We were lucky to catch up with Hillary Caltagirone recently and have shared our conversation below.

Alright, Hillary thanks for taking the time to share your stories and insights with us today. Let’s kick things off with a hypothetical question – if it were up to you, what would you change about the school or education system to better prepare students for a more fulfilling life and career?

In my own educational experience, I wish there was more of a focus on practical business skills and discussions on the potential to be an entrepreneur, rather than just leading kids to assume the best option is for them is to get a degree and go work for a company. I think this is true across the board, but especially so with creative occupations and the trades.

I was fortunate enough to go to a high school with a robust arts department that lead me to pursue photography as a career. I envisioned a job as a staff photographer, maybe for a newspaper or magazine, because I had no frame of reference for contract work or small business. No one ever said: you might end up working for yourself one day, so maybe you should take some business classes too. It was always, get good grades and a degree and you will find a good job. I enrolled in a fine arts program at a SUNY school, and took many more amazing classes that challenged my creativity and technical prowess.

I got a job right out of school with a small, event photography studio. I worked there for over a decade and it was a lovely experience, at which I learned a lot. The downside was my growth potential was limited. There was no where to get promoted to, and all my working hours and creative energy were spent serving the studio. I looked for other opportunities, but full time photography jobs were few and far between, and the ones that did exist had entry level salaries that would have me taking a pay cut. In the years since I had decided to make photography my career, the switch to digital had completely changed the job market from full time positions to contract work. The only path I could see to grow my earning potential was to go into business for myself.

Luckily for me, I had many years of inside experience with the inner workings of a photo studio. Starting a business was still challenging, but manageable and I came into it with practical knowledge on how to handle clients, price my services, and generally run a sustainable business. I also took it upon myself to find opportunities for business coaching and entrepreneurial guidance from both private coaches and a local organization called The Women’s Enterprise Development Center. I believe all of this has been essential to my (moderate level of) success.

All that to say, my only regret is that I didn’t go into business for myself sooner. If I had been guided towards classes about basic small business principals or entrepreneurship, I may have had the courage to make that choice sooner. I’m sure there are lots of other young people out there who have never even thought that they could build their own business and I think we should be encouraging them instead of feeding into the antiquated dream of climbing the corporate ladder.

Hillary, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m a Westchester County based photographer focusing on weddings, events and families. My origin story is on the previous page, but I am a lifelong photographer with a background in film and fine arts. I don’t really know why, but I have always loved taking and looking at photos. I took my first darkroom class in middle school, and I just knew immediately that this was my gift. The ability to freeze in time a person or emotion is so special, this is what I’m trying to do for my clients. I want to help them create family heirlooms that their kids and grandkids will marvel at decades from now.

What do you find most rewarding about being a creative?

I love the opportunities I get to make people feel good. Whether that’s by making them feel beautiful, or empowered, or just heard.

What do you think helped you build your reputation within your market?

Always be positive! I think I have a reputation as being easy to work with, which goes a long way towards getting referrals from other vendors. Be gracious, don’t be a diva and always try to come from a positive place when speaking to others.

Contact Info:

• Website: https://www.hillarycphotography.com
• Instagram: hillarycphoto

Image Credits

Beth Zink took my photo, all other photos are by me