The Thin Line Between Success and Failure: What Sidney Crosby's 2016 Stanley Cup Can Teach Lawyers

In 2015, Sidney Crosby was going through the worst slump of his career. He had 15 points in 23 games and instead of being in his usual top 5 spot among the NHL scoring leaders, was ranked somewhere in the hundreds. Sports writers started to write him off as going through an inevitable decline that happens with age and following injuries. Other sports reporters were saying that the Penguins should trade him while he still had some value. Advanced stats reporters (I love advanced stats) were showing charts that demonstrated that his decline could actually be explained by a steady decline that had started years earlier and the decline was simply proceeding as expected. Then the calendar year changed. In 2016, Crosby broke out of his slump and went on a tear. He finished the year third in NHL scoring and then won the Stanley Cup and the Conn Smythe trophy as the most valuable player in the NHL playoffs. Two months later, he won MVP of the World Cup of Hockey while leading Canada to a gold medal. How could the people who had written him off have been so wrong? And what does this have to do with lawyers?

In my view the people who had written off Sidney Crosby were not exactly wrong. I always thought Sidney Crosby described it best himself in his article ‘it´s ok to doubt me: sometimes I even doubt myself:

I won´t rest on my laurels. I just can´t. Winning is special. If last season taught me anything, it was how thin the line is between being ‘washed up’ and lifting the Stanley Cup.

The truth is that the line between being washed up and a Stanley Cup champion and MVP is thin. The sports writers who had written Crosby off were not wrong as much as they were unaware how much small changes in circumstances could greatly impact his outcomes.

There are a small number of law students that are legal superstars from the outset and up doing amazing things like Supreme Court clerkships and there are a small number of law students who probably do not belong in law school to begin with and really struggle. For everyone else, the vast majority of law students, it is my view that success and failure teeters on a razor´s edge.

Ask anybody who has been through, for example, the on-campus interview and in-firm process for the Bay Street firms how much luck is involved. A bad night´s sleep or a disconnect with one of the many people you interview with can be the difference between a high-paying job and unemployment. One of the elements of the in-firm interview process on Bay Street that causes so much stress is because it is obvious to all the law students that everyone who got in-firm interviews has enough merit to get the job, but not everyone will get a job. The process is almost diabolical in the sense that it generates winners and losers for what are usually the most random reasons.

In my own experience, I often think of how I felt when I started my own criminal law firm. I was in a very fragile state at the time. I was determined to try going out on my own, but I was also full of fear. I was on the receiving end of a lot of discouragement from people telling me I could never make any money practicing criminal law, especially from the older generation, including many lawyers. I felt like a scared kid much more than I felt like a confident young lawyer.

I lived at Bathurst and Lakeshore at the time with my then fiancé (now wife). I sent out e-mails looking for people renting office space and got a response that a young criminal lawyer named Sean Robichaud had started renting office space for criminal lawyers and was looking for lawyers to join. It so happened that this new office was at Bathurst and King just a block away from where I lived. He called it King Law Chambers and I remember thinking that it had a nice ring to it.

It was February 28, 2011. I remember walking from my condo at Lakeshore to King Street filled with very little except determination and self-doubt. My wife and I walked into the office and met Sean. We liked him immediately. He was full of energy, walking around the office with quick and determined steps and waving his arms vigorously while explaining how he intended to build out the office space into more offices. He did not treat me like the scared kid full of self-doubt that I was and instead encouraged me by saying that his chambers would love to have a young lawyer with my profile (flattery will get you everywhere). When I told him about my fears, he told me he would rent to me for the first two months for free and that he often had bail hearings he could not do and would send to me. I looked at my wife and we agreed that it was perfect. I hung up my shingle the next day, March 1, 2011.

In my first few weeks of practice, Sean asked me to do an adjournment application for him in Barrie and offered to pay me $500.00. When I attended for the adjournment application, I happened to see James Lockyer there who was acting for a female client having her conviction vacated because the conviction was supported by the evidence of disgraced pathologist Dr. Charles Smith. I remember speaking to James Lockyer that day and telling him what an inspiration his work overturning wrongful convictions had been for me. I came home with $500.00 in my pocket that day, but got something much more valuable than money. I couldn´t believe I could get paid to have such a fun and exciting day.

Sean must have known that I would have done that adjournment application for free. He offered to pay me to encourage me and teach me to value my time, an absolutely vital skill to succeed as a criminal lawyer. About a week later, Sean offered me $1,000.00 to do a bail hearing for a client of his. I attended for the client´s bail hearing that day, but the hearing did not get reached and I asked Sean what I should do:

Sean: “Ask him for another $500.00 for your attendance tomorrow.”

Ryan: “It´s ok, I think I´ll give him a break. I feel bad for the guy. It is not his fault his matter didn´t get reached.”

Sean: “That is the problem with criminal lawyers, we are very sympathetic people. It´s great to be sympathetic, but we need to get paid for our court time. Ask him for another $500.00.”

After our conversation, I went to the cells and told the client that I would need another $500.00 for my attendance tomorrow. He said “No problem, just ask my mom”, who was his surety.

The next day I got the client out on bail and had $1,500.00 in my pocket. I had made about $2,000.00 in the span of a week, which seemed like a huge amount of money to me at the time. That week helped build my confidence and made me realize that it was possible to make a living as a criminal lawyer, despite what all the doubters and naysayers had said.

Like the adjournment application, Sean must have known that I would have done that bail hearing for free. But he insisted on paying me not just because that was the right way to treat a young lawyer, but to teach me, encourage me and help me build my confidence. It is now almost exactly eight years since that scared kid walked into King Law Chambers. And though there are still times I feel like the scared kid, I much more often feel like the confident lawyer.

I still often think about the luck involved in finding someone who treated me with kindness when I was in a state of weakness. What if I had encountered a lawyer who was all talk and never had any work to give? What if I encountered a lawyer who was prepared to exploit a young lawyer looking for work and asked me to do work for free? What if I had encountered a lawyer that was too busy to give me advice or didn´t care or experienced a setback and was in no mood to help a young lawyer?

I ask myself these questions because I believe that the line between a scared kid who cannot make a go of it and a successful, confident lawyer is very thin. Most people that imagine when they become a success that they were born for greatness or they pulled themselves up by their bootstraps are fooling themselves. The truth is that for the vast majority of lawyers, meeting a kind-hearted mentor, being in the right place at the right time or getting a lucky break can make all the difference between success and failure. And for most people, you can easily end up on either side of that line.

For most lawyers, the line between success and failure is very thin. If you are a successful lawyer, the thin line is a good reason to remain humble. Show kindness to those in a state of weakness, it is truly one of the greatest things you can do and make all the difference to someone in their career. Remember that anyone can end up on either side of that line and that the strong can easily become the weak and the weak the strong. Just ask the greatest hockey player of his generation.