Running a small business is both deeply rewarding and undeniably relentless. From making day-to-day decisions to juggling finances, marketing, and staffing while staying true to their vision, entrepreneurs face no shortage of challenges. Despite this constant pace and ongoing economic uncertainty, small business owners remain remarkably optimistic. In fact, VistaPrint’s 2025 Small Business Happiness Report reveals that they’re not only managing—they’re happy.
According to findings, 81% of small business owners reported being either “somewhat” or “very” happy, and over half say they’re even happier today than when they first opened their doors. Notably, there is a specific “sweet spot” where small business happiness spikes: Business owners with 51 to 100 employees and those who have been in operation for 6 to 10 years report the highest levels of happiness.
What makes this combination such a winning formula? And what can newer or smaller businesses learn from it? The findings reveal key patterns in growth, team dynamics, and long-term planning, offering valuable insights for businesses at any stage seeking to build lasting success and fulfillment.
Growth, But with Stability
Running a small business with 51 to 100 employees is no small feat. It requires scale, structure, and strategic hiring. According to the survey, 68% of owners at this size say they’re “very happy,” far outpacing their peers at smaller team sizes. Just 36% of owners with 1 to 10 employees say the same.
This jump likely comes down to support from staff. At this team size, owners can begin to delegate responsibilities, focus more on vision and strategy, and spend less time wearing every hat in the business. They may also have more resources to invest in tools, training, and culture-building, all of which contribute to a more balanced and fulfilling work life.
Similarly, businesses that have been operating for 6 to 10 years report the highest levels of satisfaction. At this stage, many have weathered the early growing pains, found their rhythm, and established systems that allow for sustainable growth. Of these owners, 60% report being “very happy,” compared to just 38% of those in business for less than three years.
Passion Meets Practicality
While size and tenure are strong indicators of happiness, they’re not the only factors at play. VistaPrint’s research shows that internal, day-to-day elements like having control over one’s schedule, doing meaningful work, and engaging with a loyal customer base matter more than external economic conditions when it comes to happiness.
Owners cited their top sources of joy as: Freedom to set their own schedule (42%), doing something they love or are passionate about (41%), and interacting with customers and the community (30%). This blend of autonomy, passion, and purpose creates a powerful emotional return on investment. It’s not just about running a business. It’s about building a life – and a business – that aligns with one’s values and ambitions.
The Power of Learning and Leadership
Another happiness driver is continued learning. Nearly three-quarters of small business owners (73%) said that acquiring new skills contributes to their overall fulfillment.
Whether it’s mastering financial management, refining a marketing strategy, or streamlining operations, entrepreneurs are eager to evolve. This appetite for self-improvement often marks the difference between a good business and a great one – and between a stressed-out founder and a confident, empowered leader.
This drive to learn doesn’t fade with time. Many of the happiest business owners have been in the game for years, continually seeking new ways to adapt and improve, which is proof that curiosity is a long-term asset in entrepreneurship.
Rooted in Relationships
Beyond team size or years in business, one of the most consistent sources of happiness for small business owners is connection—30% say that engaging with customers and their community brings them joy.
These relationships go deeper than transactions. They offer a sense of belonging, purpose, and shared momentum. Whether it’s a loyal customer who roots for your success, a neighboring shop owner who offers advice, or an online community that celebrates your wins, these connections make the journey less lonely and a lot more meaningful.
Entrepreneurship can be isolating, especially in the early days. However, finding your people, whether they’re down the block or in your direct messages, can be the difference between burnout and lasting motivation. Community doesn’t just support your business. It fuels the heart behind it.
A Blueprint for Sustainable Joy
So, what can emerging entrepreneurs take away from all of this? The “sweet spot” of small business happiness, 51 to 100 employees, 6 to 10 years in business, isn’t just a milestone. It’s a mindset.
It’s about growing intentionally, not just quickly. Building a team that shares your vision. Developing systems that give you room to breathe. And leaning on tools, partners, and communities that help you thrive, not just survive.
Joy is more sustainable when it’s baked into the culture from the start. That means defining what success looks like on your terms. Not just in terms of revenue, but in freedom, balance, and purpose.
Erin Shea is the Senior Director of North America Marketing at VistaPrint, the print and design partner to millions of small businesses around the world. VistaPrint helps small business owners bring their ideas to life through custom print products, easy-to-use digital tools, and expert design support.
Photo courtesy Getty Images for Unsplash+
