From Side Hustle to Spotlight: How Branding Photos Helped This Entrepreneur Show Up with Confidence

What does it look like when a woman decides to be seen truly?

For Sharon, founder of Digital Marketing By Design and the kind of entrepreneur who helps other small business owners finally feel confident online, being seen meant more than updating her headshot. It meant showing the world the woman behind the work.

When I met Sharon, I was running a portrait experience called the 40 Over 40. A photography project close to my heart, built around one simple but powerful idea: that women deserve to see themselves the way the world sees them at their best.

So many women carry an image of themselves in their minds that quietly undersells who they actually are. We accumulate years of doubts, of being too busy to look after ourselves, and of putting everyone else first. And somewhere along the way, we stop seeing our own strength.

What I found, over and over again, was that giving a woman the gift of a truly beautiful portrait, one where she looks at it and says “wait… is that really me?” shifted something deep. Not just in how she looked, but in how she carried herself. How she walked into a room. How she believed in what she was capable of.

That moment of recognition, that quiet realization, gives me goosebumps every time.

That’s the world I was living in when Sharon walked into my studio.

Why Branding Photos Matter for Entrepreneurs (Especially Women Over 40)

We live in a digital-first world. Before a potential client reads a single word on your website, they’ve already made a subconscious judgment based on your photo. For women entrepreneurs, particularly those those who often don’t want to be seen, professional branding photos are one of the most powerful investments you can make in your business.

Not stock photos, not a selfie. And no to that photo from a family event three years ago.

Real. Intentional. You.

Research consistently shows that personal branding photography increases trust, improves conversion rates on websites, and helps entrepreneurs attract the clients they actually want to work with. When your photos feel authentically you, your audience feels that and they lean in.

Meet Sharon: Digital Marketing Expert, Business Owner

I started my business so I could build a life with more freedom and ease — one where I could do meaningful work, be creative, and still be present for the moments that matter most. I’m incredibly grateful I found the courage (and had the support) to make that leap.

Today, I get to help small business owners and entrepreneurs show up confidently online through thoughtful website design and digital marketing support. It’s truly been one of the most fulfilling chapters of my life (aside from raising my kids!).

“Every day I quietly celebrate how far I’ve come — the joys and challenges that come with entrepreneurship and everything I’m still building. It’s a reminder of what we’re capable of when we choose courage and step beyond our comfort zones.”

That same intention carries into the work I do for my clients — creating thoughtful online spaces where their businesses can grow with clarity and alignment. 

— Sharon, Digital Marketing By Design

What Is the 40 Over 40 Portrait Experience?

The 40 Over 40 Portrait Experience at Ellahrika Photography (based in Milton, ON) is a luxury, fully guided photoshoot created specifically for women over 40 who are ready to be celebrated not despite their age, but because of it.

This is not your standard headshot session. It’s a transformational experience that doubles as stunning personal branding photography the kind that makes you look and feel completely unstoppable.

Here’s what’s included:

• Pre-session style consultation — we discuss your vision, your brand, and what you want to communicate in your photos
• Professional hair and makeup artistry — you arrive, you’re pampered, you leave looking extraordinary
• Fully guided photoshoot — no awkward posing on your own; you’ll be directed every step of the way
• In-studio reveal session — view and select your favorite images in a private, luxurious reveal experience
• One digital portrait included ($275 value), with the option to purchase additional images and fine art prints

All of this starting at just $399 — a total value of over $800.

What’s the Difference between Branding Photos vs. Glamour Photos: (Do I Need Both)?

Great question and one we hear often.

Branding photos are intentionally crafted to represent you and your business. They communicate your personality, your values, and your professionalism. Photos that live on your website’s About page, your LinkedIn profile, your email newsletters, and your Instagram grid. They say: “This is who I am, and this is what I stand for.”

Glamour photos are about you, full stop. They’re about feeling beautiful, powerful, and celebrated. They’re about feeling beautiful, powerful, and celebrated. Beautifully, they peel back the professional exterior and remind you (and the world) that you are more than your job title

The magic of the 40 Over 40 Portrait Experience? You get both.

Entrepreneurs like Sharon walk away with images they can use across every digital touchpoint and photos that simply make them feel like the incredible women they are.

The Business Case for Investing in Personal Branding Photography

Ultimately, whether you’re a web designer like Sharon, a life coach, a real estate agent, or any other service-based entrepreneur — your face is your brand. Here’s why professional branding photos are a smart business decision:

• First impressions happen in milliseconds. A compelling, professional photo tells potential clients you’re credible, approachable, and worth their time.
• People buy from people. Especially in service industries, clients want to connect with a real human — and great branding photos make that connection immediate.
• Consistency builds trust. Using a cohesive set of professional photos across your website, social media, and marketing materials strengthens your brand identity.
• Confidence is contagious. When your photos reflect how powerful and capable you truly are, you show up differently — in pitches, on sales calls, and in the content you create.

Showing Up for Your Business the Way You Show Up for Your Clients

Sharon’s story is one I see often among the women I photograph. She has spent years pouring her creativity, skill, and heart into helping other business owners look and feel amazing online. And she knows, better than most, how much professional visual presentation matters.

The 40 Over 40 Portrait Experience was Sharon’s moment to receive what she so generously gives to others: the gift of being truly seen and celebrated.

Ready for Your Own Branding Photoshoot in Milton, ON?

If you’re a woman over 40 who is ready to finally have branding photos (and glamour photos!) that match the woman you’ve become, I’d love to have you join the 40 Over 40 Portrait Experience.

My studio is located in Milton, ON, and I serve entrepreneurs, small business owners, and incredible women across the Greater Toronto Area (GTA).

Spaces are limited and they book quickly.

→ Claim Your Spot in the 40 Over 40 Experience

Or book a free 15-minute discovery call at ellahrika.com

About Sharon — Digital Marketing By Design

Sharon is the founder of Digital Marketing By Design, where she helps small business owners and entrepreneurs simplify their digital presence through custom website design, branded marketing materials, and ongoing virtual assistant support. Follow her on Instagram at @digitalmarketing.bydesign.

About Carla — Ellahrika Photography

Carla is a portrait and branding photographer based in Milton, ON, specializing in glamour photography, personal branding sessions, and transformational portrait experiences for women. Her passion is helping women see their own unique beauty and strength — one frame at a time. Learn more at ellahrika.com.