Ol' College Try

Our Journeys as Parents: How We Saved (or Plan to Save) for Our Kids’ Education—Plus 529 Tips & Big Policy Shifts


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In this candid episode of College!, co-hosts Matt Carpenter and Peg Keough pull back the curtain on how they’re approaching college savings as parents—one with twins, one with a 10-year-old—and the different paths they’ve taken. Whether you’re just starting to think about saving or wondering if it’s too late, this conversation offers relatable, real-world insights with zero judgment.

Matt and Peg also dive into the latest major policy developments, including proposed federal cuts to Pell Grants and work-study programs. What do these shifts mean for families planning ahead—and what actions can you take to “control the controllables”?

Then, they tackle one of the most misunderstood tools in college planning: the 529 plan. From tax advantages to eligibility myths, they debunk common misconceptions and explain why this savings vehicle might be smarter than you think.

👉 In this episode:

  • Two personal college savings journeys—and how values, timing & income shaped them

  • What recent proposed cuts to Pell Grants and work-study could mean for your family

  • The truth about 529 plans: who they’re for, how they’re taxed, and what qualifies

  • Why saving doesn’t hurt your financial aid as much as you might think

  • How to start where you are, and why alignment with your partner is key

🎧 Whether you're saving a little, a lot, or not sure where to begin, this episode offers honest guidance, financial clarity, and peace of mind as you plan for what’s next.

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Ol' College TryBy Matt and Peg's College Planning Podcast

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