EPISODE #158

Guest: Jen Hillenga

Owner Photographer | The Ways of the Dog
Brooklyn, New York
thewaysofthedog.com

DATE: August 28, 2025

What would you do if you had to start your photography business completely from scratch in a brand new city—where no one knew your name?

That’s exactly what longtime photographer and educator Jen Hillenga did. After decades in the portrait industry and years spent building an iconic portrait studio, Jen moved to Brooklyn, worked in the corporate world for a few years, then, during a pandemic, decided to launch an entirely new venture as a pet photographer. 

As. One. Does. 

Even if you never move to another town, if you want to build a thriving business, you must reinvent yourself on the regular, and no one has done it better than Jen. 

In this episode of The ReWork, Jen joins ATJ to talk about:

• What it’s like to go from being at the top of your game… to ground zero.
• How starting over can sharpen your skills and remind you why you love photography.
• The practical steps she took to build her brand in a new town.
• Why reinvention isn’t failure—it’s freedom.

This conversation is filled with wisdom, encouragement, and practical strategies for photographers at every level.

Episode Highlights:

• Reinvent Your Business at Any Stage – Discover how Jen went from a thriving portrait studio to a completely new niche as a NYC dog photographer—and why it’s never too late to pivot.
• Avoid the Scaling Trap – Learn why “bigger” doesn’t always mean “better” (or more profitable) and how scaling can actually steal your joy.
• Start With Your Mission, Not the Money – Hear how defining a clear “why” created a brand and business that naturally attracted the right clients.
• Measure Success Beyond the Sale – Find out why sessions that build your portfolio, connections, or visibility can be just as valuable as the ones that bring in cash.
• Shift From Scarcity to Abundance – Get inspired to rethink your money mindset so you can serve clients with less stress and more gratitude.
• Build Community, Build Clients – See how tapping into the rescue dog community gave Jen a loyal, engaged client base (and how you can do the same in your niche).
• Forget the Rules, Follow Alignment – Walk away with the freedom to design your business on your own terms, and the confidence that your people will find you.

Key Takeaways:

• Why scaling might actually cost you more than it gives you.
• Discover how a clear mission can make branding and marketing effortless.
• See why every session matters, even if it’s not a big sale.
• Understand how shifting to an abundance mindset transforms your business.
• Walk away knowing you don’t have to follow the industry “rules” to succeed.

About Jen Hillenga: Longtime photographer and creative entrepreneur based in Brooklyn, New York. After running a successful portrait studio in Minneapolis and serving as Creative Director for Adorama, she reinvented her career to focus exclusively on pet photography through her brand The Ways of the Dog. Her work blends fine art, empathy, and storytelling, earning her recognition not just for beautiful imagery but for building a thriving, mission-driven business from the ground up.

It’s never too late to reinvent your business—and that true success comes from aligning your work with your passion and purpose.

Click here to listen!

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Links & Resources:
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Do The ReWork
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Jen Hillenga – The Ways of the Dog Fine Art Portraits
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Memorable Quotes:

“The only time I’ve ever been in a rut is when I was sitting in indecision. The minute you figure out your why, the universe is like, ‘Thank goodness, we were waiting for you.’” – Jen Hillenga

“Sometimes you decide and it’s immediately wrong, but even then, that’s still valuable data. What you can’t do is live your whole life in indecision.” – Allison Tyler Jones

“We did $1.2 million in sales, and I didn’t make any more money than when we made $300,000, because it was all going to employees and overhead.” -Jen Hillenga

“There are multiple metrics for success in every session, it’s not just the sale. It might be networking, content, or visibility, and that’s just as valuable when you’re building.” – Jen Hillenga

“If clients are shocked at the sales session, you’ve already lost, better to have the uncomfortable money conversation ahead of time than lose trust later.” – Allison Tyler Jones

“When someone says, ‘This is too expensive,’ I don’t hear an accusation. I hear, ‘I can’t afford it,’ and that shift gives me empathy instead of defensiveness.” – Jen Hillenga

“If you’re looking at your calendar with dread, praying for rain so you can cancel, it’s time to stop doing that work. Life’s too short to waste being someone you don’t want to be.” – Jen Hillenga

“The secret to life is that there is no secret. There are no rules, no timeline, you can reinvent yourself anytime, on your own terms.” – Jen Hillenga