The Loneliness of Leadership: Founders, You're Not Alone

In this episode of The Ross Simmonds Show, Ross ​dives deep into a topic that many leaders shy away from: the loneliness of leadership. He opens up about his experiences as a solo founder, the mental and emotional burden that comes with leading organizations, and how success can bring unexpected isolation. More importantly, Ross offers practical and powerful advice on how leaders can build resilience, create support systems, and avoid common traps that lead to burnout and self-doubt.

If you’ve ever felt alone at the top, this is the reminder you didn’t know you needed.

Key Takeaways and Insights:

1. The Quiet Weight of Foundership

• Leadership is often glamorized from the outside, but behind closed doors, it can be emotionally and mentally taxing.

• Founders are expected to always be “on” — delivering, solving, and showing up, even during personal lows.

• “Being a founder is a gift, but it’s also one of the loneliest jobs.”

2. What Makes Leadership So Isolating

• It’s not physical solitude, but the responsibility that isolates leaders.

• You make decisions that shape careers — sometimes lives — and often have no one to share the burden with.

3. The Trap of Self-Containment

• One of the biggest mistakes is trying to carry everything alone.

• Delegating responsibility and building trust with team members can alleviate this loneliness.

4. Four Reasons Leaders Feel Isolated

• 🧠 Information Asymmetry 

1. Leaders have a different view of company data, performance, and risks.

2. Transparency can reduce the burden and build empathy.

• ❤️ Emotional Labor

1. Leaders are expected to remain steady and optimistic, even when they're struggling inside.

2. Emotional resilience is important, but suppressing emotion leads to burnout.

• 🧍‍♂️ Identity Tied to Business Outcomes

1. When your self-worth becomes linked to business success, every failure feels personal.

• 👥 Shrinking Circle of Trust

1. As you succeed, your peer group shrinks — making honesty and vulnerability harder.

5. How to Fix It: Four Strategies

• 👫 Build a True Inner Circle 

1. Join peer groups like:

1. EO (Entrepreneurs' Organization)

2. YPO (Young Presidents' Organization)

3. Hampton

2. Or start a group chat with like-minded entrepreneurs.

3. Find two kinds of mentors:

1. Someone ahead of you to guide you.

2. Someone behind you to keep you pushing forward.

• 🔄 Intentional Reflection 

1. Use journaling, podcasting, or downtime to process your emotions and gain clarity.

2. Create space to think beyond day-to-day operations.

• 🌪️ Thoughtfully Include Your Team in Pressure

1. Transparency ≠ emotional dumping.

2. Share relevant challenges and strategically invite collaboration.

3. Avoid transferring overwhelming anxiety to junior team members.

• 🧠 Work With a Coach or Therapist 

1. Coaches help with clarity and accountability.

2. Therapy can help unpack the deeper emotional toll of leadership.

6. From Loneliness to Connection

• Celebrate wins publicly to avoid harboring joy alone.

• Share successes with your team, friends, and family.

• “You shift from performing to living.”

7. Final Reflections: You’re Not Alone

• Loneliness is common but not permanent.

• “You can go further with people, with honesty, and with emotional openness.”

• Wise closing quote: “He who wears the crown must bear the weight — but not alone.”

Resources & Tools:

🔗EO (Entrepreneurs' Organization)

🔗YPO (Young Presidents' Organization)

🔗Hampton

🔗Ross Simmons Show Archive

— 👋🏾 Let's stay connected —

╰ Subscribe to my channel:  @RossSimmondsTV 

╰ Instagram:  @thecoolestcool  

╰ Twitter / X: @thecoolestcool  

╰ LinkedIn: linkedin.com/in/rosssimmonds