Your Retirement Checklist: What You Need to Do Before Retiring

By Jaclyn Madrid

So you’ve finally decided to retire in the next six to 12 months. Congratulations!

Now that preparing for retirement is really real, it’s time to get things squared away before you make it official. There are questions to ask, research to dig into, moves to make … all so you can transition into retirement with confidence. 

But what if worries pop up along the way? Does that mean you’re not ready to retire just yet? To that we say, take a beat. Retiring is one of the biggest decisions you’ll ever make! And remember, retirement for women is just different. It’s OK if new factors ‌come into play that could modify your retirement game plan. The trick is to get ahead of them, so you can retire on your terms.  

We’ve compiled a retirement checklist to help you gather the information you’ll need to set yourself up for that finish line in sight (can you believe it!?).

Here’s your retirement checklist:

What to ask your employer / HR department when you’re preparing for retirement

Beyond notifying HR that you’re preparing for retirement, be sure to ask your department contact these retirement questions, the answers to which you should discuss with your financial advisor:

  • What retirement date will benefit me most based on my pension plan (or other defined benefits)? (Sometimes, your birthdate or tenure could influence your schedule.)

  • If a pension plan (or other defined benefit) is available, what are my options — a lump-sum amount, a monthly benefit, a rollover into another retirement account, etc? And which is right for me?

  • Are there stock options or any other benefits that need to be exercised before (or within a specific timeframe after) retirement or “separation from service”?

What to ask about health insurance options when you’re preparing for retirement

If you’re employed with health insurance right now, your coverage will likely change with retirement. You should know what your options are now and in the future, if and when other health care costs come up during your retirement.

If your state has an insurance marketplace, there may be representatives or licensed agents who can help you navigate that system. If it doesn’t, you might want to ask your HR representative or your financial advisor these questions:

  • How much insurance do I currently have — both now and lined up for retirement (via exchanges and / or Medicare, depending on my age)? How much will I need? What will it cost?

  • Do I have the option(s) to extend coverage under my current health care plan (aka COBRA)? If so, how much would that cost me?

  • Do I have a health care exchange where I can shop for coverage? Can I add myself to my spouse’s health care plan?

  • I’ll be filing for Medicare three months before turning 65. (Filing late can incur a penalty.) What options are available (part A, B, C, D, etc), and which is/are the best fit(s) for me?

  • Am I prepared for long-term care (or LTC) in retirement? What options do I have in planning for LTC?

  • How will I pay for health care costs in retirement? What accounts (HSA, IRAs, investment accounts, etc) will I be able to pull from, and when?

What to ask about social security when you’re preparing for retirement

Believe it or not, navigating the Social Security Administration (SSA) involves a little bit of bureaucracy. But it’s worth the head-spin now to make applying for and receiving federal benefits as smooth as possible soon. Here’s what you need to ask the SSA — and talk about with your financial advisor:

  • Based on my personal work history, what will my estimated monthly benefit amounts be — at the earliest age, at full retirement age, and at age 70?

  • What other benefits are available to me (spousal benefit, ex-spousal benefit, etc)? What would those amount to?

  • At what age should I apply for social security benefits?

  • How do I apply for social security benefits?

What to ask your financial advisor when you’re preparing for retirement

At this point in your retirement checklist, you’ve gathered enough information to schedule detailed retirement planning sessions with your financial advisor or financial planner. To get the most out of your time together, ask these retirement questions: 

  • Is now still the right time to retire?

  • Should I reevaluate my goals given the current economic climate? How does it influence my retirement plan now and going forward?

  • What updates, if any, need to be made to my financial plan?

  • How much income will I need in retirement?

  • What changes / adjustments, if any, need to be made to my investment accounts?

  • What will my income sources be (pension, social security, retirement accounts, taxable investment accounts, etc)? How will these sources work together?

  • What is the plan when taking distributions from my investment accounts? Will I be pulling from each account in a specific order, or from multiple accounts at once?

  • What do I do with the retirement plan(s) (ie, 401(k), 403(b), 457, etc) I opened with my former employer?

What to ask your tax advisor or CPA when you’re preparing for retirement

Schedule a check-in with your tax pro to get a sense of your current tax situation and how it’ll change after you start taking income from sources other than a regular paycheck. Ask them:

  • What does my current tax situation look like?

  • If I’m self-employed now, what will my taxes look like when I file in the future? What deductions will I be able to take going forward?

  • Would tax loss harvesting benefit me this year? (This strategy could allow you to take advantage of  market volatility.)

  • Would a Roth conversion, either before I retire or during retirement, be a beneficial strategy for me (given my tax bracket, income in retirement, whether I’d prefer to pay taxes now or later, etc)?

  • If I stay partly employed — either via freelance consulting or in another field — how will that affect my retirement benefits and other financial obligations (social security benefits, health insurance coverage, LTC, taxes, etc)?

What to ask your loved ones when you’re preparing for retirement

Retirement is rarely a solo journey. Chances are you have family, friends, colleagues, a partner, even pets whose lives may also be about to shift now that you’re retired. Ask how you might be able to include them in your plans:

  • How will this change our day-to-day life together?

  • What expectations do you have? What expectations do I have?

  • What adjustments will we need to make to prioritize our relationship?

  • What can recently retired colleagues or friends tell me about their own retirement experience, from my company or otherwise?

What to ask yourself when you’re preparing for retirement

Retirement will no doubt mean a lot more time than you had before — time to do what you‌ want to do, rather than what you have to. Maybe you’ll have “me time” all the time, or you might not fully retire. Many people choose to keep working, either in a scaled-back position in your current industry (see: consulting, part-time work, etc). Others retire from one field, then move to a different field altogether. Regardless, it’s important to stay do you as you transition into retirement. So, ask yourself:

  • What will my new schedule look like in semi-retirement? How much time am I committing to work (if any)?

  • How will I stay focused on what I enjoy in retirement?

  • Will I travel? Volunteer? Try a new hobby?

  • How will I stay engaged with my community after I retire?

Finally, the last question on this retirement checklist might be the most important:

  • How will I celebrate that I did this?

It’s worth repeating: Retiring is one of the biggest decisions you’ll ever make! And despite all the career-building, caregiving, and life-living, you took the time to invest in your financial future — and it’s finally paying off. You made it to this day. You deserve to savor it.

If the timing feels right, but you still have more retirement questions or want to create a more personalized retirement checklist, we’re here to help. Team up with an Ellevest Private Wealth Management advisor to discuss preparing for retirement on your terms. Connect with us today.


© 2023 Ellevest, Inc. All Rights Reserved. 

All opinions and views expressed by Ellevest are current as of the date of this writing, are for informational purposes only, and do not constitute or imply an endorsement of any third party’s products or services. 

Information was obtained from third-party sources, which we believe to be reliable but are not guaranteed for accuracy or completeness. 

The information provided should not be relied upon as investment advice or recommendations, does not constitute a solicitation to buy or sell securities, and should not be considered specific legal, investment, or tax advice. 

The information provided does not take into account the specific objectives, financial situation, or particular needs of any specific person. 

Investing entails risk, including the possible loss of principal, and past performance is not predictive of future results. Ellevest, Inc. is an SEC-registered investment adviser. 

Ellevest fees and additional information can be found at

Jaclyn Madrid

Jaclyn is a financial advisor on Ellevest’s Private Wealth Management team and a CFP® professional. Her favorite part of the job is partnering with clients and their families to help optimize their financial life so they can enjoy what they love. She works closely with clients to create custom financial plans and investment portfolios for their specific financial situations and goals.