Associate Caitlin Oswald joined Pasich LLP in 2019 and has quickly become a vital part of our team. As an avid traveler and art lover, she leverages her creativity and tenacity to solve client challenges.

Caitlin has represented insured entities and individuals in a variety of complex coverage disputes, including business interruption claims and disputes arising from the #MeToo movement, under television and film production policies, commercial general liability insurance, directors and officers liability insurance, and property insurance policies.

Learn more about Caitlin both professionally and personally below:

How and why did you decide on a career as a lawyer?

I know it sounds cliché, but when I was growing up, my mom always told me that I was either going to be a doctor or a lawyer. Unfortunately, math and science were not my forte in school, so becoming a doctor was not in the cards. I guess what they say is true, mother knows best!

But being a lawyer fits my personality. I have always liked jigsaw puzzles, and the law is a never-ending jigsaw puzzle. At first, there are a lot of discrete issues that have yet to be connected. As time goes on, you sort the issues into groups, assemble the foundation, and start to piece together the solution to the problem.

What is the best advice you’ve received?

Be resilient. In college, my dad sent me President Theodore Roosevelt’s speech “The Man in the Arena.” It reads:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

As a lawyer you will face difficulties, whether in the courtroom or in life. However, as Roosevelt’s speech emphasizes, it is vital that you stay strong, learn from your mistakes, and keep pushing. Facing setbacks is simply part of the path to success.

What is one aspect of your practice that many people are not aware of?

Insurance law has a reputation for being boring, but that’s far from the truth! Insurance is behind the risks of everyday life. Because insurance covers such a wide variety of risks, we work on claims across many different practice groups, including entertainment, employment, construction, and professional services (just to name a few).

What are your hobbies outside of work?

I love to travel, and I just got back from the South of France and Monaco. I find that escaping my daily routine and immersing myself into new cultures allows me to look at life through a new lens. To me, nothing is better than discovering a new city on foot with no particular agenda while sampling the local cuisine.

When I am not working, I also like to be outside in the sun, either at the beach reading a book or going on long walks with my bichon frisé, Muppet.

If you weren’t a lawyer, what would you do and why?

I have wanderlust, so I would host a travel and food television show like Anthony Bourdain or Stanley Tucci. I would discover hidden pockets of the world while eating unfamiliar, delicious foods. I’ve also always been interested in art—I have a B.A. in Art History—and wandering around the world for a show would allow me to share my appreciation for art and culture with a wider audience.