We recently connected with Jocelyn Phillips and have shared our conversation below.

Jocelyn, thanks for taking the time to share your stories with us today Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?

Yes, I have absolutely been able to earn a full-time living as a solo entrepreneur and I love that the sky is the limit for how far I take this business. Working for others I always felt like my potential was “capped”, like I could only go so far and make so much money.

How did I make it happen? The first step was simply making the brave decision to just start. As a self proclaimed perfectionist, starting for me meant building the perfect website and making everything “look” like I new what I was doing. This was my first mistake. You see, I originally planned to launch my business as a wedding photographer. This is where I was told the money was. I had only shot a couple of small weddings (both of which I hated by the way!), but I was determined to follow the money. I spend months “building” my business behind the scenes without actually working with any clients. After listing my business on Wedding Wire, I got a couple inquiries from brides. “Yay, it’s happening!” I thought. It took one conversation with one bride to realize I’d made a huge mistake. I didn’t want to work with brides, I didn’t want to shoot weddings. WTF was I going to do.

Feeling very discouraged I leaned on my husband for support and he asked me one very simple question. “Do you even like photography?”. I remember feeling so insulted. Of course I loved photography! It’s what I wanted to be doing for a living. He gave me the best advice and said, “Go do it then. Take photos of everyone and everything until you find what clicks” No pun intended. LOL

So that’s what I did. The next day I went on Instagram and searched my area for people who had a bigger following — I guess influencers, but I didn’t know to call them that at the time – and I sent DMs offering free photoshoots to help build my portfolio. For the next couple of months I did a bunch of free sessions, a couple that turned into paid sessions after that and then one day. It happened. I found my calling.

I was doing a family photoshoot and at the end of the shoot, the mom asked if I could do a few photos of her solo so she could use them for her online coaching business. It only took a couple clicks of my camera before I knew THIS is what I’m meant to be doing.

My clarity came from taking action.

At first, it was just about the photos—creating beautiful images that captured moments and personalities. But I quickly realized I had a talent for understanding people’s visions and strategizing how to bring them to life. That’s when I shifted gears, focusing on helping entrepreneurs not just look polished but actually create brands that feel authentic and work for their businesses.

I’ve been able to grow my business into something that not only supports me financially, but a business I truly love by blending strategy, artistry, and a deep understanding of what my clients need to succeed.

Building this career meant embracing risk, constantly learning, and always looking for ways to provide more value to my clients. I’ve evolved my offerings into a mix of consulting, photography, and resources to meet entrepreneurs wherever they are in their branding journey.

Major steps and milestones:
– Pivoting from photography as a service to offering holistic branding solutions that combine strategy and visuals.
– Embracing social media, not just to market my own business but to understand how to simplify it for my clients.
– Refining my process to focus on ROI-driven strategies, ensuring my clients see measurable results from their investments.

Do you think you could have sped up the process somehow knowing what you know now?
Absolutely. If I could go back, I would do less planning and perfecting and just take more action. So many entrepreneurs want to get all their “ducks in a row” before putting themselves out there, but like I said, clarity comes from taking action. I love working with clients after they have been in business for a year or so and helping them to refine and elevate their brand at that stage. You just know more about the clients you really want to be working with, how you want to be showing up and what kind of offers make sense for your audience.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I graduated from College with a photography diploma in 2006, but didn’t make this my full time career until 2019. My career path led me through various industries including finance and non-profits until I finally made the decision to work for myself. My entrepreneurial journey began with a passion for storytelling through photography, but over time, I realized my true calling wasn’t just creating beautiful images—it was helping people turn their visions into brands that truly work.

What I Do:
I simplify the process of building personal brands that feel authentic, aligned, and impactful.

My offerings include:
– Personal Brand Consulting: Tailored experiences like the Personal Brand Identity & Direction Day, Instagram Brand Audits, and Marketing Your Brand Days, designed to give entrepreneurs clarity, direction, and practical tools to execute their vision.
– Brand Photography: More than just pretty pictures, my sessions are rooted in strategy, ensuring your visuals tell a cohesive story and deliver a real return on investment.
– DIY Brand Toolkit (Launching in 2025): Self-paced courses, workbooks, and resources to empower entrepreneurs to build and execute their brands at their own pace.

Problems I Solve:
I work with entrepreneurs who feel overwhelmed by the branding process or stuck when it comes to making their online presence reflect the quality of their work. They may struggle with social media, feel disconnected from their brand, or just don’t know where to start. My goal is to take the stress and guesswork out of branding, giving my clients a clear path to creating brands that feel like them and attract the right audience.

What Sets Me Apart:
I’m not here to push my agenda or impose my idea of a “great brand.” I get on your team, understand your vision, and work alongside you to create something uniquely yours. My process is rooted in strategy but delivered with warmth and fun. Branding doesn’t have to be hard, and selling doesn’t have to feel icky. When your brand feels authentic and aligned, marketing becomes effortless—and that’s the magic I help my clients unlock.

What I’m Most Proud Of:
I’m proud of the ripple effect my work creates. When I help an entrepreneur succeed in their business, I know they’ll go on to make an impact on the people they’re meant to serve. That’s my “why.” It’s incredibly fulfilling to know that I’m not just helping people build brands—I’m empowering them to pursue their passions, create meaningful connections, and thrive.

What I Want You to Know:
Your brand is more than just aesthetics—it’s about creating something that represents the soul of your business. My mission is to make branding simple, sustainable, and impactful, so you can focus on the work you love and the people who need you.

Has your business ever had a near-death moment? Would you mind sharing the story?

Adjusting to life as a new mom while trying to keep my business running felt like a constant battle. I was exhausted, overwhelmed, and questioning if I could even do it all. My client pipeline had slowed down, and I worried about whether my business could sustain itself.

Looking back, I wish I’d prepared more intentionally for that season, both financially and in terms of systems. My advice to other business owners planning for maternity leave—or any extended break—is to start early. Financially, build a buffer to give yourself peace of mind during the time you’re away. On the systems side, automate whatever you can. Set up workflows, email sequences, and content plans so your business doesn’t come to a halt when you step away.

And don’t be afraid to communicate with your clients. When I finally reached out to my network, I found so much support and understanding. People were more than willing to work with my timeline, and that transparency helped rebuild trust and momentum.

That experience taught me a lot about balance, boundaries, and the importance of preparation. It also showed me the value of being transparent and authentic in my business. Now, I use that perspective to help my clients navigate their own challenges—whether it’s finding their footing after a big life change or creating a brand that can weather whatever comes their way.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

Perfection doesn’t equal progress.

Growing up, I was the definition of a perfectionist. I was a straight-A student, constantly competing with my sister for who could get the better grade. For me, perfection wasn’t just about achieving—it was a safety mechanism. After losing my father suddenly at a young age, I learned to prepare for every outcome, thinking if I could control everything, I could avoid the worst.

That mindset followed me into my business. I agonized over every detail, convinced that everything I put out had to be flawless to be successful. I was so focused on getting things “right” that I often hesitated to take action at all. But over time, I started to see something important: it wasn’t the perfect, polished plans that moved my business forward—it was the messy, imperfect action.

The more I leaned into this truth, the more momentum I built. Each time I launched something before I felt ready or posted content that wasn’t perfect, I saw results. Clients resonated with the message. Opportunities came my way. And most importantly, I realized that progress—even when it felt messy—was far more powerful than standing still.

Letting go of perfectionism has been one of the hardest but most liberating lessons I’ve learned. It’s shown me that success isn’t about being perfect; it’s about being consistent, authentic, and willing to try. Now, I remind my clients that branding, marketing, and building a business are all iterative processes. The goal isn’t to have everything figured out from day one—it’s to take intentional steps forward and refine as you go. Because when you focus on progress, you’re always moving closer to your goals, and that momentum is what truly drives success.

Contact Info:

• Website: https://www.jocelynphillips.com/
• Instagram: https://www.instagram.com/jocelynphillipsbranding/

Image Credits

Liz Salzman took the photos of me. All the others are examples of my own work.