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What it takes to make it professionally in soccer!

Three success stories and practical advice for players and coaches.

By Ron Monteiro

  • Steven Caldwell’s amazing rise to the premiership & advice to coaches and players.

  • Dwayne DeRosario’s fascinating journey to becoming a Canadian soccer legend and blazing a trail for future Canadians.

  • Jason Bent’s success as a Canadian soccer player and coach and advice to the upcoming generation.

August 23, 2020 was a historic day for Canadian soccer! In my opinion, Alphonso Davies becoming the first ever Canadian to win a Champions League title was monumental for aspiring young Canadian soccer players. This ranks right up there with moments like Bianca Andrescu’s victory over Serena Williams in Tennis. I am confident that Alphonso Davies’ rise to stardom on the world stage at Bayern Munich will be a critical step in helping lead to a golden generation of Canadian soccer players and propel us to the World Cup in 2026!

What does it take to make it as a professional soccer player? Does exceptional talent like Ronaldinho, Thierry Henry, Zlatan Ibrahimovic or Seba Giovinco possessed automatically get you there? What role does hard work & mental toughness play in it? I think about Roy Keane or Gennaro Gattuso who were not as talented as some of their peers but had unrivaled tenacity and grit. Where does ‘love of the game’ fit into this puzzle? What role does great coaching play? Jurgen Klopp, Sir Alex Ferguson, and Pep Guardiola are names that clearly help(ed) elevate teams and individuals to new heights? What about the role of parents and support figures?


I had the pleasure of having in-depth conversations with three amazing individuals who can help answer these questions with their amazing ‘footy’ experience.


Steven Caldwell’s outstanding soccer pedigree combined with his amazing analytical ability and coaching experience make him a perfect candidate to educate us on what it takes to make it to the promised land in soccer.


For those younger readers who think that Stevie was a second-class citizen in his soccer career, let me squash that right now. Stevie was recruited by the biggest clubs during his ascent to the premiership. He was invited to mammoth clubs like Chelsea, Man U, Glasgow Rangers and others but had a gut instinct that Newcastle was the place for him. While Newcastle is not the powerhouse club it was in the 1990s, it was one of the clubs always fighting for the Premiership title in those years.


Steven has played with or against world class players like Alan Shearer, Thierry Henry, Didier Drogba and Michael Bradley. He has also been around world class coaches like Bobby Robson, Kevin Keagan and now John Herdman.


Dwayne DeRosario grew up in Scarborough, Ontario. DeRo is famous for his flare, creativity and famous ‘shake and bake’ goal celebration that he consistently brought to the football pitch. Dwayne started a foundation to help inner city kids in Canada and Internationally have opportunities to improve their lives.

Jason Bent grew up in Brampton, Ontario. He has successfully transitioned to coaching and is currently an Assistant Coach on TFC in MLS. He is one of the coaches who started the TFC academy which has been a huge positive step forward for Canadian soccer. He recounted how he and his colleague Stuart Neely set up an office in an equipment room in TFC academy’s infancy.


Jason scored a brilliant goal in the U20 world cup against the eventual winners Argentina and consistently showed his tenacity as a ‘hard-tackling’ defensive midfielder. Jason has played with or against, trained alongside and coached world class players like Juan Roman Riquelme, Ruud Van Nistelrooy, Samuel E’to, Harry Kewell, Michael Bradley, Jose Altidore and Alexandro Pozuelo.


Success Formula


This is a relatively long article so here are my key findings. In addition to talking to Jason, DeRo and Steven, I am currently reading a brilliant book called ‘Grit’ by Angela Duckworth which complements my analysis. The book highlights many examples of individuals who have made it to the top of their chosen field. One example is Michael Phelps who is arguably the best competitive swimmer ever. He has the astonishing record of winning 23 Olympic gold medals in swimming. Most people know that his body is freakishly built for swimming, but what gets left unsaid is the hours and hours of hard work, sacrifice and preparation that he put in to get to the peak of the swimming mountain. Similar stories can be told about David Beckham’s or Roberto Carlos’ unbelievable free-kicks, Ronaldinho’s famous ‘elastico’ move, Lionel Messi’s amazing close dribbling and shiftiness or either Ronaldo’s famous step-overs and scissors.

I believe what it takes to make it is summarized in the following equation.

Talent + Hard work + Love of the game + Mental toughness + Luck

  1. Talent – there is clearly a base level of talent required but this alone does not automatically get you there.

  2. Hard work – there is no substitute for putting in the hours and hours of hard work. All three of these individuals had and continue to show an outstanding dedication to their craft.

  3. Love of the game – there must be a love for the game and all these individuals had this. This quality helps individuals put in the hard work and develop into the fantastic players that they became.

  4. Mental toughness – this is an intangible quality but something that must be developed by playing against the toughest competition and having that ability to come back after setbacks or defeats. Learning from setbacks and using them as fuel was a very important and common trait.

  5. Luck is also a factor and when the lucky break happens it is critical to be ready to take advantage of this opportunity. All of these individuals were ready!

Angela Duckworth has a brilliant graphic that shows that effort or hard work actuals counts twice. First in skill development or mastery and secondly in achievement.

The stories that follow show how these 3 individuals made it by loving the game, putting in the hours and hours of hard work, developing the mental toughness and were prepared when the lucky breaks happened.


Laying the foundation


Steven has very fond memories of his early years where him and his brother Gary (who also made it professionally) played footy for six or seven hours at a time. He has great memories of carrying a wooden goal that his dad made to the top of the street and playing unstructured footy for hours. It was the only sport Steven played and he remembers not thinking about anything else.

Jason recounts playing soccer with his older brother and cousin when he was three to four years old. He also had a similar love for the game and this experience playing with older kids was pivotal in his early days. He started playing for Malton Soccer Club at the age of six.

DeRo also had a similar love for the game and has memories from the age of three playing with his dad, uncle and older brothers. He remembers that soccer was a way that the community came together and this experience playing with older kids and adults was clearly pivotal in his development.

As I think about our coaching in Canada, we often hear the phrase ‘let the game be the teacher’ and this is so true for all of these gentlemen. When I visited Natal, Brazil in 2014 for the World Cup, the locals would tirelessly play for hours at a time barefoot on the beach and the skill level was exceptional. The ‘Neymar’ like diving was also prolific and annoying for us who have the Canadian mentality of getting your teeth knocked out and getting back in the game.

While I am a career men’s league veteran with zero professional soccer experience, I also played soccer for hours every day growing up in Kenya. We would play barefoot and often with a tattered ball for hours at a time. When I immigrated to Canada, my skill level was above my peers on our high school team that won the TDCAA championship and was full of rep players. This presents an interesting dilemma in Canada which is such a structured and busy society (pre-Covid 19) with kids having many different sports and extracurricular options. How do we encourage kids to play the game unsupervised, so their natural skill comes out? Can we carve out enough time for our youth to play the game with several competing activities?


The role of parents


Dwayne’s father Tony De Rosario (aka Tony De) was instrumental in DeRo’s life and he recounts that his dad was his coach all his soccer life. He would call him during his professional career and give him feedback on the positive and negative aspects of each game. DeRo credits him for pushing him to be his best but also introducing the ‘Brazilian flare’ to his game.

Jason’s parents were also very supportive of his playing career. They did not push him as he was self-motivated and had the desire to play professionally very early in his life.

Stevie’s parents were both into footy and his dad played semi-pro but always played the role of encouraging the boys (rather than pushing them). We had an in-depth conversation about this, and we both agree that the role of parents is to encourage children rather than push them to the point where they do not enjoy the sport.

We talked about sporting legends like Serena Williams and Andre Agassi and whether their parent’s relentless pushing led to their success. We both agree that these amazing individuals also had a tremendous inner drive and passion and love of the game that ultimately led to their success. There are countless other examples of parents (and coaches) who pushed their own dreams on their kids and ultimately diminished the kids ‘love of the game’. Andre Agassi’s book ‘Open’ is a fantastic book that describes his love/hate relationship with the game and the effect that his dad had on life.

Stevie did recount that his parents did ensure that he fulfilled his commitments and did not ‘cut any corners’. He had a few years where it became gruelling in the middle of the season and he wanted to quit but his parents provided the ‘tough love’ that he needed and ensured he committed until the end of the season. His parents had very high standards and encouraged him to ‘do the job right’. Always do your best so you can look in the mirror and be proud of yourself. This was also true for Jason and DeRo.


I often see hockey or soccer parents pushing their kids very hard and I asked Steven his opinion on this. His take on this is that the individual must have a deep passion and love for the game inside them and this ‘pushing’ by the parents is not helpful if the individual is not self-motivated. DeRo talked about the discipline you need to make it to the pros especially now. He said that most kids and adults wake up and reach for their phone. He recommends rolling over and doing some push-ups and putting in the work first. This type of self-driven mentality was clearly common among these three individuals and was a big part of their success. Jason also talked about being self motivated and having a deep desire to be a professional soccer player. He dedicated his life to achieving his dream of becoming a professional soccer player.


Getting serious


When Steven was 10, things started getting serious. Most talented kids in Scotland found clubs at that age and Steven played for Falkirk. It was still fun for him, but it started to have a more professional feel to it. He had a kit and tracksuit which was amazing for him. The coaches started to bring in discipline and structure but did not compromise the fun side of the game.

As the years progressed, he progressed to ‘regional centers’ and often trained at different clubs on different days. He recalls weeks where he may have trained at ‘Hearts’ on Tuesday, ‘Dundee’ on Wednesday and ‘Falkirk’ on Friday. This afforded him an amazing opportunity to train at the highest level in Scotland and experience many different coaching styles and philosophies.


At age 13-14 it became even more serious and he started to feel his life get squeezed with a tremendous amount of footy, while also having homework responsibilities. He was one of the best kids at his age and progressed to ‘Scotland Schoolboys’ tryouts. He was one of a few U14 kids who tried out with U15 kids. He did not make it, but instead of sulking, he used this disappointment as fuel and ultimately led to him being very focused and determined to make it the following year. He made it and captained the side the following year. This was a big deal as this was broadcast on Sky sports on TV.


This level started with 45-60 players who played matches after which the coaches would select who would make it to the next round in the change room. He made the final squad of 18 players which was a great accomplishment but also carried a lot of pressure with it. These types of tournaments became mental battles that each of the players faced and Stevie learned a lot about himself in these situations and kept coming back for more.


Dwayne’s experience started with him playing for Scarborough Blizzard when he was 3 years old. His dad was his coach and was influenced by the great Brazilian teams featuring legends like Zico and Socrates who were magicians on the ball. He then played for Malvern and his dad always demanded discipline, respect and combined it with letting the players including DeRo ‘express themselves’.


At age 14, Dwayne joined the provincial program which enabled him to play against the best competition. He often played against men which was a significant part of his football growth. Unfortunately, the program was cancelled but DeRo joined GS United which he credits as a fantastic program. He remembers the community feel where the older guys would push the ‘younger fiery kids’ to work very hard. The families would often have barbeques, and this felt like a family to DeRo. Dwayne developed his ‘blue collar’ hard working mentality from his father Tony as well as this experience at GS United.


Jason’s experience was more linear as he played for Malton Soccer Club from age 6-18. He was coached by the same individual (Orazio DeCiantis who played semi-pro in Italy) for the entire duration which is somewhat unique. He recounts the work ethic and discipline that his coach instilled in him. He remembers his coach making the team wear garbage bags over their clothes to make them sweat more during gruelling winter running sessions outdoors.


Malton dominated the local league and produced many National team players. He remembers travelling to tournaments in many US cities and dominating the opposition. The environment in Malton was ‘competitive as hell’ and this level of competition helped improve Jason’s skill, quickness, tenacity and mental toughness.


Jason then decided to move to the University of Maryland where fellow Canadian Carmen Isaaco (who coincidently was my first coach in High School) recommended him to their head coach who was Canadian. They won the ACC tournament and the team was stacked with US Nationals. After his first year he was scouted to play professionally which ended his short but successful University career.


The professional years


The success that Stevie experienced at this high level led to many clubs in Scotland and England. He visited many clubs including Newcastle, Chelsea, Man City and Rangers. He knew inside of him that he wanted to play in England and followed that dream. Former star players and current managers like Kevin Keagan and Kenny Dalglish wined and dined him and his parents and this was an extremely special time for him. He believed that ‘Everything was possible’

Every time he felt like he was invincible on the pitch he would play against players who would remind him how hard he would have to work. He recalled going to Chelsea where the kids he was playing against were at a higher level and this motivated him to catch up which he did.


He made the decision to go to Newcastle which just felt right to him. One of his best mates (friend) was going to play at Newcastle and this helped his transition into the club. He has learned that ‘following that inner voice’ or ‘intuition’ has helped him throughout his career.

While he was at Newcastle, he was also tested. He had one period where he was almost released while his younger brother was ahead of him in the pecking order. He had a coach (Tommy Craig) who encouraged him to dig deep and not give up. He played in a tournament at Aston Villa and he was one of the standout players. After that tournament, many clubs wanted him, but Newcastle said no. He then became a regular before ultimately playing at Birmingham and Sunderland.


Jason described his experience at FSV Zwickau as turning him from a boy to a man. As an African American player playing in a foreign Country in 1997-1998, he experienced many tough situations from opposition fans, home fans and even his own teammates. Jason alongside Dwayne helped each other during this stint where they did not understand the language and were young boys in a very competitive and challenging environment.

The intensity was ratcheted up significantly versus his previous experiences. Every single training session was intense, and you could not take a day or training session off. Some of his teammates were ten-year pros who were struggling to put food on the table for their families, so the competition was intense. He played on the first team and the mental toughness he gained from that experience was fantastic. Life away from the pitch was difficult and keeping the mind busy was one of the biggest challenges. This experience developed his confidence and showed him that he could handle the mental and physical challenges of European football.


Dwayne had several trials in Europe including at Barcelona and AC Milan. He was actually offered a contact at AC Milan but was not ready to make this commitment at age 16. It was very difficult for a young man at age 16 to be very far from home and adapt to new circumstances. These experiences proved to him that he had the physical talent and mental toughness to compete at the highest level.


At the age of 17, while playing for the Toronto Lynx he played very well in the U20 World Cup and was scouted by FC Zwickau along with Jason. Similar to Jason’s experience, it was very difficult adapting to life in a German city that was not quite ready to accept everyone. They both say the coach was ahead of their time and we all know that we continue to struggle with racial equality in 2020.

Most talented players they played against

Steven said the most talented player he ever played against was Thierry Henry which brought a smile to my face (very rare these days for us lonely Gunners fans).

Jason said Juan Roman Riquelme who played for Boca Juniors, Barcelona and Villareal was just outstanding. He recalls how Riquelme’s thought process was beyond anything he had ever seen before. He was an old school number 10 whose touch was just sublime.


Dwayne tried out for Barcelona when Ronaldo was playing for them (the real Brazilian Ronaldo). His dazzling combination of quality, pace, strength, explosiveness and clinical finishing made him the best in the world in DeRo’s eyes. He also mentioned Riquelme, Henry and Trezeguet as phenomenal talents.

Between DeRo, Stevie and Jason, Thierry Henry and Juan Roman Riquelme both got two mentions so will leave it up to the reader to break the tie!


Moving Leagues and Countries


After Jason’s Germany experience, he moved to the Colorado Rapids in MLS and had a very solid career. He always had a desire to play in England and eventually got a chance to play for Plymouth Argyle in the UK.

In order for Jason to play in England, there were a few conditions that had to be met. His Country had to be ranked in the top 70 which took a while and his case actually went to a tribunal. While waiting for this to be resolved, Jason had amazing experiences training with PSV Eindhoven and FC Copenhagen in Holland and Denmark respectively. While at PSV, he trained under Bobby Robson who saw something in him and actually wrote a letter that helped his case pass the tribunal. He was very grateful to the legendary Bobby Robson. While at PSV, Jason trained with Ruud Van Nistelrooy who he recalls was an ‘assassin in the box’.


Following Dwayne’s German experience, a former teammate encouraged him to go to China where he played for 6 months. He remembers that this experience involved a lot of discipline including rigorous fitness tests in order to play. He remembers blisters on his bleeding feet as he put in the work to pass these fitness tests.

Dwayne was then in soccer limbo, but his dad convinced him to try out for the Richmond Kickers. He reluctantly did but was pleasantly surprised at the quality of soccer. There were several Jamaican and Trinidadian internationals and he signed a contract with them. This helped him get to MLS where he played for San Jose, Houston, two stints at TFC, NY Red bulls and DC where won 4 championships, scored 104 goals and developed into one of the league’s best players. He loved his time in all these cities and his return to Toronto was ‘a dream come true’.

He had a mission to create a legacy and he clearly achieved. He did recount that it was very difficult to build a legacy in the US as a Canadian player. He wonders if his legacy would have been different if he was a US citizen. He remains proud of his Canadian and Guyanese heritage and remains a role model for inner city kids who are hoping to make it big.

After his fantastic premiership experience, Steven realized that he was now at a stage where he was essentially a ‘yo-yo’ player between the premiership and the championship. The opportunity to come to MLS arose and he again trusted his gut which said to go for it!

When he arrived in Toronto, he instantly loved the city and football club! He loved being somewhat unknown in cities across North America. He along with his team-mates could explore different cities without being noticed by the general public which was practically impossible in England.


He was pleasantly surprised at the quality of MLS and things seemed to fall into place for him quite nicely. He absolutely loves the city of Toronto and Canada and is making a meaningful impact in helping to grow the beautiful game.


Concluding advice for players and coaches.


The experience that these gentlemen had was phenomenal, but they clearly had many challenging situations on and off the field that they had to overcome. Their outstanding experience helps them provide these amazing recommendations to players and coaches.


Recommendation to coaches – what does it take to coach a future pro?

  1. Do it for the love of the game and put the players first (not business first). We need to work together to develop Canadian talent.

  2. Learn your trade, stay humble and be a student of the game.

  3. Make your sessions and team culture about fun, hard work, discipline and camaraderie (the team is a family).

  4. Find mentors and consult these mentor coaches often to continue to improve.

  5. Put in the work and be patient. Getting to an elite level of coaching takes a lot of experience and practice (there are no short cuts to avoid hard work and practice).

Recommendations to players – what does it take to make it to the pros?

  1. Great talent is clearly required but is not enough to make it.

  2. Love the game & be a student of the game. All three of these individuals had a deep love for the sport and continued to learn their craft throughout their careers.

  3. Develop mental toughness, grit and a ‘never give up’ attitude by playing against the highest level of competition & using setbacks as motivation to improve.

  4. Put in the work. There is no substitute for working on your game and putting in the hours and hours of training.

  5. Find mentors & coaches who help push you to the next level with a great environment and a high level of competition.

I am confident that dedicated professionals like Steven, Dwayne and Jason will help Canadian soccer continue to improve and one day Canadian Soccer will reach the same levels of world success as Canadian Hockey!


This will clearly require amazing leadership that will keep everyone pointed in the right direction and ‘sickening’ work ethic. Will Smith famously said:


“I’ve never viewed myself as particularly talented. Where I excel is, ridiculous, sickening work ethic”

Lionel Messi said “You have to fight to reach your dream. You have to sacrifice and work hard for it.”


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