The decade leading up to retirement is one of the most important financial periods of your life. Key decisions during this time begin to shape your long-term income, taxes, healthcare costs, and lifestyle. Some choices remain flexible, but others become permanent once retirement begins. Knowing which is which helps you make confident, well-timed moves.
Below is a practical guide to the decisions that matter most in the 5–10-year retirement window, what you can still adjust, and what becomes fixed later. Insights come from trusted industry sources, including the Social Security Administration, Medicare.gov, and leading retirement research organizations.
1. Social Security Timing and Spousal Coordination
When you claim Social Security, it affects your benefit for life, so this decision deserves careful planning.
What You Can Still Change Now
- You can claim anytime between 62 and 70. Claiming early reduces your benefit, while delaying increases it by about 8 percent per year past full retirement age.
- Couples can coordinate their timing. One spouse may delay maximizing the survivor benefit while the other claims earlier for cash flow.
- You can adjust your retirement date, part-time work, or withdrawal strategy to support delaying benefits.
What Becomes Permanent Later
- Once you file, your monthly benefit is set aside from cost-of-living adjustments.
- Your claiming age determines the survivor benefit your spouse may receive.
- Early claiming limits your ability to manage taxable income in the early retirement years.
2. Roth Conversions in the Lower-Income Gap Years
The years after leaving work but before Social Security and Required Minimum Distributions begin often create a lower-income window. This period can be ideal for Roth conversions.
What You Can Still Change Now
- You can convert traditional IRA or 401(k) assets to Roth while you are in a lower tax bracket.
- Before age 65, conversions do not affect Medicare premiums.
- Delaying Social Security keeps taxable income lower, which can make conversions more efficient.
What Becomes Permanent Later
- Required Minimum Distributions begin at age 73, reducing your ability to convert larger amounts.
- Once Social Security, pensions, and RMDs start, your income may rise and push conversions into higher tax brackets.
- After enrolling in Medicare, conversions can trigger IRMAA premium surcharges.
3. Health Insurance Between Leaving Work and Medicare
Retiring before age 65 creates a coverage gap that requires planning. This is one of the most overlooked parts of retirement preparation.
What You Can Still Change Now
- You can compare ACA marketplace plans, which offer income-based premium credits.
- COBRA or private insurance may help bridge coverage for a year or two.
- Your retirement date can influence your ACA subsidy eligibility and taxable income.
What Becomes Permanent Later
- Medicare begins at 65, regardless of when you retire.
- Missing enrollment windows can lead to lifelong penalties.
- ACA subsidies end once Medicare starts, changing your cost structure.
4. Shifting Your Portfolio From Growth to Income
Your investment strategy should evolve as retirement approaches. The goal is to reduce risk gradually while preparing for withdrawals.
What You Can Still Change Now
- You can rebalance toward more stable, income-oriented investments such as bonds, dividend stocks, or annuities.
- You can stress-test your portfolio to see how it might perform during early-retirement market volatility.
- You can adjust your withdrawal strategy and build cash reserves.
What Becomes Permanent Later
- Sequence-of-returns risk becomes more significant once you start withdrawing. Early losses can have lasting effects.
- Changing your investment strategy after retirement can be more disruptive.
- Some annuity options are only available before RMDs begin.
Your Window of Opportunity Is Now
The 5–10 years before retirement offer a unique chance to shape your financial future. Social Security timing, Roth conversions, healthcare planning, and investment strategy all work together, and the choices you make now can be difficult to reverse later.
Longview Insurance and Investments helps pre-retirees make confident decisions during this critical window.
If you are ready to take the next step, schedule a conversation today.
Let’s build your long-term plan together.
Sources:
• Social Security Administration. “Family Benefits.” 2026. ssa.gov.
• Fidelity Investments. “Focused conversion: A strategy for IRAs.” 2026 https://www.fidelity.com/learning-center/personal-finance/retirement/roth-iras-roth-ira-conversion/focused-roth-conversion
• Medicare.Gov. “Avoid Late Enrollment Penalties.” 2026 https://www.medicare.gov/basics/costs/medicare-costs/avoid-penalties