Reflections on the Journey: A Veteran Educator Shares Five Surprising Truths About Homeschooling High School
After seven years of navigating the multifaceted world of alternative education, veteran homeschooler and author Shawna Wingert is marking a significant milestone. As her oldest son prepares to graduate high school and transition into young adulthood, and her youngest prepares to embark on the very same educational tier, Wingert has taken time to reflect on a journey that has proven to be as rewarding as it is challenging.
Reflecting on the passage of time, Wingert notes that her oldest child was just eleven years old and her youngest was eight when they first began chronicling their experiences on the educational platform Simple Homeschool. Looking back on the last seven years, she describes the experience as a wonderful, joyful, occasionally stressful, and ultimately worthwhile endeavor. Now, standing at the precipice of a major family transition—with just six weeks remaining in her oldest son’s K-12 education—she finds herself looking back at a phase of parenting and teaching that shattered many of her initial preconceptions.
While the high school years flew by much faster than the earlier stages of education, Wingert emphasizes that they also turned out to be remarkably engaging. Because her children grew older, their shared interests began to align more closely with her own, transforming daily discussions about current events, history, and art into deeply stimulating intellectual exchanges. Preparing her eldest for life after high school prompted Wingert to compile a list of insights she wishes she had possessed at the outset of her high school homeschooling journey—lessons designed to reassure parents who might currently find themselves standing where she stood seven years ago.
Homeschooling High School Doesn’t Have To Be Totally Different From The Younger Years
When Wingert and her son initially prepared for his freshman year of high school, a wave of apprehension set in. Like many parents, she carried the preconceived notion that high school education needed to undergo a radical transformation to be considered legitimate. The societal expectation that ninth grade onward must look entirely rigorous, formal, and far less enjoyable weighed heavily on her preparations.
However, reality proved to be quite different. Her son’s high school experience ultimately mirrored his earlier years, relying heavily on interest-led, hands-on, and project-based learning. By the time her son reached the end of his senior year, Wingert realized that this personalized approach had not only worked, but it had honored the way her child naturally learned best. Rather than forcing her student into a conventional, rigid mold dictated by traditional schooling standards, she maintained a flexible, engaging environment, proving that effective high school education does not require abandoning individualized learning methods.
Don’t Be Afraid Of High School Transcripts and Course Credits
For many parents stepping into the realm of home education for older teens, administrative tasks can loom large. Wingert admits she was initially terrified at the prospect of compiling official high school transcripts and calculating course credits. The terminology felt formal, intimidating, and far removed from the day-to-day rhythms of family learning.
Yet, as she navigated the process, Wingert discovered that transcript management was far more manageable than anticipated. Once she established a system that worked for their specific needs, tracking and organizing credits actually became a satisfying task. Rather than remaining a bureaucratic hurdle, the transcript transformed into a tangible, observable measure of academic progress—something that can occasionally elude parents who teach outside traditional classroom walls. Gaining confidence in this area allowed Wingert to relax and better appreciate her son’s academic achievements as they accumulated semester by semester.
Your Role Will Change Over The Four Years
One of the more surprising developments during the high school phase was the natural evolution of Wingert’s daily responsibilities. Early on, she anticipated remaining the primary instructor directing every facet of her son’s daily schedule and academic output. Instead, she watched as her role shifted significantly over the course of four years.
Rather than acting as the central figure of direct instruction, Wingert found herself transitioning into a supportive facilitator—managing logistics, securing necessary learning materials, and driving her student to various commitments and activities. While this shift felt slightly disconcerting at first, she quickly realized it was a necessary and healthy evolution. This changing dynamic fostered a profound sense of academic ownership and independence in her son, allowing him to take charge of his own educational path. Looking back, she notes that acting as an administrator and driver was a worthwhile trade-off for witnessing her child’s growing self-reliance.
Your Child Will Have More Opinions
As children mature into teenagers and young adults, their developing autonomy naturally brings forth strong personal perspectives. Wingert experienced this firsthand when her son formed definitive opinions regarding his post-secondary plans—specifically his desire to apply to four-year colleges, a path she initially questioned as a potential mismatch for his unique learning profile.
Navigating these robust discussions required a delicate balance of guidance and letting go. Wingert acknowledges that while parenting a high schooler inevitably involves moments of emotional adjustment, these differing viewpoints are a natural part of growing up. Steering a high school homeschooler ultimately mirrors the broader experience of raising a teenager, which requires parents to respect developing voices and embrace the gradual process of granting independence.
The Memories Are Irreplaceable
Perhaps the most poignant realization from Wingert’s journey is the enduring value of the memories created during the high school years. As her son matured into an adult, the nature of their daily interactions evolved, yielding moments and shared experiences that felt distinct from—and deeply cherished compared to—the earlier stages of childhood.
Wingert notes that these high school years represent the phase when the combination of home education and constant family proximity truly flourished. The intellectual discussions, collaborative projects, and shared milestones formed a rich tapestry of memories that she would not trade for anything. As she prepares to close this chapter with her eldest son and simultaneously embark upon it with her youngest, Wingert reflects on the experience with profound gratitude. While the road ahead brings the bittersweet anxiety of seeing her child step out into the world of higher education, her overarching sentiment remains one of deep appreciation for the journey of homeschooling high school.
