You’ve been running your own business for a while now—so long, in fact, that the idea of being someone else’s employee feels completely foreign. You’ve chosen a path filled with responsibility: growing your company, providing employment for others, and carrying the vision forward every single day. You understand that as an entrepreneur, you’re never really “off.” Sick days aren’t really a thing, and the weight of leadership is always present.
And you love it. You wouldn’t have it any other way.
But let’s be real: it can get lonely.
Entrepreneurship loneliness is a reality most founders don’t talk about enough. Sure, the gains are worth it, and the freedom is powerful—but that doesn’t make it easy. Over the years, I’ve learned how to stay energized, motivated, and connected, even during the most isolating seasons. Here are three key things that have made a difference for me:
Join an Executive or Entrepreneur Think Tank
One of the best decisions I made was to join an executive peer group—a network of entrepreneurs who meet monthly to check in, share challenges, and help each other stay grounded. We don’t jump in to “fix” each other’s problems. Instead, we approach with curiosity and strategic thinking, helping each other regain clarity and perspective.
The second half of each session typically involves a deeper dive into a topic chosen by the group’s facilitator, sparking rich conversations that push us to grow.
Even though we’re in different industries, the support is real—and it reminds me that I’m not alone, and I’m definitely not crazy for choosing this path. Regularly engaging with other founders helps normalize the ups and downs of leadership.
Align With Organizations That Share Your Values
Connection doesn’t always have to come from business strategy groups. Some of the most energizing relationships I’ve built have come from mission-aligned organizati
ons. I have a passion for empowering Canadian business owners—especially women—to feel confident in their finances. Supporting initiatives like the Her Wealth Summit as a community sponsor keeps me connected to that deeper “why.”
When you surround yourself with others who believe in what you believe, it becomes a source of strength. As Simon Sinek writes in Start with Why, knowing your purpose gives meaning to the grind. It reminds you why you’re choosing this path, even when it feels daunting.
Schedule “Human Time” Like It’s a Business Priority
This one’s simple but essential: treat social time like a meeting you can’t cancel. Schedule it and block it in your calendar; in pen! It can be a weekly coffee with a friend, a walk-and-talk phone call, or a hobby group you actually enjoy. Your brain and your nervous system need space to breathe, and isolation will sneak up on you if you’re not intentional. For me, this human time incudes motorcycle rides with my husband, hosting dinner parties at home, brunch with a girlfriend and hanging around the lobby after Sunday’s church service to catch up with everyone there. Find people and activities that fill your cup.
You’re not just a business owner—you’re a human first. Protect your connection to joy, rest, and community.
Final Thoughts: You’re Not Doing It Wrong
If you’re experiencing entrepreneurship loneliness, it doesn’t mean you’re failing. It means you’re doing something bold—something most won’t attempt. But that doesn’t mean you have to go at it alone. Two good books that I would recommend to build out this topic and learning would be Together by Vivek Murthy, M.D. and (if you are already experiencing high stress levels) Burnout by Emily Nagoski, PhD and Amelia Nagoski, DMA.
Build your circle. Anchor to your purpose. And remember, even though the journey is yours, you don’t have to walk it in isolation.
May you be empowered;
To learn more about specific tips and tricks for your company, contact Shanalisa!
Shanalisa Keller is a CPA, CGA and Coactive Trained Coach who founded and leads the team at Canadian Finance Gal. She has a desire to make personal and business finances less daunting and confusing. She loves accounting and tax and wears the respective geek label with pride. When Shanalisa is not counting beans you can find her mixing a fun new cocktail or building a tasty charcuterie board. You can read her other blogs on various small business topics here, book a chat or coffee or wine with her here, or you can find her on LinkedIn (her favourite social platform).