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All Roads Lead to Real Estate

A Maryland podcast hosted by Matt Rhine

Full Interview · November 6, 2023 · Ep. 20

Megan Winkler: Small Moments, Lasting Impact

From classroom planning to a child’s first day, Megan shares practical ways teachers and parents can help children learn, connect and grow.

Megan Winkler and Matt Rhine in their filmed studio interview
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Educator · Matt Rhine’s sister

Megan WinklerEducator · Matt Rhine’s sister

Inside the Interview

  • Understand the preparation teachers do for children with different learning needs.
  • Find a useful way to start a parent-teacher conversation when a concern comes up.
  • Help a child practice independence and feel ready for the first day of school.
  • Hear why kindness and good decisions matter alongside academic work.
  • See what a specific parent note can tell a teacher about classroom culture.

Recorded in November 2023. Megan’s teaching roles and school policies are described as they were then; confirm current school arrangements locally.

Meet the Guest

Megan Winkler

Megan Winkler, formerly Megan Rhine, is Matt’s sister and an educator. While still in school, she found that she enjoyed helping teachers and teaching math to students who needed extra support.

More about Megan Winkler

She went on to teach fourth and fifth grades, then worked as a math resource teacher. At the time of this November 2023 conversation, she was teaching preschool. Megan is candid about the planning and energy the job takes—and about the creative problem-solving she still loves when she helps a child learn.

Her perspective is warmly practical: give children room to try small tasks on their own, keep parents and teachers talking when a concern comes up, and notice the ways a classroom can help a child feel welcome. A parent once wrote to thank her for the culture in her preschool room. That simple note stayed with her.

  • EducatorElementary classroom and math resource teaching
  • Preschool teacherHer role at the time of the 2023 interview
  • Matt’s sisterA conversation about teaching and family

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Interview highlights

Three conversations worth your time.

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Megan Winkler in an authentic frame from her filmed studio interview

When the Classroom Comes Home With You

Megan describes the work that follows teachers out of the classroom and the difficulty of protecting time at home.

Megan Winkler in an authentic frame from her filmed studio interview

Start With One Thing Your Child Needs

A practical parent–teacher conversation: understand the concern, choose a small goal and keep communicating.

Megan Winkler in an authentic frame from her filmed studio interview

Choose a Consequence You Can Actually Keep

Megan explains why staying calm, understanding a child’s development and following through matter more than a big threat.

From the interview

Questions and answers.

Watch each answer at its matched video timestamp, or read the source transcript.

How should parents start a conversation about a concern?

Megan suggests asking the teacher whether they see the same issue and agreeing on next steps together, rather than assuming either side has all the answers.

How can families ease first-day-of-school nerves?

Talk through the day, visit the classroom when the school offers that chance, practice the routine and have supplies ready and labeled.

What does a welcoming classroom look like to a parent?

Megan recalls a parent thanking her for a preschool culture that helped her child connect with a classmate. The specific note showed Megan the effect of her work.

More questions

What first drew Megan to helping students learn?

While still in school, she helped teachers and especially enjoyed teaching math and working with students who needed extra support.

How did her classroom age groups change?

Megan says she began with fourth- and fifth-graders and loved upper elementary; by the 2023 interview she was teaching preschool, an age group she once found daunting.

Why does teaching take more than setting up a room?

Megan describes planning for many different learners, preparing lessons and attending meetings—work that can take time away from the classroom.

What work can teachers bring home?

Megan remembers devoting Sundays to lesson plans and grading when she taught in public elementary school. Her preschool role gave her a different balance in 2023.

What should someone considering teaching understand?

Megan says a love of children and the chance to affect their lives matter to her; she also cautions that the work is not a route to high pay.

Which lessons matter alongside academics?

Megan says she wants children to be kind, make good decisions and grow into good people—not focus only on schoolwork.

How can a preschooler practice independence?

Megan suggests gradually letting a child try everyday tasks, such as putting on their own shoes, rather than always doing those tasks for them.

What if homework keeps turning into a struggle?

Megan talks about looking for why a particular assignment causes friction, instead of reacting only to the behavior around it.

What can school redistricting change for a family?

Megan worried that a proposed 2023 change could turn her family’s short school drive into a much longer one. It was a personal example, not a current district plan.

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