The Rest of the Plan

Ten things worth reviewing before and during retirement. 

Planning for the years ahead involves more than the number on an investment statement. Through your work with Matt and Lori, you have likely discussed many, if not all, of the topics below.

Let’s take a closer look at the everyday details within those conversations.

A home repair allowance becomes more useful when we know how much life is left in the roof. Planning for healthcare becomes more specific when we ask about the crown our dentist has been watching or what our hearing coverage actually covers.

Think of this as a companion to the planning you are already doing, with ten things to check, price, schedule, or update, wherever you are in retirement.

Readiness is a whole balance sheet, not a single number.

1. Make Sure Your Car Is Reliable 

Your car takes you to the people and places that make up your life. Give it a closer look. I’m asking you to look beyond “it seems to be running fine.” A trusted mechanic can help you distinguish routine maintenance from expensive repairs that may be on the horizon.

Ask specific questions:

• How much life is left in the tires and brakes?

• Is any major scheduled maintenance due?

• What repairs are likely in the next few years, and what might they cost?

You want enough detail to assign realistic numbers and timing to car expenses. 

Consider how well the vehicle suits the way you expect to use it. Is it comfortable on longer drives? Is it easy to get into and out of? Can you see clearly, reach the controls comfortably, and load whatever you regularly carry? A dependable car that makes every outing a minor inconvenience deserves consideration, too.

If a replacement is on the horizon, bring the estimate and your likely timeline to your next appointment. Together, you can consider how keeping, repairing, or replacing it fits your plan, including whether to pay cash or finance. 

Reliability is the goal. Shiny is optional.

The check: Have a mechanic assess your car, price any upcoming work, and consider whether it still suits your daily life. If replacement makes sense, review the cost and timing with Matt and Lori.

2. Evaluate Major Home Repairs 

Walk through your home like an inspector. Look at the roof, the HVAC system, the water heater, the plumbing, the electrical systems, and the major appliances. We get remarkably good at living around things: the faucet with a personality, and the air conditioner we encourage through August. Give all of those things a closer look. 

Start with what you know. Gather installation dates, service records, and warranties. Then have qualified professionals assess the systems you are unsure about. Ask what needs attention now, what can reasonably wait, and what a replacement might cost. Age is a useful clue, but condition matters. Something does not need replacing simply because it has reached a certain age.

Put the information in one place: the item, its condition, the estimated cost, and the likely timing. Separate routine maintenance from major repairs and optional renovations. A leaking roof and a kitchen you would enjoy updating deserve separate entries on the list.

Consider your plans for the house.

• How well will it serve you in the years ahead? Look at the stairs, lighting, bathrooms, and entrances.

• Would the layout work if you were recovering from surgery or needed help for a few weeks?

• How much upkeep do you want to manage, and how easily can you reach the people and places that matter to you? A home can be beautifully maintained and still ask more of us than we want to give it.

Your plans to stay or move should guide these decisions. If you are already planning a renovation, consider whether the same project could make daily life easier. Better lighting, a more accessible entrance, or a more accessible bathroom may be worth including in the design now. The goal is a home that supports how you want to live.

Anticipate the expenses you can and leave room for those you cannot. A water heater may still surprise you on a Tuesday. Ideally, its replacement cost will not.

The check: Review major systems, likely repair costs, and timing. Identify any changes that would make the home easier to live in and maintain. Outline your plans to stay or move.

3. Plan for Hearing and Dental Needs

Add hearing and dental appointments to your calendar. Ask your dentist what needs attention now, what may need attention in the next few years, and what can reasonably be monitored. If you have noticed changes in your hearing, schedule an evaluation. If you wear hearing aids, ask about their condition, ongoing service, and likely replacement needs. The goal is to replace vague possibilities with useful information.

These expenses support what we want to keep doing: continuing the conversation, enjoying a meal, traveling comfortably, and spending time with the people we love. They deserve consideration alongside the plans they make possible.

Then check what your coverage will actually pay. Original Medicare does not cover hearing aids and generally does not cover dental care such as cleanings, crowns, and implants. Some Medicare Advantage plans offer hearing and dental benefits, but the details vary. “Dental included” is a promising phrase, but it is not a cost estimate. Look closely at covered services, provider networks, annual limits, and your share of the bill.

Whether retirement is ahead of you or already underway, review your insurance coverage before scheduling major dental or hearing care. If your coverage is changing, compare the benefits of each plan. Get a written treatment plan and estimate, and ask your clinician which needs prompt attention and which can safely wait. Let your health needs guide the timing, and have a clear understanding of the costs.

The check: Know your anticipated hearing and dental needs, their likely timing and cost, and what your coverage will actually cover.

4. Develop a Long-Term Care Plan 

Listen, this is the line item everyone would rather skip. “We’ll figure it out when the time comes” is an understandable response to long-term care. It is also a lot to ask of a future Tuesday.

I approach this subject as both a gerontologist and a family caregiver. I know how personal these decisions are. Planning ahead gives us more time to consider what we want, what is available, and what we can afford before an immediate decision is needed.

Start with the practical questions.

• If you needed help, where would you prefer to receive it? Could your home accommodate that care?

• Who could coordinate services, manage appointments, and make decisions if you were unable to?

• If family members are part of your plan, include them in the conversation. “My daughter will help” warrants a discussion with your daughter about what that would actually involve.

Then put numbers behind the possibilities. Matt and Lori are your experts in exploring long-term care funding and coverage options, including eligibility, premiums, benefits, and the impact on your financial plan. I’ll help you understand housing and care options, their costs, and how care needs associated with different conditions may affect those expenses over time.

Together, those conversations help connect the care you want with a plan to pay for it.

Please complete Five Wishes and discuss it with the people who may someday need to speak for you.

Five Wishes is a plain-language advance directive that covers more than medical orders. It asks who should speak for you, what treatment you would or would not want, how comfortable you want to be, and what you want your loved ones to know.

It helps you express who you want to make healthcare decisions, which medical treatments you would or would not want, and what matters to your comfort, dignity, and the people you love.

These preferences deserve a place alongside your financial plan.

The check: Meet with Matt and Lori to discuss funding and coverage. Complete Five Wishes, discuss your answers with your chosen decision-maker, and ensure the document is accessible. You can keep the documents you complete in your AdviceWorks portal. 

5. Invest in Everyday Comfort 

This is the line item that gets skipped because it feels like an indulgence. We will research a hotel mattress before booking a three-night stay, then spend another year sleeping in the valley of our mattress at home. 

Look at the things you use most. Do your shoes make you want to walk? Is your favorite chair still comfortable, or merely familiar? Are your glasses helping you see well, and do they look like something you would choose today?

These purchases deserve a place in your budget because they support what you want to keep doing. Comfortable shoes make a walk more inviting. Well-fitting glasses make reading more enjoyable. A supportive chair lets you settle in with a book and get up again without negotiating with the furniture. A better fit, an adjustment, or a thoughtful replacement can improve something you do hundreds of times a year. That is a respectable return on an ordinary purchase.

Did you know? If you walk 10,000 steps a day in the same athletic shoes, you could reach their typical replacement mileage in just two to four months. They may still look presentable long after the cushioning has done its best work.

The check: Review your mattress, walking shoes, eyewear, and everyday furniture. Start with the change you would most appreciate.

6. Review the Debt You Carry

Ask whether the debt you carry still earns its place in your plan.

A mortgage or other loan may have been a deliberate choice to preserve cash or support another priority. That reasoning may still hold. The key question is whether the arrangement continues to make sense for your income, resources, and plans today.

Review each balance, interest rate, required payment, and payoff date. Know whether the rate can change or whether a substantial payment is approaching. A loan that has been quietly on autopay still deserves an occasional check-in.

Give a low-interest mortgage its own consideration. Paying it off can reduce monthly obligations, but it also uses money that would otherwise remain available. Before making a substantial payment, consider where those funds would come from, any tax consequences of accessing them, and what you might need that money for later. The decision deserves a look at both sides of the balance sheet.

Your preferences belong in the conversation, too. Some of us value having fewer monthly commitments. Others prefer to preserve accessible funds and carry a manageable payment. Either choice should fit the broader plan and leave room for changing circumstances.

The goal is to understand what each debt costs, what it allows you to do, and whether that trade-off is still worthwhile.

The check: Review the purpose, cost, and terms of each debt. Confirm which debts you intend to retain or pay down, and how those decisions affect your cash flow and available reserves. Never hesitate to ask Matt or Lori to review your debt. 

7. Build an Accessible Cash Reserve 

A strong portfolio is reassuring. Knowing which money you can use next week answers a different question.

An accessible cash reserve gives you room to respond when an expense arises at an inconvenient time. It may reduce the pressure to sell investments in an unfavorable market or to make a hurried decision about how to cover an unexpected bill.

That flexibility matters beyond the numbers. If you need help at home while recovering from surgery, for example, available funds can give you time to explore care options and make arrangements. Money you can readily use helps preserve your choices.

Start by separating foreseeable expenses from genuine surprises. A renovation already on the calendar needs its own funding. Counting the same dollars toward both that project and your emergency reserve makes the cushion look more generous than it is.

The appropriate amount depends on your spending, dependable income, anticipated withdrawals, and other commitments. Coordinate the reserve with your overall financial plan, including how much should be available for everyday spending and how much should be set aside for unexpected needs.

Then make “accessible” practical. Know where the money is held, how quickly you can access it, and whether any restrictions or penalties apply. If someone may need to manage bills on your behalf, grant the appropriate authority in advance. After using the reserve, have a plan to replenish it.

A reserve earns its place by giving you more control over when and how you use your remaining resources.

The check: Confirm your reserve target, what it is intended to cover, how to access it, and how you will replenish it. Make sure planned expenses and emergency needs do not rely on the same dollars.

8. Update Your Estate Documents 

A will can sit quietly in a drawer for twenty years while the family it describes changes significantly.

Review your will, trusts, powers of attorney, healthcare directives, and beneficiary designations. Do they reflect your current life, the people you trust, and your wishes? 

Estate planning also concerns the life you are still living. A financial power of attorney authorizes someone to act on your behalf, while healthcare documents address medical decisions and preferences. An estate attorney can explain how these documents work together and whether they provide the authority someone would need to help you.

Look closely at the people you have named. Is each person still willing and able to serve? Have you named a backup? Someone who was the obvious choice fifteen years ago may now live far away, have substantial responsibilities, or need support themselves. Being named in a document should come with a conversation, not a surprise assignment.

Review your beneficiary designations directly with the institutions that hold your accounts and policies. Updating your will does not update those forms. Ask your attorney to confirm that your documents, account ownership, and beneficiary designations align as intended.

Then make the paperwork usable. Could the person you have chosen find what they need and understand where to begin? Organize current documents, essential account information, recurring bills, and contact details for your attorney and financial professionals. Include instructions for locating important digital records and for obtaining authorized access. 

Revisit these arrangements after a significant change in your family, health, residence, or the availability of a person you have named.

This is practical capital: making your wishes clear and giving the people you choose the information and authority to carry them out.

It is also a considerable kindness to anyone who may one day need to help.

The check: Confirm that your documents and beneficiary designations reflect your current wishes. Ensure the people you have chosen understand their roles, know where to find essential information, and have the authority to act.

9. Review Your Insurance Coverage

Insurance decisions often outlast the circumstances that shaped them. A policy purchased while raising children, building a business, or paying a mortgage may still be in place years after those responsibilities have changed.

Take a fresh look at what you own, what you need to protect, and the coverage you carry.

• Have property values or major possessions changed?

• Does your liability coverage reflect your current circumstances?

• Does each of your life insurance policies still serve its intended purpose?

The goal is to understand how the policies fit together, identify any gaps or overlaps, and determine whether the coverage still makes sense for your life today. 

The check: Schedule an insurance review and confirm that your coverage reflects your current property, responsibilities, and priorities. Before your homeowners insurance renewal, ask an agent to shop your coverage for competitive pricing. 

10. Develop a Social Security Claiming Strategy

Your last day at work and your first Social Security payment do not have to fall on the same day. One deserves a celebration. The other deserves some calculations.

If you have not yet claimed, confirm how Social Security fits into your retirement income plan. Your own retirement benefit can generally begin as early as age 62, but claiming before full retirement age reduces the monthly amount. Waiting beyond full retirement age increases that benefit through delayed retirement credits until age 70. No additional delayed retirement credits are available beyond age 70.

Start with your actual numbers. Review your earnings record and benefit estimates, then compare several claiming dates. Ensure the estimates reflect when you expect to stop working, as assumptions about future earnings can affect the projections.

Then consider what will fund the years before you claim. If you delay, will living expenses come from savings, investment withdrawals, part-time work, or another income source? A larger future benefit deserves consideration alongside the resources needed to reach it.

If you are married, consider what the decision means for both of you, including the income available if either spouse dies first. Have spousal and survivor benefits reviewed together, as their rules differ. If you plan to work while collecting benefits before full retirement age, understand how earnings could affect your payments.

Your health, income needs, family circumstances, and preferences all belong in the discussion. Someone else’s claiming age is a topic for conversation over dinner. It is not a strategy for choosing your own.

You do not have to sort through these choices alone. Matt works with a Social Security specialist and can help you schedule an appointment to review your benefits, compare claiming options, and explain how they fit your circumstances. Before you file, you should understand your options, the trade-offs, and what your decision means for your retirement income.

The check: Review your earnings record and benefit estimates, compare claiming dates, and coordinate Social Security with your retirement income, work plans, and spousal or survivor benefits.

BONUS: Create a Bucket List

You have reviewed the accounts, the insurance, and the paperwork. Now, for a list that is considerably more fun to complete.

What would you like more of in your life?

What have you been meaning to do? 

A bucket list asks what we want to make room for. The grand trip belongs here. So does learning Italian, having a standing lunch with a friend, or spending an afternoon with our grandchildren without checking the time.

Think about what you want an ordinary week to include. What do you want to learn? Who would you like to see more often? Is there work, volunteering, or a project you would enjoy giving your time to? Whether retirement is ahead of you or already underway, these questions deserve a place alongside the financial ones.

Write these things down, then consider the money, time, and energy they will need. Otherwise, the calendar has a remarkable ability to fill itself with things nobody particularly looked forward to.

The things we look forward to also deserve a place in the plan.

The check: Write down three things you would like more of in your life. Put one on the calendar, whether that means booking it, inviting someone, or taking the first step. “Someday” is notoriously hard to find on a calendar.

What It All Makes Possible

An investment statement can tell us what we have accumulated, but it cannot tell us whether the house is ready, the care plan is realistic, our wishes are clear, or the people we love know what to do.

That is why this review matters. Planning for what we can anticipate helps protect reserves for what we cannot. It also leaves fewer decisions for a moment when time is short and our options may be limited.

At BROKERAGE™, we look at the rest of the balance sheet, too: our biological, psychological, social, and practical capital. The capacity to participate. The confidence to make decisions. The people we can count on. The arrangements that make everyday life work. These assets help us leverage everything we have spent years building.

You do not need to check every box by Friday. Choose one. Walk through the house, open the document folder, make the appointment, or revisit a conversation with Matt and Lori. Some of this may already be settled, and some may deserve a fresh look. The value is in knowing which is which.

And give that bucket list the same attention. The trip, the standing lunch, the thing we keep meaning to learn: these deserve a place in the plan alongside the expenses.

We have spent years asking whether our money will last. Let’s give equal attention to what we want it to make possible.

After all, isn’t that what all the planning was for?

To Read More 

● Medicare.gov, What's not covered? | Medicare