Combating Entrepreneurial Loneliness with the Power of Community

By Kimberli Davino-Wilson

One of the biggest struggles I didn’t anticipate when stepping into entrepreneurship was loneliness. I don’t think many of us do. We get swept up in the excitement of starting something new, often so different from anything we’ve done before. Entrepreneurship is glorified as a path to freedom and success—which, don’t get me wrong, it absolutely can be—but what’s rarely talked about is the loneliness that comes with building something on your own.

I’ve felt that loneliness for years now. Even with a full schedule and amazing clients, I assumed staying busy would fill the void, but if I’m being honest, it really hasn’t.

The Isolation of Entrepreneurship

For many, their business journey starts solo. Whether you’re freelancing, launching a small business, or developing a personal brand, chances are you’re doing it on your own. Even as the business grows, some choose to remain a “team of one,” managing everything from marketing to client relations without bringing others on board. While this can offer control and flexibility, it also means facing the unique challenges of entrepreneurship alone, which can be isolating and, at times, overwhelming.

The long hours are one of the first signs of entrepreneurial isolation. The desire to see your vision come to life often means sacrificing weekends, evenings, and even social events. You may find yourself missing out on gatherings with friends and family because there’s always more work to be done, or because your schedule operates on a different rhythm than those around you. Your passion and dedication may be high, but it can be frustrating when others don’t understand why you’re “always working” or how exhausting the entrepreneurial grind can be.

Those who don’t run their own businesses may not fully grasp the loneliness or the mental and emotional toll of building something from scratch. They see the flexibility and freedom but don’t always recognize the late nights, uncertainty, or the pressure you carry on your shoulders every day. The sense of isolation deepens when you lack a support network of like-minded individuals who understand your challenges, celebrate your wins, and offer insights into your struggles.

This absence of community can make the highs feel less thrilling and the lows feel well, pretty low. Without others to share the journey with—whether it’s brainstorming solutions, discussing the frustrations of a tough client, or simply venting about the unpredictability of business ownership—you can start to feel like you’re drowning. It’s hard to maintain excitement when you’re carrying the weight of entrepreneurship alone. Having people around you who understand the ups and downs makes a world of difference, but without that support, loneliness can quickly creep in.

Why Having a Community is Crucial

Having a community is crucial not just for overcoming that loneliness feeling but for overall well-being and success. Building a business often feels like an uphill battle, and without a support system in place, that journey can feel even harder. Whether in-person or virtual, a community provides a space where you can find encouragement, accountability, and shared experiences—all crucial elements to keep you motivated and grounded.

One of the greatest benefits of community is having people who truly “get it.” These are individuals who understand the unique challenges of entrepreneurship—the highs, the lows, the long hours, and the constant balancing act. Unlike friends or family who may not fully grasp what it’s like to build and grow a business, a community is made up of people who have walked in your shoes or are currently walking alongside you. They can cheer you on when things are going well and offer support when the road gets tough. This shared experience creates a level of understanding and empathy that’s hard to find elsewhere.

Having a community can also provide accountability. When you’re working solo, it can be easy to lose focus or become overwhelmed by the amount of tasks at hand. But when you’re surrounded by like-minded people, you have a built-in support system that can help keep you on track. Whether it’s through regular check-ins, goal-setting, or sharing resources, a community holds you accountable in a way that helps you stay motivated and committed to your vision.

It’s also important to recognize that while clients can become friends, there’s usually a boundary that separates the business relationship from personal connections. With clients, there’s still a professional line that’s rarely crossed, no matter how friendly the dynamic. But within a community, we are able to blur those boundaries a bit more, allowing for more open and honest conversations. You can talk about anything—whether it’s business-related or not—without feeling restricted by the professional nature of your relationship. This freedom to be yourself, share your struggles, and express your frustrations without fear of judgment is incredibly freeing.

In many ways, a community becomes your sounding board. It’s the place where you can vent your frustrations, bounce ideas around, and share both the big wins and the small victories that others outside the entrepreneurial world might not fully appreciate. You have a safe space to express the worries or doubts that come with building a business, and in return, you receive comfort and validation from those who understand exactly what you’re going through. The comfort and support make having a community so crucial—not only do you feel less alone, but you also gain a sense of belonging.

Ultimately, being part of a community offers the chance to build genuine connections with people who share your values, goals, and challenges. It’s a reminder that even though entrepreneurship can be isolating, you don’t have to go through it alone.

Honestly, in the community spaces I’ve joined and surrounded myself with, I’ve found friendships that go beyond business. We lift each other up on those tough days and cheer each other on for every win. These connections have helped me grow not just as a business owner but as a person. Without my community and the connections I have made, I don’t think I would be the person I am today. Actually, I don’t even think I would still be running a business.

How to Find or Build a Community.

I truly believe community is key to feeling connected and supported on your business journey. But how do you go about doing that?

1. Start Local: In-Person Communities

Local business communities can be a great place to start. Many cities and towns have networking events, co-working spaces, or business meetups where entrepreneurs can gather. These events provide not only a chance to grow your network but also to meet people who understand entrepreneurial life firsthand and have the face-to-face contact that so many crave.

• Attend local business meetups: Look for small business associations, Chamber of Commerce events, or industry-specific gatherings in your area. These groups often host events where you can meet like-minded entrepreneurs and form connections.
• Explore co-working spaces: Co-working spaces are great not only for working but also for meeting other business owners. Many of these spaces hold events, workshops, or casual meetups, making it easier to connect with others.
• Attend networking events: Whether it’s formal conferences, casual mixers, or niche-focused gatherings, networking events are a fantastic way to meet other entrepreneurs and build relationships. They provide an opportunity to learn from others, share your experiences, and form valuable business connections.

2. Go Virtual: Online Communities

If local groups aren’t accessible or don’t fit your schedule, virtual communities are an incredible option. The beauty of online spaces is that they can connect you with people all over the world who share your entrepreneurial spirit and goals.

• Join entrepreneur groups on social media: Platforms like Facebook, LinkedIn, and even Instagram have countless groups specifically for entrepreneurs. Look for communities that align with your values and goals, and participate actively by sharing advice, asking questions, and engaging with others.
• Participate in online forums: Websites like Reddit, Slack, and specialized forums often host active discussions where entrepreneurs can share resources, ask for help, and find support. Many communities on Slack are organized around shared interests, industries, or goals. Search for whatever meets your needs.
• Consider paid subscription communities: Paid communities offer more dedicated and focused environments for entrepreneurs. These communities often provide added benefits, such as exclusive content, regular events, group discussions, and personalized mentorship. Because members pay to be part of the community, there tends to be a higher level of engagement, commitment, and value shared among participants. Subscription communities also offer a more intimate, curated experience and can be particularly helpful if you’re looking for deep connections with people who are invested in growth.

3. Build Your Own Community

If you’re not finding the right community, consider building one. Starting a community allows you to create a space tailored to your needs and invite others who are on similar paths. Whether it’s a small mastermind, an accountability group, or even a regular coffee meetup, creating your own group can be empowering and rewarding.

• Start small with a mastermind or accountability group: If you have a few entrepreneur friends, invite them to join you in a mastermind or accountability group. These groups can meet regularly (in person or virtually) to share progress, provide support, and hold each other accountable.
• Create a virtual space: Platforms like Facebook, Discord, or Slack make it easy to set up a group where people can come together, chat, share resources, and stay connected. You can focus on a specific niche or goal, like a community for women in business, neurodivergent entrepreneurs, or product-based business owners.
• Host regular meetups: If you enjoy in-person interaction, start hosting your own events. You could hold monthly coffee chats, work sessions, or networking events where local (or even those willing to travel) entrepreneurs can meet, connect, and share insights. It doesn’t have to be a big event—sometimes, the best communities are small and intimate.

4. Be Intentional and Active

Whether you’re joining or building a community, it’s important to be intentional about your involvement. Community isn’t just about finding a group—it’s about participating, contributing, and investing in relationships. Take the time to actively engage with your community. Offer advice, share your wins and struggles, and encourage others in their journeys. The more you show up, the more you’ll get out of the experience.

You Don’t Have to Go at it Alone!

Entrepreneurship may be a solo journey in many ways, but that doesn’t mean you have to face it all by yourself. In fact, you shouldn’t. I know many try to glamorize doing it all on their own, but in reality, building and running a business can be incredibly isolating if you don’t have a support system in place. The good news is, you don’t have to go at it alone.

• Find your strength in having a community by your side. That isolated feeling truly does melt away once you know you have a group of individuals behind you.
• Combat loneliness with having a community by your side. You won’t feel so lonely once you find your group of individuals who get it, who understand what you are dealing with, and who are there to not only talk about the hard but celebrate the good with you, too.
• Find that accountability and support by having a community by your side. You don’t need to get lost in the day-to-day craziness of running a business. Having a community can and will help you stay on track when you feel like you are about to lose your mind.

The journey of entrepreneurship is challenging, but it’s also rewarding. And when you surround yourself with people who understand your struggles, share in your excitement, and support you through the ups and downs, you’ll find it easier to keep moving forward, even when the road gets tough.

So, no matter where you are on your entrepreneurial path, remember this: You don’t have to go at it alone. Find your people, build your community, and let them remind you that you’re part of something bigger than yourself.

Are you feeling the weight of entrepreneurship? You’re not alone! Please reach out, and let’s connect!

You can follow Kimberli on Instagram, read her personal blog on Substack, or join her Magic Makers Community!