Retirement Readiness at 60: A Practical Guide to What Comes Next
By Craig Loken
Associate Portfolio Manager
Turning 60 does not necessarily mean retirement is right around the corner, but it often makes the idea feel more real.
The questions become clearer and not all of them are financial: When might I stop working? What will my income look like? What will I actually do with my time? What happens if markets, taxes, healthcare costs, or family needs do not unfold exactly as planned?
If you are thinking about retiring in the next five to ten years, this guide can help you focus on the right conversations, decisions, and next steps.
1. Get Clear on When Retirement Might Happen
You don’t need a firm date, but having a window helps.
Ask yourself:
- Do I want to retire at 65, 67, or “when it feels right”?
- Would I consider part‑time or consulting work?
- Do I plan to retire fully, or ease into it gradually?
Why it matters:
Your retirement timeline affects Social Security planning, income planning, investment strategy, and healthcare decisions. Even a rough retirement window you something to build around.
Note: For some investors, additional planning options may also become available after age 59½, depending on employer retirement plan rules.
2. Estimate Retirement Income Not Just Savings
Many people focus on how much they’ve saved, but what matters more is how income will show up every month. The key question is not only “How much have I saved?” but “How much can I reasonably spend?”
Key income sources to review:
- Social Security
- Pensions or annuities (if applicable)
- Retirement accounts (401(k), Traditional IRAs, Roth IRA)
- Investment or Trust Income
- Spousal Benefits
Tip: At 60, Social Security estimates are usually meaningful enough to include in your financial planning, but there is still time to adjust your strategy if the numbers do not support your goals. It is also important to remember that withdrawals from traditional retirement accounts are generally taxable, so the amount available to you as income will be different from the account balance shown on a statement.
3. Understand Your “Real” Retirement Spending
Retirement expenses are often different, but not always lower. Some retirees spend more in early retirement years on travel, hobbies, home projects, or family experiences. Spending on incidentals may settle later, then spending might rise again as healthcare needs increase.
Common areas to review:
- Housing (downsizing, remodeling, or staying put)
- Healthcare premiums and out‑of‑pocket costs
- Travel and hobbies (especially early retirement years)
- Support for adult children or aging parents
A clearer spending picture helps determine whether your savings supports 25, 30, or even more years of retirement.
4. Review Your Investment Strategy for the Next Phase
At 60, the investment conversation often begins to shift. Growth may still be important, but so is income, liquidity, and risk management.
Now is a good time to ask:
- Does my portfolio still match my time horizon?
- Am I comfortable with the current amount of market risk in my portfolio?
- Do I have a plan for market downturns early in retirement?
This next phase may be less about chasing returns and more about ensuring sustainability and peace of mind. As retirement gets closer, it is worth reviewing whether today’s investment mix still reflects your current risk tolerance and timeline.
5. Review Taxes—Before They Surprise You
Taxes don’t stop at retirement and in some cases, they can become more complicated.
Important areas to review:
- The impact of Required Minimum Distributions (RMDs)
- Impact Medicare premium impacts
- Roth conversion opportunities
- State and local tax considerations
- Sequencing of Withdrawal’s (which accounts to spend down first)
- Charitable giving strategies
- Gifting
Retirement tax planning may be best viewed across several years, not just one tax return. The goal is usually not making the one perfect move but coordinating a sustained approach that considers how one decision may affect another.
6. Revisit Your Estate Plan and Beneficiary Designations
Life changes, and your documents should keep up.
At 60, Documents and account titling designations to review:
- Wills and trusts
- Powers of attorney and healthcare directives
- Beneficiary designations (retirement accounts, insurance policies, bank accounts)
- How assets will transfer to heirs or beneficiaries
Why it matters:
Beneficiary forms can affect how assets transfer and may override designations in a trust or a will. Keeping your estate plan current t can make things easier for the people who may need to step in and help.
7. Think About Healthcare (Before Medicare)
Healthcare is often one of the biggest question marks during retirement.
Things to discuss:
- Health insurance before Medicare (if retiring early)
- Medicare timing and coverage options
- Long‑term care considerations
- Health Savings Account (HSA) usage
- How large withdrawals or income changes may affect future costs
Planning ahead helps avoid rushed decisions later.
8. Confirm Your “Team” Is in Place
Retirement planning is rarely a solo effort. As retirement gets closer, financial, tax, estate planning, and insurance decisions often overlap.
Make sure you know who to call for:
- Financial and investment guidance
- Tax planning and preparation
- Estate planning and legal advice
- Healthcare Insurance and risk management
Coordination matters as decisions become more connected.
Final Thought: Retirement Planning Is About Confidence, Not Just Numbers
The first eight items on this list are primarily about money. This part is about everything else and for many retirees, it turns out to be the hardest part.
A career provides more than income. It provides routine, identity, social connections, and a sense of purpose. When that structure goes away, even people with strong financial plans can feel disconnected. The retirees who tend to thrive are the ones who planned ahead about how they want to spend their time and not just their money.
That might mean travel in the early years, volunteering, spending more time with grandchildren, picking up a hobby that never fit into a working schedule, or even continuing to work in some. There is no right answer, but it is worth having the conversation with yourself and the people closest to you before retirement arrives. As we have written before, Retirement is not a Date, It’s a Transition.
Lastly, at 60, retirement planning is not about having every answer. It’s about knowing which questions matter most and giving yourself time to make thoughtful decisions before retirement arrives.
If you are nearing retirement and want to better understand where you stand, we would be happy to help you talk through the next steps.