We Have to Have a Talk (or Several)

  • Child Development
Jessie Skipwith

I am having multiple conversations with a variety of members from our Aspen Academy community and I am receiving so many wonderful questions. Not “wonderful” because I have the answers; no - wonderful because these questions are bringing our community to a place where we must have dialogue - healthy conversations - about where we currently are, where we have been, and where we want and NEED to go.  Working among educators and families familiar with education, we often find ourselves looking for a checklist of things to accomplish and so we can say to ourselves, “I’ve done that” and then we look to move on. Well this dialogue, this ongoing conversation, is going to be different.

Affinity Space for Self-Identified Families of Color

One way we can support families in our community who self-identify as Families of Color is by creating a group to discuss challenges and celebrate one another. If you’re interested in joining us for that conversation, please click this link to receive more details or email me.

Conversations and Self-Reflection Set in Motion

In the world today, people’s conversations are teeming with substance and details surrounding the observations following the death of George Floyd, the global movement surrounding Black Lives Matter, the language involved in learning to be anti-racist, and recontextualizing our nation’s history.  In conversations with parents and faculty through our online Inclusive Community Conversations, we’re exploring questions including:

  • What are the next steps for parents as we raise our children?
  • What are the next steps for educators as we pivot in this moment to better form the hearts and minds of this future generation of leaders?
  • What are the next steps for our future and our shared communal livelihoods? 

What Can I Do?

Our collective next step is to learn as much as we can about people different than ourselves, their respective lived experiences, and what we are seeing in the systems that we live in and how these systems promote justice for all people. We can work to learn more and increase awareness about ourselves and how we operate in these systems.  We can acknowledge that many components of these systems are not, and have not been, congruent with the ideals we hold dear to our hearts: kindness, fairness, justice, equity, inclusion and goodness. 

Sometimes it Won’t be Easy, and it’s a Start

I have relished some of the questions presented to me by parents, as these questions have invited the necessary conversation that we all need to have in order to bring together our collective wisdom and to do our part to oppose and usurp any systems that exist that prevent the pursuit of our ideals.  These conversations are where we need to begin.  They will not always be comfortable. In fact, they are not likely to be. We are being called to engage in conversations that many of us have avoided for most of our lives.

Recently, I’ve been asked questions about Black Lives Matter and systemic racism and how these concepts will be addressed with our students in school. Parents have shared questions regarding curricular change and instruction, newly created lessons, and ongoing conversations with our students regarding anti-racism and anti-bias instruction. These are questions that we will need to answer, and I look forward to exploring answers to these questions, alongside you in community conversation.

Listen, Listen, Listen… to Understand Others

It is really hard to listen -- and hear -- when we are so busy talking or forming our thoughts for our next commentary.  We need to provide a healthy and safe space for others to express themselves and to be heard as we seek understanding. The time has come to look closely at who we are as individuals. It is the time for us to self-assess and to strive for empathy as we try to see life through the lens of our fellow human beings. We are afforded the opportunity to partner as parents and educators to guide our students and one another through what we can see will be a life-long process of growth. 

Inclusive Community Conversations

Through our Inclusive Community Conversations with students, parents and colleagues, through personal one-on-one conversations, and in observing the in-depth lessons that our teachers will be providing to our students, we look forward to engaging, learning and facilitating new and positive change.

We recognize that these are not humanity’s worst days - that certainly things used to be significantly worse. However, by acknowledging past historical injustices, we can begin a process of reconciliation and healing and move collectively towards progress. We can invite people who are in a position of power and influence to help brainstorm strategies where perhaps only they have the power to influence change. We can educate ourselves. We can continue to preserve a deeply held sense of hope for our collective future. We can do better.

Thank you for joining in and I look forward to seeing as many of you as possible at our next Inclusive Community Conversation.


Join an Upcoming Inclusive Community Conversation



Be Safe and Be Well,



About the Author


Jessie Skipwith is the Director of Elevate & Diversity, Equity and Inclusion and Licensed School Counselor at Aspen Academy.

Jessie comes to Aspen Academy with over 20 years of experience in educational leadership and student engagement. He has held head of school positions at elementary, middle and high schools, ran an all-school counseling department, provided private practice counseling services for families and individuals, and has served as the executive director of an education non-profit supporting low-income, English language learners from throughout the greater Denver area. He is a voracious reader of books about how students learn, how families and communities support developing young people, as well as books on progressive, innovative and dynamic new solutions to many of today’s life challenges. Jessie loves that Aspen Academy provides families and students with a small, nurturing and safe environment that encourages students to take healthy risks, to push themselves beyond their comfort zones, and that it inspires insatiable curiosity and wonder in students as they pursue their passions to help make the world a better place to live for all people. Outside of work, he loves to spend time with his wife and two children and enjoying Colorado’s great outdoors while hiking, golfing or skiing.