The Loneliness Of Leadership: Founders, You're Not Alone The Ross Simmonds Show podcast

Content provided by Ross Simmonds. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Ross Simmonds or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.

The Ross Simmonds Show »
The Loneliness of Leadership: Founders, You're Not Alone

23h ago 25:54

MP3•Episode home

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:

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.”

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.

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.

Four Reasons Leaders Feel Isolated

🧠 Information Asymmetry

Leaders have a different view of company data, performance, and risks.
Transparency can reduce the burden and build empathy.

❤️ Emotional Labor

Leaders are expected to remain steady and optimistic, even when they're struggling inside.
Emotional resilience is important, but suppressing emotion leads to burnout.

🧍‍♂️ Identity Tied to Business Outcomes

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

👥 Shrinking Circle of Trust

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

How to Fix It: Four Strategies

👫 Build a True Inner Circle

Join peer groups like:

Or start a group chat with like-minded entrepreneurs.
Find two kinds of mentors:

Someone ahead of you to guide you.
Someone behind you to keep you pushing forward.

🔄 Intentional Reflection

Use journaling, podcasting, or downtime to process your emotions and gain clarity.
Create space to think beyond day-to-day operations.

🌪️ Thoughtfully Include Your Team in Pressure

Transparency ≠ emotional dumping.
Share relevant challenges and strategically invite collaboration.
Avoid transferring overwhelming anxiety to junior team members.

🧠 Work With a Coach or Therapist

Coaches help with clarity and accountability.
Therapy can help unpack the deeper emotional toll of leadership.

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.”

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

124 episodes

#Entrepreneur #Business #Ross Simmonds #Tech #Marketing