How to Choose a Mastermind as a Creative Business Owner

Masterminds for Creative Business Owners | The Systems & Workflow Magic Podcast

Note: This podcast/blog was originally based on a conversation from a past episode of the Systems and Workflow Magic Podcast. Some links, offers, or references may have been updated since the original recording to reflect current resources.

Listen to the full podcast here (or scroll down to read the blog post) ⬇️

If you have been sitting on the fence about joining a mastermind for your creative business, you are not alone.

The word “mastermind” gets tossed around constantly in the online business space, but very few people actually explain what a mastermind is, how it differs from group coaching, and what kind of systems a good mastermind leader puts in place behind the scenes. That matters because your investment of both money and time deserves more than a leader who is building the plane while it is taking off.

In this post, I am breaking down what I learned firsthand as a mastermind participant, what my former mastermind leader, Kat Schmoyer, taught me about sustainable coaching systems, and what you should look for before you commit to a mastermind of your own. If you are a family photographer (or any creative business owner) who has been wondering whether a mastermind could help you grow, this one is for you.

And speaking of growing your business with real systems, if you are looking for a starting point, grab my free Lead Magnet Master Idea List to see how a simple lead magnet can become the first piece of a marketing system that actually works for you.

What Is a Mastermind, and How Is It Different from Group Coaching?

A mastermind is a peer-to-peer learning experience led by a coach, where members learn from each other and receive coaching tailored to their individual business needs. That definition might sound similar to group coaching, but there is a real difference. In a group coaching program, the coach walks you through set content.

Think of it like a course on steroids: you sign up, you get modules or live calls, and you walk away having learned A, B, C, and D. Everyone in the group covers the same material. A mastermind, on the other hand, is shaped around each member’s specific needs. One person might need to focus on the pricing strategy. Another might need help building a client workflow. A third might be working through a rebrand.

The coach adjusts the teaching to meet each person where they are, and the group members learn from each other’s experiences along the way.

Both formats are valuable. But understanding the distinction helps you choose the right one for your season of business.

Why Would a Creative Business Owner Want to Join a Mastermind?

Creative business owners benefit from masterminds because they receive personalized coaching, peer accountability, and real-time feedback in a small group setting. If you are a solo photographer running everything on your own (marketing, editing, client communication, finances, all of it), you probably know what it feels like to make decisions in a vacuum.

A mastermind puts you in a room (virtual or in-person) with other business owners who are navigating similar challenges. You get the benefit of a coach who can see your blind spots, plus the collective wisdom of your peers.

I joined Kat Schmoyer’s mastermind in early 2021, and it was a turning point for my business. Kat did not sprinkle magic fairy dust on me and promise that I would make six figures overnight.

What she did was set realistic expectations, help me build traction slowly, and remind me that organic growth takes time. That kind of grounded, honest coaching is what separates a good mastermind from a flashy sales page.

If you want that same kind of grounded approach to your marketing systems, my Family Photographer’s Marketing Society membership is built to help you create a consistent marketing rhythm without the overwhelm.

What Systems Does a Good Mastermind Leader Need?

A sustainable mastermind requires project management tools, a clear onboarding workflow, structured communication timelines, and a feedback system for continuous improvement. This is where things get real.

If you are thinking about running your own mastermind someday (or you just want to evaluate whether a mastermind leader has their act together), pay attention to the backend systems. Kat Schmoyer shared the exact systems she uses to keep her mastermind running smoothly, and they are worth noting:

Project management in Trello. Kat uses a dedicated Trello board for her coaching and mastermind workflow. Every step of the process is mapped out: responding to initial emails, sending invoices and contracts, distributing questionnaires, and creating shared Google Drive folders for each member. Every task has a due date so nothing gets lost. Even if you do not have a team, having a project management system helps you remember what you have done and what is coming next. (And yes, Trello is free, so there is no barrier to getting started.) If you want a similar system for your own business operations, check out my Backend Organization System for Family Photographers. It is a ready-made Trello board that gives you a clear structure for managing your business tasks.

A brain dump turned into a workflow. Before Kat launched her first mastermind, she did a full brain dump of everything that needed to happen to make it work. Applications, sales emails, onboarding materials, call schedules, retreat logistics. She wrote it all down, then organized it into a repeatable checklist inside Trello. That brain-dump-to-workflow method is something any creative business owner can replicate, no matter what you are building.

Dates set in advance. Kat sets every single call date for the full six months at the start of the program. Members know exactly what to expect, and there is no scrambling to schedule calls month by month. That kind of clarity is a hallmark of a well-run coaching experience.

Mid-program feedback surveys. Instead of waiting until the end of the program to get feedback, Kat started sending a survey at the halfway mark. This lets her make adjustments while the mastermind is still in progress. Small changes mid-program can make a big difference in how each member experiences the rest of the cohort.

How Do You Know If a Mastermind Is the Right Fit for You?

Research the coach’s strengths, ask for testimonials from past members, and evaluate whether the coaching style matches your personality and business stage. Choosing a mastermind is a personal decision, and it should involve more than just reading a sales page. Sales pages are designed to sell. They will always look polished and persuasive. That does not mean the experience behind them matches the promise. Here is what I recommend before you invest:

Research the coach. Look at their Instagram, their website, their podcast, their YouTube. Get a feel for how they communicate, what they prioritize, and whether their strengths align with what you actually need help with. Kat’s top StrengthsFinder results are Futuristic, Strategic, and Relator, which means she is wired to see a vision, map out a plan, and walk alongside you as you get there. That combination made her an incredible fit for me, but it might not be the right fit for everyone.

Ask for real testimonials. Do not be afraid to reach out and ask the coach if you can connect with a past member directly. A good coach will welcome that kind of transparency. Kat has done this for her applicants, and it speaks volumes about her confidence in the experience she has built.

Consider your season. Are you in a phase where you need a structured curriculum (group coaching might be better), or do you need personalized guidance and peer feedback (that is mastermind territory)? There is no wrong answer, but knowing your own needs helps you avoid spending money on something that does not match where you are.

What Makes a Mastermind Sustainable for the Leader?

Sustainability comes from repeatable workflows, honest self-assessment, a willingness to receive constructive feedback, and a pricing structure that supports the leader’s capacity. Kat started with a three-month program to test whether she even enjoyed the mastermind format before committing to a longer timeline. That is a smart move. She ran two rounds of the three-month version, confirmed she loved it and had the systems in place to support it, and then expanded to six months. She also built in a StrengthsFinder training component, bringing in a specialist coach to walk members through their top strengths. That is not just a nice bonus. It gives the mastermind leader better insight into how each member processes information and makes decisions, making coaching more effective for everyone. The biggest takeaway? A good mastermind leader is not winging it. They have built the backend, tested their process, and are constantly refining it based on real feedback. If you are a photographer who wants to start building your own backend systems (even if you are not running a mastermind), my Blogging and Organic Visibility System walks you through creating a repeatable content marketing system that grows your visibility over time.

What Should You Expect from a High-Level Mastermind Experience?

Expect clear communication, organized scheduling, personalized coaching, peer-to-peer feedback, and a leader who values transparency over perfection. A high-level mastermind should feel organized without being rigid. You should know the call schedule before you start. You should have access to shared resources, a clear application process, and a coach who checks in with you individually, not just during group calls. You should also expect honesty. Kat once told me (more than once, actually) that traction takes time. I would launch something, get impatient when results were not immediate, and she would calmly remind me that organic growth requires six, seven, eight, even nine months to build momentum. She was right every time. That kind of realistic, no-hype coaching is worth more than any promise of overnight transformation.

Frequently Asked Questions About Masterminds for Creative Business Owners

How much does a mastermind typically cost? Mastermind pricing varies widely, but most high-quality programs for creative business owners range from $1,500 to $10,000+, depending on the length, the coach’s experience, and what is included (retreats, one-on-one calls, etc.). The investment should reflect the level of access and personalization you are receiving.

Can I join a mastermind if I am still in the early stages of my business? You can, but make sure the mastermind is designed for your stage. Some masterminds are geared toward established business owners generating consistent revenue, while others welcome newer entrepreneurs. Ask the coach about the typical business stage of their members before applying.

What is the ideal size for a mastermind group? Most effective masterminds keep the group small, typically between 4 and 10 members. Kat Schmoyer’s groups have around eight members, which allows for deep personal attention while still benefiting from diverse peer perspectives.

How do I know if I need a mastermind or a course? If you need to learn a specific skill or process from start to finish, a course or group coaching program is likely the better fit. If you already have foundational knowledge and need personalized strategy, accountability, and peer feedback, a mastermind will serve you better.

Do masterminds work for photographers specifically? Yes. Photographers face unique challenges around seasonal income, client communication workflows, and marketing consistency. A mastermind with a coach who understands the creative industry can address those challenges in ways that generic business coaching cannot.

Meet Your Favorite Marketing Strategist and Business Coach for Family Photographers (Dolly DeLong Education)

Hi, I’m Dolly DeLong, a Nashville-based family photographer, marketing strategist, and systems educator for family photographers who want structure, clarity, and consistency in their marketing.

My photography journey began in 2006, and over the years, I built a sustainable family photography business while navigating motherhood, client work, and the realities of running a solo creative business. Along the way, I discovered something unexpected: I loved the backend just as much as the creative side.

What started as organizing my own workflows turned into helping other family photographers simplify their marketing, build repeatable systems, and stop relying on last-minute posting or panic marketing.

Today, I focus exclusively on helping family photographers intentionally market their businesses (not with trends but with consistently showing up).

I offer two ways to work with me:

• The Family Photographer’s Marketing Society: a systems-first membership that provides a clear weekly marketing cadence for Instagram and email, so you always know what to focus on without starting over.

• 1:1 Strategic Marketing Support for established family photographers who want hands-on guidance in building a sustainable, SEO-supported marketing system.

Through my blog, podcast, and YouTube channel, I teach family photographers how to think like marketers, plan ahead, and create marketing rhythms that support both their business and their family life.

I still photograph families around Nashville because it’s one of my greatest joys. But helping family photographers build calm, consistent marketing systems that actually fit real life is a close second.

I’m so glad you are here, reading this blog, listening to the podcast, or watching the embedded YouTube video. I hope this educational content was helpful. Please let me know what future systems content you would like me to create!