Most of us got into creative work wanting to do everything, then spent years drowning in all of it. Sean McCormick did the opposite on purpose.
Sean spent years as a public school special education teacher before he walked away from the steady paycheck, with two young daughters at home, to bet on one narrow lane: executive function coaching. He built Executive Function Specialists, founded the Executive Function Coaching Academy to train other coaches, and co-founded a practice for adults. His newsletter reaches about 6,000 people who actually open it.
This one runs deep. Matt and Sean trace the whole road: a summer meditating at a remote fishing lodge in the Misty Fjords of Alaska, a failed run as a rapper, a stretch ghostwriting papers he wasn't proud of, and the hard no from his school district that finally told him the system would never bend for the life he wanted.
What we get into:
- Finding the intersection of what you love, what you're good at, and what people will pay for
- Why "think huge, act tiny" beats chasing the big swing
- The real reason people never reach their vision, and how task switching drains your resolve
- Protecting your floor and actually investing in yourself
- Flow state, craft, and what AI can and cannot do for a creator
- Getting small on purpose, and why Sean chases depth instead of reach
- The status game vs the wealth game
- Evicting the critical roommate in your head
- Five years sober, service, and not being the center of the universe
- His goal of training 10,000 coaches by 2032, and the educator poverty behind it
- The two beliefs that changed everything
CHAPTERS
00:00 Intro: the guy who got smaller on purpose
04:04 Alaska, the lodge, and learning to seek
07:40 The breaking point: a hard no in teaching
12:04 The kitchen table and the rapper years
16:02 Product-market fit and your "bang"
21:06 Explore, then exploit: finding your one thing
25:35 The exercise: what you love meets what pays
29:37 Why people never reach their vision
32:51 Protect your floor and invest in yourself
36:35 Flow state, craft, and what AI can't do
39:53 Getting small: depth over reach
44:36 The status game vs the wealth game
46:06 What he wants his daughters to absorb
50:10 Removing what holds you back
53:15 Evicting the roommate in your head
55:46 Sobriety, service, and purpose
01:00:55 10,000 coaches, ADHD, and educator poverty
01:09:25 The two beliefs that changed everything
01:16:13 Where to find Sean
About Sean McCormick
Sean is a former special education teacher turned executive function coach and founder of the Executive Function Coaching Academy. He helps educators build small businesses that liberate them, and coaches creators and entrepreneurs on focus, self-direction, and purpose.
Find Sean
Executive Function Coaching Academy: https://www.executivefunctioncoachingacademy.com/Sean's site: https://seanmccormick.meEmail Sean: support@seanmccormick.meSean's book is free on Audible and YouTube, recorded in his own voice.
Generator Live is a show for working creatives who are building something and want to talk about what that actually looks like. No highlight reel. No tactics dressed up as wisdom. Just honest conversation about the doubt, the financial reality, the isolation, and the question every creative eventually asks themselves: is this worth it?
Some weeks we talk about the business side of creative work. Some weeks I just think out loud about whatever is on my mind, and you get to be there for it.
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