Windsor Wealth Management LLC

Investment service in Topsfield, Massachusetts

Planning Your Final Days of Work Before Retiring

by

The Calm After the Work Is Do

Today, we:

  • Discuss eight actions to take before you give retirement notice to your employer.
  • Provide a detailed checklist of essential pre-retirement tasks.

As you start thinking seriously about your final days of work before retirement—whether that’s at age 62, 67 or another time—there are a few key actions that help things go more smoothly.

Now, let’s look at eight actions to take before your last day of work:

#1—Retire to Something, Not Just from Work

Retirement isn’t just about leaving your job.

It’s about building a life you want to live. Whether that means a part-time job, volunteering, spending time with the grandkids or finally joining “that” gym—it’s important to have a purpose.

Beyond what you’ll be “doing” in retirement, it’s equally important to understand how you might feel and how your health could be impacted by this major transition.

Quick Tip by Dave Bunker, Watch the Video Now >

#2—Understand the Emotional Shift and Health Impact

The first year of retirement can bring a surprising health risk: stress-related heart issues spike.

The transition from earning and saving to drawing down what you’ve built is a big emotional adjustment.

Background:

Harvard School of Public Health researchers looked at rates of heart attack and stroke among men and women in the U.S. Health and Retirement Study. Among 5,422 participants, those who had retired were 40% more likely to have had a heart attack or stroke than those who were still working.1

The increase was more pronounced during the first year after retirement, before leveling off. Overall, research on retirement’s health effects is mixed.2

Our Recommendation…

Retirement isn’t a one-time event; rather, it’s a transition.

Many retirees experience changes in identity, routine and social connection. That’s why it’s important to prepare not just financially, but emotionally as well.

To better understand the emotional journey, check out this helpful TED Talk: 4 Phases of Retirement…and the Psychological Challenges.3 The four phases include: Vacation, Feeling Lost, Trial and Error, and Reinvent and Rewire.

#3—Clean Up and Consolidate Your Financial Life

Now is the time to tidy up your financial accounts, including:

  • Review and possibly consolidate old 401(k)s or other workplace plans into an IRA. While some 401(k)s are worth keeping, IRAs usually offer more flexible withdrawal options and simplify things for your heirs.
  • Open any needed accounts before your final day to avoid delays. For instance, give us a call about a month before you retire so we can help you set up the IRA account you’ll use to roll over your 401(k), 403(b) or similar.
  • If you’re receiving a pension, let’s analyze your options (lump sum vs. monthly annuity, single life vs. joint life, etc.) using our Income Lab modeling tool. Keep in mind, most pension decisions need to be made at least 60 days before retirement. Also, if you’re taking a lump sum, put it into an IRA. If you leave it in your brokerage, you’ll pay taxes on ordinary income. 

TIP: If you’re receiving a bonus or cashing out unused vacation time, it may impact your taxes or final 401(k) contributions. Therefore, timing your retirement date matters. Also, hold off rolling over your 401(k) into your IRA until your final contribution, unused vacation time, bonus, etc. hit.

#4—Secure Healthcare Coverage

Are you eligible for Medicare (typically at age 65)? Or will you need COBRA or private insurance? Will you want Medicare Advantage?

While pondering the latter, you’ll also want to revisit your healthcare proxy, powers of attorney and estate documents.

Important: If you’re 63 or older, let’s analyze your income to avoid triggering IRMAA surcharges (Income Related Monthly Adjustment Amount) on Medicare premiums. Being just one dollar over can cost you thousands.4

Free Medicare Counseling Resources:

#5—Plan Your Retirement Paycheck

We’ll help you set up a retirement income stream that feels like a paycheck.

Resource: Read our detailed blog post about how we help you create your monthly retirement paycheck.9

#6—Watch for Tax Triggers & Withholdings

Be sure to double-check your tax withholding rates for Social Security and pension income. Common options include 7%, 10%, 12%, 22% and higher.

Many retirees forget to set withholdings on these payments, which can lead to surprises at tax time. Alternatively, you can opt to pay quarterly estimated taxes.

As a general rule, use a 20% withholding rate as a starting point. It may need adjusting, but it offers a solid baseline.

Remember, while you’ll no longer pay into Social Security or Medicare, you’ll still owe taxes on retirement income.

Finally, if you’ve had a one-time income event, it’s important we run a tax analysis together.

For Example:

If your total income was $200,000, but $80,000 came from a one-time bonus, we’ll want to explore whether that bonus can be excluded when calculating your Medicare IRMAA.

Lastly, consider if there is anything else you should be doing right now, e.g., taking capital gains.

#7—Decide What Insurance to Keep (and What to Let Go)

As your needs change, it’s smart to review any life or long-term care insurance policies.

Key questions to ask yourself include:

  • Is your life insurance portable?
  • Do you still need it?
  • Should we evaluate or add long-term care coverage?

#8—Finalize Your Budget

A budget is a living, breathing document; it’s never truly final. Still, it’s important to think about how your spending patterns will shift in retirement.

For example, retirement may mean:

  • Less spending on commuting, work clothes or lunches out, but more on travel, healthcare, hobbies or RV maintenance.
  • Mortgage payments disappearing, but insurance or family support costs rising.
  • Savings on payroll taxes, but higher utility bills from being home more.
  • Dropping life insurance premiums, but adding Medicare costs, prescriptions or home repairs.

Resource: Download our handy budgeting worksheet.10

Understanding these trade-offs now helps set realistic expectations and keeps your retirement income plan on track.

RESOURCE: Retiring Checklist

To help you think through additional retirement considerations, here’s a detailed checklist: What issues should I consider before I retire?11

Within the above checklist are links to other checklists and flowcharts that help answer the following questions:

  • Will I Avoid IRMAA Surcharges on Medicare Part B & Part D?
  • What Issues Should I Consider When Purchasing Long-Term Care Insurance?
  • Should I Consider Doing A Roth Conversion?
  • What Issues Should I Consider When Establishing My Charitable Giving Strategy?
  • What Issues Should I Consider Before I Update My Estate Plan?
  • Am I Eligible for Social Security Benefits If I Have Been Divorced?
  • Am I Eligible For Social Security Benefits As A Surviving Spouse?
  • Can I Make A Deductible Contribution To My HSA?

Next Steps

If you’d like an updated look at your retirement income and tax projections, give us a call. We’re happy to revisit the numbers as often as you need, regardless of how close or far off your retirement may be.

–David Bunker, Financial Advisor & Licensed Fiduciary

Before You Go

Get help optimizing your retirement income. Download our FREE “Prolonging Retirement Income” checklist.

Also, receive help retiring to the life you want, schedule a complimentary financial planning consultation.

This communication was prepared with financial writer Sharron Senter’s assistance, based on interviews with David Bunker, a financial advisor and licensed fiduciary.

Sources:

1: Harvard Health Blog, Is retirement good for health or bad for it? https://www.health.harvard.edu/blog/is-retirement-good-for-health-or-bad-for-it-201212105625

2: National Library of Medicine, Transition to retirement and risk of cardiovascular disease: Prospective analysis of the US Health and Retirement Study https://pmc.ncbi.nlm.nih.gov/articles/PMC3367095/

3: TED: 4 Phases of Retirement…and the Psychological Challenges, https://www.ted.com/talks/dr_riley_moynes_the_4_phases_of_retirement

4: Northern Trust, Avoiding the IRMAA Cliffs, https://www.northerntrust.com/united-states/institute/articles/avoiding-the-irmaa-cliffs

5: Mass.gov, Serving the Health Insurance Needs of Everyone (SHINE) Program, https://www.mass.gov/info-details/serving-the-health-insurance-needs-of-everyone-shine-program

6: New Hampshire DHHS, Aging and Disability Resource Centers, https://www.dhhs.nh.gov/programs-services/adult-aging-care/aging-and-disability-resource-centers

7: Fidelity, We are Fidelity Medicare Services, https://medicare.fidelity.com/about-us/

8: Fidelity, Learn about Medicare, https://medicare.fidelity.com/learning-center/

9: Windsor Wealth Management, How To Spend Confidently & Without Regret in Retirement, https://windsorwm.com/how-to-spend-confidently-without-regret-in-retirement/

10: Windsor Wealth Management, Budgeting Worksheet, https://windsorwm.com/wp-content/uploads/2023/10/Budget-Worksheet.xlsx

11: Windsor Wealth Management, What Issues Should I Consider Before I Retirement, https://windsorwm.com/wp-content/uploads/2025/05/What-Issues-Should-I-Consider-Before-I-Retire-2025.pdf