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Why Leadership Feels So Lonely — And How to Fix It
“It’s lonely at the top” isn’t just a cliché — it’s the structural reality of leadership. The higher you rise, the fewer people you can talk to honestly. Your circle shrinks, your guard goes up, and the pressure to hold everything for everyone else grows heavier.
In this episode of Leadership, Actually, we break down why leaders feel so alone, what’s actually happening beneath the surface, and how to build the support systems you need to stay grounded, connected, and human.
We explore:
• Why the structure of work makes deep connection difficult for leaders
• The three levels of friendship — and why most leaders lack the deepest one
• What to share with your team (and what not to)
• The difference between healthy vulnerability and oversharing
• The real cost of leadership loneliness on judgment, empathy, and burnout
• Practical ways to rebuild your support system inside and outside of work
• How to create connection without crossing boundaries
✨ Lead Better 1:1s, Team Meetings & More with these FREEBIES
Practical guides, toolkits, and resources for leading better meetings, holding better 1:1s and having hard conversations.
👉 Sign up here
https://everground-advisory.myflodesk.com/1-1-freebies
📊 FREE HR Layoff Crash Course
In this free course, you'll discover step-by-step strategies to plan, communicate, and execute layoffs with professionalism and empathy. Self-paced and available 24/7.
👉 Register here
https://semerie.learnworlds.com/course/hr-layoff-crash-course
🌀 Lead Differently. Read Differently.
Join This Isn’t a Leadership Book Club — a free, low-pressure community for curious, thoughtful leaders who believe the best leadership lessons come from unexpected stories.
You’ll get a curated reading list, reflection prompts, and invites to quarterly conversations designed to help you lead with more clarity, care, and intention.
👉 [Join the Book Club Here]
https://everground-advisory.myflodesk.com/this-is-not-a-leadership-bookclub
✨ Lead Like You
A three-month private coaching experience that helps leaders uncover their authentic leadership style, build confidence, and navigate challenges with clarity and intention.
Get an exclusive discount with the code PODCAST10 for 10% off
👉 Start now
https://www.evergroundadvisory.com/lead-like-you
Join 12 Months of Leadership Mastery — a completely free 12-month program designed for leaders and founders who want to grow with clarity, confidence, and purpose.
✨ Get monthly themes, reflection prompts, and live leadership trainings — all free. https://everground-advisory.myflodesk.com/12-months-leadership-opt-in
View all episodes
By Everground Advisory“It’s lonely at the top” isn’t just a cliché — it’s the structural reality of leadership. The higher you rise, the fewer people you can talk to honestly. Your circle shrinks, your guard goes up, and the pressure to hold everything for everyone else grows heavier.
In this episode of Leadership, Actually, we break down why leaders feel so alone, what’s actually happening beneath the surface, and how to build the support systems you need to stay grounded, connected, and human.
We explore:
• Why the structure of work makes deep connection difficult for leaders
• The three levels of friendship — and why most leaders lack the deepest one
• What to share with your team (and what not to)
• The difference between healthy vulnerability and oversharing
• The real cost of leadership loneliness on judgment, empathy, and burnout
• Practical ways to rebuild your support system inside and outside of work
• How to create connection without crossing boundaries
✨ Lead Better 1:1s, Team Meetings & More with these FREEBIES
Practical guides, toolkits, and resources for leading better meetings, holding better 1:1s and having hard conversations.
👉 Sign up here
https://everground-advisory.myflodesk.com/1-1-freebies
📊 FREE HR Layoff Crash Course
In this free course, you'll discover step-by-step strategies to plan, communicate, and execute layoffs with professionalism and empathy. Self-paced and available 24/7.
👉 Register here
https://semerie.learnworlds.com/course/hr-layoff-crash-course
🌀 Lead Differently. Read Differently.
Join This Isn’t a Leadership Book Club — a free, low-pressure community for curious, thoughtful leaders who believe the best leadership lessons come from unexpected stories.
You’ll get a curated reading list, reflection prompts, and invites to quarterly conversations designed to help you lead with more clarity, care, and intention.
👉 [Join the Book Club Here]
https://everground-advisory.myflodesk.com/this-is-not-a-leadership-bookclub
✨ Lead Like You
A three-month private coaching experience that helps leaders uncover their authentic leadership style, build confidence, and navigate challenges with clarity and intention.
Get an exclusive discount with the code PODCAST10 for 10% off
👉 Start now
https://www.evergroundadvisory.com/lead-like-you
Join 12 Months of Leadership Mastery — a completely free 12-month program designed for leaders and founders who want to grow with clarity, confidence, and purpose.
✨ Get monthly themes, reflection prompts, and live leadership trainings — all free. https://everground-advisory.myflodesk.com/12-months-leadership-opt-in