BRYAN & SHANNON MILES: Leading Through Change and Loneliness
Mar 12, 2025
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Bryan and Shannon Miles reveal the real challenges of entrepreneurship, including the loneliness that often accompanies leadership roles. They discuss the importance of prioritizing relationships while navigating the complexities of business and family life. With insights on decision-making, they emphasize finding balance and creativity by learning to say no. The couple shares valuable experiences from their journey in founding Belay and highlights the significance of mentorship and community in overcoming feelings of isolation as business owners.
Effective communication during organizational changes is crucial for leaders to ensure employee engagement and morale throughout transitions.
Business owners must prioritize saying no to maintain focus on core priorities, preventing overwhelm and burnout from overcommitment.
The loneliness and isolation experienced by business owners highlight the need for open dialogues to foster connection and empathy within the workplace.
Deep dives
Communicating Change Effectively
Effective communication is essential for business owners and leaders when implementing changes within their organizations. Leaders must frame these adjustments from the employees' perspectives to ensure understanding and acceptance. By addressing how changes impact their roles, employees are more likely to stay engaged and supportive of the shifts. This type of communication not only fosters a sense of security but also enhances overall morale during transitional periods.
Learning to Say No
Business owners must learn the importance of saying no to prevent overwhelm and maintain focus on their core priorities. Initially, it is common to say yes to many opportunities in search of growth; however, this can lead to burnout and reduced effectiveness. By adopting a more selective approach and evaluating each opportunity against their long-term goals, leaders can safeguard their time and energy. Setting clear boundaries allows for greater clarity in decision-making and helps maintain personal well-being.
The Loneliness of Leadership
Business owners often face feelings of loneliness and isolation due to the unique burdens of their roles. They experience stress and responsibility that employees may not recognize, leading to a disconnect in understanding. This highlights the need for open dialogue between business owners and employees to foster empathy and connection. Encouraging a culture where business leaders can share their struggles can help bridge this divide and create a more cohesive work environment.
Navigating Growth and Complexity
Rapid business growth can lead to complexities that are difficult to manage, as witnessed by established companies when they expand too quickly. Leaders need to evaluate their operational structures and adapt as necessary to maintain efficiency and effectiveness. This might involve consolidating multiple entities or rethinking strategies that once proved successful. Embracing adaptability is crucial for long-term sustainability and can prevent organizational stagnation.
The Role of Mentorship in Business
Mentorship plays a vital role in nurturing future business leaders and fostering a supportive environment for growth. Establishing platforms like Owner allows business owners to share their experiences and provide guidance to those facing challenges. This exchange of knowledge helps create a community where entrepreneurs can openly discuss the complexities of ownership and leadership. By valuing these relationships, business owners can cultivate a thriving ecosystem that benefits all members.
Entrepreneurship promises freedom—but it also comes with a unique set of challenges that many don’t talk about. In this episode, The Double Win Show welcomes Bryan and Shannon Miles, co-founders of Belay and the nonprofit O’nr, to pull back the curtain on what it really takes to build a thriving business without losing yourself in the process.
From hiring their first virtual assistant in 2011 (who later became CEO!) to navigating the emotional weight of selling a business, Bryan and Shannon share their hard-won lessons on leadership, transitions, and making decisions that align with your values.
Memorable Quotes
“Here’s the magic phrase: ‘In order to be faithful to my existing commitments, I have to say no.’”
“I am responsible for myself and my leadership. And I know that if I extend myself too far, I’m not the best version of who I want to be.”
“If I’m saying yes to everything and I’m overcommitting and my schedule is absolutely full, there’s no space for creativity. There’s no space for dreaming. There’s no space for new ideas or realizations.”
“A lot of business owners are lonely, actually isolated.”
“As leaders, part of our job is just kind of to help people settle and know they’re safe.”
“Stewardship is just simply managing something for a season of time… While we’re there with our employees and leaders, we’re stewarding our relationships with them.”
Key Takeaways
The Loneliness of Leadership. If you’re feeling isolated as a business owner, there’s good news: You’re not the only one.
The Skill of Saying No. Implement this mental shift to help you stop overcommitting without the guilt.
Getting Buy-In For Change. What leaders get wrong when making major business changes—and what to do to help your team ride the wave.
Living Your Priorities Today. Why Bryan and Shannon took a vacation nine months after starting a business—and the opportunity that followed.
The Operator/Owner Difference. Are you owning a business or trapped in it?