We celebrate Thanksgiving with some light hearted banter, and exploring the question of whether "High Watermarking" can lead to disappointment (even if it's hypothetical). We hope you're enjoying time with your family and friends this week, but if you want your weekly dose of personal finance content, we're here for you!

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Could a half-century loan be the answer to the housing crisis, or is it a financial nightmare waiting to happen? We break down the pros, cons, and the brutal amortization schedules of 50-year mortgages to see who actually benefits. Plus, we’re emptying the mailbag to cover the specific financial hurdles you are facing right now. Tune in to this week's mailbag episode!

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This week, Ross and Dan tackle a fun question... If you had to invest $100,000 without using the stock market, what would you do? Would you become a landlord and try to buy real estate? Would you try to start a business or invest in something truly "passive?"

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Send your questions for upcoming show to checkyourbalances@outlook.com
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Does the average financial plan have "retirement tunnel vision," with a focus on pouring every spare dollar into your retirement accounts. We're all told to save for the future, but what happens when that focus makes us 'house poor' or 'life poor' today? Big goals like buying a home, funding college, or starting a business can't always wait until you're 65. Is it possible to be too focused on saving for your golden years?

#retirement #financialplanning #balance

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Send your questions for upcoming show to checkyourbalances@outlook.com
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First up: A listener challenges our take on Dollar Cost Averaging out.

Then, we confront the fear: How spooky is this market? Ross and Dan bust the financial ghouls and tell you what’s truly frightening for your portfolio (and what’s just noise).

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Send your questions for upcoming show to checkyourbalances@outlook.com
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The October Mailbag is here! Ross and Dan open up the mailbag to answer your pressing financial questions, tackling everything from navigating the costs of college to whether you can Dollar Cost Averaging (DCA) out of a position as you approach retirement. Plus, they dive into the latest listener stories and tips on spotting and avoiding financial scams. Tune in for practical advice and a breakdown of the things you need to know right now!

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Send your questions for upcoming show to checkyourbalances@outlook.com
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Is the grueling pace of your job fueling your desire for FIRE (Financial Independence, Retire Early)? This week on Check Your Balances, Ross and Dan tackle the reality that for many, burnout is the primary driver of the movement, not just aspiration. We discuss how to re-evaluate your aggressive savings strategy, explore more balanced options like Coast FIRE, and ensure your pursuit of freedom doesn't cost you your current well-being. Stop letting the corporate grind dictate your financial plan—it's time to find a path to independence that's sustainable.

#FIREMovement #Burnout #FinancialIndependence #CheckYourBalances #CoastFIRE

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Send your questions for upcoming show to checkyourbalances@outlook.com
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When it's time to sell your personal home, do you treat it like a purely emotional move or a smart financial transaction? This week, our resident real estate expert, Dan, is under contract on selling his personal home.

Join us as Dan breaks down the process, from pre-listing prep and pricing strategy to staging secrets and negotiation tactics. Whether you're moving next month or just planning for the future, this episode is packed with must-hear, actionable lessons on maximizing your home's sale price and minimizing costly mistakes.

#RealEstate #personalfinance #Investing #HomeSale #PropertyInvestment #WealthBuilding

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Send your questions for upcoming show to checkyourbalances@outlook.com
@checkyourbalances on Instagram