Podcast Ep 430 - What a $200K Photographer Would Do If She Had to Start Over

What If Growing Your Photography Business Didn’t Have to Be So Hard?

Have you ever wondered if you're making your photography business harder than it needs to be? You can spend hours planning your next marketing move, worrying about where your next client will come from, comparing your bookings to someone else's, or trying to figure out the “right” way to grow. Meanwhile, the thing that might actually move your business forward could be much simpler: meet people, try something, learn from it, and keep going. That is one of the biggest clues Heather wants photographers to notice in her conversation with Jess Wasik, a photographer who has built a business generating around $200,000 a year.

Jess's story is interesting because she isn't presenting some complicated formula for six-figure success. In fact, Heather says the point of the series isn't to hand photographers a magic formula, but to look at how successful photographers think, how they get clients, what they do when something doesn't work, and what they've stopped making so complicated. Jess's answer, over and over again, is to experiment, meet people, stay visible, and figure out what to try next instead of getting stuck analyzing what went wrong.

That sounds simple. But if you've ever run a photography business, you know simple doesn't always mean easy.

If you had to start over, where would you begin?

Heather asks Jess an interesting question: if everything disappeared tomorrow and she had to rebuild her business from zero, what would she do first? Jess doesn't say she'd redesign her website, spend three months creating Instagram content, buy new equipment, or perfect her portfolio. She says she would make connections with humans—other business owners, nonprofits, and people in her community—and make sure everyone knew what she did.

That answer is worth sitting with because photographers often spend a tremendous amount of time trying to make themselves look ready before actually making themselves known. We polish the website, adjust the bio, edit another portfolio, research hashtags, redesign the pricing guide, and wonder why inquiries aren't coming in. But how many actual people know what you do?

Jess is very direct about it: people have to know you exist before they can book you. Social media can help people see your work, but if nobody knows to look for you, you can end up with nothing more than “a bunch of pretty pictures sitting in a grid.”

What if your next client isn't waiting for your next post? What if they're waiting to meet you?

That doesn't mean social media isn't useful. It means it shouldn't become the place where you hide from the uncomfortable work of being visible in real life.

Stop waiting for people to find you

One of the most practical things Jess does is deliberately put herself where potential clients already are. If she had no past clients, she says she'd follow dogs around Pittsburgh, connect with pet-related businesses, and look for other businesses that serve the kinds of people she wants to photograph. Her goal would simply be to get on people's radar.

For an introverted photographer, this can sound exhausting. Jess actually describes herself as extremely introverted and says she doesn't enjoy small talk, yet she learned that she could talk to people about something she genuinely cared about: their dogs. She didn't need to become the loudest or most outgoing person in the room; she simply needed to show up as herself and make it easier for people to know what she did.

That distinction matters. Networking doesn't have to mean becoming someone you're not. It can mean finding the conversations that feel natural to you and having more of them.

So if the thought of networking makes you want to disappear, ask yourself: Do you actually hate meeting people, or do you hate the idea of having to perform a version of yourself you don't recognize? Jess found a way to make connection feel like her instead of forcing herself to become a different personality.

Your experiment doesn't have to work

Jess's “breed of the month” campaign is one of the clearest examples of her approach. She launched it knowing that if she didn't enjoy it or it didn't work, she could simply stop it. Her first month produced only three applications, which could have been enough for many photographers to conclude, “Well, that didn't work.” Instead, she tried again with a different breed, and the second month performed extremely well.

This is where a lot of photographers get stuck. We don't just try something; we make it mean something about us. A campaign doesn't work, so we're bad at marketing. A Reel doesn't perform, so social media is pointless. An event doesn't produce immediate bookings, so the event was a waste of time.

But what if the first version wasn't supposed to be the final version?

Jess's mindset is different. She takes an idea, adapts it to her business, watches what happens, and decides what to do next.

What if “this didn't work” is actually the beginning of the experiment instead of the end?

That's a much more useful place to operate from.

Don't give away your work just because you're afraid to ask for the sale

There's another important lesson in Jess's campaign that photographers shouldn't overlook. She didn't create an offer where everything was simply free. She was clear about what the winner received, what artwork credit was included, and what clients could expect. Applicants could understand that there was still an investment involved before they participated.

That clarity helped her attract people who were actually interested in artwork rather than people looking only for something free. She says the application was one of the most important parts because it helped her identify whether someone was emotionally, logistically, and financially ready to make the investment.

This is a useful reminder if you've been afraid to run a promotion because you don't want people to think you're “baiting and switching.” You don't have to hide the fact that you're running a promotion, and you don't have to pretend that your business doesn't need to make money. You can create something that benefits the client and benefits you.

The question is: Why have we convinced ourselves that a marketing idea can only be generous if the photographer gets nothing from it?

Your business is allowed to benefit too.

You don't have to do everything yourself

For years, Jess resisted outsourcing because she believed she was the only person who could do things the way she wanted them done. Eventually, she realized she didn't want to spend her life glued to her computer, and she began handing off parts of her workflow.

That change wasn't really about editing. It was about control.

She now uses AI for base edits, has a human editor check the work, and has a retoucher handle the images clients actually purchase. The result is a much faster workflow, with the complete process taking roughly a week and a half or less.

And here's the part photographers might need to hear: your clients probably care far more about receiving beautiful photographs than whether you personally touched every image. Jess even points out that clients don't know or care about many of the small tasks photographers spend hours obsessing over.

So look honestly at your workflow. What are you doing because you're the only person who can do it—and what are you doing because you've never allowed yourself to imagine another way?

If there's a task you dread, that matters. Jess suggests tracking how many hours you're spending on each part of a session and noticing where you're doing work you don't really want or need to be doing.

Someone else might actually love doing the thing you're tired of doing.

Being stubborn isn't always a bad thing

Jess describes herself as stubborn, and in many ways that stubbornness helped her build the business she has today. She failed when Heather challenged her to make $1,000 early on, but she kept going. She stayed persistent because she wanted the business badly enough to keep figuring things out.

But she learned something important about stubbornness: you have to know what you're being stubborn about.

Sometimes persistence builds resilience and determination. Other times, it keeps you trapped in something that is making you miserable. Jess says she can tell the difference by paying attention to how the struggle feels: if it's still driving her to figure things out, she'll keep going; if the uphill battle is simply making her miserable, it's time to pivot.

That's an incredibly useful distinction for photographers.

Are you refusing to quit because you're committed to the goal—or because you're afraid to admit this particular approach isn't working?

You can be persistent without being rigid. You can believe deeply in your business while still changing the strategy.

Your brain doesn't have to be quiet before you take action

Jess has a fantastic name for the place her anxious thoughts live: the “overthinkatorium.” She describes waking up at two in the morning with her brain running through financial worries, bookings, business decisions, and everything else she could possibly worry about.

The difference isn't that she somehow eliminated those thoughts. She accepted that her brain is always going to be active and learned to turn down the volume. Her rule is simple: she doesn't work the night shift.

How many photographers are doing unpaid overtime inside their own heads?

You're lying in bed wondering why someone hasn't replied. You're replaying a sales conversation. You're calculating next month's revenue. You're imagining what a client might think. You're trying to solve tomorrow's problem at two in the morning.

Jess's approach is a good reminder that a thought can exist without requiring your immediate attention. You don't have to solve every business problem the second your brain produces it.

Sometimes the most productive thing you can do for your business is go to sleep and deal with it tomorrow.

Look outside photography for evidence

When Jess feels frustrated, she doesn't only look at other photographers. She looks at other industries. She pays attention to advertising campaigns and ideas from businesses like Chick-fil-A, then asks herself how she could adapt what they're doing to her own business.

That's a powerful habit because photography can become a very small bubble. If everyone around you is using the same mini sessions, the same promotions, the same social media strategy, and the same messaging, it can start to feel like there are no other possibilities.

But there are millions of businesses solving the same fundamental problems you're solving: How do I get someone's attention? How do I create interest? How do I make an offer? How do I stay memorable? How do I get someone to come back?

You don't have to copy another photographer. You can borrow an idea from somewhere completely different and make it yours.

What business outside photography is doing something brilliantly that you could adapt instead of reinventing from scratch?

That is how experimentation becomes fun again.

You don't need more clients. You may need better-aligned clients.

One of the biggest misconceptions about reaching six figures is that you simply need a massive number of clients. Jess challenges that directly. She says you can have fewer clients who are more aligned with what you want to do, which means you don't have to work yourself into the ground to reach your financial goals.

That's an important shift for photographers who equate growth with exhaustion.

What if the goal isn't to photograph more people? What if it's to create a business where the right people value what you do enough that you don't need as many of them?

Jess says she's actually working less now than she ever has, and that's allowed her to have something she didn't always give herself permission to have: a life outside the business.

What if six figures didn't have to look like burnout?

What if growing your business could actually make your life better?

Stop making it harder than it needs to be

Near the end of the conversation, Jess says something incredibly direct: stop complaining and go figure it out. She isn't saying photographers don't have real problems. She's saying that spending all your time dwelling on what's not working can prevent you from seeing what might work next.

That's uncomfortable advice, especially when you're genuinely frustrated. But there's something freeing about it too.

If an idea fails, let it fail. If you hate it, stop. If you don't know how to do something, learn. If you need help, get help. If you need more clients, go meet people. If you need a new marketing idea, experiment. You don't have to turn every setback into a crisis.

Heather sums up the lesson beautifully at the end of the episode: experiment, meet people, stay visible, keep learning, stop assuming every thought in your brain is true, and when something doesn't work, figure out what you're going to do next.

Maybe your photography business doesn't need another complicated plan.

Maybe it needs you to stop waiting for certainty and start figuring things out.

Try something. See what happens. Learn. Adjust. Try again.