Tom Brady is a Tampa Bay Buccaneer, leaving behind an unprecedented legacy in New England, a fanbase that worships him above all other athletes, an ownership that publicly expresses adoration for him, a football mastermind coach that is commonly regarded as the greatest manager of all time, and an overall system (“The Patriot Way”) that has proven time and time again that it works— and works incredibly well. In 20 seasons: 20 winning records, 18 AFC East titles, 9 Super Bowl appearances, 6 championships, and a 16-0 season (yeah, yeah, I know…we’ll talk about that in a different article…). You heard right; he’s leaving this. Why? More money? He’s making less than 11 other QBs, including Ryan Tannehill and Matt Stafford. A scathing breakup with management and Belichick over in New England? Partially, maybe, but you can’t tell me that relationship has soured beyond the point of driving toward that common goal of reaching championship football yet again. A better chance to win? “Better chance?” I get that a 50/50 shot might not be the greatest scenario for simple playoff appearances, but when we’re talking about a coin flip for whether or not you make the Super Bowl? Good luck beating those odds. So, why’d he do it? Why did Brady, and why do so many other great champions and successful people, leave behind their comfortable, safe, relatively easy route to the top of the mountain? Why give up the known, the proven path, the sure thing? They do it to intentionally make it difficult—to find the spark that reignites that internal fire, allowing them to evolve, by solving different problems in ways they never have before—to chase a new challenge.
Through all my days of listening to Colin Cowherd on sports talk radio, absorbing the life lessons he preaches along the way, one of those that stuck to me most were the words he shared from Pat Riley. Riley believed that it was not just “ok”, but in fact healthy and recommended to “reinvent yourself” every 10 years or so, in order to fight off the complacency and stale nature of your current professional chase in life, and find that renewed motivation through the discomforts of a new challenge. This doesn’t necessarily mean for someone like Roger Federer to retire his racquet and grab a 9-Iron, looking to find success on the PGA Tour. Rather, (assuming you’re in an industry that you truly enjoy) it’s about adapting yourself to find a different way to chase success in your same field of specialty, via new routing. It could be a top writer like Bill Simmons departing a big-time sports company in order to boost a new upstart website. It could be a very successful direct-sales businessman like Zig Ziglar deciding to embark into the field of motivational speaking and training of others. For Federer, back in 2009, it was turning his one-handed backhand from a weakness on the slow clay into a focal point of his game in order to capture the elusive French Open; and as he gets older, it’s changing his tennis game, using a larger racquet size for more power, shortening points and winning with a more aggressive style. For Cowherd, it meant leaving a highly successful show on the sports world’s most renowned station, ESPN, and facing the new task of leading a far less successful brand, FOX Sports, to that same level of success. And for Brady, it’s departing the tried and true team, division, and conference he knows so well, and arriving somewhere completely foreign to him, with the goal of achieving that comfortable feeling of winning in an entirely uncomfortable place.
What Pat Riley was getting at is that, sure, you can live your entire life doing the same thing again and again, and very possibly finding success along the path multiple times. You can take the same path up the mountain repeatedly, reaching the top every time, celebrating as if it was some awe-inspiring achievement (despite having already proven to yourself that you’re capable). You can be the top gym salesman year after year for some big industry, using the same company-driven methods to formulaically close guests and sell memberships like clockwork, pleasing management greatly along the way. You can play the same videogame on that same “normal” difficulty level over and over, cracking your knuckles and exhaling with smug satisfaction every time you land the final hit on M. Bison, Bowser, or Liquid Snake. But while you may rack up the trophies, medals, money, fame, and “Congratulations!” game over screens…where’s the true satisfaction? Riley believed that by seeking this reinvention, you not only fought complacency, but found a new level of thrill and joy in work, constantly on the unproven path toward the unknown, with far bigger risk, yet vastly larger reward, as you challenge yourself to prove that you can be multidimensional, adaptable—-and humbled along the way.
Humbled? Absolutely. Part of the true thrill of the chase is seeking those moments where you get knocked down in defeat, finding that fresh taste of failure along your path. In the moment, are you having the ‘time of your life’? Obviously not. But how many times have you heard this same lesson: ‘You’ve got to fail forward’, ‘Life’s about getting knocked down six times, getting back up seven’, or how about the famous Michael Jordan Nike commercial, “I’ve missed more than 9000 shots in my career, lost almost 300 games, and 26 times, been trusted to take the game winning shot and missed. I’ve failed over and over and over again. And that is why I succeed.” It’s not some insightful piece of knowledge to point out that the world’s most successful people have laundry lists of failures behind them. But it does feel a bit odd to consider that they still have many failures ahead of their paths, doesn’t it? And that’s the reality of the situation— champions seek that fine line of taking a shot at success while embracing a situation where failure is a real possibility. And while it absolutely sucks when it happens, it’s those moments of failure that keep them continually adapting their skills and advancing their knowledge in efforts to work past the heartbreak of losing. In my all-time favorite book, The Subtle Art of Not Giving a F*ck, Mark Manson (an INCREDIBLE writer) talks about how we find happiness in life through solving problems. And when there are no problems? We find new ones, or sometimes create new ones, to solve. The classic problem for the highest of achievers is ‘I’m not good enough—yet’. And when they get good enough to end the issue? They find a way to recreate the problem in a different way—by reinventing themselves.
To keep the basketball analogy going, take a player Pat Riley knows near and dear— LeBron James. LeBron has been the epitome of reinventing himself throughout his career. From being a statistic machine in Cleveland, he chose instead to sacrifice his ‘number one guy’ status and join Dwyane Wade’s Heat in Miami with Chris Bosh, in an effort to win championships. Now, before you chuck spears about how this was a weak move that showed desperation, I would heavily argue that the true weak move would’ve been remaining a stat-monger in Cleveland, racking up millions upon millions of dollars, accruing MVP awards— but perhaps never winning championships. James Harden seems to have no problem doing this in Houston, and Russell Westbrook was happy doing this for a while in Oklahoma City before he finally got traded. With the Heat, LeBron won two out of four titles (Finals appearances in every season), and despite becoming the most overly criticized athlete of all time along the way, he had proven that getting championships was more than doable—it became the expectation in Miami. Seeking a new challenge, LeBron returned to Cleveland, where he won a title and once again became a dominant force (again, making the Finals every single year). He could’ve easily finished his playing career there— but constantly chasing new ways to challenge himself, Lebron hit the road and joined the far tougher Western Conference in signing with the Los Angeles Lakers, where adversity sure hit him hard, as he went from 8 straight Finals to missing the playoffs entirely. As it currently appears, this was the exact new type of failure he needed to find yet another gear to his career, as he now works on putting forth MVP-type performances while playing a position he’s never before played at the professional level (point guard), and hopes to lead the Lakers to a championship— a goal that seems not only plausible, but likely—a far cry from where people saw him at the end of the previous season, “washed up” and “done winning championships.”
It’s not just playing careers, either. Kobe Bryant found himself at the top of basketball, but when it was time to retire? He had no interest in kicking his feet up and drinking beers on the beach all day long. Rather, Kobe turned himself into an entrepreneur of different sorts— opening his own Academy, coaching his daughters in their own quests for basketball success, becoming a writer for children’s books, and even winning an Oscar for his film Dear Basketball! Any one of those would be a fine career for a normal person, let alone doing all four and on top of a Hall of Fame NBA career! Kobe’s post-playing career defined the allure of the pursuit of new challenges, and encompasses what Pat Riley expressed about reinvention, keeping yourself hungry and fresh, and seeking out new challenges and growth-via-failures en route to happiness in life.
Let me be perfectly clear: I am not saying that I believe it’s “easy” for Tom Brady to win Super Bowls with the Patriots, for LeBron to make NBA Finals appearances in the Eastern Conference, or to defeat Metal Gear Rex on the “Very Easy” difficulty setting as an 8-year old (well…perhaps that last example undermines itself a bit by definition…). Anything that requires any amount of skill, properly executed technique, and a bit of good fortune is never “easy” right off the bat. Rather, the difference in how we view the difficulty of the feat changes as a flaw in our perception, witnessing repeated and relatively sustained results. In other words, when we see Brady win three titles in five years (twice!), it appears easy. When LeBron makes a mockery of the eastern conference with eight straight appearances in the championship round, it becomes a joke. When I’m crushing through my fourth consecutive Metal Gear Solid playthrough—armed with stealth camouflage and the bandana (shout out to the nerds who understand that reference)—victory is no longer an achievement, but the expectation. And expectations are what encompass this entire concept— it’s not just that we, as fans, expect titles from these athletic greats, and are disappointed (or spitefully thrilled, depending on your fandom) when they fail to hit that ‘easy’ benchmark; Those at the highest level expect it from themselves, too. And we’re not talking the type of “I expect only the best from myself” positive mental talk; Instead, it becomes a mental game of “I have no excuse not to win this marathon by miles—anything less is flat-out embarrassing.” The challenge is no longer fun— it’s a stale, easy (in comparison) challenge, and the risk is no longer worth the reward. Reward? The knowledge and relief knowing that you’ve, once again, done something that you’ve already conquested plenty of times, and the avoidance of that gut-wrenching feeling when you fail to meet the baseline expectation. Risk? Fail to meet the benchmark you’ve established—enjoy said gut-wrenching nightmare.
It almost sounds as if I’m claiming that sustained success is a bad thing, and broods disappointment in one’s self—not at all. It’s just yet another catch-22 of a life constantly chasing better performance out of yourself. When you strive to be better in your industry day in and day out, the once-hard things will become easy ‘gimmes’ in your mind, as a 3-foot putt is to any skilled golfer. And you will find far less satisfaction in the things that used to get you fired up. To the struggling student, a 98% on a math test is a dream come true. To the elite student, a 98% is a rough slap in the face of the one question they did miss, and a taunting score of what-could-have-been if they’d just studied a bit harder, and executed a bit better on gameday. However, which student would you rather be? Exactly. It’s not about artificially withholding yourself from getting “too much success,” but rather finding unexplored areas in your passion where you have not yet proven yourself to succeed, and the ensuing exciting journey to reach that uncharted territory.
Picture the stress-continuum curve graph— the famous concept about how a healthy amount of stress brings out your top performance, but anything too much or too little will detract from your execution. Satisfaction from a life challenge is the same way; Nobody prefers to take on a challenge that they have laughably zero chance of completing. I wouldn’t feel very good about taking on Federer in a tennis match. And in the same light, as counterintuitive as it seems, nobody feels a true moment of triumph when they reach success on the far left (stress-free) side of the curve. You think I’m going to be fist-pumping when I beat a 12-year old girl in a round robin tournament with nobody else my age around to play? No way; I’m going to be agonizing over the points that I did lose to her in the process (True confession—I actually lost that match to her when I was a 16-year-old who thought he was pretty hot sh*t. You wanna talk about humbling…) When success goes from being the goal to strive for, to the expectation demanded, the challenge is no longer an enjoyable journey. You are a slave to the results you’ve created, and unless you find a way to rejuvenate your competitive drive by taking on a fresh type of challenge, your chase toward better is going to transform from a thrilling journey toward perfection, to a terrifying escape from expectations of perfection. Federer put it best after losing to Novak Djokovic in the 2008 Australian Open Semifinals—the first Grand Slam Finals he’d missed since the 2005 French Open—getting badgered by reporters about how he possibly could lose ‘so early’ when everybody had expected him to win: “I’ve created a monster.”
When the going gets easy, get the going tougher. Make life’s challenges harder on yourself, and don’t get comfortable and complacent in a job or passion that you can simply knock out on ‘autopilot’. You’re hardly advancing your prowess, you aren’t truly getting satisfaction, and whatever ‘fun’ you’re having pales in comparison to what it means to succeed when the odds are further out of your favor. Nobody plays up being the favorite; but every year, teams love expressing themselves as the underdog. When you can go out there and defeat Goliath with the odds against you, it means a world of a difference in the feeling of achievement. There’s a reason LeBron became so much more emotional after his Cleveland championship against the 73-9 Warriors, from 1-3 down in the series. Imagine how much satisfaction he’ll get if he leads the Lakers—his third franchise!— back to the top of the mountain… Tom Brady’s Patriots Super Bowl runs have been incredible, but which do you think brought him more internal satisfaction—defeating the Rams for his 6th, as a 2.5-point favorite and everybody picking the Pats, or defeating the 2001 “Greatest Show on Turf” Rams as a 14-point underdog where nobody believed in New England? And as fun as it was to beat Metal Gear Solid again and again on Very Easy, no amount of nerdy triumph there could match the ecstatic high-fiving and celebratory cheering with my best friend at 2:00 in the morning after we finally defeated Liquid Snake in a hand-to-hand duel after days of failure and hundreds of deaths. Happiness in life isn’t about finding the sure-fire path toward winning, and ‘spamming’ it over and over. It’s about choosing a course to chase, proving you can do it, and then carving out a new, tougher route to experience an enhanced version of the trek. We already know that it’s not the ‘destination’ we seek, but the journey toward it— so why subject yourself to a life of monotony, taking the same path day in and day out, seeing and learning nothing new along the way?
Colin Cowherd once explained: You should never be fully ‘ready’ for the job position you’re taking. If you’re 100% ready, it means you haven’t been pushing yourself enough, you’ve waited far too long to seize the moment, and have become far too comfortable in your current role. Tom Brady is not going to be comfortable away from the Patriots, he’s going to be tasked with teaching an entire new cast of teammates the only system he’s known for the past 20 years, and he needs to study ludicrous amounts of game film for a conference and division that he’s never played in before. Vegas has the Buccaneers likely to win less than 10 games, something that hasn’t happened to Brady since 2002. A Super Bowl appearance is NOT an expected ‘given’ for Brady and his new team. It is going to be an arduous, uphill, unique journey for Brady, forcing him to think critically as a player and team leader like he never has before— and THAT is why he happily accepts the challenge.
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