Small Business Happiness in 2025: Erin Shea of VistaPrint on Freedom, Fulfillment & the Future

1. Given that independence and passion are more valued than income predictability, how should organizations rethink their support models for small businesses? 

We often hear about the importance of financial stability and access to capital. Those factors, no doubt, contribute to a small business's success, but new research from VistaPrint reveals that small business owners (SBOs) are influenced by so much more. According to findings, internal factors - think independence, passion and community - drive SBO happiness today. SBOs rank “freedom to set my own schedule” (42%), “doing something I love or am passionate about” (41%) and “interacting with people, customers or society” (30%) as the top 3 things they enjoy most about being an entrepreneur. Not to mention, over half of SBOs are “much” or “somewhat” happier now compared to when they first opened their business. These takeaways recognize the vitality of America’s entrepreneurial spirit and power of looking inward, especially when times are tough.  

From VistaPrint’s perspective, it’s important to advocate for that mindset with products, services and resources that support SBO’s journey at any stage. When you enable that freedom, you fuel fulfillment.

SBOs aren’t just looking for tools. They’re looking for partners, especially when the stakes are personal. The best partners help SBOs feel more capable and in control, not more burdened. For example, offering great products, assisting with real-time customer support, and providing thoughtful resources for the moments in between. In VistaPrint’s case, this means helping SBOs design and print marketing materials that stand out and resonate with customers, from logo design and packaging to promotional items. 

Long-term well-being starts with trust. That trust is earned when partners show up consistently and understand the needs of the SBO – something VistaPrint has worked hard to achieve over the past 25 years.

It’s important to note that SBOs of all sizes report high levels of happiness. We think that reflects the pride millions of entrepreneurs take in shaping their own future. That said, satisfaction at scale might come from capacity – having enough help, time, and margin to focus on what matters. For micro-businesses, the pressure to wear all the hats can be a strain, especially when they’re just starting out.Prioritization and time management are crucial at this stage. Align your to-do list to your strengths and don't be afraid to seek out tools or resources that can extend capacity whether it’s automating repeatable tasks, outsourcing selectively, or tapping into peer networks for shared knowledge and support. By building these practices early, even the smallest teams can unlock more joy and long-term satisfaction.

Gen Z SBOs are redefining what leadership looks like. Their approach to entrepreneurship is deeply values-driven, tech-forward, and adaptive by design. According to our findings, they’re also the happiest generation, with 54% of Gen Z SBOs saying they’re currently “very happy”—higher than any other age group. This sets a strong foundation for future-facing businesses. As Gen Zers get more comfortable with business ownership, it’s possible we’ll see flatter hierarchies, increased transparency, and businesses that prioritize flexibility and experimentation. These shifts could spur more resilient models – ones that are not only innovative but also emotionally intelligent.

Organizations have a unique opportunity to position themselves as both enablers and protectors of the human connections SBOs care most about. VistaPrint’s research shows us that SBOs, today, prefer using AI primarily for routine or repetitive tasks. For example, 39% of SBOs said they prefer AI for audience targeting and design/content creation. These are areas where speed and efficiency often come into play. But when it comes to strategy and storytelling, the human element still matters deeply. Nearly half (48%) of SBOs say they prefer a human touch for strategy and planning and 43% still lean on people for campaign execution. That creates a clear opportunity: preserve the human touch in the moments that define a brand. The most valuable tools will be those that free up time—without stripping away the connection that makes small businesses special.

 

We need to listen to what they’re saying. Today, 81% of SBOs report being “somewhat” or “very” happy, despite macroeconomic uncertainty. This is quantifiable proof that mindset and passion are an SBO's superpower, especially during challenging times. It’s not always about scaling. It’s about staying true to your mission, building strong communities, and finding personal fulfillment along the way.  

 

This group also values upskilling. Overall, 73% say “continued learning” is one of the things they enjoy most about being an SBO, with technology/innovation (66%) and marketing management (66%) ranking as the topics of most interest. While every SBO’s path to happiness is different, they’re telling us they’re willing to put in the work to persevere.