Planning for Retirement: A Checklist and Guide

By Michael Baughman, CFP®

Wealth Manager, Principal


Kelly A. Henning, CFP®, MSFS

Wealth Manager, Principal

May 3, 2024

As financial planners we are often asked, “Will I be OK in retirement?” Before we even look at a client’s assets and expenses to answer that question, we ask them one ourselves, “What do you want your retirement to look like?”

An individual’s perspective on their retirement is unique and factors like where they have been, where they are now, and where they want to go in this next phase all come into play. For example, some people may want to remain in their current house or downsize but stay in their community. Others may want to move to an area with a lower cost of living or somewhere that is closer to family or has better weather. Some may want to retire from their current company but remain employed as a consultant or contractor. Others want to leave the 9-5 behind entirely to embark on a new passion such volunteering on a board, focusing on a beloved hobby, or becoming a lifelong learner. By understanding a client’s hopes and retirement goals, we can better determine the best ways to help make those goals a reality.

But regardless of your dreams and aspirations, there are some specific actions to take and aspects to consider as you approach retirement. And it begins sooner than you may think. From ten years before, to the week right after retirement begins, here is a guide to not only the financial, but also emotional aspects of retirement as well as a checklist of action items to consider and discuss with your advisor. Let the countdown begin!

5 to 10 years before targeted retirement: Why?

One of the biggest tasks in this time frame is defining your “why.” Why are you retiring? What is it about your current life that you want to change, improve and/or eliminate? Start to get very clear on the why. As part of this introspection, start to envision your life post-retirement. Then move on to designing that life.

4 years before targeted retirement: When?

This is the time where you confirm if you can afford to retire. You should know where your income is coming from, how long it will last and what your expenses are going to be. There are typically three phases to retirement: Go-go, Slow-go and No-go. Have you planned for these three phases appropriately? You’re likely going to spend more in the go-go phase than you will in the slow-go and no-go phases, and that’s alright. In this time period, you should re-evaluate your debt and speak with your financial advisor about whether it makes sense to pay it off before retirement or invest more money for growth instead. This is also the time when you begin to cut expenses and increase retirement savings. You are likely able to make additional catch-up contributions in your retirement accounts, so make sure you are taking full advantage of those during what are likely your peak earning years.

3 Years Out: What?

What will retirement look and feel like? What is going to get you out of bed in the morning when you don’t have to keep getting up for work? Those who don’t have something to pursue in retirement can start to lose some of their purpose. Join a board or civic club or pick up a new hobby so that you’ll have something to get you out of the house on a regular basis and help you to not lose all contact with civilization. Stay engaged. The world needs you to continue — if not expand — your contributions!

And don’t forget about health insurance/benefits. Once you turn age 65, Medicare handles pretty much everything, but if you’re retiring before that, make sure you have a health insurance strategy in place and expect it to change a couple of times before retirement.

2 Years Out: Where?

Where do you plan to retire? Do you plan to stay in your current home or community? Or do you plan to downsize, travel, or move closer to your children and grandchildren? Will you live out of an RV for a year and go where the road leads? Start to visit the places you are considering. Retirement is a big change; ideally, you’re not relocating to a new community at the same time. We often recommend renting in a location for a few months to see if you can imagine yourself living there full-time. You’ll want to see the difference between a vacation spot and a new place to call home. It’s important to determine if you have access to doctors, hospitals, stores, and restaurants in this location.

6 Months to 1 Year Out: Who?

Who is sharing your retirement journey with you? This is the time for relationship checkups. Hopefully, your spouse is on board with your retirement and looking forward to spending much more quality time with you. This period of your relationship should be the most enjoyable and thrilling. However, for many couples, this can be the hardest part of retirement. Make sure you two have some shared but also some individual interests so you can maintain your independence. And it is never too late to expand your support and friend networks. Seeking new experiences, with new people or reconnecting with old friends can be key to having emotional support and enjoyment during retirement.

0 to 6 Months Out: Retirement and Beyond

You have arrived at your destination – retirement – and are embarking on a new journey. This transition into full-time retirement can be one of the most frightening times in a person’s life. What will you do with all that newfound time? How will you adjust to having no steady paycheck? How will it feel to start spending your retirement savings versus saving for retirement? Like many things in life, once you take that first step, the rest just seems to fall into place. With proper planning, that first step can be less frightening than you imagine.

We are happy to guide you through this exciting time in your life. When you are ready to talk about your “why” and what retirement can look like for you, Modera is here to help.


5-10 years before retirement:

  • Brainstorm retirement goals and dreams of what retirement will look like.
  • Think about where you want to live and whether you want to downsize.
  • Revisit goals and time frame annually.
  • Obtain an annual credit report.
  • Revisit progress toward achievement of retirement goal and adjust retirement contributions and/or spending as appropriate.
  • Consider long-term care insurance.

4 years before retirement:

  • Create your retirement income plan.
  • Consider front loading your retirement spending to maximize good health and mobility to enjoy travel and other pursuits.
  • Review estate planning needs and update documents, titling and beneficiaries as needed.
  • Evaluate the pros and cons of paying/not paying off mortgages and other debt before retirement.
  • Focus on cutting expenses and increasing retirement savings.

3 years before retirement:

  • Attend a pre-retirement workshop and/or consider personal life coach to help prepare for the transition.
  • Request an estimate of pension or retiree medical benefits.
  • Get educated about Medicare options.
  • Get comprehensive medical, dental and vision exams while still covered by employer insurance plans.
  • Consider Social Security claiming strategies.
  • Revisit estimated budget for income and expenses anticipated in retirement.

6-12 months before retirement:

Income tax planning

  •  Speak with accountant about expected new income bracket and how to plan for it.
  • Discuss possible Roth conversion or other tax planning strategies.
  • Outside retirement plan contributions? (non-deductible)

401(k) Plan

  • Plan to max out contributions for current year.
  • Confirm all funds in 401(k) accounts are vested.
  • Confirm whether funds are pre-tax only or pre-tax and after-tax.
  •  Coordinate with your financial advisor on a plan for your 401(k) and other accounts held through an employer.
  • If rolling funds to an outside IRA, open a new account and obtain account number and custodian address/wire instructions for future deposit.
  • If retiring between 55 and 59 ½, you may want to wait to rollover, due to options to take penalty-free withdrawals from 401(k) in year of retirement or take 72t distributions for at least 5 years.
  • Obtain documentation from your company related to stock options so you understand important dates associated with the options, such as vesting, expiration, etc.

Pension Benefits

  • Obtain all pension benefits available through current employer.
  • Determine if a lump sum pension option is available and whether it is preferable for you.
  • Determine other Qualified and Non-Qualified Retirement Benefits.
  • Obtain information on all additional plans offered by the company and information on vesting, tax, and transfer of these accounts.

Social Security Benefits

  • Login to, create account, and obtain a current benefits statement.
  • Be sure to complete this step for spouse.
  • If divorced, contact Social Security directly at (800) 772-1213 and obtain information on taking benefits as ex-spouse.
  • Speak with your financial advisor about potential claiming strategies.

2 to 3 months before retirement:

Paid Time-off

  • If you have any accumulated sick days, vacation time or other PTO days, determine if/how you will be paid for these days.
  • Advise Supervisor and HR Representative in writing of desired retirement date (this timing may be dependent on your company guidelines and/or specific to your role). A specific date may be agreed upon (e.g., first week in January depending on payroll and other items).
  • Consider date which you will be eligible for year-end bonus or other benefits, including 401(k) matches, profit sharing, or stock options.
  • Request Retirement package of paperwork from HR.
  • Depending on the size of the company, HR will generally provide its own packet of paperwork and forms that need to be completed.
  • Determine date for exit interview with HR/supervisor.
  • Make final decision on all insurance, including medical, dental, vision and life insurance (timing will depend on company policies).

1 week before retirement and after:

  • Confirm that HR retirement package has been completed and all relevant documents are signed.
  • Clean-up desk/emails, etc. Remove any personal/private information from work email and computer.
  • Post Retirement 401(k) Rollover Paperwork – Submit following retirement date.
  • Obtain online/phone the paperwork to roll your 401(k) (or other retirement accounts) out of the plan into an outside account if that’s the choice you’ve made.
  • Complete paperwork and contact HR to see if plan administrator signature is required.
  •  Send in all paperwork following retirement date.


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