Erin Cowling

Erin Cowling

Building a less traditional law practice for fantastic freelance lawyers such as herself

Erin’s law school journey started with a blunt hit to the head – no, seriously. 

During undergrad, as she was organizing the basement of her Queen’s University student housing, she reached for a box on a top shelf and was startled by an old LSAT book left by another tenant that fell off the shelf and hit her. Out of curiosity, Erin cracked open the book and got hooked on the logic puzzles. She would complete them in her free time for fun and figured if she could do well on the LSAT, she might try law school. 
Prior to this serendipitous accident, Erin was unsure of the direction to pursue professionally. With an undergrad in English Literature and a minor in Women Studies and Religion, everyone told her she should teach. But becoming a professor was not appealing to her, so she decided to take a shot at law. 
First in her family to go to university, and without any lawyers in her family, Erin did not meet an actual lawyer until she attended law school. Everything that she knew about law, at this point, she had learned from TV. And while she had never heard of “Bay St” before, she decided to stick to her cohort and follow the traditional law job trajectory and take part in the Bay St summer student application process. When Erin arrived in Toronto for in-firm interviews she was less than impressed with the entire process, especially the cocktail party scene. There was only one firm where she saw herself working, McMillan Binch LLP (now McMillan LLP), and fortunately that firm recruited her for a summer position. She was asked back to article with the firm and then spent another seven years as a litigation associate. 
In the beginning, for the most part, Erin really enjoyed her time at McMillan. She worked on challenging and interesting cases, some that were on the national news and went to the Supreme Court of Canada. Since her boyfriend at the time (now husband) was also a lawyer on Bay Street, working a similar job with demanding hours, her work as a litigation associate fit with her lifestyle. It was an exciting time in her legal career. 
However, as a first-generation lawyer, Erin did not fully understand how the legal profession worked. She thought if she treated working in a law firm the same as law school (keep your head down, work hard, produce excellent work), she would be a successful lawyer. 

Unfortunately, that is not always true. Writing excellent factums and winning cases is not always enough. The bottom line is that law firms are businesses that prioritize making money. They make money by landing clients and big cases. 

While some of her fellow associates (often male associates) focused on networking (often with male partners) and business development early in their careers, Erin missed the importance of these connections. Erin now knows that often it is these behind-the-scenes contact points that can help associates land better files, more interesting work, and better bonuses. Through these experiences Erin learned the importance of networking and fostering relationships to best position yourself in the legal business environment. 
Over time, Erin’s priorities in life also shifted and the thrill of being at the office for 12-14 hours or more a day started to wear off. She no longer fit what the firm was looking for in an employee and the firm no longer offered Erin a career that fit with her core values. When looking for other employment, she took the first job offer that came her way (in retrospect she realizes taking the first offer may not be a good idea). However, feeling like the “safe” thing to do was to take the offer, Erin started working with a small estate litigation firm. Going from corporate-oriented litigation to estate litigation was very challenging. Estate litigation was much more personal and emotionally draining than what she was used to. Several months into the new role, Erin knew she had made a career mistake as her mental health began to suffer. She was also pregnant with her third child. Against everyone’s advice, she quit without another job lined up. While recognizing it would be a challenge to go from a two- income to one-income family, Erin knew it was the right decision for her own mental health.  
During this time, while waiting for her newborn daughter to be a bit older before she applied for a full-time job again, Erin started accepting overflow legal work from different solo lawyers and law firms. She would help a firm draft their blog posts or draft a factum. A few months later, when she felt ready to go back to full time work, she started applying to job openings. But every time she would send an application in to a law firm or in-house position, her stomach was in knots. She knew she did not want to go back to full-time traditional legal work. 
Listening to her gut this time, Erin decided to continue taking on overflow work from different law firms, to see if she could build a non-traditional law practice as a freelance lawyer. Instead of working for one firm, she would freelance for several. She would choose what work she wanted to take on and what she did not. Erin attended lawyer events in her area to meet as many litigators as possible. In 2013, her original pitch was: when times get busy, I am here to help, as needed, without the overhead of a full-time associate, whether it be legal research, writing and more. In 2015, the demand for her help was so overwhelming she started turning down work. This is Flex Legal’s origin story. 
Having discovered other lawyers interested in her less-traditional legal career, Erin created Flex Legal to help meet the demand, while also creating an alternative legal career for lawyers looking for something less traditional. Flex Legal started with a roster of three lawyers, and today they have over 50 lawyers helping hundreds of law firms across Canada. As a result, Flex Legal enables these experienced freelance lawyers to assist lawyers and ​law firms on a cost-effective, as needed, and flexible basis.  
Erin never thought she was an entrepreneur. In law school, she gave little thought to the business side of law. Although there was a steep learning curve when setting up Flex Legal as a business, Erin discovered she loves wearing the entrepreneur hat and learning how to improve and grow her business. Her love of learning also explains why she always has two books on the go (one of them being a business/law book, the other a detective novel or mystery). 
While Erin acknowledges that practicing as a freelance lawyer will never generate the same income as an equity partner at a Bay Street firm, and it can be a risk to choose a non-traditional legal career path, Erin has absolutely no regrets. She is more than happy to trade some of the financial rewards for the freedom she now experiences. 
Erin loves the flexibility of her not average law job. Even if she was not a mother, she would like a flexible schedule, that may still have crazy hours at times, but enables her to set boundaries and gives her more control of her workload. 
An example of a boundary she has imposed that may not work in traditional law is her email management. During the pandemic, Erin deleted her work email from her phone and has a message saying that she checks emails only from 9-5 on weekdays. Prior to doing this, the notifications on her phone would trigger work in her mind, when she was enjoying time with her family or getting ready to sleep. Although she may still be working outside those hours, she has noticed that her lawyer and law firm clients respect her boundaries which enables her to properly delineate her work from personal time.  
During the baseball season, you can find Erin making the most of her uninterrupted personal time scoring Blue Jays games. Erin finds that scoring a baseball game with a pencil and paper in hand, acts as a meditative practice and stress relief activity because you must slow down, pay attention to the game in the present moment, and be mindful of the details. And she sees the final filled out scorecard as a beautiful piece of art that tells the story of the game she just watched.