Pre-Retirement 12-Month Checklist 

Written by Canty Financial - Published on May 10, 2023

The period leading up to your retirement is a critical time to ensure that you have your financial plan in place as you enter retirement. Financial planning doesn’t stop once you retire, things change and your need to stay on top of things and adjust as needed. This is the focus of much of our work with clients approaching and in retirement. 

Here is a checklist of items to review during the 12 months leading up to retirement. 

Your Retirement Budget 

One of the most important things to do during this period is to formulate a retirement spending budget. This will drive almost everything else that you do financially in retirement. This budget should take into account your normal monthly costs plus money to cover things like travel or other activities that you plan to do in retirement. 

Sources of Retirement Income 

During this period it's important to identify all sources of retirement income that you can tap. This might include many of the following: 

  • Employer retirement accounts such as a 401(k), 403(b), Thrift Savings Accounts (TSP), or Deferred Compensation
  • IRA accounts, both traditional and Roth
  • Taxable investment accounts
  • An annuity
  • Social Security
  • A pension
  • Real estate  

Depending upon your situation there may be additional sources of income to consider as well. It's important to be sure that you have your arms around all potential sources of retirement income, and how much income you might generate from each of these sources. Additionally, you will want to be sure that you understand the tax implications of tapping each of these income sources. 

Retirement Withdrawal Strategy 

Putting a retirement withdrawal strategy in place is critical. Which accounts will you withdraw funds from and in what order? This will be driven by a number of factors including your age at retirement. When you claim your Social Security will certainly be a factor in this strategy. 

This goes hand-in-hand with your retirement budget and also encompasses tax planning in terms of whether to tap taxable or tax-deferred retirement accounts first. 

Regularly reviewing and adjusting your retirement withdrawal strategy is vital for effective financial planning during retirement. Our team specializes in assisting clients with this essential aspect of retirement planning.

401(k) & Employer Retirement Plans

When our clients retire or leave their employer, they often ask about what to do with their 401(k) or similar retirement plan. We assist them with rolling over their plan to an IRA, developing a retirement withdrawal strategy, and ensuring their investments are aligned with their goals and time horizon.

For many individuals, the 401(k) or employer retirement plan represents their largest retirement savings, so it's crucial to develop a well-defined strategy for managing and investing these funds throughout retirement.

Transferring a 401(k), 403(b), TSP, or Deferred Comp to an IRA account offers several advantages for portfolio management. It provides a wider range of investment options, such as individual stocks, bonds, ETFs, and a more extensive selection of mutual funds compared to employer-sponsored plans. Rolling over the employer plan allows for better integration into an overall investment strategy and alignment with other managed assets. Moreover, IRAs often offer lower-cost investment options when compared to employer retirement plans.

When taking required minimum distributions (RMDs) or taking distributions from tax-deferred accounts, it's important to consider the associated tax implications and engage in tax planning. Additionally, careful consideration should be given to selling the appropriate investments to facilitate distributions.

Healthcare Costs 

A key budget item is the cost of healthcare. Depending upon the circumstances surrounding your retirement, how you cover the cost of healthcare may vary over the course of your retirement. 

In the case of a married couple, if one spouse is still working while the other spouse retires the working spouse may be able to add their spouse to their employer’s policy. If you are retiring as part of an early retirement package from an employer, check to see if they offer any extended health insurance benefits.

Medicare is the main vehicle to cover healthcare costs in retirement and it's important to learn as much as you can about the basic coverage offered by Parts A and B as well as other options such as drug coverage and Medicare Advantage plans. You can learn more about the basics of Medicare in our article here

Social Security 

Prior to retiring, you should obtain a copy of your Social Security statement and review it for accuracy. It’s important to be sure that all of your earnings are properly credited to your record as this is the basis of how your Social Security benefits are calculated. If you find omissions it's important to contact the Social Security Administration immediately to get this corrected. 

During this time period, you should also review your benefit levels based on claiming at various points in time. This will help you determine when is the best age at which to claim your benefit as part of your overall retirement financial picture. 


If you are covered by a defined benefit pension plan from your employer, this is the time to be sure you understand how to claim your benefit and any options available to you as to how to receive your benefit and the benefit level based on when you claim it. 

Most defined benefit plans offer the benefit as a monthly annuity payment. The payment amount may differ based on the age at which you commence your benefit. Some companies may also offer the option to receive a lump-sum payment versus the stream of annuity payments. 

You will also want to ensure that your beneficiary information is up-to-date. If you are married, the beneficiary is generally your spouse, but you should verify to be sure. 

You may also be entitled to a pension benefit from a former employer if they offered a pension plan and you were vested in a benefit prior to leaving that employer. Vesting typically occurs after five years. You should contact that former employer to be sure you are on top of what needs to be done to initiate your benefit. 

Stock Compensation

If you have received any type of stock-based compensation from your employer, you want to be sure that you understand what needs to be done to take full advantage of this prior to leaving the company. 

This might include stock options, restricted stock units (RSUs), or other vehicles. Be sure that you understand when and how to convert these vehicles to shares and also any restrictions on selling the shares if desired. 


Many might think that once you retire worrying about taxes is a thing of the past. In fact, taxes are among the top issues that retirees need to focus on. During the year leading up to your retirement, you will need to do some tax planning in conjunction with formulating your withdrawal strategy. You will also want to look at the tax impact of pension payments and other streams of retirement income. Assisting clients with tax planning is a regular part of our services, both as they approach retirement and throughout their retirement years.


In the year leading up to retirement, or prior to that time, there are a number of planning issues to resolve and things to verify. The items listed above are a good starting point, your list may differ a bit depending upon your own unique situation. The more prepared you are, the more likely you are to enjoy a financially successful retirement. 

If you are looking for guidance about your retirement plan or any other financial issues, please contact us to discuss. We are here to help.

Bill Canty, CFP®, CPA

Ed Canty, CFP®, Investment Advisor

Joe Canty, Investment Advisor

Maureen Walsh, EA, Tax Advisor

Tina Alteri, CPA, Tax Advisor

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