Jill on Money with Jill Schlesinger Terrified of Making the Wrong Move
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Nov 6, 2025 Chris, a private caller and listener, shares his journey after receiving a $2.2 million inheritance while facing retirement decisions and managing real estate investments. He discusses the balance of a mortgage-free beach house and the financial implications of possibly stopping work at 60. Jill provides insights on health insurance costs, the importance of estate planning, and diversification strategies to mitigate risks. Their conversation highlights the critical need for professional advice in navigating significant wealth and thoughtful planning for a secure future.
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Caregiving Led To An Unexpected Inheritance
- Chris explains he stopped working to care for his ill parents and recently inherited money after they passed.
- He and his wife face a life decision about whether he should return to work or remain retired while she continues working.
A Big Real-Estate Heavy Balance Sheet
- Chris and Jill map assets: paid primary home, beach house, two rentals, $1M brokerage, and cash.
- The couple's net worth jumps to about $3.2M pre-primary-sale once the $2.2M inheritance is included.
Match Spending To Sustainable Income First
- Calculate your monthly spending and compare it to conservative portfolio income before quitting work.
- Use safe withdrawal math and confirm you can sustainably cover $12,000 monthly expenses from assets and rentals.