Getting Ready to Retire? Follow This Checklist


By Louis Horkan
Reviewed by Nathan Kattner

Table Of Contents

    Preparing to retire is a process that should start well in advance of the actual big day. You can make this easier by following a checklist.


    Quite often people look at retirement as an event and/or a date on the calendar. In fact it is a process. And it requires tons of consideration and planning.

    To ensure you are properly prepared, you need to start sooner than later, which will make the process easier to understand and follow. And much more likely to succeed.

    Keep in mind this isn’t something you can do in a day or two – it will require real thought and consideration.

    This is all about your life in retirement. There are plenty of key areas to cover and you definitely want to treat this seriously, as the decisions you make today will impact your money and your retirement tomorrow.

    Follow this checklistFollowing this checklist will help you get ready for the big day…and all the ones that follow thereafter.

    1) Decide what you want to do

    As you start on your checklist you need to determine what you envision for retirement. This is even more important if you and a spouse or partner plan to live out retirement together.

    By the time you are approaching retirement you should have figured some things out in terms of who you are and at least some of what you’d like to do. Playing golf everyday isn’t a plan, no matter how much you love playing some stick.

    If there are two of you doing so, both should have ideas, and should take the time to discuss these things openly and honestly. Often some of those things won’t align.

    That’s fine and to be expected. This is about being honest. And being willing and even wanting to compromise. To take time before you get there to lay out how you each view what retirement will look like in terms of your interests and what it will take for each to be happy and fulfilled.

    Expect to cover a wide array of issues, ranging from work in retirement and travel to hobbies or interests, charitable work, giving and more, as well as day-to-day living.

    2) List what’s yours

    Once you’ve thought about how you want retirement to look like and the things you want to do (individually and collectively), then you have to prepare to create a budget and a retirement plan that will act as roadmaps and provide guardrails.

    But before doing those things, you have to assess where you are now. What do you have now pre-retirement?

    Best way to go about doing this is to create a worksheet. Be sure to include all assets. This should encompass cash, savings, brokerage accounts (non-qualified), qualified retirement accounts, insurance policies, trusts, properties, vehicles of all types, travel or recreational memberships or clubs that are paid up, valuable possessions, disaster funds, inheritance that is due to you, and more.

    3) Determine current bills and debt

    Pretty straightforward, but you want to be sure to account for everything so you don’t get surprised when you do retire.

    This includes what you spend currently. Regular monthly bills, long-term debt (mortgages and vehicle loans), credit cards, charge cards (e.g., furniture and store), personal loans, medical debt, travel and/or recreational memberships you pay for regularly, monthly entertainment, spas treatment, health clubs, monthly clothing allowance, beauty and health products, annual travel, et, cetera.

    Two items not included here are long term care (LTC) which can be very expensive, and taxes, which are expensive and necessitate the need for a tax plan within your overall retirement plan.

    Additionally, you will want to consider your goals and plans, such as charitable giving while you’re alive, gifting to loved ones, and legacy if you plan to pass on assets to families, friends or organizations after you pass.

    While going through the “cost side,” it’s important to be exhaustive, as you won’t be getting that check from an employer once you retire. What you will need to cover bills will depend on your expenses, but for context, many experts ball park a figure of at least $1 million to retire comfortably.

    For further context, the U.S. Bureau of Labor Statistics (BL) reports that the average expenditure for American households in 2022 was nearly $73k. Whichever benchmark you use, it will at least give you something to measure your current status against.

    4) Time to budget

    While you've determined what you have in terms of assets, you need to break down income sources that will be there in retirement.Now that you have a handle on what you have and what you are likely to spend on a regular basis once retired, it’s time to move forward with budgeting.

    While you’ve determined what you have in terms of assets, you need to break down income sources that will be there in retirement.

    Income sources will include the following:

    • Retirement savings – pension income (if any), qualified savings accounts (IRAs, employer-sponsored such as 401(K), some types of annuities, et. cetera)
    • Social Security – Average social security benefit for the typical individual in 2023 is $1,782 if starting at full-retirement age of 67, according to the Social Security Administration
    • Investment income – you’ll probably want to keep invested in the market to drive savings growth and help address inflation and taxes, with new investments as well as those existing
    • Employment in retirement – part/full-time, owning your own business, consulting, and more
    • Passive income – a good example is rents from rental properties

    When you compare your income and your expenses, you can get a good idea of whether or not you are looking at a surplus or a deficit. If there is a surplus, you are probably going to be okay in retirement.

    If instead there is a deficit, then you have to find more income or you may be looking at the real possibility of decreasing your monthly expenditures, which will mean adapting goals and adjusting your standard of living lower in order to ensure you don’t outlive your assets.

    5) Create the retirement plan before you retire

    Once you’ve gone through the aforementioned steps and have a good picture on what your goals are, as well as your budget, you can now do the real planning that will guide you into retirement and onward.

    As you work on the plan, consider the fact that you and/or your spouse or partner might live for 20 to 30+ years in retirement on a fixed budget. And that’s with nothing more than savings, social security and whatever other income streams previously created.

    This should start to drive home the importance of retirement planning. And the need to do it before you retire.

    Whether working with a retirement planner or financial advisor during your pre-retirement years, which is highly suggested, or doing the planning on your own, it is essential that it occurs starting before you retire.

    Keep in mind that your plan will not just encompass formalizing your budget. Because you will likely need to bring in income over the course of your retirement, you’ll need an investment plan that takes into account your comfort with risk, as well your need for income, and the period of time you’ll likely need to stay invested in the markets.

    A comprehensive plan will cover major issues such as diversification (not placing all eggs into one basket to minimize risk) and in what manner to allocate those assets. The goal will be safely increasing your savings with the least amount of risk encountered and while minimizing taxes you’ll owe.

    Part of your retirement plan will focus on spending. It will guide you on how you’ll strategically spend down your assets (income streams) over the years of your retirement so you have what’s needed to achieve goals and ensure you don’t outlive your assets. Part of your spending plan will adjust over the years as you age upward and spend less as you become less active.

    You will also need a tax plan that enables you to pay the least amount of money to Uncle Sam. A good plan could potentially save you tens to hundreds of thousands of dollars (maybe even more) in taxes, which means more money left in your pocket to use or pass on.

    Additionally, you want to include estate planning. This will serve to protect assets and have a plan in place to dispose of your assets once you do pass on.

    That can include protecting your spouse or partner, family members and other loves ones, and even entities or organization you want to help. You definitely want to ensure beneficiaries get what you want them to receive in the timeliest and most tax efficient manner, and to be able to avoid the hassles and expense of probate.

    When it comes to your estate and the disposition of assets, your planning should take into consideration issues such as final directives (documents that spell out how you prefer to be treated if incapacitated), final expenses (e.g., burial costs) and funeral wishes.

    6) Create a plan for paying off debt

    This sounds like a no-brainer, but lots of people make the mistake of carrying expensive debt into retirement, which acts as a tax on your available income. This is especially true today given the higher than usual rates you’re probably paying on everything from mortgages and vehicles to credit cards, personal loans, and more.

    There are different ways to target debt (example: chose the highest rate item and concentrate on paying as much as possible each month while paying minimums on all other items), but whatever you decide, start on a plan in advance of retiring and try to eliminate as much as possible before making your move.

    During this period take advantage of overtime, part-time with another employer, or gig work, all with a goal of paying that debt down sooner rather than later, when you may have less opportunity to do so.

    Decide when to retire and where to live

    We list these separately because they will have a big impact on your plans, but to some extent they depend on what you determine as you go through the checklist.

    Where you wish to retire is also a bit of a wildcard.Depending on circumstances, you may or may not have the opportunity to decide when you will retire. If you or a spouse/partner or family member becomes incapacitated, you may be forced to retire before planned or preferred. Same might occur if your employer decides to let you go.

    Assuming you do get to decide when you wish to hang up your boots and walk away on your own timing, the aforementioned planning will help you decide when that might be and the triggers that might precipitate doing so.

    That might be age driven, such as 65 when you are eligible for Medicare health coverage, or 67 when you reach full retirement age and wish to start withdrawing Social Security. Or when you have saved a specific amount of money.

    Whatever the case, by having taken all the steps and considerations above, your decision will likely be made easier.

    Where you wish to retire is also a bit of a wildcard. You may find you that you can’t fulfil your lifelong dream of retiring to an exotic locale after you’ve gone through this process.

    By working through this preparation process in advance, either you can take steps while there’s potentially still time to find a way of funding your dream, or you can adjust your desire on where to retire to a more realistic locale.

    Just as with timing of when to retire, knowing what you’ll have and comparing that with affordability data will likely make your decision about where to retire to easier.

    One last suggestion

    There’s one last step you should take while you are going through this process – gathering all documentation into one place that is easily accessible. This includes all financial accounts, ranging from savings and retirement accounts, websites, insurance policies and anything else financially related.

    Also, contracts and information on debt you might still carry, legal documents (example – lawsuits), and anything else that your estate will have to deal with.

    You’ll want to include contact information for important people that they will need to communicate with, a list of all user names and passwords, and any other pertinent documentation they will need to have access to.

    Gathering all of that information into a single place, such as a home safe, with an adviser or within a safe deposit box at your bank is prudent and will save the surviving partner time, energy and hassle at a time when they will probably be grieving.


    We did mention at the start this isn’t something that will take a day or two. Serious thought has to go into each of these key areas. Some areas like putting together your comprehensive retirement plan, and all that entails, definitely takes some time.

    Beyond your retirement plan, there are so many considerations and decisions to be made. This gets tougher when there are two people involved.

    As such, it’s important to discuss retirement and all it will entail in advance, alleviating the stress that can arise when dealing with these issues in real time, after you retire.

    Given the complexity of retirement, you should do yourself a favor and work with a professional who knows all the issues and can help you create a plan and assist you in navigating your retirement efficiently, ensuring your “happily ever after” ends up being what your envision.

    if you are currently utilizing a retirement plan (either your own or one created for you), our team would be happy to review it to determine if it is capable of actually meeting your goals.

    Or we can assist you by creating a customized retirement plan capable of helping you to retire with confidence, utilizing our proprietary Retirement Success Plan (RSP) approach.

    We’ll build a holistic, comprehensive retirement plan addressing relevant issues, utilizing strategies that cover Social Security, taxes, income, spending, healthcare, LTC, legacy, and more, customized to your family’s specific needs.

    A plan created with the goal of ensuring you can successfully live out the retirement you envision.

    If you are ready to take the next step and talk to a team of retirement planners who can advise on all your retirement needs, and who will put your interests first, Schedule a call today!


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