How to Effectively Teach Youth the Importance of Grit & Never Giving Up

In my 6th season of Florida Pop Warner tackle football, I had gone from playing every snap of the game 3 years in a row, always focused on learning more and improving, to barely seeing the field the entire next year. I was mad because I was passionate about the game and gave it everything I had whether it be in practice, the games, or in my neighborhood playing backyard football. 

The year I didn’t play often: I felt helpless and confused because I knew I worked so hard for hours every day. I studied the details and physics of football every night after practice while most kids played video games, and knew I was a better player than others because I was obsessed with mastering technique, angles, and how to use my limited physical stature to hit people 3x bigger/stronger/faster than me in the right spot to ensure 100% of the time they go down. But these particular coaches decided who was going to play, and where, in the first practice of the season.

6 games later of giving my all every practice and zero change each game, I felt like my freedom was taken from me and for the first time in my life, I told my parents I wanted to quit the league: Quit standing on the sidelines, quit getting my hopes up every Saturday, and quit the very thing that motivated me to get better and work hard for my passion every single day since I was 7 years old.

My parents knew that one unique gift I had was passion, enthusiasm, and execution in everything I was responsible for. I never quit anything I believed in.

My dad, who passed away from brain cancer in 2010, was working in Taiwan on a project at the time and the email he sent me in response to this critical moment as a kid… Well, it’s my most prized possession and was such an important part of my nature vs nurture growth. He always spoke to me like an adult when teaching me about life. He always taught me what the right thing a good human-being does, not what a kid should do. 

Here it is, think deeply when you read this:

That next year: I played every single snap as starting safety and wide receiver + special teams. I was a defensive captain and was moved up to varsity later in the year as a freshman in Florida 5A High School football. 

If my dad let me quit that day, I may not have developed the rare grit I possess. Which I absolutely agree is necessary for long-term success as an entrepreneur.

It put a chip on my shoulder and taught me what it means to persevere through the hard times when you feel powerless. It taught me what is important is to know you did your best that day, and will be even better that next day because you wake up every single morning with a dream you’re working towards. I value all the chips on my shoulder that have come since. They are my daily fuel to put in 5 more hours each night when most people are sleeping.

Whenever I am discouraged, feeling down, having a bad day, don’t get the answer I want from a prospect, or someone tells me I can’t do something, or to just give up and move on… I read this letter word for word like I’ve never read it before. It relates to so much of life and what it means to keep going forward and never give up. 

To work hard for something you love, are passionate about, something that serves a purpose more important than just personal gain, and when you look forward to working for it every single moment: I think that’s a meaningful life and a real source of truth, authenticity, and purpose. 

My grit is what I am most fortunate for in terms of skill set and mentality. Some people are taller, stronger, smarter, better-looking, or many other things but one thing I know is that I will never give up in pursuit of my dreams, goals, and doing what I feel is right/important. 

My dad taught me to be a good person by example and made me the person that no one can successfully bet against when it comes to drive, passion, perseverance, courage, patience, the will to be the best, and using discouragement as a positive source to fuel motivation. 

His advice was real, it was original, and it’s translated to every situation in life when I needed someone to tell me to keep going but had no one to go to. Winning means proving the doubters wrong through your results, not through vengeance, and as long as you stay true to who you are and be the best you can possibly be — through character, commitment to your word, perseverance, courage, execution, integrity, and have that true internal motivation to be a great asset during your limited time here — all the hard times you will always inevitably encounter in every single meaningful venture in life — they won’t seem so hard. Because they aren't.

Here’s what I had to say 2 years later (2004), on my boarding school admissions application, about who has inspired me most in my life and why. Note the underlined last sentence.

That’s who I was fortunate to learn from and am proud to say that I am carrying that torch every second of every day. 

Someday my future kids will learn the same thing about their own dad: “He doesn’t ever give up.”