Pre-retirement checklist
Short answer: In the five years before retirement, build an income plan, decide on healthcare until Medicare, model Social Security timing, map tax moves such as Roth conversions, and consolidate accounts. In the final year, confirm the numbers, pension choices, and paperwork. In the final 90 days, set up the first paychecks from your savings.
Five years out
- Estimate spending in retirement, including the first few active years
- Map income sources: Social Security, pension, portfolio, part-time work
- Decide how you will cover healthcare before age 65
- Model Roth conversions and which accounts to draw first
- Review how much is in employer stock
One year out
- Confirm your retirement date and any pension election deadlines
- Choose a Social Security claiming age for each spouse
- Rebuild a cash reserve for the first year or two of spending
- Update wills, powers of attorney, and beneficiaries
- Run a tax projection for the retirement year
90 days out
- Set up a monthly transfer from savings to checking that acts as your paycheck
- Confirm final paycheck, unused PTO, and deferred comp payout dates
- Enroll in health coverage that starts the day employer coverage ends
- Decide what to do with your 401(k): leave, roll over, or both
Get the tax side right
The years around retirement often have unusual income: a last partial year of wages, then low income before benefits start. Those years can be useful for conversions or gains. Bull Oak’s profile lists tax planning, tax prep, and filing with its retirement planning.
Related: Roth conversion calculator, bridging to Medicare, retirement mistakes in your 50s, retirement planning advisors.
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Frequently asked questions
When should I start pre-retirement planning?
Five to ten years out gives time to adjust savings, taxes, and healthcare plans.
What is the biggest pre-retirement mistake?
Not having a written income plan that shows where each year's spending will come from.
Should I pay off my mortgage before retiring?
It depends on your rate, liquidity, and taxes. Model it rather than assuming.
Is this financial advice?
No. It is a general checklist. Work with a professional on your situation.
Bull Oak is a fee-only fiduciary advisor, helping high-net-worth individuals and families navigate the transition into retirement through financial planning, investing, and tax planning and filing.
See Bull Oak’s profileRelated reading: questions a pre-retiree can ask a financial advisor, financial advisor directory for retirees.
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