Rethinking Success in a Modern Legal Career

In the summer of 1998 I was a freshly called lawyer working in the regulatory policy shop of a national phone company. As we gathered in the boardroom to celebrate a colleague’s 25th anniversary, I leaned over and whispered to a co-worker “wow, I’m not sure I’ve even been toilet trained for 25 years.” To that point, five and a half years delivering the local newspaper to my own house was the longest I had ever done a single job. A personal longevity record that stands unbroken today.

Point of fact, I eventually did spend over 10 years with that company, albeit spread over two provinces, thirteen calendar years and about 7 different roles. The skills gained in those and other roles got me hired as CanLII’s CEO (a four year stretch that concludes on April 30th) and helped prepare me for what comes next. But here’s the thing, it all feels like stages in a legal career that others may increasingly regard as normal.

Structurally unsuited to job stability

I’m taking about the legal profession here, not me.

Using Ontario as an example, a quick glance at some basic legal market employment stats makes it evident that variety of experience and charting your own path is the norm (at least in the aggregate). At the end of 2013, the Law Society of Upper Canada reports that Ontario was home to 11,375 law firms – nearly 78% of which were solo practices. At the other end of the scale, in this province of over 13 million people there are only 40 firms that employ more than 50 licensees (this includes firms where lawyers+paralegals >50 people). Beyond private practice, over a third of employed Ontario lawyers ply their trade in education, government, corporate, non-profit and other environments.

We don’t even need to consider different legal specialties to look at these high level stats and conclude that none of us can claim to follow a traditional path to becoming a real lawyer because there is no traditional path. There may be traditional roles – criminal defence comes to mind – and we may find ourselves in such a role at one point or another, but any sense of stability and clarity we believe exists with those roles simply can’t be extrapolated as emblematic of all legal careers.

Your legal career begins in the direction set by your first legal employer, and the time you spend on that path is subject to many circumstances within and outside your control. It can take a few years to get your head wrapped around your activities and to begin to understand your own preferences and passions.

Employability and a range of personal goals

All is not lost and there is much to be gained.

Every experience is a learning experience and though it can seem that way sometimes, few doors are permanently closed. This isn’t a generic “JDs are good for many careers” pep talk, but an appeal to make choices that broaden your skills, strengthen your resiliency and have some rational connection to long-term career goals. I’m not talking about a linear career development path. There are simply too many extraneous factors. Why narrow your view and adopt a single definition of success?

I’ve always looked at career development in a few ways.

The first, when looking 10 years ahead, I think about a dozen or so roles that I believe I would enjoy doing. When evaluating a new work or learning opportunity, I ask myself how it will contribute to getting me closer to one or more of my 10-year-out dream jobs. This lens can reveal the advantages of opportunities that might otherwise seem like a career detour.

The second involves recognizing that even if moving closer to one goal moves you further from another, it needn’t necessarily foreclose the opportunity forever. Imagine a golf course where the 18 holes are laid out around the perimeter of circle and each hole is accessible from a single tee box at the centre. You can play toward any, or even several, holes (goals!) without leaving the course, and you can change direction at any time.

Finally, the third is about taking ownership of your own success. By all means, seek out teachers, mentors, sponsors, promoters, subject-matter experts and others who can help you along the way, but accept that only you can define what you want out of your legal career and only you can assess whether you are successful in your efforts.

A step in the right direction

In my view, law students, new lawyers, mid-career professionals, and near or long-since retired lawyers have never had it so good. There is not one type of lawyer and there is not one way to develop a successful legal career. For the increasingly small minority of lawyers who believe there is and act accordingly, I wish you well. For the rest of us, a step back, to the side, up or down can be a step in the right direction when you can see how it strengthens your ability to handle change and how it can build you into the kind of success you want to be.


  1. Nice post Colin.