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