Quit Your Job and Become a Photographer


We are pumped to feature Kyle Dempsey! Kyle is pretty big on the Instagram with over 100k followers.  Kyle was born and raised along the Westfield river in the Berkshires of western Massachusetts. He grew up building forts along the river bank, fishing and skipping rocks. Kyle has always had a love for creating art whether it be through painting and drawing, building with his hands, or a myriad of other channels. He acquired his degree in creative advertising and starting getting very seriously with a camera during his time at college. He filmed commercials and photographed ads for his college’s advertising team and taught himself almost everything behind the lens. After college, Kyle had a few scattered jobs and ended up working for a small marinara sauce company as a right hand man. In May 2016, Kyle quit his job to pursue his dream of becoming a full time photographer. We did a little Q & A with Kyle. Check it out!

HFDG: What was your first experience with exploring that made you love it so much? Kyle: In late Summer 2013, my best friend and I hopped in his Subaru Impreza wagon and started heading West from Massachusetts. We had just over two weeks to get to San Francisco, where I had a plane ticket to fly back home. It was the most amazing trip I’ve ever been on and started an ever-burning fire in my gut that made me addicted to traveling and living on my own.

HFDG: Where have you been that is special to you? K: There are so many places I’ve been that hold very special places in my mind, but a few that stand out are The Badlands in South Dakota and the Crystal Mill in Colorado.

HFDG: What is your advice to those who have not explored yet? K: Plan less and let the experiences come to you. Take the random backroads. Go places you don’t feel comfortable going. The best experiences come when you least expect them.

HFDG: Who have you met along the way that has made a difference to you? K: I’ve met so many people through social media that have made a huge impact on my career as a photographer. People such as mrtommyblades, taylormichaelburk, btonevibes, and hbmertz have given me great advice and helped me grow as an artist.

HFDG: How has your life changed since you started to adventure? K: Since my first road trip in 2013, my life will never be the same. I will always have a deep desire to leave no stone unturned, to go places I’ve never been, and to meet new people. I’m addicted to the adrenaline of chasing the dying light in new places and the feeling you get when you capture moments that you will remember forever. Adventure is what makes me feel alive.

HFDG: For someone who is looking to do photography full time, what advice do you have for them?

K: My advice is to find a niche and spend everyday pushing yourself to become the best in your niche. The photography market is so saturated that if you don't have a differentiating factor to your work, it will be very hard to stand out. It's going to be slow to start, so make sure to keep your head down and keep creating every single day.

HFDG: Where is the next place you plan on going?

K: In early November I’m taking a road trip to Minnesota to work with a music producer on some new songs of mine!

Thank you to Kyle for sharing some advice!

Follow Kyle and his adventures on Instagram