What You Need to Know Before Retiring: A Checklist

By Jaclyn Madrid

So you’ve finally made the decision to retire. Congratulations!

Given the volatility and uncertainty we’ve been seeing in stock and bond markets — not to mention the economy in general — you likely have more questions than you expected to have. You may even be wondering if now is still a good time to retire. To make the move official, there are a few concerns beyond the “when” that you’ll need to address. This is one of the biggest decisions you’ll ever make, so you’ll want to prepare yourself (and your loved ones) for the change.

We’ve compiled a list of questions and sources to help you gather the information and answers you’ll need from various sources to feel confident in all aspects of this transition.

What to ask your employer / HR department

Beyond notifying HR of your plan to retire, there are plenty of other important questions the department can discuss and help you answer concerning your pension (if one is available to you) and any other company-provided benefits and accounts. Here’s what to ask:

  • What retirement date will benefit me most (pension plan credits)?

    Ask a financial advisor if there are any income or other considerations. Examples: For pension participants, sometimes your birthdate is a factor. Are you close to Social Security FRA and want to wait until you’ll have that income instead of pulling from your investment portfolio while the market is down?

  • If a pension (or other defined benefit) plan 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? (In the event that markets rebound in the near future, you may want to consider a plan that can account for that.)

  • 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 your financial advisor

A financial advisor or planner is often your first point of contact in the retirement discussion. After all, they’re usually the one(s) best prepared to answer the most important question: “Can I afford to retire now?” They’re also able to contextualize the details of your portfolio against the current climate of the markets.

If you have created a financial plan with your advisor, the two of you should review it and make any necessary updates. Doing so now can provide clarity for your retirement planning. Your advisor can walk you through recent changes in the economy and analyze how they may impact your retirement picture, both now and going forward. Go through it with these questions:

  • Is now still the right time to retire?

  • What are my goals? Have any of them changed, especially given the current economic climate?

  • 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

Taxes are a big part of retirement planning. Schedule a quick check-in with your tax advisor to get a sense of both your current tax situation and how it’ll change after you start taking income from sources other than a regular paycheck. Ask them these questions:

  • 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 the current volatility of the markets.)

  • 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 find out about social security

In addition to your own retirement savings, you’re also going to be navigating the Social Security Administration (SSA) — and believe it or not, there’s probably going to be a little bit of bureaucracy involved in receiving those federal benefits. Here are the details you’ll need to get straight — first via your own research, then discussed with your financial advisor once you have the numbers — before you take the leap:

  • 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 find out about your health insurance options

    If you’re employed with health insurance right now, your coverage will likely be changing with retirement. You’ll want to know what your options are now, and you’ll want to think through various potential health care costs that may come up throughout 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 talk to your HR representative or your financial advisor about 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 (of or about) your colleagues and loved ones

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

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

    • What adjustments will I need to make?

    • What expectations do they have? What expectations do I have?

    • Do I have any recently retired colleagues or friends I can talk to about their own experience retiring, from my company or otherwise?

    Your retirement is your own

    And of course, with retirement will no doubt come a lot more time than you had before — time to do what you actually want to do, rather than what you have to. You might not be retiring altogether — many people choose to keep working, perhaps in a different field or in a scaled back position in your current industry (see: consulting, part-time work, etc). Regardless, it’s important to stay in touch with yourself as you embark upon this new journey, too!

    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?

    Whatever you do, allow us to say congratulations again. You’ve worked long and hard to get to this day, and you deserve to savor it. If you’d like to connect with an Ellevest Private Wealth advisor to discuss your plans, we'd be happy to help.


© 2022 Ellevest, Inc. All Rights Reserved.

This information is for educational purposes only and is not intended to be an exhaustive list of questions to consider when approaching retirement. The information provided does not take into account the specific objectives, financial situation, or particular needs of any specific person.

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. Investing entails risk, including the possible loss of principal, and there is no assurance that the investment will provide positive performance over any period of time.

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.