From International Model to Award-Winning Immigration Lawyer: Q&A with UTM Alumna Lorraine D’Alessio

An upbringing as the daughter of immigrants in Mississauga, combined with the city’s unique diversity and multiculturalism, laid the foundations for Lorraine D’Alessio’s (HBA 2003) international career in Immigration Law.

Paving her way through her studies at UTM with a successful, international modelling career, she quickly learned the importance of understanding one’s rights and advocating for them. Now, living in the United States, a first generation-immigrant herself, she has made it her life’s mission to help other immigrants.

As the CEO and Founder of D’Alessio Law Group, which is intentionally comprised almost exclusively of women, Lorraine D’Alessio was nominated as a 2017 Leader in Law by the Los Angeles Business Journal and is the recipient of the 2018 Enterprising Woman Award.

D’Alessio has provided counsel and advice to US embassies across Canada, the Maple Business Council, World Trade Center, as well as UBCP National and various national branches of labor unions including ACTRA. She has also provided counsel to hundreds of prominent entertainment agencies, unions, private companies and academic institutions including New York Film Academy, Next Models, Food Network, Sub Pac, Pepperdine University, Plug and Play, Expert Dojo, and 500 Startups.

Lorraine D’Alessio sat down with us to talk about her path into law, her international career, her time at UTM, and the joys and perils of working in Immigration Law in the United States.

Can you tell us more about your personal background?

I grew up in a loving household right in Mississauga with my parents. My father is a first-generation English-immigrant, having moved as a young child. I’ve had a lifelong passion for supporting and holding up immigrants from all over the world. My family taught me many of the values I carry with me today; and it’s exactly these values that have shaped my dedication toward helping people understand their rights.
 

What brought you to UTM and what was your UTM student experience like?

I was very interested in U of T’s international presence and reputation. I always knew I wanted to work abroad; so, knowing that UTM had this level of prominence in the international community, I specifically sought an education there rather than at other universities that had offered me a full ride!

I had something of an atypical campus experience. Having been exposed to the party scene when I was younger, by the time I got to UTM I was all hustle! Both of my parents are teachers, and I knew the value of hard work and perseverance, often juggling multiple jobs in modelling and retail at the same time as my studies. In spite of my hustle, I always felt that UTM was a welcoming and diverse environment that shaped and defined the woman and leader I am today.
 

You graduated with a specialist in Political Science and a minor in English. What were some of the most interesting lessons or classes that stayed with you? Any professors that come to mind?

Professor Braun had a wonderful influence over my development at UTM, and the lessons I learned, not only from the courses, but also from the one-on-one feedback and discussions – something I’ll never forget.

Through modelling, I had a lot of exposure to people from Europe and their work regimen, especially people from Russia. I think that was part of the reason why one of my favorite elements of my education was European Studies. Being able to combine my experience as a model with the educational aspects of my studies is still helping me today in connecting with my law firm’s Russian clients.
 

Did you continue working as a model throughout your student days? If so, how were you balancing your modelling career with academic life? Was it challenging?

Modelling was a huge part of my life in university, having been involved ever since I was 14. When I was 16, I was scouted by FORD Models at a dance club in Toronto and was quickly asked to attend an ‘on call day’ at their Toronto office, where I was presented with a contract and noted for my resemblance to Giselle Bündchen. I happily kept up with modelling, especially participating in editorials, until I was 24. It was a great way to make some money while earning my degree, but I always knew that immigration law was the future for my career.

So, you always knew you wanted to be a lawyer?

I always knew I had a certain empathy with other immigrants in my school and community, knowing them to be hard-working, tenacious and successful people. I wanted to combine this with my own experiences traveling internationally for business, and my desire for helping people.

During business travels as a model, I sometimes felt very fearful of paramilitary officers at border crossings. There’s a very skewed power dynamic where the officer can often act at their discretion – that fear and dynamic encouraged me to learn what my rights actually were. After experiencing countless personal violations and facing fears of being denied or searched at the border, or being barred access without explanation, it became my goal to demystify the process and guide immigrants through the complexities of immigration as a shield from that fear.

So, that’s how you got started in Immigration Law?

Yes, through my courses at UTM, I found that immigration law sat perfectly at the intersection of my greatest passions. Mississauga is the most multicultural city in Canada and, growing up, I appreciated that, unlike other parts of North America that can be defined as a ‘melting pot,’ Mississauga is a true mosaic. I have always loved that Mississauga is a collective of international cultures and art where the entire city’s identity is defined by each of its parts that make it whole, rather than an assimilation of cultures.

Growing up with a multicultural group of friends from around the world, including friends from Serbia, Croatia, China, South Korea, and the West Indies, I always loved that we could coexist together not just despite of, but with a love for our differences – it’s been one of my greatest aspirations to share this experience with others through immigration law.


You champion female empowerment. You set up your own firm, hired a legal team that is mostly comprised of women, and were awarded the 2018 Enterprising Woman Award. What motivates you to keep pushing the boundaries?

It is precisely these women, who make up my firm, that motivate me to keep pushing the boundaries. Seeing how hard they work each day, going above and beyond to help our clients achieve their dreams while providing for their families – those are my reasons! They are the true power behind our firm and the reason why I work from sunrise to sunset to ensure this is a place where they can continuously grow as, both, professionals and individuals. One of my greatest goals with my team is to create a support system that transcends typical work relationships, but has a positive impact on the family and home life of our incredibly hard-working team.

And, related to that, what were the challenges and boundaries you had to face in your law career? What advice do you have for others facing similar challenges?

Like so many others in immigration, the last few years have been difficult. Between surviving an administration openly opposed to immigrants, followed shortly after by a pandemic that caused a global lockdown, immigration law and those that practice it have faced some of our toughest challenges in the last five years. My best advice to others is this: start foundationally. When you have a strong structure with a team that cares and will back you just as strongly as you back them, you can survive anything. When your team is strong, your clients will notice, and building and holding onto that reliability, both internally and externally, will help you ensure not only survival but success.
 

What motivates you?

Our clients! Seeing what they’ve accomplished in their careers and where they want to go is exactly what inspires me to open those doors to make their dreams of working in the Unites States a reality.

One of our most inspiring clients is a company called Hyperloop. Hyperloop has been bringing in some of the brightest minds from all over the world to develop clean energy, high-speed travel that will revolutionize public transportation, and it’s this level of innovation that motivates me to open every door I can for our clients.
 

What advice can you share for students interested in a career in law?

Immigration law is a practice, not a science; 2+2 doesn’t always equal 4 in immigration law. You can follow the exact same formula 10 different times and still get 10 different results.

My family used have a saying, “you can please some of the people some of the time, but you can’t please all of the people all of the time.” So, my advice is this: help as many people as you can, and fight for every single client, and learn to grow from your failures rather than dwelling on them. Don’t be discouraged by failure. Learn from it, and as long as you do what your experience, intuition, and knowledge tells you is right, you will find your successes outweigh the rest.
 

You were born and raised in Ontario. What brought you to California? What do you like about life there versus Canada? What do you miss?

What isn’t to love about California? The incredible weather, the cultural diversity, the opportunity – California represents everything that’s great about America! Like many immigrants, I knew my career goals would eventually take me away from my home country. And, although Ontario will always be my first home, California feels as much a part of my identity as Canada. California weather can’t be beat, but I do miss the natural beauty of the changing seasons in Ontario, its incredible people and, of course, my family. I make every effort to return as frequently as I can!
 

You've accomplished a lot in the last decade. Where do you see yourself ten years from now?

In the last ten years, D’Alessio Law Group has expanded from me writing my own cases, managing my clients, and, basically, doing everything myself, to being a proud, multinational company with hundreds of active clients and an equally diverse team of dedicated employees around the world. I hope in ten years, I can look back on our growth the way I look back now: loving the people and clients who have come and gone, fostering old and new relationships with some of the most creative and intelligent minds from around the world. I hope I can look back, as I do now, at the wonderful things our clients have accomplished, knowing that my team and I have helped make America the best place it can be for everyone who calls America home.