8 Step Retirement Planning Checklist

Retiring within the next 12 months

Retirement checklist

You are within a year of retiring, congratulations!

While it is time to be happy, there are a few items to get out of the way.

At this point you have identified you have enough money, you have an idea how you will spend your time, and invested in a way that fits your goals. If not, then you need to take care of those three items prior to your retirement date.

Assuming you have the money, know how to spend your time, and invested wisely here are your final action steps:

  1. Get Organized
  2. Social Security Timing
  3. Retirement Income Draw Down Strategy
  4. Establish Health Insurance Coverage
  5. Finalize Long-Term Care Insurance Plan
  6. Complete Rollovers
  7. Give your Employer Notice
  8. Estate planning update

Get Organized

Entering retirement, you probably have a swath of financial tools. Savings, investments, insurance, bills, and much more scattered in different places or under any reasonable system.

Simplify your life and consolidate those accounts. Maybe you have to wait until your last day of work to consolidate every account, but make sure you have a plan.

To simplify your life even more, automate as many of your financial transactions as possible. When you are traveling the world, you may not have time to make a last minute bill payment. If you’re not traveling the world, why waste space in your mind to remember it anyway?

Automation also protects you from becoming a forgetful lapser on your long-term care policy. Don’t stop paying important bills because you forgot. Technology is too good to let that happen!

Another idea is to consider a credit freeze. Now that you are retiring, you should have fewer needs for obtaining new loans, and higher risk for fraud. A credit freeze is an inexpensive and great way to protect yourself from losing your hard-earned nest egg to identity theft.

Social Security Timing

If you don’t need Social Security on day one of retirement, plan on when you should start it.

We all know waiting until age 70 and living a long time yields the highest lifetime benefit. Yet, it might not be the life-optimal benefit.

You should know your break-even age and lifetime benefit differential between the timing options. After knowing this, consider how it fits into your retirement draw down strategy.

The Social Security sign-up process should take around three months. No matter when you plans to start it, keep this in mind. During the sign-up process, consider requesting direct deposit. To keep things simple, this is necessary.

Retirement Income Draw Down Strategy

Before you take your first retirement paycheck, you need to know where it is coming from and how much you need to take.

Throughout your life, you had money coming in from an outside resource. Knowing how much you had coming in every week or month made it easy to know how much you could spend.

In retirement, you need to make decisions on where your money is coming from and how much is coming in.

What accounts will you liquidate first and why? If you do it wrong it could cost you years on the life of your nest egg.

Establish Health Insurance Coverage

When you were an employee or a business owner it was a given on where your health insurance coverage comes from.

When you no longer have employer sponsored insurance you need to make your own decisions on how to fill that health insurance need.

Retiring 65 or later means you are eligible for Medicare. Medicare Part A is free and it is easy to sign up for it. Yet, this is only your hospital insurance. Your medical insurance and prescription drug coverage is completely separate.

Retiring prior to 65 requires looking at transitional coverage until Medicare kicks in.

Self-insuring health care costs is not a risk you can afford to take.

Finalize Long-Term Care Insurance Plan

Medicare does not cover long-term stays in a long-term care facility. Medicaid only kicks in once all of your resources are exhausted.

Stays in a long-term care facility might cost $10,000 per month.

What is your plan?

Complete any Rollovers

This is part of getting organized, but make sure these are completed prior to the day you need your money.

The rollover process could take up to a few months. During this period, you won’t have access to the funds.

If you need to make a withdrawal from your employer 401(k) or 403(b) you will need this completed ahead of time.

Give Notice to Your Employer

When retiring your employer will appreciate a more than two-week notice. Understand your employer’s retirement process so you do everything properly.

There are certain employee benefits that may continue or paperwork that needs to be filed. If your employer has a Pension then there might be a minimum lead time prior to receiving payment.

Update your Estate Plan

Because you are consolidating and simplifying your life make sure you have your estate plan updated.

Review your account beneficiaries, power of attorney, and Trust or Will for any new information.

Part of simplifying your life is to simplify your life for whoever is in charge after your death. Your records should be orderly and your wishes should be documented.

Overlooking your beneficiary designation could leave your final wishes up to your state or in the hands of the wrong recipient. Not a legacy you may want to leave.


Do you want to understand how to make your money work for you and keep more of what you have earned? 

Reach out to me at nbyers@jbcwealthadvisors.com or schedule a free consultation.


Disclaimer: This article is provided for general information and illustration purposes only. Nothing contained in the material constitutes tax advice, a recommendation for purchase or sale of any security, or investment advisory services. I encourage you to consult a financial planner, accountant, and/or legal counsel for advice specific to your situation. Reproduction of this material is prohibited without written permission from Nate Byers a Madison, WI CPA Financial Advisor,  and all rights are reserved. Read the full Disclaimer in the footer below.