Jill on Money with Jill Schlesinger Is Our Financial Picture Too Complex?
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Oct 13, 2025 Lisa, a listener from North Carolina, seeks advice on simplifying her family's complex finances, which include rental properties and two small businesses. Jill discusses strategies for managing retirement accounts and college savings plans for her children. They explore cash flow issues and the benefits of potentially selling a business to reduce stress. Jill encourages Lisa to consider letting go of one time-draining business to improve her financial situation and lifestyle flexibility.
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Start By Cutting Time Drains
- If your finances feel complicated, simplify by removing drains on time and energy first.
- Sell or stop activities that create stress before making wholesale changes to assets.
Household Income Snapshot
- Lisa says her husband earns about $200k base plus roughly $50k bonus for a consistent ~$250k household income.
- She framed herself as making nothing initially, though she later earns from side projects.
Healthy Retirement Base
- They have strong retirement savings: $791k across accounts with a growing tilt to Roth contributions.
- That level gives flexibility on tax planning and future withdrawals as income rises.