Q: Why did you start your business?

Erin: I started my business because, while I loved being a lawyer, I needed more flexibility in my life. At the time, I felt like law was an all-or-nothing profession where I had to work a million hours a week or quit completely. So, I started calling myself a freelance lawyer and offered my legal services to other lawyers and law firms as an independent contractor, helping them with their overflow legal work. It was a win-win situation as I was easing the burden for my lawyer clients, and I could pick and choose which work projects to take on and still do very exciting high-level legal work. When my own freelance practice got too busy, I started Flex Legal and brought on other freelance lawyers to help with the work. We've grown from 3 freelance lawyers in Toronto to over 80 freelance lawyers across Canada.

Q: What do you offer?

Erin: Flex Legal matches freelance lawyers with busy lawyers, law firms, and in-house legal departments across Canada. We offer a flexible solution for hiring lawyers who may not want to or cannot afford to hire a full-time employee but want to spend less time in the office. We also offer a flexible way for our freelance lawyers to practice law when a traditional law practice may not be right for them.

Q: Why did you want a Branding session?

Erin: I've had traditional headshot photos done in the past where I looked like a typical, conservative lawyer with my suit on and my arms crossed. As I've created my own legal career on my own terms, I no longer feel like I have to stay "in the box" of what others "think" a lawyer should look like. I wanted to be more authentic to who I am as a lawyer, CEO, entrepreneur, writer, speaker, and woman. So I sought out a branding session to express that.

Q: What advice would you give to an entrepreneur?

Erin: While it can be challenging being an entrepreneur, I find the positives far outweigh the negatives. Find a mentor or other entrepreneurs you can turn to when days are tough or when you need to bounce ideas off someone outside of your business. Find your people. It makes it so much easier.

Entrepreneur Spotlight: Erin Cowling of Flex Legal Redefines Legal Careers

Stacey Naglie Photography • June 5, 2024

Share this page:

In the world of entrepreneurship, finding a balance between professional demands and personal aspirations can be a daunting challenge. For Erin Cowling, a passionate lawyer turned entrepreneur, this journey led to the creation of Flex Legal—a dynamic solution for legal professionals seeking flexibility and balance in their careers. We sat down with Erin to discuss her inspiring journey, the unique services offered by Flex Legal, and her experience with a personal branding session with Stacey Naglie Photography.

Discovering Flexibility and Success: The Journey of Erin Cowling

Q: Why did you start your business?

Erin: I started my business because, while I loved being a lawyer, I needed more flexibility in my life. At the time, I felt like law was an all-or-nothing profession where I had to work a million hours a week or quit completely. So, I started calling myself a freelance lawyer and offered my legal services to other lawyers and law firms as an independent contractor, helping them with their overflow legal work. It was a win-win situation as I was easing the burden for my lawyer clients, and I could pick and choose which work projects to take on and still do very exciting high-level legal work. When my own freelance practice got too busy, I started Flex Legal and brought on other freelance lawyers to help with the work. We've grown from 3 freelance lawyers in Toronto to over 80 freelance lawyers across Canada.
Q: What do you offer?

Erin: Flex Legal matches freelance lawyers with busy lawyers, law firms, and in-house legal departments across Canada. We offer a flexible solution for hiring lawyers who may not want to or cannot afford to hire a full-time employee but want to spend less time in the office. We also offer a flexible way for our freelance lawyers to practice law when a traditional law practice may not be right for them.
Q: Why did you want a Branding session?

Erin: I've had traditional headshot photos done in the past where I looked like a typical, conservative lawyer with my suit on and my arms crossed. As I've created my own legal career on my own terms, I no longer feel like I have to stay "in the box" of what others "think" a lawyer should look like. I wanted to be more authentic to who I am as a lawyer, CEO, entrepreneur, writer, speaker, and woman. So I sought out a branding session to express that.
Q: What advice would you give to an entrepreneur?

Erin: While it can be challenging being an entrepreneur, I find the positives far outweigh the negatives. Find a mentor or other entrepreneurs you can turn to when days are tough or when you need to bounce ideas off someone outside of your business. Find your people. It makes it so much easier.

The Power of Flexibility and Authenticity: Erin Cowling’s Path to Success

Erin Cowling's story is a testament to the power of flexibility and authenticity in building a successful business. Through her journey with Flex Legal, she has demonstrated how embracing one's true self and stepping outside traditional roles can lead to innovative solutions and remarkable growth.

A woman is sitting at a desk with a laptop.

A woman is sitting on a white couch in front of a fireplace.

Capture Your Authentic Self with Stacey Naglie Photography

If you're an entrepreneur looking to capture your authentic self and tell your unique story through professional photography, contact us today. Let's create visuals that stand out and truly represent your brand.

Get started with a free consultation

Get Started

Share this page: