I was competing against.

This may not work for everyone, but this works for me and the way my brain is wired.

So how did Grit lead to your eventual success? How did Grit turn things around?

Grit is everything when it comes to creating success and altering circumstances to your liking.

No matter how good you are, there will always be circumstances that are not in your favor, and there will always be things that don’t work out despite your best efforts. Grit is the determining factor in whether or not you keep going and whether you figure things out when it’s not working. And everyone will have times in their life and career when things are not working. No one goes through an entire lifetime or career without needing a heavy dose of grit every now and then — some more often than others.

Based on your experience, can you share 5 pieces of advice about how one can develop Grit? (Please share a story or example for each)

  1. Develop an “until” mindset. Due to a coaching change and me getting lost in the shuffle, I didn’t even play my last year and a half of college basketball. I didn’t sign my first professional contract till nearly three years after my last college basketball game! During that time period, my mindset was always focused on making it happen in professional basketball — I was going to keep working on it and looking for ways to make it happen UNTIL I figured it out. Many people stumble with perseverance because they will only keep trying “IF” things work out. When you change that “if” to “until,” you’ll keep going for as long as it takes.
  2. Be resourceful. There are always multiple ways to get to your desired outcome; many see only one or two ways to get there and quit when those one or two ways don’t work. When I wanted to get into professional speaking, for example, I got started by connecting with and meeting knowledgeable people who I didn’t even know that well. Because I was being active and looking for opportunities, things worked out for me. My Mentor in thought leadership was a person who I barely knew, and was connected to me through a person that neither of us really knew too well. But when I met her, I took notes on everything she said, understanding that I might not get another opportunity to learn from someone who knew a lot more than me about this area that I wanted to get into. Because of my attentiveness and note taking, she took a liking to me and continued to invest her knowledge in me. And I took advantage of that because I had an opportunistic mindset.
  3. Keep showing up. Players who want to play professional basketball overseas usually attend events called exposure camps. Exposure camps are basically job fairs, but for athletes: we show up with our sneakers and shorts and actually play our sport in front of an audience of decision-makers. Exposure camps are not free to attend; it is an investment on behalf of the player who sees it as a way to get into the professional basketball world or advance their career. Over the course of my career, I attended probably 15 different exposure camps and tryout events, all with the intention of furthering my career. Some of those events were fruitful for me, and some of them were not. The ones that were worth it more than paid for the ones that were not. The fact that I continually showed up not only helped start and further my career, but also continue to pay me back nowadays, as I share my knowledge and experiences with other players who are now in the position that I was in 15 years ago. The fact that I continually showed up makes my experience valuable to others these days.
  4. Make your confidence bulletproof. I had to believe in myself for a very long time before anyone else even recognized me or would have been willing to believe in me — both as a professional athlete and as a thought leader. With very few exceptions, when you are first starting out in an area that does not have a clear path to success, you probably won’t have many people in your corner, telling you that they’re sure you’ll make it. Maybe your friends and family, but you know they will say that anyway! You have to be willing and able to run off of your own personal energy and self-belief in between the time you get started in the time you get established as someone people can believe in. When no one else has any idea that you even exist, you have to have the confidence in yourself that continuing to show up and putting yourself out there will pay off in the long run. Without this confidence, you will not stick to it and likely give up before you even get close to your success.
  5. Keep moving. Even when things were not working for me, I stayed active. I was always trying out new techniques, looking for new ways to get my work seen and known, and never checked out of the game, so to speak. As a professional athlete, I told you about the many exposure camps I invested in going to. What I didn’t tell you about is the thousands of emails that I sent out, or the many team managers I spoke to trying to sell myself as the player they should sign to a contract. In the thought leadership / consulting space, I couldn’t even count the number of emails and cold phone calls I’ve made to sell my products and services. Or the number of products and offers I’ve presented to my own audience through my websites, sales funnels, and landing pages. I’m always active and trying new things, and when something isn’t working, I get rid of that and try something else! That is the game in a nutshell.

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 you when things were tough? Can you share a story about that?

I mentioned my mentor in thought leadership earlier. What’s funny about how we met is that the person who connected us was not a close friend of either of us! But because I was active and opportunistic, and because she noticed my discipline, we connected immediately. She taught me a lot about the speaking business, how to position myself as a thought leader on my topics of expertise, and gave me belief in the fact that my experience in the sports would be valuable to a business audience.

How have you used your success to bring goodness to the world?

That’s all that I do!

Here at Work On Your Game, we are giving “game” to people every single day, and our aim is always to make our free material better than other people’s paid material. I think we are succeeding at doing that; your readers can take a look at our content and decide for themselves.

Are you working on any exciting new projects now? How do you think that will help people?


We have our daily podcast (which I call a “MasterClass”) that publishes every single day on the topics of discipline, confidence, mental toughness and personal initiative. I am also always working on new books; we have at least two coming in 2021.

What advice would you give to other executives or founders to help their employees to thrive?

The simplest thing they can do is direct their teams to consume more Dre Baldwin content! Haha… not joking though.

In addition to that, executives must first of all set the example: show up every single day and do the work, and keep showing up, even when things are not working, so you are the standard-bearer for everyone else. As the person in charge, everyone else is following your lead even when you don’t notice.

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. 🙂

The answer to that question is the Work On Your Game movement that has been going since 2009.

I didn’t even know it when it started, but when people first heard that phrase, they jumped on it and have continued to love it ever since. Our movement has touched over 70 million lives over the past decade plus, and we have another 7 billion + to go!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Work On Your Game.” — Dre Baldwin

It’s relevant because that has been the story of my entire life and career. Show up every single day and do the work, put myself out there boldly and authentically, continue showing up doing the work, putting myself out there, even when the success I’ve expected to achieve has yet to be achieved, and being a go-getter: making things happen instead of waiting for things to happen.

That is all that I do, and it is what I teach other people to do. I practice what I preach, and preach what I practice.

How can our readers follow you on social media?

You can reach me through the following social media:

Thank you so much for joining us. This was very inspirational.

That’s the goal! Thank you for having me.

Dre Baldwin of Work On Your Game: Five Ways To Develop More ‘Grit’ was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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