CheckBox Pro founder, Missy Couch, interviews experts in the field of education to offer tools, tips, and insights to make the life of a charter school leader even more sustainable.
In this summer edition of What's Saving My Life, Missy shares 10 things that brought a little more joy, ease, and sanity to life from July through September.
The list is a true mix of meaningful and delightfully ordinary, from World Cup soccer, family video compilations, and welcoming a new rescue dog after saying goodbye to a beloved longtime pup, to finally unclogging the bathroom sinks and embracing overalls as a summer uniform. She also shares what happened when she ditched her Apple Watch and removed social media from her phone, the family card game everyone can finally play together, and the unexpected joy of watching her youngest step confidently into kindergarten.
There's also plenty of summer survival, including a reality TV binge while solo parenting during her husband's theater rehearsals and a paper calendar that helped make camps, travel, visitors, and family logistics feel a little more manageable.
As always, this episode is a reminder that the things saving us don't have to be big or profound. Sometimes they're simply the people, routines, tools, and small joys making a busy season feel a little lighter.
Connect with Missy: LinkedIn: https://www.linkedin.com/in/missy-couch-5626b8176/
About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/
Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ
21 Sept 2026
59: Strategic Sense Making
In this episode of the CheckBox Pro Series, Missy sits down with Dr. Remy Washington, CEO of Uplift Education, to talk about stepping into leadership at scale while staying connected to the people doing the work every day.
Remy shares her unconventional path into education, from pre-med student to car sales to high school math teacher, and the opportunities that eventually led her to Uplift. Now eight months into the CEO role, she reflects on leading a network serving more than 23,000 students while navigating enrollment, financial pressures, staffing decisions, and organizational change.
At the center of Remy's leadership is what she calls strategic sense making. She shares how listening sessions, campus visits, focus groups, data, and highly intentional planning help her understand what is happening across a large organization and make better decisions because of it.
Remy also gets practical about managing a demanding role, including how she structures her week, prepares for check-ins, protects time to stay close to schools, and is learning to delegate more to her executive assistant.
This episode is an insightful look at leading with curiosity, proximity, and the discipline to gather the right information before deciding what comes next.
Connect with Dr. Washington:
LinkedIn: https://www.linkedin.com/in/remy-l-washington-edd-72496913/
Learn more about Uplift Education: https://uplifteducation.org/
About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/
Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ
31 Aug 2026
58: Seeing What's Possible
In this episode of the CheckBox Pro Series, Missy sits down with David Williams, founder and leader of Village Tech Schools, for a conversation about reimagining what school can look and feel like.
David shares how he stumbled into education, fell in love with teaching, and eventually helped build Village Tech around a belief that students should do meaningful work connected to the world beyond the classroom. From public exhibitions and community partnerships to cross-age learning and design thinking, he explains how Village Tech creates opportunities for students to build confidence, creativity, and a strong sense of belonging.
David also reflects on the realities of leading a growing charter network, including school finance, enrollment pressures, and the challenge of translating a nontraditional school model to people who have not experienced it firsthand. Through it all, he returns to a people-first philosophy: schools should be people driven and data informed. He also shares the meeting structures his leadership team uses to protect time, strengthen accountability, and keep the organization focused on the work that matters most.
This episode is a thoughtful reminder that while school leadership is complex, the heart of the work remains simple: create the conditions for students and adults to do meaningful work together.
Connect with David:
LinkedIn: https://www.linkedin.com/in/david-williams-15914865/
Learn more about Village Tech Schools: https://villagetechschools.org/
About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/
Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ
Who has been a guest on CheckBox Pro Series
Names identified in recent episode analyses. Showing up to five guests.
ShaVanety Jones
Missy Couch
Daniel Casselli
Kela Small
Sam Brobeck
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Apple Podcasts (US)
5.0 / 5
9 ratings
Spotify
5.0 / 5
1 ratings
Podcast Authority Score: 58 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
87
Social presence
0
YouTube
0
Engagement
71
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