This Can't Be That Hard

This week, we're shifting gears. The busy season is upon us, and from now straight through the holidays, we're all going to be chasing our tails in one way or another - with marketing, with sessions, or even just with general pre- and mid-holiday chaos. So instead of hitting you each week with a longer, meatier episode, I've put together a series we're calling "Stories & Shorties." These are bite-sized tips and stories from some of my favorite photographers and educators, intended to give you those little boosts of business-focused inspiration you need each week.  

We're kicking things o...

Here's something  see all the time (and have fully been guilty of myself): you run a marketing campaign, it does what it does, and by the time it's over, you don't want to think about it any more... you're just onto the next thing. You skip the debrief. You promise yourself you'll remember what worked. But then six months later you're reinventing a wheel you've already built two or three times.

To close out our back-to-school marketing challenge, I brought on my friend Tiffany Crenshaw from Animal House Photography and Tiffany Crenshaw Education. Tiffany - a business o...

You know that feeling when you get a client email, a phone call, or even just an inquiry and your heart starts racing... Maybe it's excitement, maybe it's fear, or maybe it's a combination of the two, but according to our nervous system, it's all the same.

We talk a lot on this podcast about what to say to fill your calendar. What we don't talk about enough is how what's happening in your body when you respond tends to show up in your words whether you mean it to or not.

That's exactly why...

Most restaurant menus have a handful of apps, a handful of entrees, and a handful of desserts: enough to give people choices and accommodate dietary restrictions, but not so many that people get overwhelmed.

So why do most of us limit our photography "menu" to one or two items? When your business only has one package, one price, the offer is take it or leave it: you're handing hesitant clients an easy way to say no by saying nothing at all.

In this episode, I'm breaking down:

It's August, which means it's probably feels way too early to think about Black Friday, holiday cards, or filling your calendar for Q4... but that's exactly why now is the time to do it!

Every year I watch the same thing happen: photographers coast through summer, and then the second Starbucks rolls out everyone's favorite seasonal latte, panic sets in: empty calendar, no plan, reactive scramble. This month on the podcast, we're running something we're calling the Back to School Marketing Challenge, and this episode is step one: getting organized.

My marketing director Dayna and...

Here's a pattern I've noticed: photographers spend months chasing a version of growth that sounds right, but never actually sits right. Typically this is because they've heard advice or purchased a course that may be well-intentioned, but doesn't really align with their unique circumstances or goals. Before they know it, they've spent their valuable time, money, and energy heading in the wrong direction, and now have to spend more of each of those things to get themselves back on track.

I'm wrapping up our Beyond the Bottleneck series this week, and although this episode may sound a...

You can streamline and automate every last thing in your business, but there are still only so many clients you can take on because there's only one of you... unless you build an associate team.

This week, I'm sharing my conversation with Ali Leigh, a Minneapolis-based wedding photographer who has been running an associate team for almost a decade. Ali was an open book, sharing the actual nuts and bolts:

My dad had a "system" for organizing his office. You could ask him for anything - any book or file or piece of paper - and he'd be able to locate it in 30 seconds. The problem? No one else had any idea what his system was, and if he wasn't available, nothing could be located.

Maybe your office is super organized, maybe your desktop is as clean as the day you got your computer, but I'd be willing to bet that somewhere in your business, there are "systems" that only you have the keys to.

...

There's an old story about a fisherman who keeps going out every day with holes in his net. Even though he knows the net leaks, he doesn't think he can afford to take the time off from fishing to mend the holes. I've been that fisherman more times than I'd like to admit, and I'd be willing to bet there's a good chance you have been too.

At some point in business, most of us will get in our own way. Of course that bottleneck isn't obvious - instead, it shows up as exhaustion, as the feeling...

This last episode in our Summer Essentials series dates back to 2021, but don't let its vintage fool you: it's message is as true - and important - now as it was then: most of your clients don't actually know what they want. 

Here's what we're chatting about:

This conversation with copywriter and brand strategist Courtney Fanning changed how I think about copywriting. The premise is simple (if a little uncomfortable): we all instinctively write for the type of consumer we are, and if there are four types, that means we're only effectively speaking to maybe 25% of our potential clients.

Courtney shares a framework she adapted from Spanx founder Sara Blakely that breaks buyers into four types: the director, the socializer, the relator, and the thinker. Each one needs something different from your website and your copy in order to feel confident enough to reach...

There's this cookbook my mom had when I was growing up called More With Less. The whole premise was: here are big, satisfying meals made with humble ingredients. It was on her shelf my entire childhood, and honestly... it's basically how I think about business strategy too.

This episode is one of our most popular ever, and I'm re-sharing it as part of our Summer Essentials series because right now - in this slower-before-it-gets-busier stretch - is a great time to re-engage your most valuable marketing asset: your past clients.

In this episode, I’m sh...

This month, we're taking a little break from new episodes and digging into our (big) archive to reshare some of our past faves. Today's replay originally aired in 2022, but if anything, it feels MORE relevant now than it did then: how do you keep showing up and promoting your business when the news is heavy. How do you send out a sales email or post about your upcoming mini sessions when those things seem trivial at best compared to what's happening in the world?

Here's what I'm covering:

I was talking to a photographer friend who - by every outside measure - is killing it. On the inside, though? She admitted she was struggling with feelings of self-doubt and stress about the future of her business.

I think a lot of us carry around a mental image of some summit - a destination that we will reach where things in our business will finally feel settled and all the hard work will be behind us. But the longer I do this, the more convinced I am that there is no such destination. And in a...

Having concerns about AI isn't a bad thing: it means you're thinking critically about an issue that warrants critical thought. But nor do concerns mean you have to (or should) avoid AI altogether.

The issues surrounding this world-changing technology are big, and I didn't want to gloss over them: What does "authenticity" mean in the AI era? What happens to your brain when you outsource thinking? What is the environmental cost of data centers? Are the companies building these tools considering anything beyond their bottom line?

So in this episode, I'm opening the whole can...

I remember the exact moment I first heard about ChatGPT. I was walking my dog, talking to my dad on the phone, and he mentioned this thing he'd heard about on NPR - some AI tool where you could just type any question and get an answer. My reaction? "Huh. Why would I need that when I have Google?"

That was not that long ago. Wild.

Just a couple of short years later, and AI is literally everywhere. But a lot of photographers I talk to are genuinely conflicted about using it - and I...

Okay, I'll just say it: I am an Airtable evangelist. I have been for years. It runs my episode archive, my client data, my business dashboard, my production workflows - honestly, it runs a lot of my personal life too. And I know that sounds like something I'm pitching, but I genuinely make zero money on Airtable. I just really, really believe in this tool.

The problem is that what Airtable does can be hard to explain - and that makes a lot of photographers click around in it for a few minutes, get confused, and close...

Tech tools and software are an easy thing to accumulate. Most of us add tools when we find them, promising ourselves we'll dive in "as soon as we have time. Before long, we've got a giant tech stack that just kind of happened.

In this episode, I'm talking about the costs of "tech debt" - not just the financial expense, but the minutes, hours, even cumulative days that we all spend on workarounds, redos, and tweaks, all the while thinking, "I'm sure I had a tool that was supposed to do that!"

We'll also cover...

Ever wonder what it actually looks like to build a profitable photography business on lower prices and higher volume? That's what this conversation with Naomi Boyer is all about.

After a rough year in 2024 where inquiries were down and the business just felt like an uphill battle, Naomi decided to try going all in on something she'd been developing on the side: school and event photography built on a high-volume, streamlined model.

The result? Was so great that she shifted her entire business model.

This episode gets into the real mechanics of making...

What if the most profitable thing in your business isn't your highest-priced offer?

That's the question behind this episode - and the answer might surprise you. I brought in two photographers, Jenn Chen and Allison Maxwell, who have each built something I find genuinely fascinating: a lower-priced, accessible offer that sits at the front of their business and funnels clients into their higher-ticket work. Not as a loss leader or freebie, but as an actual profit center that also happens to grow their audience and warm up ideal clients.

Jenn runs a family and newborn...

You know that moment when you look at your bank statement and realize you're still paying for software you stopped using three months ago? Yep. We've all been there.

Profitability isn't just about what you charge - it's about what you keep. And for most photographers, there's money unnecessarily leaking out of the business every single month that a little attention could stop.

In this episode, I'll walk you through my strategic approach to evaluating business expenses - not as a slash-and-burn exercise, but as a way to make your spending actually work for your...

What if "Just raise your prices" is the wrong advice for right now?

That's a question a lot of photographers have been sitting with lately - and honestly, it's one worth taking seriously. When budgets feel tight and bookings feel uncertain, the standard advice can start to feel a little tone-deaf. But here's the thing: there are real, strategic ways to increase your profitability without ever touching your prices.

In this episode, I'm revisiting a framework I introduced way back in Episode 38 - the Donkey, Workhorse, and Unicorn business models - and looking at it...

What if the reason your marketing isn't converting has nothing to do with your content... and everything to do with the part that comes after it?

In this episode, Annemie and Dayna get a little theatrical to break down one of the most important (and most avoided) distinctions in your business: the difference between marketing and selling, and why you genuinely can't have one without the other.

Using Wicked as their framework, they make the case that Glinda (your marketing) gets all the love, while Elphaba (your selling) gets an unfair bad rap. But here's...

Picture this: you're cruising down the highway, passing billboard after billboard without really registering any of them. Then hunger strikes, and suddenly that McDonald's sign is the only thing you can see.

That's how marketing works: you're not introducing yourself once and hoping for the best. You're showing up again and again, so that when your client's _"I need a photographer!"_ moment finally hits, yours is the name that comes to mind.

But here's the catch: even when someone is ready to pull off at the next exit and book, their brain starts throwing up...

For a long time, SEO gave us a set of rules to follow. There were a lot of rules, and following them all wasn't ever _simple_, but at least the playbook was fairly clear. These days, though, the landscape has shifted…

With the proliferation of AI tools and search algorithms, the way people find information online is evolving quickly. The rules around SEO are changing as well, and many photographers are wondering what actually matters now.

This week I’m joined by Corey Potter of Fuel Your Photos. Corey is a former wedding photographer who now...

If you’re anything like most photographers, the thought of walking into a fundraiser, hosting an event, or introducing yourself at a networking mixer makes you want to put on your soft pants and climb back into bed. Which is exactly why I’m betting the rock quadrant of your marketing system is probably the one that needs the most attention.

The truth is, in-person marketing can be one of the fastest ways to build real momentum in your business… but that requires finding opportunities that feel aligned and doable!

For this episode, I went back t...

As the slow season fog lifts and spring energy kicks in, it can be tempting to try to chase the perfect marketing strategy… only to end up overwhelmed, second-guessing every move, and wondering why marketing always feels like a gamble.

This month, we're doing something brand new on the podcast called March Marketing Madness, and for the first time ever, we have a guest host! This Can't Be That Hard's very own marketing director, Dayna (who many of you know from the Consistency Club) is taking over the mic to walk us through a fun, practical way bu...

If you want your photography to be more than a hobby, getting your finances organized isn’t just a “nice to have” - it’s the foundation for a profitable, sustainable business. If you’ve ever promised yourself that “next year will be different” when tax season rolls around, this episode is for you.

Today, I’m joined by Tiffany Bastian, a no-nonsense accountant with over 20 years of experience who works exclusively with photographers across the US. Tiffany’s not a photographer herself, but she’s made it her mission to help creative entrepreneurs ditch the shame, get organized, and f...

Organization is not just about what your clients see… it's also about how your business feels to you.

In this episode, we dive deeper on our organization theme by looking at internal systems… the behind the scenes structure that keeps everything running smoothly.

I’m joined by Stacey Rolfe of Tog Hub, who helps photographers build streamlined, sustainable systems inside their CRMs. Stacey shares why burnout isn't usually about talent or motivation; instead, it's about capacity. When your schedule, pricing, and workflows are built around someone else’s life instead of your own, things start to crack...

Organization isn’t just about tidy desks and color coded planners… it’s about how your business feels to your clients. This episode is part two of our organization series, and we’re digging into external organization… the systems, workflows, and processes your clients experience from inquiry to delivery.

I’m joined by systems strategist and photography specific VA Erin Wissig, whose work helps photographers take their workflows out of their heads and turn them into clear, repeatable systems. We talk about the difference between being organized behind the scenes and creating a client experience that feels confident, p...

What if the secret to a calmer, more creative business isn’t another color-coded planner or a prettier desk, but a system that actually works for you - quirks, chaos, and all? If you’ve ever felt like organization is just another thing on your to-do list (or that you’re “bad” at it), today's guest has a message you're going to want to hear.

Ashley Rose of Systems Over Stress joins us to share her refreshingly real approach to organization - one that supports your creativity instead of adding clutter to it. Ashley’s journey from feeling over...

If you’ve been following along with our systems theme, you’ve already worked through marketing, sales, and fulfillment, the three core systems that can absolutely run your business. But even with those dialed in, many photographers still feel stuck on the income rollercoaster… great months followed by scary quiet ones.

In this episode, we focus on the final piece of the puzzle: building a repeat and referral system that turns great client experiences into steady, predictable income. Instead of crossing your fingers and hoping happy clients send people your way, we’re talking about how to support...

Last week, we talked about building a marketing system that helps you consistently attract new leads without burning out, but great marketing alone isn't enough. If inquiries aren’t converting into bookings, or bookings aren’t turning into great client experiences, your whole business starts to wobble.

That’s why this week I’m zooming in on sales and fulfillment. Instead of chasing yeses or worrying about being pushy, I walk you through how to design a sales process that helps the right clients feel informed, confident, and excited to book. From there, we move into fulfillment… the system...

If there is one thing that burns photographers out faster than almost anything else, it’s marketing. What is supposed to feel like connection often feels more like an endless cycle of posting, scrolling, and second guessing… all while the rules keep changing.

In this episode, I’m kicking off our Systems Theme by talking about how to build a marketing system that actually feels like connection (and supports your business instead of draining it). We look at why chasing trends and algorithms isn’t the answer, and how focusing on trust, local connection, and clear priorities leads to...

We're kicking 2026 off with some big milestones around here! At the time this goes live, we're crossing the six year anniversary of the launch of Simple Sales and the almost six-year anniversary of the podcast. On top of that, we recently crossed half a million downloads AND this is episode 350! With all these stars aligning, it felt like the right time to pause, reflect, and make some intentional decisions about what comes next.

In this special episode, I'm share why the mission behind This Can’t Be That Hard hasn’t changed, even though the industry and the...

If you’ve ever felt stuck between pricing models or frustrated by sales systems that don’t quite fit, this episode will hit home.

For our final episode of the year, I’m resharing a conversation I had with Jill Smith on The Business Focused Photographer Podcast about the story behind Simple Sales, how it came to be, and why it’s still the system that completely changed the way I run my photography business.

We talked about bridging the gap between all inclusive and in person sales, how to raise your prices with confidence, and what...

Marketing can feel like a mystery sometimes… especially when you’re trying to figure out what actually works versus what just burns time.

This week, I’m resharing a conversation I had with Kim Box on The Motherhood Anthology Podcast where we talked about one of my favorite topics… marketing that actually moves the needle.

We got into the difference between marketing tactics and marketing systems, how to balance consistency with creativity, and how to make your marketing feel more like flow and less like force. I also shared a new metaphor for planning your strategy...

AI is everywhere right now… and whether it excites you or makes you want to pull the covers over your head, it’s here to stay.

This week, I’m resharing a conversation I had with my friend Colie James on her podcast Business First Creatives. Colie is one of those people who always gets my wheels turning, and this episode is a perfect example of that. We talked about how AI is showing up in our businesses, what it’s actually good for, and how photographers can use it to create content faster without losing their voice.<...

Most photographers know the feast-or-famine feeling all too well… one month you’re booked solid, and the next you’re wondering where the next client will come from.

In this week’s episode, I’m resharing a conversation I had with Kimberly Espinel on her podcast Eat, Capture, Share, where we dig into one of my favorite topics: building recurring revenue through a portrait membership.

We talk about how the idea was born out of an ankle injury (yep, really), why recurring revenue has been the single biggest stabilizer in my business, and how you can apply...

When you’ve been in business for a while, it’s easy to fall into the habit of focusing on tactics… what to post, what to charge, what to offer next. But sometimes the real growth happens when you zoom out and look at the bigger picture.

This week, I’m sharing a conversation that originally aired on Leah O’Connell’s podcast Photo Fuel. Leah and I dove into the parts of business that don’t always make it into strategy guides; risk, failure, ego, and what it really means to build something that lasts. We talked about c...