A few weeks out from the first photography retreat and mastermind in Virginia, I’m sharing the honest debrief — five things I learned, what I’d do differently next time, and one big decision I made about the future of the program.
Lesson 1: I got a lot of things right and did what I set out to do.
I took a lot of swings with this photography retreat and mastermind, and most of them landed exactly how I hoped, which was a huge confirmation.
The chef-prepared welcome dinner set a great tone to start on the first night. I wanted the weekend to feel warm and unhurried as we all got settled, so a local private chef made us a beautiful dinner, and it immediately put everyone at ease.
The house — an old restored farmhouse in a small Virginia town — was exactly the vibe I was after: cozy, and comfortable, but spacious enough to spread out.
The group size felt right too: five people, small enough to give each person real attention but big enough for everyone to contribute different perspectives.
Putting the retreat in the middle of the four-month program was a gut call I questioned at first, but in hindsight felt just right. We had months to build relationship before sharing space, and then the in-person experience deepened everything that followed.
Also, using Voxer as the connective tissue between sessions proved to be a huge bonus. Voice notes in the car, hiding in a closet to ask a quick question, doing life together in the in-between – that kind of trust and community weaved into our regular lives is exactly what I envisioned.
2. The in-between moments were king
I knew going in that the unplanned conversations would be the magic, but I didn’t know what they’d be about. I planned the sessions and the agenda, but the spontaneous rabbit holes developed our time in an unpredictably wonderful way. One person would surface a struggle, the whole group would light up, and we’d follow it somewhere I never could have pre-planned. That’s not something you can manufacture when you have a tight schedule. If anything, it’s an argument for protecting the space between.
3. What I’m going to adjust: adding an on-location session
Every family session during the retreat was in-home because that’s what I promised and what these photographers were there to practice. And those sessions were wonderful— real families in real homes, winter jackets and slightly dirty backyards, the full range of it.
But I recognized that most photographers who do or want to do in-home work are in transition and/or not wanting to completely elminate outdoor work. They just want to adjust the tone and feeling around the work as a whole. The skills we practiced in-home are ones they also want to carry into their outdoor work. So next round, I want to include at least one session in a park or downtown setting that shows how you can bring that same unraveled feeling to a different environment.
4. Doing it differently is why it worked
I went into hosting this photography retreat and mastermind with quite a bit of imposter syndrome. I wondered at first if it needed to be more bougie, more edgy, more something. But I decided to lean into exactly how I approach my photography — grounded, real, not performing anything — and I learned that trusting my gut was a good move.
It meant I wasn’t nervous going into it because I wasn’t stepping into a performance role. And the ripple effects — seeing how the conversations and skills are showing up in people’s work, in the sessions they’re booking, in how alive they feel doing them — that’s been fuel I didn’t know I needed and a confirmation that I’m in the right place with this offer.
5. Hosting is really fun — and more demanding than I realized
I already knew I love hosting. In the last year, I’ve started hosting monthly gatherings as part of my photography business marketing, and those have been really energizing me, too, so I think it’s a trend for my work overall.
During the retreat I was fully on. I cooked soup on the rainy night, prepped the morning coffee, sat around a table of flowers talking about pictures and families and business and it was all pure delight. I didn’t feel tired at all. And then it ended, and I felt the drop in a way I hadn’t anticipated.
Now I know what it takes AND that I want to keep doing it.
The big decision: one photography retreat & mastermind a year
Right after the first round ended, I started marketing a summer retreat. The energy was high and the momentum was real. Within a week and a half, I had a lot of conversations with people saying “this sounds incredible, but the timing doesn’t work for me.”
I started listening to that — and more importantly, I started looking honestly at what I was basing the decision on. Excitement and capacity are not the same thing. I had the excitement. I didn’t have the readiness – logistically within my family life and photography business – to turn around and run another full round three months later.
The summer timing would have put the coaching portion straight into my busiest season as a photographer. It would have done the same thing to participants. The timing that seemed like an asset — practicing new skills right before your busiest season — can also be overwhelming when you have all those implementation ideas and no bandwidth to act on them.
I’ve decided to run the retreat & mastermind only ONE TIME per year, in the spring, for five participants. It may change in the future, but in order to protect the quality and magic of this approach, that’s where I’ve landed.
If you’ve been watching and thinking – heck yes, I want that – you can claim your seat whenever you’re ready. There’s no waitlist, just rolling enrollment on a first come, first serve basis.
Check out the next upcoming retreat dates and details here and grab your spot when you’re ready.
Find It Quickly:
0:00 – Free resources at leahoconnell.com/learn
1:15 – Intro
3:00 – What I got right
8:30 – Why the in-between moments were king
12:30 – What I’m changing for the next round
16:30 – The biggest reason I think it worked
21:30 – The surprising tax I wasn’t expecting
24:30 – A big decision about future rounds
Mentioned in this Episode:
PhotoFuel Retreat: leahoconnell.com/retreat
Episode 68: Why I Started a Retreat for Family Photographers
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Episode 67: How to Break Through a Growth Plateau in Your Photography Business
