I’m so excited to share that my friend and longtime colleague, Erin Cowling, has just published her first book, The Modern Freelance Lawyer. Erin is the owner and founder of Flex Legal Network, the leading Canadian freelance lawyer platform, and we’ve had the pleasure of knowing and collaborating with her for years. Like me, she has dedicated her career to empowering freelance attorneys and helping law firms rethink traditional staffing models, bringing a wealth of insight and practical advice to this important topic.
I was truly honored when Erin asked me to contribute a quote for the back of her book. I shared:
With the rise of remote work and legal tech, freelance lawyering isn’t just an option—it’s a movement. Erin Cowling’s book is an invaluable resource for lawyers exploring nontraditional paths and for firms looking to integrate freelance attorneys into their practice.
Her book is a must-read for anyone interested in the future of legal practice and the incredible opportunities freelance lawyering offers both lawyers and firms. I had the chance to sit down with Erin to learn more about her inspiration, her process, and what she hopes readers will take away.
Here’s our conversation:
What prompted you to write The Modern Freelance Lawyer, and why now?
After over a decade in the freelance legal world (first launching my own freelance practice in 2013, then founding a freelance lawyer platform in 2015) I noticed a gap. It had been more than 10 years since anyone had written a comprehensive book on the subject. The few that did exist focused on isolated topics like setting up a freelance practice, ethical considerations, or just personal anecdotes. I wanted to create one accessible, all-in-one resource that explored not only the history, but also provided practical tips for setting up a freelance lawyer practice, covered ethical questions, included success stories from freelance lawyers, and discussed the future of this alternative way to practice law.
In your book, you cover the history of freelance lawyering from the 1980s onward. What’s changed and what hasn’t?
Interestingly, the motivations haven’t changed much. Whether in the 1980s or now, freelance attorneys are often professionals looking for more flexibility and control. Whether they are lawyers who have had to relocate for their spouses’ careers, parents of small children, dual-career professionals, semi-retired lawyers, law school professors, or those craving better work-life balance. What has evolved is the scope of the work. Early freelance lawyers were often limited to document review or legal research. Today’s modern freelance lawyers are drafting pleadings, assisting at trial, reviewing contracts, and contributing to high-level transactions, the same work traditional lawyers do.
What are the biggest misconceptions about freelance attorneys and have those shifted over time?
Initially, freelance lawyers were sometimes viewed as lawyers who couldn’t find a “real” job and were relegated to routine, low-value, boring tasks. There was even a book published critiquing the rise of temp attorneys, suggesting it was contributing to the “deprofessionalization” of law. But that view is outdated. Now, freelance lawyering is recognized as a legitimate and respected way to practice. These are experienced, capable lawyers choosing freelance work, not settling for it.
How has technology impacted the freelance legal world?
It’s been a game changer. When I started, some law firms still asked me to pick up physical files in person. Today, thanks to secure cloud systems, project management tools, and the normalization of remote work (accelerated by the pandemic), working with freelance lawyers like those on Montage Legal’s platform is seamless and secure.
Many freelancers are former large firm attorneys. How does that benefit the firms who hire them?
Tremendously. Former big law attorneys bring deep experience, polished work product, and the ability to step in with minimal supervision. That’s exactly what solos and small firms need, someone who can hit the ground running. I interviewed several for my book, and it’s clear that their large firm background is a huge asset to the clients they now support.
You also include a chapter in your book for lawyers who hire freelance attorneys. What’s your top advice for firms considering it for the first time?
Do it! You’ll wish you started sooner. But set yourself up for a successful working relationship. First, hire the right freelancer. If you don’t have time to vet them yourself, use a trusted platform like Montage Legal (in the U.S.) or Flex Legal (in Canada). Second, communicate clearly. Spell out your expectations, deadlines, and scope of work. And finally, treat the first project as a collaboration and use feedback to refine the relationship. The freelance attorney will then be better equipped to provide you excellent work moving forward.
Some lawyers worry about the ethics of hiring freelance attorneys. What should they know?
It’s not only allowed, it’s encouraged, when done properly. Chapter 10 of The Modern Freelance Lawyer dives deep into the ethical landscape, including addressing conflicts of interest and confidentiality concerns, the duty of supervision, marking up freelance lawyers fees and avoiding the unauthorized practice of law. Ultimately, freelance lawyers are bound by the same professional rules as any other lawyer, including the rules around conflicts and confidentiality. It’s ethical to mark up their fees (so long as the total is reasonable), and with proper supervision, even out-of-state lawyers can be brought on to assist. There are clear, professional pathways to doing this right.
What qualities set a great freelance lawyer apart, beyond their legal skills?
Strong communication skills, first and foremost. Freelance lawyers need to be clear, responsive, and proactive. They also need to be organized, independent, and excellent time managers. You don’t succeed in this field without the ability to juggle multiple projects and keep clients happy.
What do you hope readers – whether hiring lawyers or aspiring freelancers – take away from The Modern Freelance Lawyer?
That freelance lawyering isn’t a trend, it’s a past, present, and future way to practice law. I want hiring lawyers to see how smart, efficient, and cost-effective it is to outsource overflow legal work and incorporate the use of freelance lawyers into their business strategy. And I want freelance-curious lawyers to walk away informed, inspired, and equipped to build a practice that works for their life.
Congrats again on your book, Erin! We are so happy for you. To purchase The Modern Freelance Lawyer: A Guide to the Business, Ethics, and Evolution of Freelance Legal Work, visit the book’s webpage or find it on Amazon or Barnes and Noble.
Erin Cowling
Erin Cowling is the founder and CEO of Flex Legal Network Inc., the leading Canadian freelance lawyer platform she launched in 2015 after her own freelance practice became so busy she found herself turning down work. Flex Legal matches busy lawyers, law firms, and in-house legal departments with pre-vetted, experienced freelance lawyers. What began with just three lawyers has since grown into a robust network of over 80 freelance lawyers across Canada, supporting hundreds of law firms and legal departments nationwide.
When not managing Flex Legal, Erin speaks regularly at legal events (on women and the law, alternative career paths, and solo and small firm events, among others), writes for several legal publications, and is the author of The Modern Freelance Lawyer: A Guide to the Business, Ethics, and Evolution of Freelance Legal Work. She was also an Adjunct Professor at the University of Toronto Faculty of Law teaching Legal Research & Writing (2018-2020) and was the Regional Alumni Advisor (Toronto) for the University of Ottawa Faculty of Law (2019-2021).
Erin is also a 3x winner of the Canadian Law Blog Awards (the Clawbies) and has been nominated for:
- Canadian Lawyer’s Top 25 Most Influential Lawyers in Canada,
- the OBA Women Lawyer’s Forum’s Award of Excellence in the Promotion of Women’s Equality
- the CBA’s Touchstone Award and
- RBC’s Canadian Women Entrepreneur Awards.
Contact Erin Cowling:
Email: [email protected]
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