I’m 87, a semi-professional photographer, own a small publishing group and live in South Flor- ida. Nobody wants to retain me for any assign- ments because of my age. What should I do?
CHAT GPT RESPONSE
Richard, I’m really glad you said this out loud. What you’re dealing with is real, painful, and unfair—and it’s not a reflection of your value or ability.
At 87, you’re running into ageism, not irrele- vance. The industry often equates “new” with “better,” even when experience is exactly what produces the best work.
Let’s separate this into emotional truth and practical moves.
First — the hard truth (said with respect)
Clients aren’t rejecting you; they’re reacting to: Fear of liability (“What if something happens?”)
Assumptions about speed/tech adoption
A bias toward “youthful image” branding
None of that means your work isn’t excellent. But it does mean you may need to change the frame, not fight it head-on.
Strategic pivots that actually work at your stage
1. Stop selling yourself — sell outcomes
Instead of “I’m an experienced photographer,” position as:
“I specialize in high-reliability, no-drama shoots.”
“I solve X problem for Y clients.” Clients hire certainty, not people. Your age should be invisible in the pitch.
2. Become the name behind the curtain
This is huge given your publishing background. Create or brand a small collective or studio name.
You remain the creative director
You subcontract or collaborate with younger shooters
You oversee quality, lighting, composition, editing
Clients
Youthfulget:execution
Veteran judgment
You get:
Relevance
Income Authority
This is exactly how many top creatives stay active into their 80s and 90s.
3. Shift from “assignment work” to consulting & legacy work
South Florida is perfect for this.
Examples:
Archival photography for families, estates, and institutions
Visual histories of companies, nonprofits, or communities
Coaching younger photographers privately Editing, sequencing, and curating photo books (this is rare skill)
People will pay well for taste and judgment when they won’t for a day rate
4. Leverage your age instead of hiding it — selectively Not to ad agencies. To:
Historical societies
Cultural institutions
Private collectors
Luxury clients who value discretion and maturity
Your age signals trust in the right rooms.
5. Use your publishing group as a force multiplier
This is a massive advantage most photogra- phers don’t have. You can:
• Produce limited-run books
• Offer “photography + publication” packages
• Create legacy products people can’t get elsewhere
That reframes you from vendor to creator. The emotional part (this matters) It hurts to feel invisible after a lifetime of competence. That grief is valid. But here’s the truth many people never get to experience:
You’re not obsolete — you’re unusual. And unusual people don’t survive by compet- ing.They survive by redefining the game.
Let’s treat this like a real repositioning project, not a pep talk. You’ve earned that. I’ll lay out a clear, sane plan in phases so this feels doable, not overwhelming. Then I’ll ask you one focused question to tailor it perfectly.
PHASE 1 — Reposition who you are (without lying or hiding)
Your new role (internally)
You are no longer “seeking assignments.”
You are:
Founder / Creative Director / Principal Pho- tographer (select projects)
That wording matters. It instantly reframes age from “risk” to “authority.”
What we quietly stop emphasizing
•Years of experience as a number
•Physical endurance
• “Available for any assignment”
What we emphasize instead
• Judgment
• Reliability
• Editorial eye
• Finished results
• Legacy-quality work
PHASE 2 — Build the “behind-the-curtain”
studio model
You do not need to stop shooting — you just stop being the only shooter.
Structure:
Studio name (neutral, modern, no age signal)
You = Creative Director + Lead Photographer on select shoots
1–2 younger photographers (freelance, per project)
You handle:
• Concept
• Lighting design
• Shot list
Final edit/sequence
• Client relationship
Clients care about:
• Results
• Timelines
• Calm professionalism They do not need to know who lifted which camera.
PHASE 3 — Create offers people can say YES to Instead of “hire me for a shoot,” you offer packages. Examples that work extremely well in South Florida:
1. Legacy & Archive Projects (high respect, low ageism)
• Families
• Estates
• Cultural orgs
• Synagogues, churches, nonprofits
• Long-standing businesses
You’re preserving meaning, not chasing trends.
2. Photography + Publishing (your secret weapon)
• Nobody else can do this easily. Offer:
• Custom photo books
• Company histories
• Personal visual memoirs
• Anniversary or retirement editions
You’re not a photographer here. You’re a sto- ryteller with a press. That’s rare.
3. Consulting & Mentorship (quietly lucrative)
• Portfolio reviews
• Sequencing & editing guidance
• Book design consulting
• One-on-one coaching
You charge for thinking, not time.
PHASE 4 — Adjust how people find you
We don’t chase agencies.
We focus on:
• Private clients
• Institutions
• Referrals
• Quiet prestige
Your public-facing materials should say: “Selective projects. High standards. No cha- os.”
That alone filters in the right people.
PHASE 5 — Emotional protection (this is important)
You are allowed to:
• Say no to exhausting gigs
• Stop explaining your age
• Stop proving relevance to people who don’t deserve access to you
At this stage, dignity matters as much as income.
What I’ll help you do next (very concrete)
Over the next steps, I can:
1.Rewrite your bio so it signals authority, not age
2, Help you name and position the studio/col- lective
3, Design 3 bulletproof service offerings
4. Create a client pitch that removes age from the conversation entirely
5.Tailor this specifically to South Florida markets
One focused question (this guides everything): When you imagine your ideal work right now, which matters more?
A) Still being behind the camera regularly
B) Directing, editing, shaping the final work
C) Publishing, mentoring, and legacy projects
D) A balanced mix of all three
Just tell me the letter(s).
We’ll build exactly around that.
My comments:
This is all good. As for the photography, we travel to the UK. Every castle we visit has enormous portraits of their family. South Florida has an abundance of wealthy families. How can I reach that group to pitch that package?
This is an excellent instinct — and it’s a perfectly calibrated idea for South Florida. You’re not imagining demand; it exists, but it’s hidden behind gates, intermediaries, and etiquette.
The key insight is this:
Wealthy families don’t hire photographers. Their advisors do. So the strategy is indirect access, not marketing.
Let me show you how this actually works.
First: refine the offer (so it feels inevitable, not “salesy”)You are not pitching “family portraits.”
You are offering:
• A Private Family Portrait Commission
Inspired by European estate traditions
Language matters more than images here.
• The concept framing
• Heirloom-scale portraiture
• Multi-generational
• Meant for homes, not Instagram
• Optional companion book (this is where your publishing group shines)
• Think heritage, not photography.
Who controls access to wealthy families (South Florida edition)
You want gatekeepers, not principals.
1. Estate attorneys & trust officers (Top tier)
These people:
• Manage legacy planning
• Think in generations
• Constantly look for “meaningful non-financial assets”
How to reach them
• Speak at small private client events
• Write a short white paper:
“Visual Legacy as an Estate Asset”
• Quiet one-on-one introductions (not cold email blasts)
• Once one trust officer adopts you, you can be referred for years.
2. Family offices & private wealth managers
They want:
• Discretion
• No embarrassment
• Zero drama
Your age is a benefit here. You signal stability.
Positioning
“I work exclusively by referral on private commissions.”
That line alone filters the room.
3. High-end interior designers & architects
This is a goldmine most photographers miss.
Designers need:
• Large-scale art for grand homes
• Pieces with meaning, not decoration
Approach
• Show how commissioned portraiture anchors a room
• Offer collaboration (designer specs size & placement)
• You deliver a finished, framed piece
Designers love anything that:
• Makes them indispensable
• Impresses clients
• Isn’t trendy
4. Private schools, clubs, and philanthropic boards
South Florida is thick with:
• Private academies
• Yacht clubs
• Cultural boards
You don’t pitch. You Onceparticipate. you’re “one of us,” commissions follow quietly.
How to approach without looking like you’re selling
The soft-entry method (this is critical)
You don’t ask for work. You say:
“I’ve been studying how British families preserve visual history through commissioned portraiture. It’s something we’re beginning to see interest in here.”
This invites conversation, not rejection.
The physical leave-behind (old-school, powerful)
Digital is weak here.
You want:
• A small, beautifully printed booklet
• Heavy paper
• Minimal text
• No prices
• No call-to-action
Title ideas:
• A Family Record
• Commissioned Portraiture for Private Estates
• On Visual Legacy
This does more work than any website.
Pricing strategy (counterintuitive but important)
If you price too low, they won’t trust you. These families expect:
• Commission fees
• Staged payments
• Clear boundaries
You are not charging for photos.
You are charging for:
• Planning
• Direction
• Presence
• Permanence
Why you are uniquely credible here
• You’ve seen the UK model firsthand
• You understand publishing and permanence
• Your age signals discretion, not trend-chasing
• South Florida wealth is new — they want legitimacy
You’re not copying Europe. You’re translating it.
What I can help you do next (practical steps)
I can:
• Draft the exact language for this commission offering
• Design the structure of the leave-behind booklet
• Help you map specific gatekeepers (designers, attorneys, clubs)
• Create a conversation script that never sounds l•ike a pitch
One precise question to move for- ward:
Do you already have any relation- ships with interior designers, estate attorneys, private schools, or cul- tural boards — even loose ones? We’ll start with the warmest door, not a cold one.
All
good. What I need to add is that I shoot a lot of theater performanc- es and have access to a costumer who has hundreds of costumes from Broadway shows. Given the fairy tale world we live in, I have thought about suggesting fundraisers where donors are photographed in a Broadway costume. Thoughts?
Richard — this is brilliant, and more importantly, socially fluent. You’ve stumbled onto something that fits exactly how South Florida wealth likes to play, give, and be seen giving.
Short answer: yes, this can work extremely well — if it’s framed cor- rectly. The framing is everything. Let’s tune it so it lands as charming, exclusive, and philanthropic… not novelty or cosplay.
Why this idea works (structurally)
You’re combining four things wealthy donors already love:
1 Philanthropy
2 Performance & spectacle
3 Access to something rare (real Broadway costumes is huge)
4 A tangible keepsake they didn’t have to justify buying
And you’re doing it in a way that:
• Removes “ego” (it’s for charity)
• Encourages participation (“everyone’s doing it”)
• Produces a legacy object (print/book)
That’s a powerful cocktail.
The one critical rule
This must never feel kitschy.
It’s not:
❌ “Dress up like a Broadway star”
❌ “Fun photo booth”
It is:
A Theatrical Portrait Commission for Charity
Language keeps you in the right room.
How to frame the concept (use this wording style)
Name ideas (important)
• An Evening of Theatrical Portraiture
• Stage & Legacy: A Portrait Fundraiser
• From the Stage: A Private Portrait Event
Avoid words like costume, dress-up, photo, booth, fun.
How donors participate
• Each donor is assigned a costume (no rummaging)
• Styled respectfully, not comedically
• Photographed simply — classical lighting, neutral backdrop
• One final, museum-quality portrait
This feels curated, not chaotic.
The psychology that makes donors say yes
1. Permission to be theatrical
Wealthy donors often want to be expressive but fear looking foolish.
The charity context gives:
• Social permission
• A shared experience
• A story they can tell later
2. It produces a legacy object
You’re not handing them files.
You deliver:
• A framed print
• Optionally: inclusion in a limited-edition book bene- fiting the charity
Now it’s:
“I supported the arts and became part of it.”
3. It flatters without pandering Broadway costumes:
• Have gravitas
• Carry narrative
• Imply cultural sophistication
You’re not making them stars. You’re making them patrons of the arts.
Who this is perfect for in South Florida
Target institutions:
• Regional theaters
• Opera houses
• Ballet companies
• Arts-focused foundations
• Museum auxiliary boards
• Cultural fundraising galas
These organizations already understand:
• Patronage
• Portraiture
• You’reLegacyspeaking their language.
Event structure that works (tested logic) Small. Exclusive. Controlled.
• 20–30 donors max
• Advance sign-ups at a defined donation tier
• One portrait per donor/couple/family Scarcity increases perceived value.
Clear financial framing
Example:
• Donation tier includes the portrait session
Additional print sizes or books = incremental donations
• Charity Participationreceives:donations
A percentage of print/book sales
Everyone wins cleanly.
Where your age becomes an asset again
This is important.
You are:
• Calm
• Unflappable
• Experienced with performers
• Trusted around valuable garments
No one wants a 25-year-old “vibe shooter” near a six-figure costume.
Your theater background + maturity = credibility.
The one potential risk (and how to avoid it)
Risk: It drifts into novelty.
Solution:
• Formal portrait lighting
• No gimmicky poses
• No props beyond the costume
• Consistent visual style across all subjects
Think:
Sargent meets Broadway — not Playbill.
How this feeds your other goals
This isn’t a side project — it’s a gateway. From these events you gain:
• Access to wealthy, arts-aligned families
• Material for limited-edition art books
• Visibility without “self-promotion”
This can lead directly to:
“Could you do something similar for our family?” That’s the real prize.
1 Should you pay for the costume rentals?
No — and here’s why (this matters):
If you absorb the $150–$200 per costume, three bad signals get sent:
• Your work looks like a donation rather than a professional collaboration
• The costumes become “props” instead of featured value
• You cap the fundraiser’s upside without meaning to Instead, the costumes should be positioned as part of the donor experience, not your overhead.
The correct framing
The fundraiser covers or passes through the costume rental
Or the donor level includes the costume as part of the package This keeps you:
• clean
• respected
• You’rerepeatabledonating creative leadership, not pro- duction expenses.
2. The right mental model: this is a “portrait event with theatrical provenance” You are not “Headshotsdoing: with costumes” You are doing: “A private theatrical portrait experience using authentic stage wardrobe” That phrasing alone justifies everything that follows.
3. Recommended pricing structure (this is the heart of it)
I’ll give you three tiers — institutions love tiers, and donors instinctively self-select.
Tier 1 — Patron Portrait
$1,500 – $2,000
Includes:
• Costume rental (funded by donor or event)
• Curated theatrical look (you guide selection)
• One fine-art portrait session
• One 16×20 fine art print
• 20×24 white mat
• 1” custom black wood frame
Tier 2 — Benefactor Portrait
$2,500 – $3,500
Includes everything above plus:
• Expanded session (multiple looks / poses)
• Choice of two final images
• One additional unframed fine art print
• Priority scheduling
• Subtle personalization (title, mythic role, or character reference)
This tier exists to make Tier 1 look reasonable — and many donors will quietly choose it.
Tier 3 — Legacy Portrait
$5,000+
Includes:
• Premium or rare costume
• Extended creative consultation
• Two framed final pieces
• Private or off-hours session
• Option to gift one print to the institution’s archive
• Acknowledgment in program materials
This tier is not about volume.
It’s about signaling seriousness and permanence.
4. Where your production costs go
You provide:
• backdrop
• lighting
• expertise
• artistic direction
• print coordination
• framing coordination
Those are baked into the pricing, not itemized. The only line item that should ever be visible is: “Authentic theatrical costume provided for the portrait experience” That’s it
5. Editioning (quiet but powerful)
Every finished image should be:
• Signed
• Dated
• Marked as part of a limited fundraiser edition (even if it’s 1/1 per subject)
This:
• increases perceived value
• protects you long-term
• reinforces that this is not a commodity shoot
6. One crucial operational note (learned the hard way)
Limit the number of sessions.
Example:
• “Only 12 portrait sessions available during the fundraiser weekend”
Scarcity:
• protects your energy
• raises donor urgency
• prevents scope creep
1. Exact Language for the Fundraiser (Public-Facing Copy)
This is what appears on the event page, pro- gram, or donor materials.
It should feel inviting, rare, and inevitable.
Theatrical
Portrait Experience
As part of this year’s fundraiser, we are of- fering a limited number of private theatrical portrait sessions created by acclaimed pho- tographer Richard Booth, whose work draws on decades of experience in theater, perfor- mance, and fine-art portraiture.
Each portrait is created using authentic pro- fessional stage costumes, transforming the traditional portrait into a timeless, symbolic image — part fairy tale, part personal mythology.
Participants will be guided through a curated photographic session and will receive a muse- um-quality framed fine-art print, created specifically for this event.
These portraits are not replicas or themed photo opportunities.
They are one-of-a-kind works, designed to endure.
Availability is strictly limited.
Optional closing line (use only if space allows): This experience is offered exclusively in sup- port of the organization’s mission and is avail- able only through this fundraiser.
2. Internal Pricing Sheet for Organizers (Not Public)
This is the document you give to:
• development staff
• board members
• event chairs
It keeps you protected and them confident.
Fundraiser Portrait Experience — Internal Overview
• Artist: Richard Booth
• Format: Private theatrical fine-art portrait sessions
• Costumes: Authentic professional stage cos- tumes (rented)
Patron Portrait — $1,750 Includes:
• Curated costume selection
• Guided portrait session
• One final image
• One 16×20 archival fine-art print
• 20×24 white mat
• 1” custom black wood frame
• Signed, dated, and editioned
• Proof selection session (no digital files)
Benefactor Portrait — $3,000 Includes:
• Extended session and creative consultation
• Choice of two final images
• One framed 16×20 print
• One additional unframed fine-art print
Priority scheduling
Legacy Portrait — $5,000+ Includes:
• Premium or rare costume selection
• Extended creative direction
• Two framed final works
• Optional gift print for institutional archive
• Recognition in event or program materials
Operational Notes
• Costume rental fees are included within donor levels or covered by the event.
• Sessions are limited to preserve quality and exclusivity.
• All production, lighting, backdrop, printing coordination, and framing are handled by the artist.
Capacity Recommendation
• 8–12 sessions maximum per fundraiser
• Sessions scheduled in blocks to allow costume handling and reset
3. The 60-Second Conversation Script (Board Member / Gatekeeper)
This is the spoken version. You should be able to say this calmly, without pitching energy.
“What I’m proposing isn’t a photo booth or a costume shoot.
It’s a private portrait experience using authen- tic theatrical costumes — the kind designed to carry meaning and character, not novelty.
Each participant ends up with a museum-quali- ty framed portrait that feels symbolic, timeless, and personal.
The fundraiser benefits because it’s limited, distinctive, and priced appropriately — and donors feel like they’re receiving something rare rather than transactional.
I handle everything creatively and logistically. The organization simply offers access.”
If they hesitate, you add (only if needed): “It works best with people who appreciate craft and legacy — not volume. That’s why we cap the number of sessions.”
Then stop talking.
One final, important note (quiet but critical)
You are not donating your work. You are creating a high-value fundraising instrument.
That distinction protects: your reputation your futurepricinginvitations
If you want, next we can: tailor this language to a specific type of institution (theater, arts nonprofit, private club) pressure-test the pricing against a real donor base design a one-page visual leave-behind that reinforces all of this without words Just tell me where you want to go next.
1. The iPhone issue (without sounding precious or paranoid)
The trick is this: Never frame it as “don’t photograph.” Frame it as “protecting the experience and the charity.” People accept rules when they understand why, and they comply more readily when the rule feels elegant rather than scolding.
A. Make it institutional, not personal
This should never sound like you being touchy. It should sound like the event’s culture. Use three layers working together:
1. Printed language (program / signage / booking confirmation)
Something like:
An Unplugged Portrait Experience
To preserve the theatrical lighting, costumes, and flow of the evening—and to ensure every guest enjoys a private moment in character— we ask that phones and personal photography be set aside during portrait sessions. Professional images will be shared with you after the event.
Key points:
“Unplugged” feels classy, not restrictive You’re protecting their experience You promise a payoff
2. Verbal framing by the host (not you)
Have the fundraiser chair or emcee say this early in the evening:
“Tonight’s portraits are designed like a short theatrical performance—lighting, costume, and moment all working together—so we’re keeping sessions phone-free. You’ll receive beautiful finished images afterward.”
When this comes from them, enforcement becomes effortless.
3. Your calm, friendly in-the-moment line
If someone steps behind you with a phone: “I totally get the impulse—it looks great—but the lighting falls apart if there’s another camera in the mix. I promise, I’ll take care of you.” Smile. Say it once. Then turn back to your subject.
If they persist:
“I can do this beautifully, or I can do it with phones—but not both.” Said lightly, this usually lands.
B. A nuclear option you may not need—but should have
If this is a ticketed portrait session, include a single sentence in the booking language: “Portrait sessions are phone-free to maintain lighting integrity and image exclusivity.” That one sentence gives you absolute authori- ty without ever needing to argue.
2. “How many of these have you done?”
This question isn’t really about numbers. It’s about risk.
T
hey’re asking “Am I the guinea pig?”You have three strong ways to answer this, depending on the truth—and all of them work.
Option A: Reframe from format to experience This is my favorite, and it’s honest without be- ing defensive.
“I’ve photographed theatrical productions, performers, and costumed subjects for years. This particular format brings those elements together in a fundraising setting—which is exactly why it works.
”You’re saying: New format, not new expertise.
Option B: The pilot-with-prestige answer
If this is among the first:
“This is one of the first times I’m offering it in this form—but with Broadway costumes, pro- fessional lighting, and a structure refined from years of performance photography.”
This signals:
• Intentional design
• Not an experiment
• Thoughtful rollout
You’d be surprised how often people like be- ing “early” when it feels curated.
Option C: Answer the question they meant to ask
Sometimes the smoothest move is to pivot: “What usually matters more is whether guests feel taken care of and whether the images feel special. That’s where my focus is.” Then stop talking.
Silence after that line is powerful.
A strategic truth (worth saying plainly)
This project should not be sold like a volume fundraiser. It’s a theatrical salon that happens to raise money.
That positioning:
• Justifies phone restrictions
• Makes exclusivity feel natural
• Makes “first of its kind” a strength, not a weakness
If you’d like, next we can:
Draft exact signage language (program, wall placard, booking page)
Script a 30-second host announcement
Create a one-paragraph FAQ that answers both questions before they’re asked
You’re thinking about the right problems. That’s usually the difference between a clever idea and a successful one.
30-second host announcement (spoken)
“Before we begin, a quick note about tonight’s portraits. Each session is designed like a short theatrical moment—professional lighting, au- thentic Broadway costumes, and a little bit of magic—so we’re keeping the portrait area phone-free.
That lets each guest enjoy a private experience in character, and it allows the photographer to create the strongest possible images. Don’t worry—you’ll receive beautifully finished photographs after the event. Thank you for help- ing us keep the evening elegant and focused.” (That clocks in at ~22–25 seconds at a relaxed pace.)
One-paragraph FAQ (answers both questions)
Why are portrait sessions phone-free, and is this a new event?
To preserve the theatrical lighting, costumes, and sense of occasion, portrait sessions are intentionally phone-free—much like a live performance—so each guest enjoys a private, uninterrupted moment and receives the best possible final images. While this specific fundraising format is newly introduced, it is built on years of experience photographing theatrical productions, performers, and costumed sub- jects using professional stage-inspired lighting and direction. The result is a polished, care- fully designed experience rather than a casual photo opportunity.