Jon Macaskill
Dad First 🔹 Men Talking Mindfulness Podcast Cohost 🔹 Keynote Speaker 🔹 Entrepreneur 🔹 Retired Navy SEAL Commander
Colorado Springs, Colorado, United States
144K followers
500+ connections
About
Who am I?
I’m Jon Macaskill, a retired Navy SEAL Commander turned mindfulness teacher, leadership coach, and resilience practitioner. My journey has taken me from the battlefield to the boardroom… from leading elite teams under pressure to helping leaders navigate complexity with clarity and composure. I’m a Christian, and my faith is a steady compass guiding how I lead, serve, and show up.
At the heart of it all, I lead with clarity, courage, and compassion to help others unlock their potential. I use my voice, presence, and past...especially the hard parts...to empower people to live and lead with integrity, resilience, and heart.
What do I do?
I help leaders and teams grow by blending mental toughness with emotional intelligence. Through 1:1 coaching, workshops, and keynotes, I teach practical tools to build clarity, trust, and resilience. I’ve worked with Amazon, Microsoft, PepsiCo, and more—and across every high-performing team, one truth holds: you can’t lead others well if you don’t lead yourself first.
What makes my approach different?
I believe grit and compassion are two sides of the same coin. My leadership lens is forged through discipline and refined by deep work in presence, empathy, and connection. I help leaders navigate stress, communicate with impact, and build cultures that elevate performance and people while staying anchored in what matters.
I model what it means to be strong and compassionate… disciplined and self-aware… driven and deeply human. Every interaction is a chance to build trust, challenge the status quo, and make life better for my family, my teams, and everyone I encounter.
I also co-host Men Talking Mindfulness, a podcast about leading, living, and showing up fully… especially when it’s hard.
Let’s connect if you’re:
• A leader building a high-performing team
• Someone facing stress or decision fatigue
• Ready to lead with greater awareness and purpose
Message me to start the conversation—or follow along if you’re here to learn. Either way… welcome.
Articles by Jon
Activity
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What can LEGO teach us about leadership? More than you’d think. Will and I, Men Talking Mindfulness Podcast cohosts and workshop team, ran reps…
What can LEGO teach us about leadership? More than you’d think. Will and I, Men Talking Mindfulness Podcast cohosts and workshop team, ran reps…
Shared by Jon Macaskill
Experience
Education
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The Tuck School of Business at Dartmouth
Next Step: Transition to Business
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This highly selective on-campus program is taught by MBA faculty and designed for elite military veterans, public sector leaders, and Olympians. Next Step focuses on leadership development, strategy, financial analysis, spreadsheet modeling, and business communication.
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Licenses & Certifications
Volunteer Experience
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Member Board Of Directors
Trails of Purpose
- 2 years 8 months
Social Services
Trails of Purpose is a 501c3 located in the Nation's most densely Veteran populated area, Hampton Roads, Virginia. We operate as a Certified Professional Association of Therapeutic Horsemanship International (PATH int'l) Center.
We are driven for innovative Veteran community. We are passionate about creating a safe environment in which relationships with both humans and horses can thrive in. We believe in natures ability to heal. We see the value in reigniting purpose in the lives of…Trails of Purpose is a 501c3 located in the Nation's most densely Veteran populated area, Hampton Roads, Virginia. We operate as a Certified Professional Association of Therapeutic Horsemanship International (PATH int'l) Center.
We are driven for innovative Veteran community. We are passionate about creating a safe environment in which relationships with both humans and horses can thrive in. We believe in natures ability to heal. We see the value in reigniting purpose in the lives of Veterans.
In addition, we also believe in the healing capabilities of equine partnerships. Horses, as prey animals, have mastered the skill of listening and sensing over the previous centuries. They are highly sensitive and incredibly honest. They cause their human partners to be open to trust and willing to work. Our program utilizes Equine Assisted Activities to grow the bond between horses and humans alike. Powerful growth can happen when we step along side each other and a horse. -
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Skills
Courses
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Mindfulness Based Stress Reduction - Center for Mindfulness in Medicine, Health Care, and Society
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Honors & Awards
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Alumnus Under 40 Distinction Award
Ruston High School, Ruston, LA
Organizations
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COMMIT Foundation
Member
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UDT SEAL Association
Member
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Elite Meet
Member
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The Honor Foundation
Ambassador
Recommendations received
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LinkedIn User
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