How to Thrive as an Underdog: Lessons From a Legend Nobody Wanted

“If you want to play with the big boys, you gotta learn to play in the tall grass.”

Tom Brady,
Quoted from his high school yearbook


A young Tom Brady watched the NFL Draft on television with his family, anxiously waiting on his name to be announced, along with the team that he would be drafted into. A round passed, and his name still wasn’t on the screen. Then another round passed, then another, and then another.

Into the sixth round, Brady was more than worried. His family was heartbroken as well, as it seemed more and more likely that not one team even wanted him. “I don’t understand this,” he said to himself. “I don’t understand this.”

At one point, Brady decided it was too much for him to bear. “I gotta get out of here,” he said. He went upstairs to his bedroom and took a baseball bat with him before heading back down and out the door.

There was no hope, or so he thought. He really loved football, and it was his life. But everything seemed to point out to him not being good enough. After all, he had read the scouting reports written about him, saying that he “didn’t look like an NFL quarterback.”

A while later, his parents went out searching for him. They found him in tears, as a gloomy question clouded his mind: “What am I going to do with the rest of my life?”

His mother wrapped her arms around him, while his father patted him on the back.

Meanwhile, the time was ticking for the New England Patriots to pick their drafts. They weren’t in a position of needing another quarterback, but for head coach Bill Belichick, he couldn’t stop thinking about Tom Brady. He couldn’t believe Brady still wasn’t drafted at that point. “Brady’s too much value,” he told his staff. “Why is he still there?”

On one hand, Belichick considered similar concerns as others who had passed on Brady — that physically, he was skinny, frail, and slow.

But on the other hand, the personal recommendation of a fellow coach, Dick Rehbein had stuck with him. Rehbein had met Brady personally on a scouting trip, where he was impressed by Brady’s character, particularly his work ethic, concentration, intelligence, maturity and mental toughness. Upon returning home that day, Rehbein told his wife that one day everyone would know Tom Brady’s name.

Belichick thought too about Brady’s performance. Even though he got to play very few games as a backup quarterback in college, he would time and again rescue his team to victory. In the many high-pressure situations that Brady found himself in, he always kept a cool head — he never flinched, and was able to calmly focus on making just the right plays.

It was obvious that he didn’t have the tangibles, like a great physique. But he did have the intangibles that a team desires in a capable leader. As author Jeff Benedict wrote, “Intangibles were hard to measure, but they were so often what distinguished the great ones. And when it came to quarterbacks, there was perhaps no greater intangible than the ability to produce under pressure.”

Belichick made his decision. Soon enough, the telephone rang in the Bradys’ home. And the rest, as we now know, is history. It was perhaps the best decision that Belichick had ever made for the team.

The draft was officially announced on TV: “With the one hundred and ninety-ninth pick in the draft, the New England Patriots select Tom Brady.”

During his twenty years in the New England Patriots, Brady led the team as a starting quarterback through nine Super Bowl games, and winning six of them — an incredibly exceptional feat in the NFL. After leaving the Patriots and joining the Tampa Ray Buccaneers, Brady went on to have his seventh Super Bowl win. And recently, he has officially announced his retirement, bidding farewell to a long and prosperous career, for good.

Tom Brady’s journey as an NFL quarterback is easily one of the greatest underdog stories we have. And understandably, we just love these stories — because at different points in our lives, we may find ourselves in challenging situations where we are seemingly at a severe disadvantage, as though all odds are stacked against us. In times like these, a story like Brady’s is exactly what we need to keep pushing forward.

And as Brady demonstrated, the key to thriving as an underdog is to nurture an impeccable character in ourselves — to have the intangibles in place. In other words, who are we when no one else is watching? Because ultimately, having good character and working towards being a good person are the glue that binds everything else together.

The following lessons from Tom Brady, then, have very much to do with our character. Success first comes internally.



1. Have a Deep Hunger for Learning. For Brady, football is very much a mental game. He had a competitive edge in his ability to quickly discern patterns in his opponents’ playing and to capitalize on their weaknesses — and this certainly had a part in how he was able to stay calm during games and make the most informed decisions possible. 

While many in the team questioned why Brady was even around early on, no one could deny how extremely hardworking he was. Even during off-seasons, he would practically live in the stadium, as he relentlessly sought to learn and improve himself. Alongside his rigorous physical training, it was not unusual for coaches and staff to find him logging hundreds and hundreds of hours in a tiny room in the stadium called “the dungeon”, where he watched video recordings to study his mistakes and his opponents — endlessly pushing the play and rewind buttons. It was odd for a backup quarterback to be that hungry to learn, when no one else was doing what he was doing. 



2. Always Be Prepared for Opportunities. “Fortune favors the prepared mind,” as chemist Louis Pasteur remarked. It’s always better to prepare for an opportunity when you have none, then to have an opportunity and not be prepared. Being a backup quarterback, Brady didn’t have a chance to play in his rookie year. Yet, he embraced it as his training camp to learn as much as he can, as well as to practice his leadership skills in managing his fellow rookies.

The opportunity eventually came for Brady to step up as a starting quarterback after veteran Drew Bledsoe sustained a severe injury. Brady proved himself to be a valuable asset to the team in game after game, even leading them towards the team’s first ever Super Bowl win. Brady’s position as starting quarterback then became permanent, while Bledsoe was demoted to being a backup quarterback after his recovery. This inevitably put a strain on their then-close relationship, though both agreed that it was for the best of the team. 



3. Don’t Look Back. One of the most essential traits that high-performers need to possess is resiliency, or the ability to bounce back from failure. Brady might have had a formidable work ethic, and so did his team, but this doesn’t at all mean that they didn’t have their share of bad games. In fact, the team went through a ten year drought between 2004 and 2014, where they didn’t win another Super Bowl. But as always, especially for Brady as a leader, it came down to owning up to his mistakes and doing his best to minimize them the next time.

One particular instance in his career shaped his mindset. The team had lost an important game, and when they returned to the stadium the next day for practice, they saw Belichick standing next to a hole, with a shovel in one hand and a football in the other. “You guys see this ball? This is the ball from the game yesterday,” said Belichick. “And this is what I think of it.” The team watched as he tossed the ball into the hole and buried it. “The game’s over,” he said. “We’re burying it and moving on.”



4. Don’t Let Success Change You. Even as a seasoned player, Brady was still always the first to arrive to the stadium, and the last to leave. And especially after his first Super Bowl win, he turned down multiple endorsement deals, parties, and even an offer from his hometown to designate a “Tom Brady Day”. Instead of overindulging in his success, he cut his offseason vacation short to get back to work in the stadium. Essentially, he was always careful to keep his work as the number one priority, to minimize distractions and to keep demanding more from himself. Another reason was that as a leader, he was careful to not lose the respect of his team due to slacking or complacency. 

Throughout his career, he also remained humble in that he was willing to be paid much less as compared to his high-performing peers. This way, the team could allocate a higher budget to recruit more of the best players. As Brady commented on being humble, “I don’t think we have very grand illusions of ourselves. I don’t think we put ourselves on this pedestal of being unbeatable, or being great players. I think we pride ourselves on our humility, on being a good player, and contributing in whatever your role on the team is. And because of that, nobody is ever satisfied.”



5. Look Towards Other Arts for Inspiration. An especially interesting aspect of Tom Brady’s success is his unusual choice of role models. Rather than solely looking up to footballers and athletes, Brady’s major sources of inspiration were figures of other arts and walks of life. And from that, he was able to have a unique mental and emotional agility in how he approached football.

For instance, one of those figures is spiritualist Don Miguel Ruiz, who wrote the book The Four Agreements. A book that teaches the acceptance of what one can and cannot control, it has since been “a mantra” for Brady’s life and work. Another inspirational figure for Brady is the chef Jiro Ono, who is known as one of the greatest sushi craftsman in the world. Brady has learned several practical lessons from Jiro’s work, such as “doing the same thing over and over again, and improving one bit at a time”, “to always be yearning to achieve more, “to keep climbing, even as no one knows where the top is”, and “to love your work and dedicate your life to mastering it.”


  1. #2 is so important. David Goggins has come out with a new book, so he’s been giving talks again, and I relate with the term ‘performance without a purpose’, because it’s the only way you’ll be ready when the time comes.

    Sure, you might look at the day and think you could slack off just today, because it won’t matter, right? But the person who always does the right thing, day after day, will be the one who’ll be able to jump onto a passing opportunity.


    1. Izzat Zailan says:

      Ah, that’s interesting! I’ve actually never read or listened to any of David Goggins’s content. I second that, though. I think at best, it has a lot to do with having a deep love for what we do. If we show up to work every day because we’re in love with the process itself, it doesn’t really matter when the opportunity might come, because we would definitely be prepared

      Liked by 1 person

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