What to Do Before Retirement: A 5-Year Planning Guide for Ages 55, 60, and 65

The final five years before retirement are often the most impactful planning window. For high-net-worth individuals, decisions made during this period — around income timing, liquidity, healthcare, and estate structure — can meaningfully influence long-term outcomes.

Rather than treating retirement planning as a one-time exercise, this period is best approached as an ongoing process. As assumptions become clearer and circumstances evolve, the financial plan should be revisited and refined over time.

What Should You Do in the 5 Years Before Retirement? (Quick Answer)

In the five years leading up to retirement, high-net-worth individuals should refine their retirement income strategy, model withdrawal sequencing across account types, evaluate Social Security and healthcare timing, reassess portfolio risk, and update estate planning. Treating the financial plan as one that is refined over time allows for adjustments as new information becomes available.

Age 55: Laying the Foundation

At age 55, while retirement is still several years away, this is often when structural planning decisions have the greatest flexibility.

This is a good time to revisit retirement timeline assumptions and stress-test projected cash flow under varying market conditions, inflation assumptions, and spending scenarios particularly where future income depends on business value, equity compensation, or other concentration factors. Updating the financial plan early allows for gradual portfolio adjustments, especially if a significant portion of net worth is tied to illiquid investments.

Age 55 is also an opportunity to confirm that retirement savings strategies remain aligned with long-term goals. Maximizing contributions and evaluating the mix of pre-tax and Roth savings can help create tax flexibility in retirement.

Age 60: Refining Income and Healthcare Strategy

By age 60, retirement typically shifts from a future plan to an active planning priority. Financial plan assumptions should be updated with greater precision as retirement timing, lifestyle spending, and anticipated income sources become more clearly defined.

This stage is also when many individuals begin evaluating Social Security claiming strategies. While eligibility begins at 62, delaying benefits may increase lifetime income, particularly for households with other sources of retirement funding.

Healthcare planning becomes more immediate as well. If retirement is expected before age 65, individuals should evaluate insurance coverage options alongside projected out-of-pocket costs and potential gaps between retirement and Medicare eligibility.

Age 65: Executing the Retirement Transition

Age 65 often marks the shift from accumulation to implementation. At this stage, the financial plan should transition from savings projections to income distribution modeling.

This includes establishing a tax-efficient withdrawal strategy across taxable, tax-deferred, and Roth accounts, while coordinating distributions with Social Security timing. Medicare enrollment also becomes a priority, with initial enrollment periods beginning three months before age 65.

Retirement is also a natural time to revisit estate planning documents, beneficiary designations, and insurance coverage. Aligning these elements with updated goals ensures the financial plan reflects both current circumstances and long-term legacy intentions.

Refining Your Financial Plan Over Time

Markets shift, retirement dates evolve, and income projections change. Regularly revisiting the financial plan and adjusting it as circumstances evolve supports more deliberate, incremental decision-making rather than reactive course corrections.

For high-net-worth individuals, an evolving plan can enhance tax efficiency, manage risk, and preserve flexibility as retirement approaches.

Frequently Asked Questions

When should I start refining my retirement plan?

Ideally five to ten years before retirement, with annual updates as income projections, investment performance, and personal priorities evolve.

Is Social Security timing still important for high-net-worth households?

Yes. Even when Social Security represents a smaller portion of retirement income, optimizing timing can improve tax efficiency and portfolio longevity.

How often should a financial plan be updated before retirement?

At least annually, and more frequently when major changes occur, such as liquidity events, shifts in retirement timing, or tax law updates.

Final Thoughts

The five years leading up to retirement represent a critical planning window. For high-net-worth individuals, coordinating investment strategy, income timing, healthcare planning, and estate considerations — within a plan that is refined over time — can help create clarity and confidence as retirement approaches.

To learn more, connect with a Freestone advisor to discuss strategies tailored to your situation.

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