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6-Step Retirement Planning Checklist to Get the Ball Rolling

Senior Couple at Kitchen Table Completing Retirement Planning Checklist with laptop and pads of paper

Retirement Planning Checklist: 6 Bite Size Steps

Before you start your next big chapter of retirement, help make sure you are financially on track for the golden years you want. Like many important to do’s, breaking them down into a retirement planning checklist can make the exercise much easier to tackle. 

Plus, your sense of accomplishment from checking off each task can encourage you to stick to your mission. Here is a 6-step checklist to help get the ball rolling on retirement planning and determining what kind of budget you will need in the future.

#1. Make a retirement budget

Use these next few months to get a handle on your spending needs and wants so you can be prepared for the day the paychecks stop, says Dan White, firm founder and asset protection consultant of Dan White and Associates. Keep in mind the budget you create today will not be set in stone, as most people have a U-shaped financial retirement. 

That means they spend more in the earlier years, less in the middle years when the routine is in place, and more again in later years when health issues drive expenses back up. You can use our Retirement Income Planning Worksheet to help simplify this task of budgeting. It is a fillable PDF and will do the calculations for you.

Woman completing retirement planning checklist on graph paper with calculator, ipad with bar charts on screen and pie chart on paper

#2. Calculate your Social Security benefit

To look at your earnings and get an estimate of what you’ll get from Social Security, you can create a login at If you’re not sure when to start taking your benefits, you can also use the Social Security Administration’s Quick Calculator to determine how your benefit will change depending on how old you are when you sign up. It’s an important part of your retirement equation since the dollar amount can drop by about 30 percent if you take it before you reach full retirement age.

If you are married there are Social Security strategies for married couples to coordinate and maximize their Social Security Benefits.

#3. Calculate your pension payment

If you have a pension, you can talk to your human resources department or pension benefit manager to get an idea of what your monthly payout will be. If you are married, also ask if the pension provides a survivor benefit, and if your regular payment will be cut to provide that benefit.

#4. Balance your portfolio

If you are about to retire, your investments should likely be taking on a more defensive position, which means that they carry less risk. That way, you will protect your savings against any potential market downturns. Sequence of returns is the biggest risk for someone who’s just retired, or within a couple of years of it.

#5. Reset your insurance

Review your insurance contracts which may include homeowner’s insurance, life insurance, long-term care insurance, and car insurance to make sure you have the right level of coverage. If you need to cut expenses in retirement, you can raise the deductibles on certain policies. 

Review your options for health insurance too. Options to consider if you’re too young for Medicare are: going on your spouse’s policy, buying COBRA from your employer, taking advantage of a pension plan’s health benefit, or buying individual insurance on your state’s exchange or on

#6. Determine where you will live

Where you live, especially if you will still have a mortgage, is an important part of the retirement puzzle, says White. If your dream is to relocate, he suggests possibly renting in a location to see if you really like it first. Your plans should also address where you will live while you age. 

Will you want to age in your current location? What costs will be associated with that kind of care? Or will you move to a 55-and-up community? What about assisted living? These should all be factors in your future retirement budget.

If you are looking for ideas; check out this Forbes List, “Best Places to Retire in 2020.”

Simplify Your Path to a Financially Secure Retirement

By completing this 6-step retirement planning checklist you’ll gain a better understanding of your finances. Identifying your sources of retirement income and thinking about the life of your future self can be a motivating factor nudging you to create a strategy that helps checks all the boxes toward gaining the financial security you seek in retirement.

At after completing your retirement planning checklist you realize you are not quite on track you’ll have to work longer, spend less or make more.  The sooner you get the ball-rolling the better!

Jason Caudill, MBA

Jason Caudill, MBA

Jason is passionate about annuities and the important role they can play inside a retirement portfolio. He's distributed more than $1.5 Billion in annuities over a 17-year career; serving in many roles, including RVP at the largest independent Annuity Brokerage Firm, VP of Marketing at a top Insurance Company, and Regional Director in the Private Client Group at a Fortune 500 Company.

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