Why Leaders Feel Lonely — and How to Find Real Friends Again
“When someone stepped into my story, I finally began to heal. One real friend changed everything.” — David Cherry
Leadership often looks inspiring from the outside — full rooms, packed calendars, meaningful work.
But behind the momentum, many leaders quietly face the same hidden truth: it’s lonely at the top.
Recent research from the U.S. Surgeon General found that nearly half of adults (49%) report feeling lonely on a regular basis, and leaders are among the most isolated groups. A Harvard Business Review study revealed that 61% of executives struggle with loneliness, which directly impacts their focus, creativity, and emotional health.
That’s why our latest episode of the Table Network Podcast hit a nerve.
We sat down with Coach Jayme Shiarla, an executive wellness coach and NLP practitioner, and David Cherry, better known as “The Friendship Guy,” to explore what authentic connection really looks like for high-capacity people.
🎧 Watch the full conversation → YouTube Episode: Why Leaders Feel Lonely (and How to Find Real Friends Again)
The Friendship Gap
David shared his personal story — decades in full-time ministry, surrounded by people but secretly struggling with addiction and isolation.
It wasn’t until a friend stepped into the middle of his mess that everything began to change.
“When someone stepped into my story, I finally began to heal. One real friend changed everything.” — David Cherry
That experience inspired David to launch The Friendship Project, a six-week course that helps leaders identify, build, and sustain deeper friendships that bring emotional and spiritual health.
The 3 Levels of Friendship
In the episode, David breaks down what he calls the “Levels of Friendship” — a framework for auditing the relationships in your life:
Level 0 – Digital Connections: Social media followers or distant acquaintances.
Level 1 – Familiar Faces: You recognize each other, maybe chat occasionally.
Level 2 – Good Friends: You share life events, support each other, but rarely go beneath the surface.
Level 3 – Deep Friends: These are the people who know your story — the wins, wounds, and weaknesses — and love you anyway.
Most people have around 500 name/face connections, 50 casual friends, and just 1–3 deep friendships, according to Dunbar’s Number research.
And that’s okay — if those few friends are intentional and trusted.
Building Real Connection (Even When You’re Busy)
David and Jayme share several simple rhythms that anyone can apply:
✅ 1. Schedule Consistency, Not Perfection.
David’s “Saturday Breakfasts” — weekly meetups with a trusted friend — have continued for 12 years straight. It’s not about the meal; it’s about the rhythm.
✅ 2. Send Monday Morning Messages.
Each Monday, David sends short encouragement texts to pastors and friends — what he calls his “Monday Morning Messaging Ministry.”
Most replies sound like: “You have no idea how much I needed this today.”
✅ 3. Lead with Curiosity, Not Judgment.
Coach Jayme says curiosity is what unlocks connection:
“Instead of asking what’s wrong with you, ask what happened to you.”
✅ 4. Risk Small, Then Go Deep.
Test trust by sharing something small and see how the person handles it. Safe friends lean in — they don’t dismiss, fix, or shame.
✅ 5. Make Space Before the Casseroles Go Away.
Jayme reminds us that true friendship is shown after the crisis fades — when the “casseroles go away.” Consistent check-ins build real belonging.
Friendship Is Good for Business
It’s not just emotional—it’s strategic.
Research from Gallup shows that employees who have a best friend at work are 7x more engaged, more productive, and far less likely to burn out.
In David’s words:
“When my friend processes a bad day instead of bottling it up, he goes back to work lighter, focused, and stronger. Friendship is good for business.”
Next Steps to Rebuild Connection
Audit Your Relationships – Write down your 10–15 closest connections. Identify which level each one falls into (Level 1–3).
Reach Out to 3 People This Week – Text encouragement, set up coffee, or simply check in.
Join the Friendship Project – A 6-week small group experience that walks you through building deeper relationships.
Attend the Next Table Network Gathering – October 16th, where we continue these conversations live around real tables.
Subscribe to the Table Network Podcast – Hear honest stories and practical wisdom that connect faith, work, and community.
Final Word
True friendship takes time, risk, and humility — but it’s worth it.
As Jayme said so perfectly in the episode:
“We aren’t meant to do life alone. When we start better, we treat people better — because we’ve finally learned to treat ourselves with grace.”
Listen on YouTube → Why Leaders Feel Lonely (and How to Find Real Friends Again)
Join the 6-week Friendship Project → Sign Up Here
Follow The Table Network for more conversations on leadership, purpose, and community.
