MONDAY MATTERS with Jen Schwanke and Will Parker – 10 Lessons from Masterminds

MONDAY MATTERS with Jen Schwanke and Will Parker – Lessons in Sailing Upwind

LESSONS IN SAILING UPWIND William D. Parker, July 9, 2026 When my friend Dave Sandowich, a retired principal with 20+ years of admin experience, invited me to go sailing with me off the Chesapeake Bay, I was thrilled. This would be the third time he had taken me on the water, and my son Jack, now 20 years old, was coming along. We sailed 60 miles over three days, from Dave’s place on Kent Island to Annapolis, Maryland, and then south to a quiet cove. Sailing upwind was the most challenging and exhilarating part of the trip. Calm waters and quiet moments were nice too, but Dave was quick to point out that sailing upwind takes work – a mastery of understanding the sail and jib, the use of crewmates to help you come about, and knowledge and skill to stay on track. As Dave told me the first time we sailed together in 2019, “Sailing is a lot like leadership,” he said. “On a sailboat your destination may be directly from where the wind is coming from. A sailboat can’t sail directly into the wind but it can work its way up wind by sailing at angles off the wind and working its  way up wind to the destination. It is more work and will take more time but you will get there if you stay the course, apply your sailing knowledge and get the feedback from your instruments and instincts and adjust along the way.” Whenever I think about resistance in leadership, I think about sailing into the wind. Leaders have a destination in sight for their teachers, students and communities. The question is: what do you do when you experience pushback and resistance toward reaching those goals. WHAT HAS FACING RESISTANCE TAUGHT YOU? This week, I met with a group of leaders for a retreat, and I posed that question to them. Some of their responses included: “Pushback causes me to reassess my own understanding of mission and vision and if I’m effectively and clearly communicating it with others.” “Perhaps there is misunderstanding or misrepresentation of our goals that I need to recommunicate.” “It’s my responsibility to realign expectations while keeping in mind that relationships are complex. Reaching my goal may not be a straight shot. Sometimes I have to work with people until they come around to a clearer perspective.” “Leadership is more like chess than checkers. It requires wisdom to know how to maneuver among people and systems while still reaching the right outcome.” Each one of these statements reminds me that the work of leaders is complex, and navigating complexity takes more than just a good handbook or code of conduct. It requires wisdom to step into the complexities and determine the next best step for moving forward. Having said that, here are a few thoughts to keep in mind as you sail a route in the coming school year: 1. People – Investing in people means taking time to know who is on your team, gaining their trust, and remembering that development is not a one time event. 2. Systems – Developing systems means analyzing your operations, processes, routines, and procedures in light of your students, teachers, and community members. Ask yourself what it is like to be on the other side of any activity at your school. How are you aligning the system involved for the outcome you want them to experience? 3. Belief – Encouraging collective efficacy among your team members means being clear on what you believe is most important for the outcomes and impact happening around student learning. These three reminders bring us back to commitments to people, systems, and belief – the essentials for any flourishing school community.  Anyone trying to navigate or move forward an entire organization or community must be prepared to face some winds of resistance. You can either allow the pushback to cause you to throw anchor, drop sails, or turn around.  CHOOSE YOUR HARD Our last day together, Dave and Jack and I were having breakfast together, when I asked Dave what were some lessons in leadership he’s learned along the way. Dave is enjoying retirement and a lot of time on his boat with family and friends. When I asked him what lessons he was learning, he looked at me and Jack and said, “You have to learn to choose your hard.” “What do you mean by that?” I asked. “Take my physical fitness, for example,” he continued. “I choose the hard by keeping my workout routine. I don’t really want to do pullups, planks and pushups, but I choose that hard over the hard of declining health, higher blood pressure, or losing my mobility over time. You choose your hard one way or the other.” Life and leadership teach us a lot of lessons along the way if we slow down enough to listen and reflect. In leadership, the harder and wiser option often requires sailing into the winds of resistance. If it wasn’t hard, everyone would do it by default. But good outcomes often require hard choices.  When I think about the goal of schools to build a community of learning, I’m encouraged that the task is worth it for students, for teachers, and for communities. It’s also worth it for leaders.  On our last day of sailing, Dave navigated the boat back toward Kent Island. He gave each of us a turn at the helm. I tried to soak in the memories of sun, waves, and the warmth of friendship and family.  Your school year ahead will be full of unexpected situations, and the truth is: you don’t choose the winds you encounter. But you can choose how you respond to them.  As you sail into the winds of a new school year, may you learn to pivot, to navigate, and to recalibrate along the way.  The destination and experiences you reach will look different in each journey, but the mindset you have along the way may be what makes all the difference. NOW IT’S YOUR TURN What are some experiences in pushback or resistance you’ve faced, and what lessons did you learn? How can you apply those lessons to navigating with wisdom “upwind” in the school year ahead? The post MONDAY MATTERS with Jen Schwanke and Will Parker – Lessons in Sailing Upwind [https://williamdparker.com/2026/monday-matters-with-jen-schwanke-and-will-parker-lessons-in-sailing-upwind/] appeared first on Principal Matters [https://williamdparker.com].

PMP509: A Complaint Free World with Will Bowen

MEET WILL BOWEN [https://williamdparker.com/wp-content/uploads/2026/07/PMP-Template-34-1024x1024.png] Will Bowen is an internationally recognized speaker, author, and founder of the Complaint Free® Movement. This movement has inspired millions of people across more than 100 countries to live with greater positivity and personal accountability. He is best known for his bestselling book A Complaint-Free World [https://www.amazon.com/Complaint-Free-World-Revised-Updated-dp-0593581318/dp/0593581318/ref=dp_ob_title_bk], which introduced a simple yet powerful idea: by becoming more aware of our words, especially complaints, we can transform our mindset, relationships, and results. His challenge has helped individuals, teams, and organizations break the habit of chronic complaining and replace it with intentional, solution-focused thinking. His message has been featured on major media outlets, including Oprah, NBC’s Today Show, and People Magazine. Whether speaking to schools, corporations, or leadership groups, Will Bowen equips people with tools to elevate their thinking and ultimately, their lives. COMPLAINING, MINDSET, AND PERSONAL GROWTH In this conversation, Will Bowen shares the origin of his global initiative, which began with a simple purple bracelet and a challenge: go 21 days without complaining. What started as a small experiment quickly grew into a worldwide movement, helping millions become more aware of their thoughts, words, and habits. At the heart of Bowen’s message is the idea that complaining is not just harmless venting; it reinforces negativity, limits growth, and shapes how we experience the world. Instead, he encourages individuals to take responsibility for their responses and focus on solutions rather than problems. THE G.R.I.P.E. FRAMEWORK A key takeaway from the conversation is Bowen’s practical acronym for understanding complaints: G.R.I.P.E. G – Get Attention Complaints Will makes an important distinction between honest reflection and complaining; complaining is expressing something primarily for selfish appeal or ego. Response Tip: When others complain for attention, redirect their thinking toward gratitude. Ask: “So what is going well with __________?” For example, if someone complains about students, ask: “What’s going well with your classes?” This shift moves the conversation from misery to possibility. R – Remove Responsibility Complaints Complaining is often used as a way to get off the hook. When faced with accountability, people may point to others’ failures or claim circumstances are beyond their control. This keeps them stuck and avoids ownership. Response Tip: Shift from excuse-making to solution-seeking by asking: “If it were possible, how might you do it?” This question removes the escape route and opens the door to action. I – Inspire Envy Complaints (The Humble Brag) Sometimes complaints are really disguised attempts to appear superior. For instance, pointing out someone else’s shortcomings may actually be a way to highlight one’s own strengths. These “humble brags” create comparison rather than connection. Response Tip: Will Bowen suggests “complimenting the opposite.” If someone points out another’s flaw, you might respond by affirming their strength: “It’s great that you’re always on time.” This can gently expose the motive behind the complaint and shift the tone. Changing the subject is also an effective way to disengage from this pattern. P – Power Complaints People who feel powerless sometimes use complaining as a way to gain control—often through gossip or criticism of others. This can be especially toxic in teams. Response Tip: If someone comes to you to complain about another person, respond with: “It sounds like the two of you have a lot to talk about.” If they continue, you might add: “Would you like me to arrange a meeting?” This redirects them toward resolution instead of reinforcing the complaint. E – Excuse Complaints (Excusing Poor Performance) Complaining is one of the quickest ways to avoid accountability. Instead of addressing areas for growth, individuals may focus on obstacles or limitations. Bowen notes that, like in team sports, those who resist coaching often weaken the team dynamic. Response Tip: Replace excuses with ownership by asking: “How do I plan to improve next time?” This shifts the focus from justification to growth and from problems to solutions. COMPLAINING, SOCIAL MEDIA, AND LEADERSHIP A powerful part of the conversation focused on how social media platforms often amplify and reward complaining. Bowen explained that algorithms are designed to prioritize emotionally charged content (especially negativity) because it drives engagement. As a result, complaints, outrage, and criticism tend to spread faster and wider than thoughtful or solution-oriented messages. In a world where complaints are often rewarded with attention, leaders stand out by modeling steadiness, responsibility, and solution-focused thinking. LISTEN FOR EVEN MORE! Will Bowen reminds us that eliminating complaints does not mean ignoring real problems. Instead, it means choosing to address those problems in a way that is constructive, responsible, and focused on solutions. Listen to the entire conversation for even more great takeaways, and as always, thank you for doing what matters! CONTACT & RESOURCES To learn more about Will Bowen and the Complaint Free® Movement, visit https://willbowen.com/ [https://willbowen.com/], where you can find resources, tools, and information about his work.  The post PMP509: A Complaint Free World with Will Bowen [https://williamdparker.com/2026/pmp509-a-complaint-free-world-with-will-bowen/] appeared first on Principal Matters [https://williamdparker.com].

MONDAY MATTERS with Jen Schwanke and Will Parker – The Problem with Certainty

Welcome back to another episode of Monday Matters! This week, Will Parker and Jen Schwanke talk about the problem with certainty [https://jen-newsletter-c4287d.beehiiv.com/p/the-problem-with-certainty]. Certainty is not a bad thing. It is very soothing and comforting for us, but it doesn’t equal growth. In fact, being certain is a terrible substitute for growth. The idea of leadership as a single individual who believes they do not need help or input is a dangerous one. It’s important for leaders to lean into their relationships with others. Surrounding yourself with people who you can collaborate with to grow is powerful. We don’t want to shut out the voices of other people who might see things that we can’t see ourselves. By welcoming input from other principals, teachers, staff, and even students, we can truly grow as leaders. Listen in to the full conversation to hear more about the problem with certainty! The post MONDAY MATTERS with Jen Schwanke and Will Parker – The Problem with Certainty [https://williamdparker.com/2026/monday-matters-with-jen-schwanke-and-will-parker-the-problem-with-certainty/] appeared first on Principal Matters [https://williamdparker.com].

PMP508: Rigor, Routines, and Relationships with Dina Langston & Stacey James

A QUICK NOTE TO LISTENERS: Before this week’s interview, Will Parker and Jen Schwanke take some time to answer a listener question. This week’s question is: How can I discover my teacher’s unique “professional work languages?” Listen in to hear their response! You can use these questions to help discover those “work languages”: How do would you describe your leadership style in three words? What are your best working conditions? How does appreciation feel like for you? How do you communicate early warning signs? What is your genius zone? What is my learning zone? MEET DINA LANGSTON & STACEY JAMES: [https://williamdparker.com/wp-content/uploads/2026/07/PMP-Template-33-1024x1024.png] Stacey James and Dina Langston are experienced educational leaders from Armwood High School in Hillsborough County, Florida. [https://www.hillsboroughschools.org/o/armwood]  Stacey James currently serves as a Magnet Lead at Armwood High School and has held this role for several years, leading schoolwide efforts to align rigor, routines, and relationships to support instructional improvement and student success. With over 17 years in education, she has previously served as a classroom teacher, AVID coordinator, and instructional coach. James also has more than five years of experience as an AVID staff developer, facilitating professional learning for educators at AVID Summer Institutes and national conferences. Dina Langston serves as principal of Armwood High School, where she leads efforts to improve instructional quality, school culture, and student outcomes through aligned systems and collaborative leadership. Her work has contributed to significant school improvement, including increased graduation rates and academic performance. In recognition of her leadership and impact on student achievement, Langston was awarded the 2026 Principal Leadership Award from Florida TaxWatch. Together, Stacey James and Dina Langston design and deliver professional learning grounded in real school contexts and focused on sustainable improvement for educators and students. THE TRIPLE R FRAMEWORK: Today’s guests center their leadership work around what they call the Triple R Framework: rigor, routines, and relationships. These three elements work together to create strong learning environments where students and educators can thrive. When schools intentionally focus on all three, they create both the structure and the culture necessary for sustained improvement. RIGOR: Rigor is not simply about giving students more difficult assignments. Instead, it involves designing learning experiences that require students to think deeply, engage meaningfully, and apply their knowledge in authentic ways. When educators maintain high expectations while also providing the support students need to succeed, rigor becomes a pathway to greater engagement and stronger learning outcomes. Key ideas: * Maintain high expectations for every student * Design learning that requires critical thinking * Connect instruction to real-world applications * Pair high expectations with strong student support ROUTINES: Predictable routines create stability in classrooms and throughout schools. When students understand procedures and expectations, they can spend less time navigating uncertainty and more time focused on learning. Clear routines also help teachers manage classrooms effectively and maintain a consistent learning environment. Examples include: * Clear entry and exit procedures * Consistent assignment submission processes * Structured discussion and participation norms * Reinforcing routines regularly so expectations remain clear RELATIONSHIPS: Relationships are the foundation of a healthy school culture. When students feel known, valued, and supported, they are more likely to engage in learning and take academic risks. Strong relationships among educators, students, and families build trust and create a sense of community that strengthens the entire school environment. Effective strategies include: * Community-building activities * Meaningful conversations with students * Learning about students’ interests, backgrounds, and goals * Creating a culture where students feel safe to participate and grow STAYING CONNECTED: Listen to the full conversation with Dina Langston and Stacey James for more insights on leading with rigor, routines, and relationships! You can stay connected with Dina Langston and Stacey James via the following channels: * School website: https://www.hillsboroughschools.org/o/armwood [https://www.hillsboroughschools.org/o/armwood] * Dina’s LinkedIn: https://www.linkedin.com/in/dina-langston-60b0a7249/ [https://www.linkedin.com/in/dina-langston-60b0a7249/] * Email: dina.langston@hcps.net  * Stacey’s LinkedIn: https://www.linkedin.com/in/stacey-james-m-ed-m-s-i-d-38391130/ [https://www.linkedin.com/in/stacey-james-m-ed-m-s-i-d-38391130/] * Email: stacey.james@hcps.net  The post PMP508: Rigor, Routines, and Relationships with Dina Langston & Stacey James [https://williamdparker.com/2026/pmp508-rigor-routines-and-relationships-with-dina-langston-stacey-james/] appeared first on Principal Matters [https://williamdparker.com].

MONDAY MATTERS with Jen Schwanke and Will Parker – Why Vacation Matters

Today’s Monday Matters discusses the importance of summertime for mental break and the importance of disengagement from the worries. Will Parker and Jen Schwanke discuss the benefits of giving yourself a mental break from the stress of a leadership job. They talk about how taking a break will make the next school year better, and will allow you to re-connect to yourself and the things that you love. Will and Jen also talk about how taking a break from work is easier said than done. Sometimes you need a few days for your brain to reset and get into vacation mode. If you feel like you can’t stop working, or don’t want to, you don’t have to take the whole summer to stop working, but it’s important to take some time to mentally and emotionally detox. Take a few days in the summer to spend time enjoying time with family and friends, enjoying nature, and remembering what is important. Listen in to hear more about the importance of summer vacation! You can also read this article [https://williamdparker.com/2021/pmpencore028-four-reasons-your-vacation-matters-2/] Will wrote several years ago about the importance of vacation. As always, thanks for doing what matters and enjoy your summer break! The post MONDAY MATTERS with Jen Schwanke and Will Parker – Why Vacation Matters [https://williamdparker.com/2026/monday-matters-with-jen-schwanke-and-will-parker-why-vacation-matters/] appeared first on Principal Matters [https://williamdparker.com].