Jill on Money with Jill Schlesinger Maximize Our Assets and Optimize Our Taxes
10 snips
Dec 23, 2025 Dave, a listener from North Carolina, seeks advice on retirement timing and tax strategies. He discusses household income, plans to retire soon, and a significant concentration in company stock. Jill dives into his 401(k) and after-tax conversion strategies while emphasizing the importance of diversification. They explore his real estate holdings, healthcare options, and the potential of 529 funds for his son. Jill encourages simplifying investments and reassures Dave he's on track for an early retirement.
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Build A 10-Year Retirement Plan
- Work toward a clear retirement timeline and savings plan for the next decade.
- Max out retirement contributions and use catch-ups to accelerate savings while working.
Employer Stock Is Wealth And Risk
- Concentration in employer stock creates both wealth and risk that needs deliberate handling.
- Diversification is critical even if you feel loyal to your company.
Use Professional Help For Tax Planning
- Hire a fee-only financial advisor or tax professional to plan tax-aware diversification.
- Consider paying hourly for targeted planning to avoid a big taxable hit from selling concentrated stock.