We were lucky to catch up with Charles Chessler recently and have shared our conversation below.

Alright, Charles thanks for taking the time to share your stories and insights with us today. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?

I started out life as an actor. From the time I was 14 years old it was all I wanted to do. In the late ’90’s I gave it up because I had a mound of debt and it just wasn’t fun anymore.
I worked my way out of debt as a cater-waiter and eventually became a personal trainer.
But, there was an enormous creative void.
In 2005 I picked up a digital point and shoot camera as a way of coping with my father being ill.
He had 4 major surgeries over a two year period and I would carry that camera everyday as I walked back and forth across Central Park to see him at Mt. Sinai Hospital.
I became addicted to the act of taking photographs and had what many folks have when they start out – a good eye. But I didn’t understand anything about light or camera settings.
I bought my first DSLR in 2008 so that I could photograph the glorious bird life that we get in Central Park.
In 2011 I decided that I wanted to make my living as a photographer since it was all I wanted to do all the time.
The best decision I ever made was to focus on headshots since there’s always a market for them and I love working with people.
I studied and practiced for about 3 years before I started charging.
About 4 years ago, at the age of 57 I finally achieved the goal of making my full time living as a photographer. And, it feels great.
I work with actors, musicians, authors and corporate clients and love all of it.
Advice would be to always work on your skills, post consistently on social media and carry business cards everywhere.
I don’t like to be pushy with marketing…I do it from the point of view of sharing that I’m doing something that I love and I let people find me.
This has worked for me. Word of mouth has been king in my world.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

Looks like I answered some of that in the previous question. In a nutshell, I am a NYC based headshot and portrait photographer who works with a wide range of clients.
They may be actors, musicians, authors, business folks, convention attendees and corporate clients.
Depending on a client’s needs we work outdoors with either natural light or a combination of natural light and strobe or we can work in a studio or I can bring a studio to a client’s office and set up in a conference room or hallway. I bring everything necessary for a professional headshot.
If I have a special sauce that sets me apart it’s that I love connecting with people and bringing out the best in them.
Once the technical stuff is set, it’s all about the connection.
I may have extended time on a longer shoot with an actor or a musician or I may have 5 to 10 minutes with a business person who needs to get back to work. Either way a connection is made and I strive to make the process as enjoyable as possible for my subject. For those who don’t necessarily like being photographed I try to make it as quick and painless as possible. For those who do enjoy it there is the pleasure of collaborating and exploring.

What do you think is the goal or mission that drives your creative journey?

I think I’ve had three main goals with my creative journey:

1) To make my living doing something I love.
2) To be respected for what I do.
3) To be able to help others.

I finally achieved goal #1, as mentioned above, about 4 years ago, at 57 years of age.
(I’m the poster child for never giving up, always believing and having the talent to do the work.)
Goal #2 is something I’m lucky to feel all the time..
Goal #3 is a total joy and takes the following form:

There are two organizations that are near and dear to my heart:

1) Opening Act, which brings theater to underserved public schools around NYC.
2) Wild Tomorrow, a wildlife conservation non-profit based in Kwazulu-Natal, South Africa. I am an ambassador for them.

I’ve been working with Opening Act for about 6 or 7 years now. I started out being hired to photograph their fundraising galas, then started doing free headshots for their summer program students (usually about 20) and now do free headshots for their annual YesFest where all their students perform in a weekend of shows at the 52nd Street Project in NYC. A couple of weeks ago, as a matter of fact, I spent 4 days at YesFest and photographed all 150 – 200 students who were participating. These kids would never have the money for a professional headshot and doing this is truly a joy. I also started mentoring one of their students about 5 years ago and he is thriving and has become like a son to me. It’s a beautiful thing.

I’ve been working with Wild Tomorrow for about the same amount of time and also started out photographing their fundraising galas. This progressed to becoming an ambassador with them and being the photography teacher on yearly 2 week trips to South Africa which help us raise money for what we do.
And, what do we do? We are saving wild spaces and wildlife and supporting the local community.
(Tons of info can be found on our website: https://wildtomorrow.org/)

This is dream-come-true work. The guy who was working his way out of debt in the late ’90’s and early 2000’s never thought he’d be going to South Africa, documenting Rhino Dehornings and helping to feed school children.

There’s an essence to working with both Opening Act and Wild Tomorrow that I’d like to mention.
Both of these opportunities came about because I focused on doing work that I love which created real connections with people who share my sensibilities and passions. I cannot stress enough how important it is to surround yourself with people who “get you” and to do the work that lives in your heart.

In your view, what can society to do to best support artists, creatives and a thriving creative ecosystem?

This one is easy:

Buy the book.

Buy the music.

Pay your photographer.

Do not undervalue what we contribute and work so hard to provide.

I also want to answer “What’s the most rewarding aspect of being an artist or creative?”:

Getting up and doing something you love every damn day.

Contact Info:

• Website: https://charleschesslerfaces.com/
• Instagram: https://www.instagram.com/charleschesslerphotography/
• Facebook: https://www.facebook.com/charleschesslerphotography

Image Credits
Photo of me by April Anderson. All other images my own.