Deep Dive - A Wedding Photography Retreat with John Dolan
Your body is the sum of your ancestors — it’s the story of their time and yours.
The photograph is a record of those magical accumulation of moments.
It’s history.
John Dolan is a photographer known for his eloquent wedding photography. He has an incredible ability to create timeless photos, without imposing on the moment.
John has been featured by Martha Stewart Magazine and has photographed weddings for Will Smith, Ben Stiller, AnnaSophia Robb, and he’s photographed the first White House wedding since Nixon’s presidency. John recently made one of Over the Moon’s Best Wedding Photographers of 2024.
He wouldn’t describe himself as a celebrity photographer, but celebrities do seem to be drawn to his trustworthy, anti-paparazzi, approach. By showing up without expectations and shot lists he moves with the day, instead of fighting against it.
John’s Instagram / website johndolan.com
On a whim, I decided to attend his workshop in New England. His philosophy fit with the honest direction I sought for my own photography in wedding, landscape, and editorial. The workshop was a review of my current work and a “deep dive” into the self.
Prior to arrival we printed out work for review and read up on photography philosophy, and history. Already, questions began to form. How can we honor the art of photography and elevate weddings to a higher standard while offering work that stands out?
John Dolan reviews portfolios during a photography retreat in North Adams, MA.
Arrival
Before heading to the workshop I had a client photoshoot in Boston (this was a big reason I was able to attend the workshop at all). Prior to the photoshoot I stayed in a hostel just above Boston’s Chinatown, which coincided with celebrations for Chinese New Year. After a cross-country flight — and hard rest — I awoke groggy as the Year of the Dragon, Jia Shen (Wood Dragon), was being ushered in by firecrackers, drums, and offerings. As a dragon myself (1988), I decided to take sail and join the festivities.
After the celebration, client photoshoot, and visit to Rhode Island to see family, I made my way to the workshop at Tourists Hotel in the Berkshires (pronounced Burk-sheers, not Berk-shires…weird).
Tourists is a stunning hotel in the small town of North Adams, Massachusetts.
It’s tucked in the Northeast corner of the state and was surrounded by dormant trees, winter mountains, and art museums. Tourists itself reminded me of a warm Scandinavian building focused on Hygge (coziness) and congregation here seemed tradition.
The lobby of this hotel invited people from their already comfortable rooms. Every morning the fire was lit around 7:30am and stayed fed into the night, dying in the late hours around 11pm. The fire’s end prompted guests to return to plush comfortable beds.
In the rooms, heated floors kept out the last bite of February’s winter. The radio played Tourists Radio during the day, and Tourists Sleepytime at night. Spring felt within reach, but on the last days of the retreat flurries would fall, reminding us of winter’s hold. The ambience here settled the soul — a perfect place for creative processing.
The Crew
The other photographers at the retreat were incredible both in artistry and heart. (Photo by John Dolan) Attendees left to right:
Alice Thigpen, Alabama (Family Photography)
Carolina Rivera, New Jersey (Wedding Photography)
Laura Billingham, New Jersey (Wedding Photography)
Amber Vickery, Texas (Wedding Photography)
Mel Toms, South Carolina (Wedding Photography)
Julie Cate Christman, Florida (Wedding Photography)
Samantha Dean, California (Wedding Photography)
Nathan Chapman (& Zoey), Texas (Wedding Photography)
Blake :D
The photographers at the retreat were well versed in the wedding world (one in family photography). Because of this I learned an incredible amount, not just from John, but from them. Their processing and questions were immensely helpful.
The quickly forged bond between us reminded me of those I created while in the Coast Guard. In the Coast Guard we showed up to training from all over the country and immediately were connected by shared purpose, passion, and struggle. In this same way, the endings are often abrupt and sad to me — for just as quickly as we unite — we return to our prospective corners of the map.
The Workshop
In addition to the workshop, portfolio reviews, and hikes we had our three meals together each day and we spent a lot of time conversing here. The night of the first dinner the question came up:
Imagine your photography as a dining experience that you found memorable. Think about a meal that humbled you and brought you into the moment. What stands out?
For me I think back to our honeymoon in Greece. Nearing off-season, we were losing the crowds that usually grace the Aegean Sea. We disembarked the ferry from Athens to Mykonos exhausted by heat and travel. Having arrived to our first island we sought out a friend-recommended restaurant for brunch.
The restaurant was open to the bleach white alleys of Mykonos. The doors and windows were open, allowing the sea’s comforting breeze to traverse the warm dining area. The white interior was complimented by vibrant decor.
We were seated by the owner, a bright green-eyed fellow who held the look of the sea. We ordered a Greek coffee and fava while listening to Fevgo by Orfeas Paridis. Fava feels like a comfort food; it’s a pureed yellow split pea that’s grown in the volcanic soil of Santorini then topped with capers. Rather simple but it held the space in both fragrance and taste.
The whole moment was absurdly beautiful and I’ll take that memory for as long as my mind allows.
So the question becomes: how can we make our photography business like this experience? A unique restaurant in the Greek Islands over something bland, dulled by ease and access — say like a Chipotle — good but nothing stands out. How can we serve a few people well, rather than many people sub-par?
Here begins some tips derived from the retreat:
Not everything will be covered here, such as portfolio reviews and 1-1 sessions, but there will be some general lessons learned.
I believe this information is helpful for both photographers and couples to consider.
Treat your business like the restaurant in Mykonos.
John Dolan says, “weddings are too important to be vanilla.” Many wedding photographers play it safe but in doing so they miss the point of it.
We may be driven to meet trends, to achieve what sells, pursue shot lists, but weddings are huge, dynamic moments. They are historical records of friends, families, and lovers. To place the focus on posing and items over people we remove love’s authenticity from the record.
Seek heritage photos that the client will want to hold onto. Imagine a childhood photo, or family photo that is important to you. Now bring that into your photography and try to create those photos for the couple.
Raise wedding photography up as art and history and not a banal form of familiar photos.
Understand art vs. commerce. Where are you focused and what are you selling? If you’re too focused on commerce i.e. marketing, SEO, money, then you aren’t going to be creating art. However, if you work on your art the clients who value that will follow.
Weddings are sociological events and you’re the intimate witness.
Relationships are specific to each couple and to each family. As a photographer. you come into this intergenerational event and it’s important to be a kind, gracious observer.
Weddings, like life, are not perfect and the photography can reflect this. Mix in the salt with the sweet.
The wedding industry will push obligations on your art forcing busy into the celebration. Resist.
Posing is time. Don’t give in hour to your photographer when you only have 8-10hrs to celebrate. We come together for few events, relish the uniting of friends and family.
We are not perfect families. The myth of American culture is perfectionism. Don’t assign emotions to a wedding based on myth. Pictures should come from the excitement and the exhaustion of the moment.
It’s about the feel over the look (or the emotional over the sentimental, we’ll approach this in a bit).
Feel it, frame it, then shoot it. Collect the photos, don’t direct them.
Create generational photos and stop hustling for social media, hustle for the photograph. With social media pressures this can feel impossible. Online all eyes can feel trained on you, which is not conducive to creativity.
Find the stories.
Presence. Empty the plan and approach in the right state of mind. Absorb the energy of the event and capture slivers of emotion. A shot list will distract and pull you from the experience.
Create don’t chase. Remember, you’re on stage with the couple. You can be positive or negative force. The less you say the more room for couples to feel. Be a positive presence in the room and keep your ego out. Note: You should not be moving faster than the couple.
Add layers to a photo to achieve elegance. In the same way a landscape photographer adds layers, a wedding photographer can achieve more storytelling by adding depth to the image. For example if a group is together and you want that group shot don’t pose it just prompt to the group: “Don’t change, just turn.”
Imagine the photo as a 50s craftsman home. The care and intention that goes into that should go into your photography. Stop trying to appeal to every type of client; instead find those that value your craft.
Always follow the bride and listen to the wedding. Use sound to find the vibrations of the moment. Find where the flock is.
Strive for emotional photographs over the sentimental.
A few more general tips for business operations.
Strive for engaged engagement sessions. Go where your couple likes to haunt. Where does this couple love and habit?
Hand deliver the final photos. Box up 15 of your favorite prints and, either invite the couple over to review photos, or meet them.
Find the couples you jive with. Set the expectation by reducing obligatory photos to enhance the creativity.
When anxieties arrive, such as imposter syndrome, take pictures to ease that stress. The only way past the anxieties is to do it. Do some storytelling “pushups” to stay fresh — volunteer your photography services in-between weddings.
Find inspiration and continue learning.
Create a wall of your photos that are inspiring to you in the moment. Swap them out for more inspiration.
Create an admire list of artists who’ve had a long career. Pick a writer, musician, actor, and study their career.
Study photographic history and add photography books to the shelf.
Have a balanced diet by trying new things.
Takeaway
Using what I’ve learned from John, the others, and my own approach I’d like to take the following forward into my photography: presence by coming in to the wedding empty and ready to receive the moment. The couple knows their love. You do not need to tell them how to be. Embrace what they bring to the photo and let them have their love.
I’m arriving to a wedding as an artist and observer ready to create and record, not to chase. By upholding myself to higher artistic standards, studying photographic history, and trying new things, I’ll find the couples that value that work.
