Rejection, unpredictable income and self-doubt can be harder to manage than lighting or posing. Photographer and filmmaker Ajani Charles joins Nikki Closser to talk about the mental side of building a photography business—and the relationships, routines and practical business habits that help him keep going.

Ajani shares the story behind Project T-Dot, his long-running documentary project on Toronto's hip-hop culture, community and history. He explains why he stayed with it for 15 years before monetizing it, how commercial work supported him along the way, and what a personal project can offer beyond an immediate paycheck.

The conversation also gets practical about finding photography clients: being useful, solving a client's problem, defining an ideal client and following up. Alongside those business habits, Ajani discusses the role that meditation, therapy, journaling and a trusted support system have played in his own life.

In this conversation:

• Personal photography projects, long-term relationships and creative identity
• Rejection, financial uncertainty and clearer business goals
• Remembering your wins and finding support during difficult periods
• Marketing through usefulness, trust and client problem-solving
• Ideal client profiles, CRM follow-ups and consistent outreach

Build your photography business with PortraitSystem.com. Use code PODCAST7 for your first month for $7.

Chapters

00:00 The mental side of a photography business
01:34 Ajani's start in art and photography
04:10 Project T-Dot: photographing Toronto hip-hop
10:11 15 years to monetize a personal project
17:34 Rejection, money and creative-career uncertainty
22:15 Remembering your wins when criticism sticks
27:32 Meditation, therapy and journaling
33:58 Photography marketing: trust and usefulness
37:24 Ideal clients, CRM and follow-ups
39:46 Taking action after a no
45:27 Mentors and a creative support system
47:51 Four final questions: routines, gear and getting started

Drew Forsyth is an award-winning portrait photographer and director based in the North West of England, working with commercial and advertising clients across the UK and internationally. His work centres on people who've given everything to be extraordinary at what they do — from dancers with English National Ballet and musicians of the BBC Philharmonic and the Hallé Orchestras, to Nobel Prize-winning scientists, politicians, and performers at the height of their careers. His photography has been featured by BBC News, The Guardian, The Times, and Rolling Stone, and recognised by the Royal Society of the Arts. He's an AOP Accredited Photographer and Fellow of the RSA, and speaks internationally at events like Photo North, Pas de Deux Photo Conference, and the Royal Photographic Society.

In this episode, Drew and Nikki trace his path from a JCPenney-style family portrait studio to photographing world leaders, Nobel laureates, and major corporate campaigns — and he breaks down exactly how he prices that work today. They dig into setting boundaries on set (and how to say yes to more without losing your mind), why those early "conveyor belt" studio years became his real technical training, and why he believes his biggest competition isn't other photographers — it's being forgotten. Drew also walks through how he actually quotes corporate jobs (day rates, itemized breakdowns, and the cautionary tale of a client who blamed him for "cheap-looking" dresses), how personal passion projects like his "Breaking Ground" series and a helicopter shoot over Manhattan became his best marketing, and the "Helsinki Bus Station Theory" — his framework for why so many photographers give up on their style right before it becomes distinctive.

Topics covered:

• Setting boundaries with clients without losing bookings
• Why "conveyor belt" studio work builds indispensable technical skills
• The accidental path from individual sessions to corporate/organizational clients
• Pricing corporate shoots: day rates, itemized quotes, and scope questions
• Why past-client relationships and personal introductions beat cold outreach
• Marketing through consistent presence, not constant hard-selling
• Passion projects as a client-acquisition strategy
• The Helsinki Bus Station Theory: staying the course creatively

If you're building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.

👉 For more videos like this, visit: https://theportraitsystem.com/

ABOUT THE PORTRAIT SYSTEM:

The step-by-step system to turn your portrait photography into a profitable business.

Build a solid foundation for the portrait business you want. Attract the right clients over and over again. Confidently create the work you're proud of. Streamline, scale, and grow with purpose.

Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.

With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.

Whether you're starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.

FOLLOW US:

JOIN The Portrait System: https://theportraitsystem.com/

FB: /theportraitsystem

IG: /theportraitsystem

Caroline White has been a professional photographer for 21 years — starting as an actress shooting headshots on the side before a burglary wiped out her equipment and pushed her into photography full-time. Since 2011 she's averaged six figures a year shooting personal branding for women entrepreneurs and coaches, and more recently has pivoted into a passion project: underwater portrait photography.

In this episode, Caroline and Nikki dig into pricing high-touch branding packages (from $2,500 simple sessions to a $20,000 two-and-a-half-day shoot), the "asshole insurance" strategy that protects her boundaries while letting her overdeliver for great clients, how AI is affecting (and not affecting) the personal branding photo market, and her transition from packages to in-person sales for underwater work — including handmade, rhinestone-embellished prints. Caroline also opens up about the near-drowning experiences that shaped her fearlessness in the water and her ability to help nervous clients feel safe underwater.

Topics covered:

• Building a 6-figure business without weddings or paid ads
• How marketing lag works — and what happens when you stop
• Add-ons that increase average sale (rush orders, retouching tiers, split-day shoots)
• "Asshole insurance": overdelivering for good clients, holding boundaries with difficult ones
• AI's real impact on personal branding photography
• Underwater photography: gear, safety, and working with non-swimmers
• Transitioning from packages to in-person sales (IPS)
• Handmade art pieces: painting on prints, Swarovski crystals, double exposures

If you're building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.

👉 For more videos like this, visit: https://theportraitsystem.com/

ABOUT THE PORTRAIT SYSTEM:

The step-by-step system to turn your portrait photography into a profitable business.

Build a solid foundation for the portrait business you want. Attract the right clients over and over again. Confidently create the work you're proud of. Streamline, scale, and grow with purpose.

Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.

With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.

Whether you're starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.

FOLLOW US:

JOIN The Portrait System: https://theportraitsystem.com/

FB: /theportraitsystem

IG: /theportraitsystem

What happens when a portrait photographer stops thinking like a freelancer and starts thinking like a CEO? Jaren Collins did exactly that — and built JCi Creatives, a nationwide creative agency specializing in conference and event storytelling, with clients including AT&T and the Thurgood Marshall College Fund.

In this episode, Jaren breaks down:

• How he quit his corporate job (with almost nothing saved) and matched his salary within a month
• Why he walked away from 52 weddings a year to pursue corporate clients
• How one $1,000 gig turned into nearly $100,000 in annual spend from a single client
• His approach to project-based pricing and asking "what's your budget" upfront
• High-volume headshot strategy — including doing 75 headshots in 23 minutes
• The systems, AI tools, and team structure that keep his business running efficiently
• Why referrals in the corporate world are massively underutilized

Jaren also co-owns Greenwood Co., a creative coworking and content space in DeSoto, Texas built to empower creators and entrepreneurs — and his mission is to help others turn creativity into sustainable, legacy-building businesses.

Whether you want to break into corporate photography or scale what you've already built, this episode is full of real-world strategy you can use today.

If you're building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice. 👉 For more videos like this, visit: https://theportraitsystem.com/

ABOUT THE PORTRAIT SYSTEM: The step-by-step system to turn your portrait photography into a profitable business. Build a solid foundation for the portrait business you want Attract the right clients over and over again Confidently create the work you're proud of Streamline, scale, and grow with purpose

Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.

With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.

Whether you're starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.

FOLLOW US: JOIN The Portrait System: https://theportraitsystem.com/ FB: /theportraitsystem IG: /theportraitsystem

In this episode of The Portrait System Podcast, Nikki sits down with photographer and educator Meg Loeks to talk about how she built a photography business rooted in storytelling, color, and creativity. Meg shares how she went from a corporate marketing job to running a thriving portrait business, and how life circumstances eventually led her to focus fully on photography education.

They talk about building momentum through social media, finding clients through your network, evolving your style, using color intentionally, and how education can become a powerful second income stream for photographers. Meg also shares her approach to photographing families, styling sessions, working with created light, and growing a loyal audience online.

If you’re a photographer interested in building a business, refining your artistic voice, or eventually stepping into education, this conversation is full of insight and encouragement.

Meg’s work is known for its rich storytelling, cinematic lighting, and thoughtful use of color, and this episode gives a great behind-the-scenes look at how she thinks about both art and business.

If you’re building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.

👉 For more podcasts like this, visit: https://theportraitsystem.com/

ABOUT THE PORTRAIT SYSTEM:

The step-by-step system to turn your portrait photography into a profitable business.

Build a solid foundation for the portrait business you want

Attract the right clients over and over again

Confidently create the work you’re proud of

Streamline, scale, and grow with purpose

Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.

With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.

Whether you’re starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.

FOLLOW US:

JOIN The Portrait System: https://theportraitsystem.com/

FB: /theportraitsystem

IG: /theportraitsystem

In this episode of The Portrait System Podcast, Nikki sits down with South Africa–based photographer Simone Dorfman to talk about real-life marketing strategies that actually work. Simone shares how she built a photography business with a $2,000 average sale in a small town by offering personal branding photography, product photography, and content creation services for small businesses.

They discuss:

• Photography marketing strategies for small markets

• How to increase photography pricing through value-adds

• Running simple Instagram and Facebook ads

• Partnering with stylists and content creators

• Packaging B-roll social video with photography sessions

• Booking branding clients through networking

• Creating photography packages for small business owners

If you’re a photographer looking to increase your photography pricing, attract better branding clients, and simplify your marketing strategy, this episode is packed with actionable advice you can use right away.

If you’re building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.

👉 For more videos like this, visit: https://theportraitsystem.com/

ABOUT THE PORTRAIT SYSTEM:

The step-by-step system to turn your portrait photography into a profitable business.

Build a solid foundation for the portrait business you want

Attract the right clients over and over again

Confidently create the work you’re proud of

Streamline, scale, and grow with purpose

Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.

With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.

Whether you’re starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.

FOLLOW US:

JOIN The Portrait System: https://theportraitsystem.com/

FB: /theportraitsystem

IG: /theportraitsystem

Most photographers don’t fail because of their photography, they fail because of pricing and marketing. In this episode of The Portrait System Podcast, Nikki sits down with Vanessa Joy (working photographer + educator, in business since 2008) to talk about what it really takes to keep a photography business profitable and sustainable.

In this conversation, Vanessa breaks down:

• Why “I need more leads” is usually the wrong problem
• How to market with a wide net (and why there’s no magic bullet)
• The biggest fix when you’re “posting everywhere” but still not getting inquiries
• How to audit your first impression (website + social + messaging)
• Sales + branding: why “branding” is really voice + communication
• Pricing without emotion: how to use math + data to set prices that actually support your life
• Outcome-based selling: stop selling “hours + number of images” and sell the transformation
• Raising prices without panic: keeping some clients, losing others, and finding the next pond
• Systems that prevent burnout: CRM workflows, email templates, SOPs, automations
• Hiring associate photographers: how to sell “the studio/team” (not just you)

If you’re serious about building a photography business that lasts, this episode will save you years of trial and error.

Find Vanessa:

VanessaJoy.com (photo work + corporate work + education)

If this helped, subscribe, share it with a photographer friend, and drop a comment: What’s harder for you right now — pricing or marketing?

If you’re building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.

👉 For more videos like this, visit: https://theportraitsystem.com/

ABOUT THE PORTRAIT SYSTEM:

• The step-by-step system to turn your portrait photography into a profitable business.
• Build a solid foundation for the portrait business you want
• Attract the right clients over and over again
• Confidently create the work you’re proud of
• Streamline, scale, and grow with purpose

Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.

With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.

Whether you’re starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.

FOLLOW US:

JOIN The Portrait System: https://theportraitsystem.com/

FB: /theportraitsystem

IG: /theportraitsystem

Taxes don’t have to be the thing you avoid until April. In this episode of The Portrait System, Nikki sits down with Heather Leicy (tax prep educator + bookkeeper + working photographer) to break down photographer tax deductions, year-round tax prep, and the biggest “can I write this off?” mistakes.

You’ll learn:

• What to do monthly so you’re not scrambling at tax time
• A simple system for setting aside 20–30% for taxes
• Common photographer deductions: education, software, gear, website costs, client gifts
• The truth about meals/coffee write-offs (when it counts, when it doesn’t)
• Home office deduction basics and “dedicated space” rules
• Why mileage tracking is one of the most missed deductions (and the app Heather recommends)
• A simple breakdown of LLC vs S-corp taxation and why it’s a math decision
• Why sales tax rules vary so much by state (digital vs physical vs services)

Important: This episode is for educational purposes only and is not tax, legal, or accounting advice. Tax laws vary by location and change over time. Always consult a qualified CPA/tax professional about your specific situation.

Find Heather

• Instagram: @heather.marie.Leicy
• Community: Conquer Community – theconquercommunity.com

If you enjoyed this episode, please subscribe, leave a review, and share it with a photographer friend who needs a tax reset.