Struggling to stand out and create consistency in bookings
Wanting to ditch weddings to get weekends back with your family
Feeling stagnant in sessions, needing fresh posing + direction tools
Editing queue never-ending, yet profits aren’t where you want them
Does This Sound Like You?
Craving a weekend away with likeminded women who inspire me to spark creativity, new ideas, and business growth in the year to come.
I've been there too.
But here’s the good news — you don’t have to stay stuck.
It’s time to fall back in love with your work, feel proud of every session you deliver, give your clients an experience they’ll never forget, and finally rest in your enough.
Your next level is waiting — and this retreat is how you get there.
I'm so ready!
Meet Your Host
After years in the wedding industry, I found myself craving a different kind of business — one that didn’t take me away from my family every weekend, but instead celebrated the beauty and sentiment of family and motherhood.
Through trial and error (and plenty of lessons learned the hard way), I transitioned from weddings to a six-figure portrait-only photography business. Along the way, I discovered what truly makes sessions flow, clients feel valued, and photographers feel confident and supported.
Chelsea Hollis
chelsea allegra photography
If I can build a thriving business in the family and motherhood space, so can you!
This retreat marks my ninth workshop, and I’m thrilled to host you for it — pouring all of my experience, knowledge, and heart into helping you grow your business, master family posing, create systems that give you time back, and serve your clients beautifully.
I can’t wait to spend the weekend with you — laughing, learning, and leaving you inspired, encouraged, refreshed, and ready to take on your biggest goals!
– Samantha D.
"The Prosper Retreat gave me clarity, confidence, and breathed new life into my business."
- Samantha d.
I decided to attend Chelsea's Prosper Retreat to take my business even further and it was the best weekend full of fun and revitalization! I am now able to scale my business like never before. Talking to her is like talking to a lifelong friend. The amount of care and attention she gives is truly unmatched. I left with such an immeasurable amount of knowledge, new friends, and a fresh vision for the future."
"A fresh vision for the future.
- Madison z.
Chelsea’s retreat didn’t just pour into me with invaluable education — it left me feeling refreshed, inspired, and deeply connected to an incredible community of women. I walked away feeling called to slow down, refocus, and approach my business with greater intention so I can grow and scale in a way that truly aligns with me."
"So, so worth it.
- Confidence to direct families naturally + create standout images
- A client experience that makes people rave about working with you
- Workflows + systems that free your time and lift the mental load
- A plan for pricing + profit that supports your family goals
- Fresh portfolio images + styled shoots to attract dream clients
- Business besties + community that inspires you long after the weekend
What if you could leave this retreat with...
- Posing with Purpose – tools, games, and cues for stress-free, joyful sessions
- Client Experience Mastery – wow families so they return again + again
- Workflows & Systems – run your business with ease + efficiency
- Albums & Profit Growth – add heirlooms seamlessly + increase revenue
you'll learn
the four core pillars of prosper workshop
What You'll Learn
a peek at the content
next
Never have those “umm… what do I do next?” moments again.
You’ll learn exactly how to guide your clients into natural, flattering poses, handle tricky moments with grace (yep — even crying toddlers and less-than-thrilled dads), and create beautiful images no matter what the day throws your way. You’ll leave feeling confident, prepared, and ready to make magic in any situation.
Master Your Family Posing
next
You know your clients are investing so much in their photography — don’t let those images live and die on one Instagram post! If your heart says every family deserves to have their love displayed in a tangible way, then albums should be part of your process.
I’ll walk you through my step-by-step approach to offering albums in a way that feels natural and exciting for your clients, while also creating more margin and income for you as a photographer. By the end, you’ll feel confident making albums an easy, joyful, and profitable part of your business.
Master Your
Album Sales
next
Being your own boss isn’t easy. You want to serve your clients wholeheartedly, but balancing that with the financial integrity your business (and life!) needs can feel overwhelming.
Here’s your reminder: you belong here, and you are absolutely worthy of doing what you do. It is possible to run a purposeful, client-focused business that still leaves room for profit and growth — and I'm going to show you exactly how.
Master Your
Numbers
$1699
$1,499 early bird rate
Cozy community + connection
Hard copy workbook (no frantic note-taking needed) + welcome gift
Hands-on learning + portfolio building
3 fully styled family sessions (beach, studio/in-home, farm)
All meals, snacks, + coffee (no meal planning, no dishes 🙌)
3 Days + 2 Nights lodging in Wilmington, NC
all general admission tickets include the following:
Your Ticket Includes:
✨ VIP Upgrade (limited to 3): All of my digital products, templates, 2 coaching calls ($1000+ value for $499)
– Alexis V.
"It was the perfect blend of learning and enjoying a meaningful girls’ weekend. I left feeling inspired with a clearer vision for my business, a new perspective on pricing and marketing, and the confidence to build a business that truly serves me.
I truly can’t recommend this retreat enough. If you’re on the fence, just do it!! You won’t regret it."
I’m so excited to welcome you into my brand new home in Wilmington, NC for the ultimate cozy + inspiring weekend!
We’ll kick things off Friday night with a fun dinner out (so pack a swirly outfit for photos!) and a hands-on session in my natural-light studio the next morning — perfect for building your portfolio and learning in real time.
All weekend, you’ll enjoy delicious meals, snacks, and plenty of coffee (my love language), plus thoughtful welcome gifts when you arrive. Cozy communal spaces make it easy to relax, brainstorm, and dream big with your new business besties.
It’s part workshop, part slumber party, part creative recharge — and 100% designed to leave you refreshed and inspired.
MINUTES FROM WRIGHTSVILLE BEACH + DOWNTOWN WILMINGTON
Where we'll stay
omg COUNT ME IN!
On the farm
Sunset at the beach
Natural light studio
Cozy at home
Sunset at the beach
Natural light studio
- Alexis v.
"The weekend itself was incredibly life-giving. Chelsea is easily one of the most talented photographers I know, but she shows up without any ego. She’s genuine, passionate, and truly invested in the people she’s teaching, and that energy is contagious.
The photo sessions were a huge highlight. They reflected her real shooting style, and it was so valuable to watch how she poses and directs families. Everything was thoughtfully curated while still reflecting the kinds of families and situations we photograph every day, not something overly extravagant or unrealistic."
- Gerrianna P.
"My time spent at the Chelsea's Workshop was transformative for my business! I had my "why" nailed down but I couldn't exactly pinpoint my "how." Chelsea encouraged me to analyze my business in ways I never had before. After using her tips and knowledge to implement workflows and maximize my profits, I'm now able to quit my full time job to focus on my business and prioritize my family."
- Gerrianna P.
"My time spent at the Chelsea's Workshop was transformative for my business! I had my "why" nailed down but I couldn't exactly pinpoint my "how." Chelsea encouraged me to analyze my business in ways I never had before. After using her tips and knowledge to implement workflows and maximize my profits, I'm now able to quit my full time job to focus on my business and prioritize my family."
- Laura b.
"Chelsea's workshop was a game-changer for my business. Her attention to detail in the educational material and styled shoot, coupled with her willingness to be honest about her success and failures made the day feel incredibly authentic and valuable.
I left feeling inspired and ready to make significant changes in my business. My experience was willed with information, creativity, community, and it has truly changed my business."
- Jenny b.
"Chelsea's workshop teaches you how to turn leads into profit, and add value to your offerings all while Chelsea makes you feel cozy and at home. She sets up a styled shoot to beautifully enhance your portfolio, too!"
- Tallison B.
"I've attended a workshop and a retreat with Chelsea and I believe it has helped my business grow tremendously. I highly recommend the workshop to any photographer who wants to improve their business and workflow at any level."
- Samantha D.
I decided to attend Chelsea's Prosper Retreat to take my business even further and it was the best weekend full of fun and revitalization! I am now able to scale my business like never before. Talking to her is like talking to a lifelong friend. The amount of care and attention she gives is truly unmatched. I left with such an immeasurable amount of knowledge, new friends, and a fresh vision for the future. Thank you Chelsea!"
- Cayce F.
"I have attended workshops, coaching, etc with Chelsea in the past, so my only hesitation going in was that the information provided would be things I’ve learned in prior spaces with Chelsea. But, I’m so glad I didn’t let that stop me. Each time I've attend a coaching event with Chelsea, I learn so many new things and ways to improve my business. As Chelsea evolves, she shares her wisdom and lessons learned, which then helps me evolve and grow too."
love notes from past attendees
a timeline of the entire retreat weekend
We’ll kick off the day with a hands-on session in my natural light home studio — perfect for practicing poses, styling, and capturing gorgeous images.
Morning Studio family Session
Saturday, August 1
Sunday, August 2
Get comfy and settle in for a day of learning, laughter, and inspiration as I share all of my behind-the-scenes secrets and wisdom. Don’t worry about taking endless notes — you’ll get a hard copy of the workbook so you can stay fully present and soak it all in!
daytime workshop
After sunset, we’ll return to the house for a cozy, relaxed dinner and more time to connect, unwind, and share the highlights of the day. We'll play some fun games and maybe cuddle up by the fire!
dinner at home
After breakfast, we’ll dive into one last styled session — likely at nearby farm with horses and other animals— giving you one more hands-on opportunity to practice everything you’ve learned. Our rain plan will be an in-home session here instead!
breakfast + optional yoga flow
Friday, July 31
Everyone arrives and settles into the house. Pick up your welcome gifts and enjoy appetizers and mocktails as we mingle before dinner.
Arrival at the house
We’ll return to the house for a final round of workshop time, more learning, and an open Q&A to answer all your questions.
We’ll wrap up and check out around 12:30PM, leaving you inspired, refreshed, and ready to bring all your new skills back into your business.
quick q+ a at lunch before departure
girl's night out
We’ll head to one of my favorite Wilmington spots for a fun, girly night out — think delicious eats, laughs, and plenty of photo ops!
evening chill + business brainstorm
Back at the house, unwind, get to know your new business besties, and kick off the weekend with a fun, interactive business brainstorming activity. Share ideas, set intentions, and get inspired for the sessions ahead!
sunset session at the beach
We’ll head to the beach to capture a stunning sunset session, putting all your new skills into action and creating breathtaking images to enhance your portfolio,. Maybe we'll take a quick dip in the ocean ourselves before heading home!
on the farm- styled shoot
Choose to sleep in a little later OR roll out your mat and join us for a gentle yoga flow. Think mindful movement, a touch of meditation, and the perfect mix of recharge + relaxation after a packed weekend of learning, connection, and growth.
FREQUENTLY ASKED QUESTIONS —
FAQ
No. 1
Your first payment will secure your ticket to the retreat! You may pay in full or in 4 monthly payments. Write it off for 2026 taxes! If you opt for the monthly payment plan, your first payment is due at booking to reserve your space.
This retreat is open to photographers of all experience levels! That said, we won’t be covering the basics of shooting, lighting, or editing — so you’ll want to feel confident shooting in manual before you arrive.
If you’re newer to photography, I recommend brushing up with some YouTube tutorials and getting plenty of practice so you feel comfortable behind the camera. Once you’ve got those fundamentals down, everything we dive into at the retreat will be incredibly valuable no matter where you are in your journey.
Absolutely! I will be sending out a questionnaire to all attendees prior to the retreat. Please let me know if you have any food allergies and/or restrictions and we'll make sure we have the right meals provided for you.
ILM airport, with RDU being the second closest. You are more than welcome to join us from out of state and the airport is just a short 20 minute ride from where we'll be staying.
It depends on how many attendees join us. If we fill to maximum capacity, some rooms will be shared — but don’t worry, all attendees will have their own bed.
One of the sweetest parts of this retreat is the friendships that bloom along the way — it’s a little bit girl’s weekend sleepover, a little bit business mastermind. You’re also welcome to bring a friend and request to room together.
If you’re local to Wilmington, you’re more than welcome to sleep at home and rejoin us in the morning for all the fun.
Just note that the retreat ticket price is the same whether or not you stay overnight. Since I don’t have to book an outside venue, I’m able to keep the cost much lower overall. Your ticket goes directly toward all the education, materials, meals, gifts, and activities that make this weekend so special!
Because spots are limited and a lot of love (and investment!) goes into planning your experience — from venue preparation, food to materials and styled sessions — your retreat ticket is a non-refundable investment.
If something comes up and you need to cancel at least 60 days before the event, we’ll do our best to fill your spot. If we’re able to find another attendee, we’ll happily refund anything you’ve already paid toward the retreat. You may also use your payments toward private one on one coaching and/or a session should you need to cancel.
Book now
VIP Ticket
Tickets are sold on a first come, first served basis. Reserve your spot today as spots for this retreat are very limited!
limited spots available
Book this ticket to add all digital products and 2 private coaching calls to your retreat experience.
early bird rate through 5/31!
$
best value!
book now
early bird rate through 5/31!
1499
QUESTIONS?
🎶 (Yes, I’m singing in full Taylor Swift mode!)
Spots are limited, and this intimate weekend is going to fill fast! Don’t miss your chance to learn, laugh, and grow alongside an amazing group of photographers. Early Bird tickets end 04/10— grab yours now before it’s too late!
Are You Ready For It?
book now
payment plan
Spread your payments over a four month period.
4 monthly payments
380
$
flexible option!
general admission with vip add-on
General admission
payment plan for general admission
1699
1998
2198
Early Bird Ends 5/31 before monthly payments jump to $428/month.
$
payment plan available
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