Photo by Robin Rayne

In 2002, I left a full-time job to launch my freelance career as a visual storyteller.

I had a couple of cameras, a good amount of hope, and just enough naivety to think it might actually work out.

At the time, I didn’t know that most freelance businesses fail.

According to small business statistics, around 50% fail within 5 years, and only a small fraction survive beyond 20. The creative world — especially photography, video, and storytelling — is notoriously tough. And freelancing? That adds a whole new layer of uncertainty.

But somehow, 23 years later, I’m still here.

So, how did I beat the odds?

If I had to sum it up in one word, it would be adaptability.

The world I started freelancing in looked nothing like the one we’re in now:

• Digital cameras were just beginning to replace film.
• YouTube didn’t exist yet.
• Social media wasn’t part of any marketing plan.
• Clients mailed checks.
• And no one was asking about “vertical video” or “AI editing tools.”

Through all of that, I’ve continued to build Storyteller & Brand Builder Stanley Leary into something that has stayed relevant and effective for clients — not by doing everything, but by doing the right things at the right time.

Here are a few truths I’ve learned:

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1. Clients don’t just hire services — they hire trust.

When clients trust that you understand their mission, care about their message, and will deliver — they come back. And better yet, they refer others.

2. You can’t afford to stop learning.

I’ve taken courses, learned new software, upgraded gear, and adjusted workflows more times than I can count. The moment I get too comfortable is the moment I start slipping behind.

3. Being a storyteller is more valuable than being a technician.

Lots of people can shoot video. Fewer can find the story, frame it in a meaningful way, and create emotional impact. That’s where real value — and longevity — lives.

4. You have to be more than “just a creative.”

I’ve taught workshops around the world, consulted with businesses on branding, coached young storytellers, and helped nonprofits raise support with visual messaging. Those things not only diversify income — they deepen the impact.

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The Real Secret? Keep Showing Up.

There were slow months, canceled contracts, hard pivots, and seasons where I questioned whether this path was sustainable. But each time, I focused on what I could control: my skillset, my attitude, and my relationships.

This isn’t a story about getting lucky.

It’s about showing up consistently — for clients, for causes, for community.

If you’re a freelancer or creative trying to find your way, let me encourage you:
Longevity isn’t built in a sprint. It’s earned over time — one project, one pivot, one person at a time.

Thanks for reading. And thank you to every client, student, colleague, and friend who’s helped make this 23-year journey possible.

Let’s keep telling stories that matter.

Photo by Dorie Griggs

One of the strengths I bring to my workshops, especially the intense one-week kind, is discernment. I often see very clearly where someone needs help or correction. It’s not a guess or a vague hunch; it’s a sharp awareness and part of my brain’s workings.

Being on the Autism spectrum, I know that directness often comes with the territory. For me, it’s less about being blunt and more about being efficient, honest, and helpful. If someone is doing something that could be better, I want them to know, because I also want to know when I can grow or improve.

But I’ve learned that this can be hard for others to accept, especially in a condensed, emotionally charged learning environment like a one-week creative workshop, where students are already being stretched in vulnerable ways.

The Challenge: How do I lead with clarity and kindness?

It’s something I continue to wrestle with. I care deeply about my students and want to give them my best. I want them to grow, to see what I see in their work and rise to it. But I also want them to feel safe, seen, and not crushed by my critique.

What I’m Learning (and Relearning) About Communicating with Warmth

Here are a few things I’m putting into practice—and maybe they’ll be helpful for others too, especially those of us who are more naturally wired for truth than tact:

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1. Ask Before Advising

Instead of jumping in with a correction, I’ve started asking:
“Would you like some input on that?” or “Can I offer an observation?”

This slight pause respects their autonomy. It shifts the dynamic from “Here’s what’s wrong” to “I noticed something—would you like to know?”

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2. Affirm What’s Working First

It’s easy to focus on what needs fixing, because that’s often what stands out. But I’m learning to discipline myself to notice and say what’s working.

Example:
“Your use of natural light in this shot is so strong—it feels honest and intentional. There’s one element that’s distracting from that, though. Want to take a look together?”

This frames feedback as refinement, not rejection.

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3. Be Curious, Not Just Correct

Instead of saying, “This doesn’t work,” try:
“I wonder what would happen if you tried this differently?”

This shifts the posture from teacher-as-authority to teacher-as-co-explorer, and that builds trust.

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4. Let Silence Help

Sometimes, my directness is less about what I say and more about how fast I say it. Pausing for a breath or letting a moment sit before speaking helps me better gauge the emotional space. Slowness can be kindness.

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5. Let Students Reflect First

Instead of jumping in with my take, I’ve begun asking:
“How do you feel about this work? Is there anything you wish had turned out differently?”

Students often already sense what needs improving, and saying it themselves gives them ownership and dignity.

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Teaching is Not Just About the Work—It’s About the Person

I’m still learning to hold this tension: giving honest, helpful, transformative feedback, without stripping the humanity out of it. It’s easy to prioritize information over connection, especially in short workshops, where time is tight. But connection is what makes the information stick.

My discernment is not a flaw. My directness is not wrong. They’re strengths. But strengths need refinement, just like the students I’m trying to help.

And maybe that’s the lesson underneath all of this: we’re all learning how to see better, speak better, and love better—even when it’s uncomfortable.

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If you’re someone who also struggles with how to confront or correct others, maybe start with this question:

“What would it feel like for me to hear this?”

Or even better:

“What tone would help me stay open to this feedback?”

Because that’s what we want—for people to stay open, not shut down. To grow, not retreat. And that starts with how we speak.