Deciding to retire is one of the biggest financial and lifestyle transitions you’ll ever make. Whether you’re planning to retire in the next 6 to 12 months or just beginning to map out your strategy, ensuring a smooth and confident transition takes planning, research, and key conversations.  

For women, retirement comes with unique considerations: longer life expectancy, financial independence, career pivots, inheritance, and changing health needs, all requiring careful thought.  

This checklist is designed to help streamline your retirement preparation so you can retire on your terms, with a clear financial plan.

Conversations to Have with Your Employer  

Before you officially retire, you’ll need to discuss the details with your employer and HR department. Here’s what to ask:  

• Pension and Retirement Benefits
  • What retirement date benefits me most based on my pension plan or tenure?
  • If I have a pension plan, what are my payout options (lump sum, monthly benefit, rollover into another retirement account)?
  • Do I have stock options or other benefits that must be exercised before retiring?

Health Insurance and Long-Term Care

Women typically face higher healthcare costs in retirement due to longer life expectancy. Knowing your options before you retire will help you prepare for future expenses.

• Health Insurance Planning
  • What are my options for extending coverage under my employer’s plan (COBRA)?
  • Do I have access to an insurance exchange where I can shop for coverage?
  • Can I add myself to a spouse’s health insurance plan?  
• Medicare & Long-Term Care Considerations
  • What Medicare options (Part A, B, C, D) are available to me?
  • What’s the best fit based on my health and financial situation?
  • Am I financially prepared for long-term care? Should I consider LTC insurance or alternative strategies?  
    • What is the plan for any level of long-term care need?
    • Will adult children stop their lives and have the resources, especially if out of state?
    • If single what is the plan to use which account first spending down for care?
    • Does my current advisor model out the future need for care?
  • Which accounts (HSA, IRAs, investment accounts) can I use to cover healthcare costs?

Understanding Social Security Benefits  

The decision of when to claim Social Security can significantly impact your financial stability in retirement.

• Key Social Security Questions
  • What will my estimated monthly benefit be at the earliest age, full retirement age, and at age 70?
  • Am I eligible for spousal or ex-spousal benefits?
  • When should I apply for Social Security to maximize my benefits?

Conversations with Your Financial Advisor  

You’ve gathered important retirement details—now it’s time to fine-tune your plan with a financial advisor.  

• Investment & Income Planning
  • Is now the right time to retire based on my financial situation and current economic climate?
  • How much income will I need in retirement, and where will it come from (pensions, Social Security, investments)?
  • How should I structure withdrawals from my investment accounts?
  • What should I do with my 401(k), 403(b), or other retirement plans from previous employers?  

Retirement Tax Considerations  

Taxes don’t disappear in retirement - they simply change. Your advisor and/or CPA can help you minimize tax burdens while optimizing withdrawals.  

• Key Tax Questions
  • What does my current tax situation look like?
  • Would a Roth conversion benefit me before or during retirement?
  • How will partial employment or consulting impact my tax obligations and benefits?  

Conversations with Loved Ones  

Retirement is rarely an individual journey - it often affects spouses, family, and close friends. Open discussions can help set expectations and strengthen relationships during this transition.  

• Family Conversations
  • What changes will retirement bring to our day-to-day lives?
  • What expectations do I have? What expectations do my loved ones have?  
  • How will we maintain connection and fulfillment after retirement?  

Planning for Life After Retirement  

Retirement isn’t just about leaving the workforce - it’s about stepping into the next chapter of your life with purpose and excitement.

• Lifestyle & Fulfillment Planning
  • What will my new schedule look like? Will I travel, volunteer, start a new hobby?
  • How will I stay engaged with my community and social circle?
  • Will I continue working part-time or consulting?  

The Final Step: Celebrating Your Retirement  

Retirement is a milestone worth celebrating. You’ve spent decades building financial security - now it’s time to enjoy the rewards of your efforts.  

• Final Reflection
  • How will I celebrate this transition?
  • What small moments will remind me that I did this - I made it to retirement?  

Retirement is a deeply personal journey, but with the right preparation, you can make it an exciting new beginning rather than an uncertain transition. If you're feeling overwhelmed, now is the time to team up with an advisor who understands your unique financial needs.

Representatives do not provide tax and/or legal advice. Any discussion of taxes is for general informational purposes only, does not purport to be complete or cover every situation, and should not be construed as legal, tax or accounting advice. Clients should confer with their qualified legal, tax and accounting advisors as appropriate. Some health insurance products offered by unaffiliated insurers. Securities and investment advisory services offered through qualified registered representatives of MML Investors Services, LLC. Member SIPC. CRN #202807-9084953