Not only has technology changed over the last decade, but so has the industry, the way we form relationships and lets not even get started with the rise of social media. No matter what facet of the industry you serve, you really have to either adapt or die. Today’s guests, Rick and Sarah Pendergraft of PenWeddings have been in the industry for over 15 years. They have learned first hand how important it is to not be stuck in their ways and how to evolve with the times. They truly follow the mantra of “Don’t be afraid of the unknown. Learn it. Embrace it. And move forward.” We have a feeling that you will be singing the same tune after listening to this conversation.
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There comes a point in every wedding creative’s career when you realize that what got you to where you are won’t get you to where you want to go. You’ve likely raised your prices, added new gear, improved your skills. But then something shifts, and suddenly what used to set you apart is now the standard.
That’s the moment you face the decision: adapt—or fall behind. Have you felt this before? We certainly have once or twice in our careers.
We recently sat down with Rick and Sarah of PenWeddings, who’ve been in this industry for over 15 years, to talk about what it really looks like to stay relevant and successful in a space that’s constantly moving. During this conversation, what stood out most to Taylor and I was their willingness to keep reinventing themselves—creatively, strategically, and in terms of pricing and positioning.
They didn’t go from $1,000 weddings to $19,500 overnight. It took time. It took learning when to raise prices, when to shift deliverables, and when to reposition their brand to reflect the level of clients they were serving. It took letting go of comparison and leaning into the needs of the market they actually wanted to work in.
One of the biggest takeaways from this conversation was the realization that luxury clients are different. They don’t need two years to save for their wedding. They don’t care about being first to book—they care about finding the right creative. And they often book much closer to the date, which means you have to stop treating open dates on your calendar like missed opportunities.
Some of our best weddings have booked 2, 3, 4 week out. It’s true!
If you want to break into the luxury market and build a business that truly reflects your value, you can’t afford to keep waiting. You have to shift the way you see your pricing, your client experience, and your brand positioning.
The industry has changed. Fast. And while it’s easy to get nostalgic about how things used to be—DSLRs, glidecams, endless hours of pulling manual focus—the truth is, it’s not 2010 anymore. The technology and client expectations have evolved. And the businesses that thrive are the ones that choose to keep evolving too.
If you’re sitting in a season that feels uncertain, or if you’re watching others pass you by while you wonder what’s missing—this is your sign to adapt. To reframe. To move forward.
If you know your work is luxury-level but your bookings don’t reflect that yet, it’s time to change more than your price. The Luxury Mastermind is our 12-week program designed to help photographers and filmmakers break out of the mainstream market and build high-end, highly profitable businesses.
Inside, you’ll learn how to position yourself as a luxury expert, attract ideal high-end clients, and price your work with confidence—without burning out or second-guessing every move.
Join us inside the Luxury Mastermind at thelevelupco.com/mastermind and start building a business that reflects the level you’re truly capable of.
