How Deep Thinking Creates Better Coaches With Jason Macauley
Struggling to connect with your coaching clients?
Jason Macauley spent 25 years climbing the tech ladder before discovering that his philosophy degree was actually his secret weapon for leadership.
In this episode of the Ace Coach podcast, he reveals how curiosity trumps control, why treating people like objects destroys relationships, and how a simple shift from "extraction" to "generation" can transform your entire approach to coaching.
📚 What We Talk About:
02:15 Jason's unexpected journey from philosophy student to tech executive to executive coach over 25 years
06:30 How working as one of the internet's first content moderators at Tripod.com shaped his perspective on human behavior
09:45 The burnout moment that forced him to choose between coding and leading people—and why his "philosopher brain" craved the complexity of human problems
12:20 Why he left a lucrative retail tech career selling "red bottled shoes to people with closets full of them"
15:40 The harsh reality check of transitioning from corporate security to entrepreneurial uncertainty
18:25 How packaging yourself for others' approval kills authenticity and attracts the wrong opportunities
22:10 Why curiosity about others prevents the toxic cycle of disappointment, resentment, and workplace conflict
28:35 The philosophy behind his coaching: constantly questioning your own assumptions and staying intellectually humble
31:50 His profound success story of a leader who stopped chasing certifications and started asking better questions
38:20 Why believing in people's potential creates bigger results than setting limiting expectations
42:15 The mental shift from building what others want to creating what you find valuable—and trusting others will too
💭 Key Quotes:
"Life only looks like a path if you're walking backwards."
"We are trapped in our own conception of others... If I'm not curious, then I am only reacting to myself."
"Leadership becomes less about figuring out how to get stuff out of people and more about believing in what we can accomplish together—not extraction, it's generation."
"We're not here to be fixed because we're not broken."
"If you blame it on someone else, you are nowhere near the truth. If you blame it on yourself, you're halfway there. If you realize no one is to blame, you're all the way there."
"When we try to define the purpose of something narrowly... we miss everything else that we are."
📖 Resources Mentioned:
🔗 Connect With Our Guest:
Website: www.anotherviewcoaching.com
Socials: LinkedIn
