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My Retirement Checklist

Use this checklist to prepare for transition into retirement.

This will help you, your spouse and adult children ensure that all major steps are covered.

Let’s Start Now:

Note: We have checklists grouped by time length to retirement and by types of people retiring.

Step 1:

Pick the date when you would like to retire.

Why do this?

  • This is the date on which all other aspects of your retirement depend.

  • For example: the date you retire and how much savings you have at that point relates to how much money you should take from savings each year and when you will start drawing social security.

Write down the date you plan to retire. If your finances can’t support you retiring on that date, then we will go through a step for you to come up with a plan to make a new date or make a plan to earn income while retired.

Step 2:

Figure out the date you will start getting social security.

Why do this?

  • You have a choice of when to start getting social security and you can pick a different date than the date of your retirement.

  • How much money you will get each month from social security for the rest of your life will depend on both how much money you made during your lifetime and when you decide to start getting social security.

How do I get started?

1. Know your full retirement date. To get what the government says is your “full” monthly payment from social security, you need to wait until you reach your “full retirement age”. This age is different depending on the year you were born. If you decide to start getting social security early, which is any time between age 62 and your full retirement date, you will receive less money each month for the rest of your life. However, if you choose to start social security later than your full retirement date, up to age 70, then you will receive more money each month than your full monthly payment for the rest of your life.

2. Think about your particular situation. Social security payments are designed so that if you live to the same age as the average life expectancy for someone your age, than you will receive the same amount of money whether you start getting benefits at 62 or 70. However, most people live longer or shorter and so how long you actually live will impact the total amount you get from social security over your life. So think about your benefits based on how you think you’ll need them.

Do you expect to live a long time? Think about your health and family longevity. Many people, especially women, live longer than the average life expectancy. So if you are very healthy and have a history of family members living to be 90+ then you may want to start benefits later so as to receive more over the length of your life. Alternately, if you have little income or are unwell or have a family history of dying young, you may get more if you start receiving social security early.

Do you have a spouse? If you have a spouse, they may be able to receive social security benefits based on your work record, especially if they made less over their lifetime than you did. Your spouse will receive less money each month once you pass away if you start receiving social security early.

Do you plan to work in retirement? If you think you may work while you are retired, know that the government may give you less money each month if you sign up to receive benefits before you reach full retirement. However, each year after you reach full retirement, they will recalculate your monthly social security payment and the amount of your benefits will go up each month based on the total amount of money you’ve made. Also, once you reach full retirement age, you can earn as much as you want and the government will not reduce your monthly payment from social security.

4. Calculate how much you will receive. The government’s social security website page has a handful of benefits calculators that can help you calculate what percentage of your benefit you will receive at different ages and how much you will receive if you were to retire. Click here to be redirected to that site.

5. Pick a date to sign up for social security. For example, you may choose the date that you turn 67. Remember that the date you actually retire can be different than the date you start getting social security. Write down the date that you plan to sign up for social security.

TIP :Want to receive a reminder to sign up for social security? Then just sign up for our newsletter/reminder.

Step 3:

Figure out when you will sign up for Medicare.

Why do this?

  • Most people need to sign up for Medicare to start receiving health insurance benefits from the government.

  • If you don’t sign up for Medicare during the initial enrollment period set by the government, you may have to wait to start getting coverage or you may end up paying a penalty to get medical and prescription drug insurance.

  • Picking a Medicare Plan can take a while and you want to give yourself time to research your options. For example, some people choose to sign up for Part A/Hospital Coverage, Part B/Medical Coverage and Part D/Prescription Drug Coverage separately, while others choose to receive these types of coverage through Part C/Advantage Plans (sometimes called Health Plans).

  • Figuring out when you can sign up for Medicare also helps you know if you’ll need to buy private insurance for a period during retirement.

How do I get started?

1. Know the Sign Up Basics:

For most people, when you sign up for Medicare depends on how old you will be when you plan to retire and whether you will have health coverage through your employer. Remember that to receive Medicare you must be 65 and have worked or have a spouse that worked at least 10 years during which you paid Medicare taxes.

Most people are first able to sign up for Medicare (including Part A/Hospital Coverage, Part B/Medical Coverage, Part D/Prescription Drug Coverage or Part C/Medicare Advantage Plans) three months before they turn 65. The initial window to sign up, called the initial enrollment period, lasts seven months, through the three months after the month you turn 65.

  • If you plan to retire before or when you turn 65, you may want to sign up for Medicare in the three months before you are 65. That’s because your Medicare benefits will then start the first day of the month you turn 65, (if your birthday is on the first day of the month then your coverage will start the first day of the month prior to your birthday). If you sign up the month that you turn 65 or in the three months after you turn 65, you will have to wait between one to three months to start getting your benefits.

  • If you plan to retire after you turn 65 and you are eligible for health insurance through your job, you should talk with your employer about how your health benefits work with Medicare to decide whether you will sign up for Medicare when you first become eligible. If you do not sign up for Medicare and then retire after age 65 you have 8 months from the time you leave your job to sign up for Medicare Part B/Hospital Coverage and Part D/Prescription Drug Coverage without penalty.

  • Avoid a late sign up penalty: If you plan to carry Part B/Medical coverage and Part D/Prescription Drug Coverage, and you sign up late, you may need to pay a costly late enrollment penalty. To avoid this, you can sign up:

  • Within 8 months of retiring, if you retire at 65 or later and have had health coverage through your employer, or

  • During the initial enrollment period, if you are retiring before or at age 65 so that you do not have to pay a late enrollment penalty.

The late enrollment penalty can be costly. You will need to pay an additional 10% each month for every 12-month period that you could have signed up for Medicare and the penalty lasts as long as you have coverage!

  • There are important exceptions for some people who will get Part A/Hospital Coverage and Part B/Medical Coverage Automatically. This may apply to you if you are:

  • Already receiving social security or railroad retirement benefits,

  • Under 65 and have a disability,

  • Have ALS (Amyotrophic Lateral Sclerosis), or

  • Live in Puerto Rico and get benefits from social security or railroad retirement benefits.

You can read more about what to do if this applies to you

Step 2. Write down the date that you plan to sign up for Medicare.

If you would like to receive a reminder to sign up for Medicare, click here.

What Are Your Medicare Options?

To see our primer on what the different Medicare options are, click here.

Ready to Sign Up for Medicare?

Click here.

Step 4:

If you will be retiring before age 65, figure out where you will purchase health insurance.

Why do this?

  • The federal government requires everyone to have health insurance or pay a fine and if you have a serious injury but no health insurance you run the risk of losing your savings or even your home due to health bills!

  • Getting an idea of how much health insurance will cost you will also help you figure out your retirement budget and plan.

What are your health insurance options?

  • If you have health insurance from your employer, you are eligible to keep your health insurance for a number of months through a program called COBRA, which allows you to have the same insurance for up to months.Keep in mind, though, that if your employer pays some portion of your health insurance, you will need to pay the full premium or price for it while getting COBRA.

  • If your spouse is still working, you may be able to join his or her insurance plan.

  • To buy health care insurance on your own, you can buy it directly from a health insurance company, or you can use your state’s health insurance exchange.If you use your state’s health insurance exchange, you may be able to get a discount based on your expected income.Looking at insurance rates on your state’s health insurance exchange can give you a rough idea of how much to expect to pay and what benefits plan are available to you.

Step 5:

Decide where you will live during retirement.

Why do this?

  • How much it costs to retire depends a lot on where you will live during retirement and whether you own your own home.

  • Making a plan of where to live will help you to launch your retirement well prepared.

How do I get started?

  1. Write down how much money you plan to spend monthly on your mortgage or rent. Ideally, you would find a place to live that you can pay off completely, so that you do not have a monthly cost for your home beyond property tax.

  2. Consider your options. Are you looking to remain where you are or to make a change in where you will live during retirement?

  • Will you remain in your current home? Many people choose to stay in their current home to remain near family and friends and/or because they already own their home. If you plan to stay in your home, look carefully at its condition. Are there any major repairs that need to be done? You may also want to make some changes to allow you to remain in your home as long as possible.

  • Will you find a new home in your current community? Some people want to remain near family, friends and the community they are used to but want to find a new home. It may make a lot of financial sense to downsize to a smaller home to access some of the money tied up in your home or if you have a home that is larger than you need that is not paid off. As you are looking for a new home keep in mind that most people experience two phases of retirement, one where they are young and healthy and a second phase where they are aging and may be experiencing mobility issues. To remain in your home while you age, look for a home that has design elements that will allow you to stay such as a bedroom and bathroom on the first floor, minimal stairs and storage cabinets that are easily reachable to you.

  • Will you live in a new place, either in the U.S. or abroad? Living in another state or country can allow you to live somewhere cheaper while exploring a new place that you may always have been interested in. You can find a list of cities to consider ranked by best weather and cost of living.

Forbes 25 Best Places to Retire in 2015 (

U.S. News and World Report – 10 Sunniest Places to Retire (

Step 6:

Decide how much you will save each month between now and your retirement date.

Why do this?

  • It is important to continue to save up until you retire so that you can start out with the biggest nest egg possible.

How do I get started?

Look at your monthly income and expenses.

  • As a general rule of thumb, throughout your working life you should save about 10 percent of your income towards retirement through your life.If you save this much over time, you will likely have a very solid next egg at retirement.

  • You may need to adjust this amount down if you are young and getting an education or adjust it higher if you are older and have not saved before.

  • Think creatively.Are their ways to cut down on current expenses to help you save a little more?

Write down how much money you will save each month. You can set up an automatic payment to a mutual fund or your savings account going forward.

Step 7:

Figure out how you will manage your savings during retirement.

Why do this?

  • Ideally, you are going into retirement with some savings. Finding out how to manage the money you have will help you to support yourself during retirement.

How do I get started managing my savings?

  • A general rule of thumb for managing your savings during retirement is to take out no more than 3 to 4 percent of your savings each year.This number is given as an amount that will insure your savings last your lifetime.

  • Keep in mind that you may need to draw less if your portfolio is doing poorly or that you may actually be able to take out more depending on how long you actually end up living.

  • Go to our section on to learn more about how to structure your investment portfolio during retirement.

  • If you have the means, you may want to consult a financial advisor who can advise you on how to handle your particular situation.

What is an annuity?

Another option is to take out an annuity. An annuity is an insurance product that allows you to pay an insurance company a set amount of money in return for getting regular payments. You can opt to get these payments monthly, quarterly, yearly or even in one lump sum. You choose to receive the payments for the rest of your life, or for a set number of years. The idea is that an annuity can provide you with certain income for the rest of your life. The downside is that they have been criticized for having high management costs. So think about how comfortable you are in managing your own money and carefully research any annuity before you buy one. To explore getting an annuity, click here to visit.

Now, write down your estimate of the monthly income that you anticipate receiving from your savings.

Step 8:

Decide if you will carry any insurance products designed to support retirement.

Why do this?

  • Insurance products exist that may benefit you depending on your financial situation and the health of you and your family.Common products created for retirees include:

  • Annuities

  • Long Term Care Insurance

  • Accidental Death and Dismemberment (ADD)

  • Long Term Disability

  • Whole Life Insurance

How Do I Get Started?

Educate yourself on what these products are and how they may or may not help you so that you will have a better idea if they can benefit you. To see our primer on insurance products and how they can help here.

You can get an idea of how much this may cost by contacting a reputable insurance company. Three companies that have been around a long time are:

But there are many, many others. Take the time to explore your options and find a plan that meets your needs.

Step 9:

Figure out if there are any large one-time costs that you need to take care of before you retire.

Why do this?

  • It can be hard to come up with the money for unexpected or large costs when you are living on a fixed income.

  • If you can take care of costly one time needs, such as replacing an old roof on your house or replacing a broken down car, before you retire, you will help to secure your financial situation.

How Do I Get Started?

Make a list of any large, one-time costs that are needed to maintain the integrity of your home or your car. Then figure out a rough estimate for how much each might cost. Add up these costs.

Step 10:

Decide whether you will work a paid job during your retirement.

Why do this?

  • Having a full- or part-time job in retirement can increase your monthly income if your savings are low, and it will end up increasing the amount of social security you draw each month once you reach the age of full retirement.

  • Having a part-time job that draws on your talents and passions can also help you to stay healthy, socially active and provide meaning.

How Do I Get Started?

To read more about what makes a great job for retirees and to see some examples, click here.

Step 11:

Calculate a budget for your retirement.

Why do this?

  • So that you know how much you will have each month when you retire, and whether you can afford to retire when you want to or if you need a new plan.

How Do I Get Started?

Calculate your expected expenses and income and compare the two. A list of common expenses and income are given below. You can also use our budgeting template to estimate your needs. You will need to have Microsoft Excel already downloaded on your computer.

Add up the expenses you will have during retirement. Common expenses are:

  • Housing (rent or mortgage/taxes)

  • Food

  • Medical insurance (such as medigap or a supplement)

  • Dental insurance

Now add up the income you will have during retirement. Common income sources are:

  • Social security

  • Pension

  • Job income

  • Annuity payment

  • Scheduled withdrawal from savings/investments

Readjust Your Plan If Needed. If your expenses will exceed your income, consider how you can plan to set yourself up for success. Is it time to consider downsizing? Would you be willing to take on a part-time job during retirement? Are you able and willing to post-pone your retirement date?

Step 12:

Do a trial run to see if you can live for a month on your anticipated monthly income.

Why do this?

  • If the budget you plan to live on doesn’t match the reality of your expenses over a few months, you will still have time to adjust your retirement date or rethink your retirement strategy.

How Do I Get Started?

Pick a three month period and try to live on your budget. Is your food budget enough? What unexpected costs came up that you didn’t plan for?

Step 13:

Establish a will or trust.

Why do this?

  • Figure out what will happen to your money when you no longer need it while you are young and have a clear mind. This can bring you peace of mind and help you to enjoy your retirement.

How Do I Get Started?

You will need to decide if you would like to create a Last Will and Testament, a Living Will or a Trust. To decide which would be best for you, please see our summary of pros and cons here. Once you have decided which makes sense for you, you can have yours written up relatively easily and inexpensively online or you can work with a private attorney to draft these documents.

It may be in your best interest to work with an attorney if your assets will be more than the federal estate exemption tax, which is currently $5,120,000.

Online providers of wills and trusts include:

  • LegalZoom: This site helps you to complete a will or trust for a fee. You have the ability to ask a lawyer questions via the website.

  • RocketLawyer: This site allows you to download and complete one document, such as a will, for free. You have the ability to ask a lawyer questions via the website.

Step 14:

Create an advanced directive.

Why do this?

  • An advanced directive or living will lets doctors and other caregivers know how you would like to be cared for should you become very sick or seriously injured and not be able to communicate your wishes yourself.

  • Having one in place before something happens helps ensure you get the care you want and provides your family peace of mind should difficult decisions about your care come up.

How Do I Get Started?

  • Each state has different laws and titles for an advanced directive, so it’s important to complete one that follows the laws in your state.

  • Once you fill one out for your state’s form you must have the required witnesses see you sign it for it to be valid.

  • Advanced directives can only guide your care if two physicians certify that you are unable to make medical decisions and that you are in a serious medical condition required by your state’s law, such as a “terminal illness” or “permanent unconsciousness”.

  • That means that an advanced directive will not affect the care provided by an emergency medical technician that responds to a 9-1-1 call.

To find and fill out an advanced medical directive for your state, click here.

Step 15:

Think through the hobbies or volunteer activities you plan to take up.

Why do this?

  • Volunteering or taking up a new activity can help you to stay engaged and fight off depression during retirement.

  • A little bit of advanced planning will help you to pick a volunteer opportunity that matches your needs and expectations and to avoid frustration as you start these activities.

How Do I Get Started?

Do you plan to volunteer? Volunteering to help your community can be a deeply meaningful experience. But do your expectations match the reality of volunteering? What’s the difference between working and volunteering? Read our primer on finding a great volunteer opportunity that matches your needs and interests. Once you’ve identified what you want to do, don’t wait until you retire to try it out. Volunteering at your local library? Trying it out can help you figure out how you like the people and culture of the organization.

Do you plan to take up a new sport or hobby? Before you invest a lot in a new sport or hobby, try it out before retirement. Want to take up golf? Try going to the golf range once a month or sign up for a lesson. You may confirm your interest of decide there are other ways to prefer to spend your time.

Step 16:

Make an exercise plan.

Why do this?

  • Many people lose muscle as they age and this is one of the main reasons for developing disabilities later in life.

  • Exercising regularly can help to build or maintain muscle and bone strength to avoid disability.

  • It’s also helpful for people with chronic pain conditions such as arthritis, osteoarthritis and back pain to keep healthy.

How Do I Get Started?

The World Health Organization recommends that adults who are 65 and older should get 150 minutes of moderate exercise, such as walking, or 75 minutes of vigorous exercise, such as running, each week. There are ways to exercise no matter how in shape or out of shape you are right now or how old you are.

To see our primer on exercise options that can meet your needs, please click here. Once you have considered the options, make a plan for what you will do to exercise, when you will do it, and where you will do it. This will help you to fit exercise into your new lifestyle.

Step 17:

Set some personal goals for yourself.

Why do this?

  • Setting personal goals for yourself during retirement can help you to enjoy your retirement, stay mentally sharp and physically healthy and keep a positive outlook.

How Do I Get Started?

Consider goals to:

  • Accomplish a challenging goal, such as learning to play chess or doing a marathon

  • Socialize regularly, which is an important part of being healthy and happy

  • Taking up a new activity, like joining a knitting group


  • Set/Confirm your retirement date. Take a close look at what your expected income will be and compare it to your expected expenses. Then come up your monthly budget for retirement. For many people, retirement will entail having a part-time job or other money-making activities. Do a trial run in the months before you officially retire to make sure you can get by on your projected income.

  • Figure out when you will sign up for social security. This decision will relate to the amount of money that you will or will not have in addition to social security. In general, the longer you wait, the larger your monthly pay check will be.

  • Take care of large one time expenses, such as replacing an old roof, or purchasing a new or used car to replace an aging one to start out retirement on a good financial foot.

  • Research and understand the benefits and drawbacks of financial products designed for retirees, such as annuities, insurance and Long Term Care insurance, Accidental Death and Dismemberment, Long Term Disability, Whole Life Insurance.

  • Set up an investment plan for how you will manage your money while you are in retirement and how you will handle large unexpected costs that arise. Financial planners can help you to think through the ins and outs of your financial plan.

  • Establish a will or trust if you haven’t already. This is a good time to think how you would like to distribute your assets once you no longer need them.


  • Decide where you will live.This could be in your current home, another home in your community or somewhere entirely new. In addition to geography, think about what you will need in your house as you age so that you can remain independent. See our suggestions for how to find a retirement home.

  • Decide how you will spend your time. Do you need to work in some capacity? What can you expect from a volunteer position? What hobbies do you enjoy or plan to take up? See our tips for picking a desirable work opportunity and/or selecting a satisfying volunteer opportunity.

  • Come up with goals for yourself. What will give you meaning in this new phase of life? Do you plan to travel the world, make a difference in your community or do things that you never had time to explore before? See our thoughts on how to start out on the right track.


  • Determine the health care insurance you will carry. For retirees over 65, this may be as simple as signing up for Medicare and purchasing private supplemental insurance. Those under 65 need to purchase private insurance. Also consider whether you will carry dental insurance or pay out-of-pocket for dental care needs.

  • Make an exercise plan. Staying physically fit will help you maintain your quality of life, so come up with a strategy. There’s also a lot you can do to maintain your mental agility. See some ideas for how to keep fit while having fun.

  • Think about how your will interact with others. This is key to mental health and happiness. How will you stay plugged in?

  • Create an advanced medical directive.The time to think through how you’d like to handle a health crisis is when you are healthy! An advanced medical directive is easy to fill out and can give you peace of mind.

Once you know how you want to live your retirement, be sure to discuss it with your family and friends. Make sure you and your spouse are on the same page and that you both understand the key aspects of your financial plans. Now get ready to launch this special time in your life!

#retirement #checklist




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