What is your name and occupation?
Sheila Drakeley — Photographer and Videographer, Owner of Sheila Drakeley Photography
How long have you been a Boston Business Women’s Member?
2+ years
What is your Instagram handle?
@sheiladrakeleyphotography
Were you born and raised in Boston? If not, what brought you here?
I was born and raised in Connecticut. I came to Boston for school and decided to stay to build my business and career.
Tell us more about your job or company and what led you to your career?
I’ve always loved photography — capturing moments from family events, trips, and everyday life. In college, I used my summer job money to buy my first camera, and that small decision changed everything.
I fell in love with capturing people’s most meaningful moments and building visual stories that last a lifetime. Over time, my business has grown to include both photography and videography services for clients across a wide range of occasions and industries.
What would your clients say about you and your company?
Clients often describe me as reliable, talented, transparent, and honest. Many share that they felt comfortable during their sessions and appreciated the quality and authenticity of my work.
What is the best advice you’ve ever received?
You cannot build your empire overnight. Everything takes time — stay focused on your end goal, and you’ll achieve it.
What is your favorite book?
The Spirit Catches You and You Fall Down by Anne Fadiman
What is your secret weapon?
For business: Trello — it keeps projects organized and helps me manage assignments for my interns.
For personal life: Full Fitness — it helps me track progress toward my health and fitness goals.
What advice would you give to your younger self?
Continue growing — not just physically, but mentally and emotionally. You can always learn something new and become a better, more well-rounded individual.
How do you enjoy your free time?
I love to travel. My family always valued experiences over things, and I’ve carried that forward. I also love to run and have completed multiple major races.
What is something that not many people know about you?
I run a travel blog called The Traveling Massholes, which was featured on Chronicle!