Jill on Money with Jill Schlesinger Can I Fully Retire in 2-3 Years?
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Jan 7, 2026 Angela, a listener seeking advice on her retirement plan, discusses her aim to retire in just two to three years. She shares insights about her household finances, including 401(k) balances and Social Security estimates. The conversation dives into options for a pension lump sum and managing appreciated company stock. Jill also highlights the importance of spending needs, flexible income sources, and the impact of taxes on retirement accounts. They wrap up by confirming Angela's estate planning is in place, setting her on a path toward financial freedom.
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Retire Early If You Can Accept Account Drawdowns
- Do consider retiring in two years if you and your husband are willing to draw from retirement accounts and accept the tax consequences.
- Plan for partial work or side income if you want more financial breathing room while bridging to Social Security at full retirement age.
Long-Held Company Stock Creates A Tax Puzzle
- Angela holds long‑standing company stock granted over 20 years ago with likely low cost basis.
- Jill frames this as a "good problem" because the stock has appreciated significantly.
Fold Property Sale Into Retirement Cash
- Do plan to add the commercial property sale proceeds to your brokerage and treat it as part of your retirement liquidity.
- Use the extra cash to bolster taxable accounts for flexibility before Social Security starts.