Mix Tape: The Hits of the 25/26 Soundtrack

Hello,

This is my last new letter of the 25/26 school year, and what a year it’s been!

As I've done for the last two years, I wanted to take a moment to spotlight some of the posts for this year in case you missed them and want something to peruse over the summer. Think of this as a mix tape that might encourage you to dive deeper into any of the other posts from this or previous years!

September 2025 

• The Choice Is Yours - In this post, I reflect on my love of audiobooks and how new text-to-audio technology has expanded the way I experience reading. While these tools are far from perfect, they have reminded me of a much bigger truth: perspective is always a choice. I explore how we can focus on imperfections and frustrations or choose gratitude for the opportunities and blessings in front of us. Through examples from family life, parenting, finances, and everyday routines, I examine how our mindset shapes our experiences. Inspired by Mel Robbins’ concept of “let me,” I emphasize that while we cannot control every circumstance, we can always control our response. Ultimately, I argue that choosing gratitude and perspective is less about ignoring challenges and more about intentionally deciding how we want to live and view the world.

October 2025

• Partnership and the Role of AI - You can't go anywhere without encountering AI, so how do we use it well? I share a parenting challenge that became a lesson in leadership, partnership, and the thoughtful use of AI. After my newly licensed daughter broke curfew on the very day her driving restrictions ended, my husband and I disagreed about the appropriate response. Feeling stuck between accountability and compassion, I turned to AI as a thought partner to help me reflect on my values, goals, and desired outcomes. Through a series of guided questions, AI helped me develop a response that balanced empathy with clear expectations. I reflect on how AI can support human decision-making, not by replacing our judgment, but by helping us think more clearly and intentionally. Ultimately, I explore how parenting mirrors leadership and how strong partnerships, both with people and technology, can help us navigate difficult moments with greater wisdom and clarity.

November 2025

• When I Say “Jump,” You Say, “But Why?” - Do you ever wonder why people often resist even well-intentioned improvements? Using examples like New York’s evolving graduation requirements, I explore how constant adaptation can leave people emotionally exhausted and hesitant to embrace yet another shift. I compare this resistance to ants trapped by imaginary boundaries and fleas conditioned not to jump beyond old limits, arguing that people often remain constrained by psychological barriers long after the actual limitations are removed. Drawing on concepts from Dan and Chip Heath’s Switch, I explain that successful change requires more than logic or enthusiasm; leaders must address emotions, provide clarity, and create supportive conditions that make change feel safe and achievable. Ultimately, I argue that effective leadership is not simply announcing opportunity but building the trust, emotional safety, and clear pathways people need in order to move forward confidently.

December 2025

• The Surprising Why Some Leaders Outlast the Rest - Our instinct for “tit for tat” retaliation can damage relationships, teams, and leadership over time. Beginning with childhood memories of conflict with my sister, I connect those experiences to the concepts of game theory and the prisoner’s dilemma, which I recently revisited through a presentation by Dean Ramirez. Using his “bird continuum” framework, I examine different approaches people take toward cooperation and conflict, ranging from endlessly peaceful “doves” to relentlessly retaliatory “hawks.” Surprisingly, the strategy that proves most successful over time is the “robin” approach: extending grace and cooperation more often than retaliation while still maintaining clear boundaries. Drawing connections to the work of Adam Grant and Simon Sinek, I argue that sustainable leadership is built not on keeping score or winning isolated battles, but on preserving trust, psychological safety, and long-term collaboration. Ultimately, I reflect on how leaders who balance kindness with accountability create stronger, healthier relationships that endure beyond momentary conflicts.

January 2026

• Don’t Hate the Player, Hate the Game - Here, I explore how workplace behaviors that frustrate us are often symptoms of larger systemic problems rather than simply individual failings. Through stories of a colleague being yelled at during a professional meeting and an innovative teacher being subtly pushed aside, I reflect on how systems teach people what is safe, valued, and tolerated. I contrast functioning systems, where accountability, professionalism, and honesty are supported, with broken systems, where silence feels safer than speaking up and leaders lack the support needed to lead effectively. I argue that organizations shape behavior through the patterns they reward, ignore, or punish, often producing the very dysfunctions they later criticize. Ultimately, I challenge readers to stop focusing solely on “fixing people” and instead examine the systems and conditions that create repeated outcomes. If we want meaningful change, we cannot simply replace individuals; we must redesign the environments that shape their behavior.

February 2026

• What Amazon Customer Service Taught Me About Leadership - A surprisingly simple comparison between Amazon customer service and leadership became the foundation for this reflection on trust, communication, and psychological safety. I share how, during my first opening day as superintendent, I told staff I wanted approaching me to feel like contacting Amazon customer service: not necessarily getting every answer they want, but always feeling heard, respected, and safe asking for help. Drawing parallels between customer service, parenting, and leadership, I explore how trust is built not through grand promises but through consistent responses that reduce fear and shame. Through a real example of a teacher voicing concerns about a decision, I reflect on the importance of listening with curiosity rather than defensiveness and creating environments where people feel safe enough to speak honestly. Ultimately, I argue that leadership is less about authority or always saying yes and more about responding to others with respect, care, and a genuine willingness to listen.

March 2026

• Not the Problem Is Not the Solution - A reflection on courage, silence, and moral responsibility, this piece challenges the comforting belief that simply “not doing harm” is enough. Drawing on examples from literature, comedy, education, and everyday life, I explore the difference between the absence of wrongdoing and the active presence of good. Whether it is ignoring degrading comments, remaining silent during uncomfortable moments, or failing to interrupt harmful behavior, I argue that neutrality often creates space for harm to continue unchecked. Inspired by comedian Daniel Sloss’s reflections on missed warning signs and by conversations about fear, love, and courage, I examine how small acts of silence can quietly normalize larger problems. Ultimately, I question how we expect students to become upstanders when adults themselves often struggle to act and suggest that true character is built not through slogans or intentions, but through consistent action that protects the dignity and safety of others.

April 2026

• Annuals and Perennials - Using the Gottman Institute’s concept of “perpetual problems” in relationships as a starting point, this piece explores how many of leadership’s greatest challenges are not problems to solve once and for all, but tensions to manage repeatedly over time. I reflect on the difference between temporary, situational issues and the ongoing balancing acts that define leadership, such as autonomy versus alignment, support versus accountability, and stability versus change. Through personal examples and reflections on my own habits, I examine how these recurring tensions often reveal deeper internal conflicts rather than simply external disagreements with others. Ultimately, I argue that effective leadership is less about achieving perfect resolution and more about remaining committed to the work of self-awareness, recalibration, and returning to the conversation again and again. The goal is not to eliminate tension, but to stay engaged with it in meaningful and healthy ways.

May 2026

• The Enemy of Good - Reflecting on my journey as a “recovering perfectionist,” this piece explores how perfectionism often prevents growth rather than encouraging it. I examine how the pressure to do things perfectly can stop us from starting, discourage us from continuing, and make progress feel invisible. Through examples from parenting, language development, technology, and running, I introduce the ideas of approximation and iteration: the understanding that growth happens through imperfect attempts followed by steady refinement over time. Just as children learn to speak through incomplete words and innovations evolve through multiple versions, personal growth also depends on allowing ourselves to begin before we feel fully ready. Ultimately, I argue that progress is not about achieving perfection but about continuing to move forward, learn, and improve. By shifting our focus from the “gap” between where we are and where we want to be toward the “gain” of how far we have already come, we create room for both growth and joy.

June 2026

• Not a Good Fit - A seemingly simple classroom scenario about proposing a student play becomes a deeper reflection on leadership, values, and the importance of alignment. I explore how our responses to conflict and collaboration are shaped by the values we prioritize, whether that is innovation, integrity, collaboration, psychological safety, or something else entirely. Through a conversation with graduate students and a retired superintendent, I examine how two people can interpret the same situation very differently because they are operating from different value systems. Rather than framing one approach as universally right, I argue that leadership requires clarity about what truly drives our decisions and the courage to act consistently with those values, even when it costs us opportunities. Ultimately, I reflect on the idea that success is not simply about getting the job or pleasing others, but about finding environments where our values genuinely align and where we can lead authentically.

~Heather

P.S. Summer has a way of drawing us back to things that matter. Rest. Family. Time outside. Slower evenings. Simple joys that somehow feel easier to access when the days are longer and the schedules are lighter. That is why my Catch of the Week this week is finding ways to plant the seeds of summer throughout the rest of the year.

Too often, we treat those things as seasonal. We tell ourselves we will slow down in June, reconnect in July, breathe again in August. Then the calendar turns, routines return, and many of the things that made us feel most alive quietly disappear. The challenge is this: maybe summer is not meant to be an escape from real life. Maybe it is a reminder of what real life needs more of. A walk outside in October. Dinner with people you love in February. A quiet evening without rushing in April. Small moments of rest and joy do not have to belong only to summer. How can we sprinkle the joys of summer throughout the year?

P.P.S. Please remember to...

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