Episode 13: Teacher By Day, Realtor By Night episode artwork

EPISODE · Jun 16, 2026 · 13 MIN

Episode 13: Teacher By Day, Realtor By Night

from Chalkboards to Cashflow: Educators Investing in Real Estate · host Michelle Kavan

In this episode of Chalkboards to Cash Flow, we sit down with Lindsay, a full-time first grade teacher who has successfully balanced a career in education while working as a licensed real estate agent for more than two decades.From juggling lesson plans and client calls to using commission checks to support her family and retirement goals, Lindsay shares the reality of managing two careers at once and why becoming a real estate agent can be a powerful side hustle for educators.If you’ve ever wondered whether you could build a real estate career without leaving the classroom, this episode is for you.In This Episode, We Cover:* How Lindsay became a real estate agent while teaching full time* Balancing education, family life, and real estate* Why teaching skills translate well into real estate* The realities of earning commission-based income* Using real estate as supplemental retirement income* Challenges of managing two careers* Building trust with clients while working in education* Why educators may have an advantage in real estateMeet Today’s GuestLindsay has spent nearly 40 years teaching first grade while also building a successful side career in real estate.After earning her real estate license in 2004 during a teaching job-share arrangement, she spent over 20 years helping clients buy and sell homes while continuing her work in the classroom.Key TakeawaysTeachers Can Successfully Build Side HustlesLindsay’s story proves that educators can pursue additional income streams without giving up teaching. Real Estate Can Supplement RetirementOne major theme of the episode is using real estate income to help offset the realities of teacher retirement benefits.Trust Is a SuperpowerTeachers naturally build trust with people, which can become a huge advantage when working with real estate clients.Systems and Support MatterLindsay discusses the importance of:* Good brokers* Transaction coordinators* Reliable people on your teamTrying to do everything alone makes balancing both careers much harder.You Can Handle More Than You ThinkOne of the most inspiring moments of the episode centers around discovering personal capacity and learning how to manage multiple responsibilities successfully.Topics DiscussedBecoming a Realtor While Teaching* Getting licensed* Passing the exam* Starting with mentorship and support* Building business graduallyBalancing Two Careers* Working during summers and breaks* Managing paperwork around school schedules* Setting expectations with clientsFinancial Benefits* Supplemental income* Paying for weddings and college expenses* Supporting retirement planning* Using commissions strategicallyLessons Learned* The importance of ethics and trust in real estate* Choosing the right people to work with* Managing burnout and exhaustionMemorable Quotes “Teacher by day, realtor by night.” “You can do more than you think you can.” “I’ve always told people upfront, I’m a teacher first.” “There’s always enough hours in the day to switch gears.”“It’s great as a supplemental income.”Connect With The ShowFollow Chalkboards to Cash Flow for more conversations around real estate, side hustles, and financial freedom for educators.Join the free Chalkboards to Cash Flow Facebook community and connect with teachers and everyday investors building wealth one step at a time.Enjoyed This Episode?If this episode inspired you to explore real estate while continuing your teaching career:* Follow the podcast* Leave a review* Share this episode with another educator* Join the Chalkboards to Cash Flow Facebook group* Reach out on Instagram for more information about becoming an agentBecause you don’t have to leave the classroom to start building wealth outside of it.

Episode metadata supplied by the publisher feed · Published Jun 16, 2026

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Episode 13: Teacher By Day, Realtor By Night

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This episode was published on June 16, 2026.

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