“Try something that isn’t certain. It’s ok to be uncomfortable. You can always change your mind if it doesn’t work.”
Strategy executive Jaclyn Ryan shared some advice she would give her younger self during our photoshoot.
“I’m naturally more risk averse. I would tell my younger self to take on something with an unknown outcome, take more risks. Especially in my early career when often everyone is more focused on the short-term. Did I get the right promotion? Make the right step? But if I had thought about the long-term journey instead of the short-term aspects, I would have had less stress and anxiety. I like to say that your career is a marathon, not a sprint.”
“After college, I didn’t know what I wanted to do, so I spent a few years in a marketing role before going back and getting my MBA. I had not studied abroad, so I did an International MBA to reset and refocus my career. I entered management consulting and it was one of the best experiences I’ve had. It opened up so many opportunities for me to work for different clients, in both the US and Europe, and gave me an understanding of how different companies work.”
“I loved helping solve problems and working with a team. It really solidified the kind of work I enjoyed. So after a number of years, I transitioned into an internal consulting role at Amex. I was able to work in a number of different roles and teams there before getting an opportunity to be a part of a strategy team looking for growth opportunities at MetLife. It’s wonderful to be a part of starting new and transforming existing businesses within MetLife.”
“Now I’m really focusing on being purposeful about my network and connecting with a wide variety of people, especially women in leadership. Even though I’m not in a career transition, this is a way for me to reinvigorate my commitment to my career and connect to others. I recently joined Chief, which led me to Alissa.”
Thank you Jaclyn, for sharing your advice with us.
About Alissa
Alissa Randall is a portrait photographer based in New Jersey and New York City, known for creating images that feel both elevated and deeply personal. While professional headshots remain a cornerstone of her work, her photography has grown to include personal branding, women’s empowerment, family connection sessions, and expressive portraits of dogs and the people who love them.
Her approach blends editorial artistry with empathy and guidance, helping people feel comfortable enough to be fully seen in front of the camera. Whether photographing an executive, an entrepreneur, a family, or a beloved dog, Alissa creates photographs that reflect more than appearance. They reflect presence, personality, connection, and story.
Alissa photographs in NJ, NYC, and on location beyond the tri-state area. Explore more of her work on the homepage and discover stories behind the images on the blog.