During lunch with my friend and client Linda Holstein — writer for Twin Cities Business magazine, mediation lawyer, and owner of Holstein Mediation — our discussion shifted to marketing, branding, self-promotion, and bragging. Linda, a confident businesswoman who is an avid cheerleader for those in her circle, offered valuable food for thought. Olio e Più, a gorgeous spot serving authentic Italian cuisine in downtown Chicago, made the perfect backdrop for this discussion. 

Small Business Owners Need to Brag. It’s the Key to Growth and Success

Marketing, branding, self-promotion, and bragging actually have quite similar meanings for business owners. While all these terms share a similar purpose, the word bragging carries a particularly negative social connotation. 

Many small business owners hesitate to step in front of their audience. Whether it’s from a desire to stay humble or a fear being viewed as boastful, keeping quiet actually hinders growth. It becomes a blanket where a business stays hidden from their potential audience (and future clients.) 

I’m here to cheer you on and tell you that it’s okay and necessary for small business owners to “brag” — or, more accurately, practice thoughtful and authentic self-promotion. Why?

1. Bragging Builds Your Brand

In a crowded marketplace, visibility is crucial. Sharing your wins helps shape your business’s identity and differentiates you from competitors. Clients are drawn to success stories because they build trust and credibility. By openly discussing achievements — whether it’s a new product launch, a big partnership, or a glowing customer review — you create a memorable narrative that attracts attention.

When you couple those successes with customized brand-specific photography it only enhances your brags. The more your audience sees your face, the more they come to know, like, and trust you. It’s like a new song. The more you hear it, the more it sticks in your head and the more you like it.

Tip: Share your milestones on social media and in newsletters. A post celebrating your 1,000th customer or a positive feature in a local newspaper engages those in your circle and attracts new people.

2. Self-Promotion Attracts new Clients

People want to buy from businesses they trust. One way to establish that trust is by demonstrating competence and reliability. Bragging — when done with thought and authenticity — showcases your expertise and the value you bring. Highlighting awards, certifications, or positive outcomes lets potential customers see the real benefits of choosing your business.

Example: Imagine you’re a bakery owner. Sharing that your cakes won a local contest or that your bakery was named “Best in Chicago” makes people want to check it out for themselves. Even better, get their lips smacking beforehand with a photo of those cakes and/or you decorating them. Photography carries so much information (and social proof) enticing busy people to stop their scroll.

3. Bragging Inspires Community Support

Small businesses thrive on community engagement and the power that comes from client referrals. Sharing your success can inspire others to root for you. People love supporting local business owners who are passionate about their work and excited to share their journeys. Bragging isn’t just about promotion — it’s about creating connections and sparking pride within your audience.

Tip: Use storytelling to show the human side of your business. Show photos of the hard work that went into your latest success and how your community contributed to it.

4. Bragging Positions You as a Leader

When you openly discuss your accomplishments, others will view you as a knowledgeable and innovative leader in your industry. This visibility can lead to new partnerships, media coverage, and speaking opportunities. As a small business owner, your personal story is usually intertwined with your brand. Sharing your journey elevates both your business and your professional profile.

Example: A landscaper who shares tips along with examples of their award-winning projects is more likely to be seen as an expert — and gain more referrals.

Don’t forget: YOU are part of your story. Your audience wants to see your face. Do a test and see it for yourself. When you post an image of yourself, how much more engagement do you receive? (I can help you out here! Humble brag: I’m really good at finding the beautiful spark that is within everyone…yes, YOU too. The beautiful spark comes from that authentic moment where you drop your guard and are your gorgeous self.)

5. If You Don’t Brag, Who Will?

Big corporations have entire teams who work on marketing and public relations to promote their successes. Small businesses, often working with tighter budgets, can’t afford to stay silent. You are your own biggest advocate. Sharing your achievements strategically and authentically ensures that people hear about the great work you’re doing.

As a fellow local business owner, I’ve got your back. I will help make bragging easier for you.

I can help you in multiple ways.

1. Use the power of your phone to create stunning imagery for your social media

Your phone has such power. Many of my personal photos are taken with my phone. It’s so much more portable than my big camera and it’s always there. As a former art teacher, I love to work with individuals, small teams, and groups of friends to elevate their own Phone-tography skills through 2 hour workshops.

2. Try out a Branding Blitz or Brand Essentials Portrait Session.

These are quick sessions personalized to you. You’ll complete a questionnaire beforehand. I’ll send you a look book and a number of preparation guides beforehand so that we maximize that time. You walk away with 3 stunning portraits with the option (and zero-pressure) to purchase additional images.

Branding Blitz sessions take place in gorgeous studio spaces throughout the city. I change up the locations to keep your photos looking unique. Learn more here.

Branding Essentials sessions take place in a location customized for you. Learn more here.

3. Dive all in with a Brand Builder Photography Session.

This is where I’ll get to know your brand as if it were my new best friend. We’ll start with a strategic plan created through a detailed questionnaire, phone calls, and my research. It’ll result in a personality-filled visual library of stunning imagery that includes images of the people, personalities, products, workspaces, process, behind-the-scenes, and/or any future promotions. We can also add some video, gifs, time-lapse video and animations to your session. Each Brand Builder is custom designed for you, with your thoughts and voices being crucial to the planning process.

What is your personal or business brag right now?

Send me a note and tell me about it. I’d love to cheer you on.

**Featured image for this blog post was created as part of a Brand Builder session for Introspective Family Therapy. They are a heartfelt therapy practice on Chicago’s Northside serving children, adolescents, and adults in individual and group settings. The owner, Anviksha Kalscheur is committed to caring for her team of therapists, knowing that creating that healthy environment will also enhance the therapy services delivered to their diverse clientele. I highly recommend checking them out if you are in search of a therapist.