Author: Kevin Lao

Moving to Tennessee in Retirement: Your Complete Estate Planning Guide

Thousands of retirees move to Tennessee every year. Maybe it’s the mountains or being closer to family. Maybe it’s the lower taxes and cost of living. Whatever the reason, there’s one critical aspect of this move that most people overlook until it’s too late: your estate planning documents are still living in your old state.

Those powers of attorney you signed in Illinois? That will you created in California? The trust you set up in New York? They might still be legally valid in Tennessee, but “legally valid” and “practically effective” are two very different things. And some of the planning strategies that worked perfectly in your previous state simply don’t exist in Tennessee.

Here’s what catches most new Tennessee residents off guard: Tennessee doesn’t have transfer-on-death deeds for real estate. If you owned property in Florida, you might have used a ladybird deed to avoid probate. That option doesn’t exist here. If you’re moving from a state with different probate rules, different incapacity planning documents, or different estate planning tools, you need to understand how Tennessee does things and what that means for your family.

This guide walks through everything you need to know about estate planning when retiring to Tennessee, from understanding Tennessee’s specific requirements to knowing which documents need immediate updating and which planning strategies work best in this state.

Why Your Old Estate Plan Might Not Work in Tennessee

When you move to Tennessee from another state, your estate planning documents don’t automatically become invalid. A will created in New York is still a legal document. A trust created in California still exists. Powers of attorney from Illinois don’t disappear just because you crossed state lines.

But here’s the problem: estate planning is highly state-specific. Each state has its own laws governing how documents must be executed, what language they should contain, and how they’ll be administered. What worked in your previous state might not work smoothly in Tennessee.

Financial Institutions

Let’s start with the most practical issue: financial institutions in Tennessee are familiar with Tennessee documents. When someone tries to use a financial power of attorney from another state at a Tennessee bank, the bank often hesitates. Financial institutions don’t make it easy to use powers of attorney in the first place—they’re cautious about fraud and protective of their customers’ accounts. When you show up with a document from another state that looks different from what they normally see, you’re giving them another reason to pause or potentially refuse to honor it.

Medical Providers

The same issue applies to healthcare documents. If your family needs to present your living will to a Tennessee hospital, having a document that Tennessee medical providers recognize and have seen many times before makes the process much smoother. An advance care directive from Tennessee looks like what they’re used to dealing with. A healthcare directive from another state might raise questions or require additional verification.

Witness Signatures and Notaries

Beyond the practical considerations, there are legal differences that can significantly impact your estate plan. Tennessee has specific requirements for how documents must be signed and witnessed. In Tennessee, wills require two witnesses, and those witnesses must be “disinterested,” meaning they don’t have any stake in your estate. Tennessee also doesn’t recognize virtual notarizations for estate planning documents—you need to be physically present with a notary to sign these documents.

Real Estate Transfers

The biggest difference for many retirees is how Tennessee handles real estate transfers. Many states offer tools like transfer-on-death deeds or ladybird deeds that allow real estate to pass outside of probate. These are incredibly useful planning tools that can help avoid the time, expense, and public nature of the probate process. Tennessee doesn’t have anything like this. If you own real estate in Tennessee and want to avoid probate, you might consider placing that property in a revocable living trust. There’s no simple deed option that accomplishes the same goal.

This catches many out-of-state retirees off guard. Some states have ladybird deeds (also called enhanced life estate deeds), which are extremely popular in those states. You can transfer your home using a ladybird deed, maintain complete control during your lifetime, and have it pass automatically to your beneficiaries without probate. When these same people move to Tennessee, they discover that tool isn’t available. If they want the same probate avoidance for their Tennessee home, they need a different strategy.

Understanding Tennessee’s Probate Process and Why It Matters

Before you can make informed decisions about your Tennessee estate plan, you need to understand what you’re trying to avoid: the Tennessee probate process.

Probate is the court-supervised process that happens after someone dies. If you only have a will (or if you don’t have any estate planning documents at all), your estate goes through probate. Your family files a petition with the local probate court. The court oversees the process of gathering your assets, paying your debts, and distributing what’s left to your beneficiaries.

In Tennessee, probate takes a minimum of four months due to creditor notification requirements. The state requires a waiting period to give creditors time to come forward with any claims against the estate. Realistically, even for a simple estate, you’re looking at six to twelve months. If there’s any complexity—business interests, out-of-state property, disputes among beneficiaries—the process can easily take twelve to twenty-four months or longer.

The costs add up quickly. You’ll have court filing fees, but the bigger expense is usually attorney fees. Most families need legal help navigating probate, and in Tennessee, you’re looking at anywhere from $1,500 on the absolute lowest end to multiple five figures for straightforward estates. Complex estates, especially those with family conflict, can generate legal fees much higher than that.

Privacy Concerns

There’s another issue many people don’t consider: Tennessee probate is public. Anyone can go to the probate court and pull up your file. They can see:

  • Your will
  • The inventory of your assets—what you owned and how much it was worth
  • Who your beneficiaries are and what each person is receiving

For high-net-worth individuals, this lack of privacy can be a serious concern. There are people who actually monitor probate records to find out who’s inheriting significant assets. It’s uncomfortable to think about, but it happens. Some families prefer to keep their financial affairs private, and probate makes that impossible.

The Tennessee probate process isn’t necessarily worse than other states, but it’s also not something most families want to go through if they can avoid it. Understanding these drawbacks helps you appreciate why certain estate planning tools—particularly trusts—are so valuable for Tennessee residents.

Tennessee’s Advanced Care Directive: Healthcare Planning Done Right

One of the most important documents you’ll need as a Tennessee resident is called an advanced care directive. This is Tennessee’s specific document for healthcare planning, and it’s different from what many other states use.

Tennessee’s advanced care directive combines two critical healthcare planning tools into a single document. Understanding what each part does helps you appreciate why this document is so important.

Healthcare Power of Attorney

The first part is your healthcare power of attorney. This section names the person who can make healthcare decisions for you if you’re so incapacitated that you can’t communicate those decisions yourself. This isn’t about everyday medical choices—you can still tell your doctor you want the blue pill instead of the red one. This is for situations in which you cannot physically or mentally express your wishes. Maybe you’re unconscious, had a severe stroke, or are in the late stages of dementia. In these situations, someone needs legal authority to make healthcare decisions on your behalf.

Without a healthcare power of attorney, your family would have to petition a Tennessee court to start a conservatorship proceeding. They’d have to prove your incapacity in court. It’s expensive, time-consuming, and emotionally draining during an already difficult time. Having this document in place allows your chosen person to step in immediately without court involvement.

Living Will

The second part of Tennessee’s advance care directive is the living will, which addresses end-of-life decisions. Specifically, your wishes regarding life-sustaining treatment if you’re in a terminal condition or permanently unconscious state.

This is perhaps the most important gift you can give your family. Without a living will, your loved ones have to make agonizing decisions about whether to continue life support. They’re already watching you suffer. They’re dealing with their own grief and emotional trauma. And now they have to make a decision about whether to remove life support, never being completely sure if it’s what you would have wanted.

A living will takes that burden off of them. You’ve already made the decision and put it in writing. They’re simply following your clearly stated wishes rather than making the choice. For families who’ve had to make these decisions without guidance, the emotional weight can be crushing. Having a living will in place is an act of love and protection for the people you care about most.

If you’re moving to Tennessee from another state, you might have similar healthcare documents from your previous state. They might still be legally valid. But Tennessee healthcare providers deal with Tennessee advanced care directives every single day. They know exactly what these documents mean and what authority they provide. When medical decisions need to be made quickly, having a document that providers instantly recognize can make a significant difference.

Choosing Your Healthcare Power of Attorney

When choosing who to name as your healthcare power of attorney, consider both location and capability. If you’re new to Tennessee and your closest family members are still in your previous state, that creates a practical challenge. Healthcare decisions often need to be made in person, with full understanding of the medical situation. Having someone local who can be at the hospital, speak with doctors, and fully grasp what’s happening is valuable.

That said, if your most trusted person lives out of state, they can still serve in this role as long as they can travel to Tennessee if needed and stay in communication with medical providers. It’s a balance between who you trust most and who can practically fulfill the responsibilities.

Financial Powers of Attorney and Tennessee Banking

A financial power of attorney is the document that names someone who can handle your financial affairs if you become incapacitated. This person can

  • Access your bank accounts
  • Pay your bills
  • Manage your investments
  • Deal with your insurance
  • Handle other financial matters on your behalf.

Without this document, if you become incapacitated, no one can access your finances. Your spouse can’t go to the bank and withdraw money to pay for your medical care. Adult children can’t access your accounts to pay your mortgage and utilities. The only option would be for your family to petition a Tennessee court for conservatorship, which is expensive and time-consuming.

Here’s where the Tennessee-specific considerations become critical. If you have a financial power of attorney from another state, it might still be legally valid in Tennessee. But when your designated person actually tries to use it at a Tennessee bank or financial institution, they’re likely to encounter resistance.

Banks and credit unions are already cautious about powers of attorney. They worry about elder financial abuse. They’re protective of their customers. They scrutinize these documents carefully. When someone shows up with a power of attorney that looks different from what they normally see—one from Illinois, California, or any other state—it gives them another reason to hesitate or refuse.

Having a Tennessee financial power of attorney that complies with Tennessee law and aligns with what local financial institutions are accustomed to seeing makes the process significantly smoother. When you need to use a power of attorney, it’s usually during a crisis. Your loved one is in the hospital or dealing with serious cognitive decline. The last thing you want is to be arguing with a bank about whether they’ll accept an out-of-state document.

Requirements

Tennessee has specific requirements for how powers of attorney must be executed.

  1. They must be signed
  2. Witnessed by two disinterested witnesses (people who don’t benefit from your estate)
  3. Be notarized

If your old power of attorney doesn’t meet Tennessee’s requirements, updating it should be a priority.

When naming someone for this role, think about who is both trustworthy and capable with financial matters. This doesn’t have to be the same person you name for healthcare decisions. In fact, it’s common to name different people based on their strengths. Maybe one family member is great with medical matters—perhaps they work in healthcare—while another is more financially savvy and better suited to handle banking and investments.

Why Tennessee Residents Need Trusts More Than Many Other States

If you own real estate in Tennessee and you want to avoid probate, you need to understand one critical fact. Tennessee doesn’t offer the simple probate-avoidance tools that many other states provide.

States like Florida, Michigan, Ohio, and several others have what are called transfer-on-death deeds or ladybird deeds (enhanced life estate deeds). These allow you to deed your property so that it automatically transfers to your named beneficiaries when you die, completely avoiding probate. You maintain full control during your lifetime—you can sell the property, mortgage it, or change the beneficiary designation whenever you want. But at death, it passes automatically without any court involvement.

Tennessee doesn’t have this option. For Tennessee residents who own real estate, there are essentially two paths:

  1. The property goes through probate
  2. It’s owned by a trust.

You could own property jointly with right of survivorship, which means when one owner dies, the other automatically becomes sole owner without probate. This works fine for married couples. But it only postpones the probate issue until the second spouse dies. And it doesn’t help single individuals or people who want their property to go to children or other beneficiaries.

Revocable Living Trusts

This is why revocable living trusts are so important for Tennessee residents who own homes or other real estate. A revocable living trust allows you to transfer ownership of your property into the trust during your lifetime. You serve as your own trustee, which means you maintain complete control. Nothing changes in terms of your ability to use the property, sell it, refinance it, or make any other decisions about it. But legally, the trust owns the property.

When you pass away, your successor trustee can immediately transfer the property to your beneficiaries according to your trust instructions—no probate required. In Tennessee, where you don’t have simpler deed-based options, a trust becomes the most effective tool for avoiding probate on real estate.

The trust benefits extend beyond just real estate. A properly funded trust avoids probate for all assets owned by the trust such as:

  • Bank accounts
  • Investment accounts
  • Personal property

This means your family can settle your estate in weeks instead of months or years. They avoid court filing fees and attorney fees. And they maintain privacy since trusts don’t become part of the public record like probated wills do.

For Tennessee retirees, especially those moving from states where they used transfer-on-death deeds or similar tools, understanding this difference is crucial. The planning strategy that worked in your previous state might not be available here, and you need to adjust your approach accordingly.

Tennessee Trust Requirements: Funding and Administration

Creating a trust document is only the first step. The most brilliantly drafted trust in the world won’t help your family if it’s not properly funded. Trust funding means actually transferring ownership of your assets into the trust. This is where many Tennessee estate plans fall apart.

When your estate planning attorney creates your revocable living trust, they’re creating a legal entity that can own property. But creating the trust doesn’t automatically transfer your assets into it. You have to retitle your assets from your individual name into the trust’s name.

Real Estate

For Tennessee real estate, this means executing a new deed. Your attorney can prepare the deed for you, transferring the property from you individually to you as trustee of your trust. But you have to actually record that deed with the appropriate Tennessee county register of deeds office. If you own property in multiple Tennessee counties, you need to record deeds in each county.

Make sure you understand the timing if you’re moving to Tennessee and selling property in your previous state before buying in Tennessee. If you close on your Tennessee home before you’ve created and funded your Tennessee trust, you’ll need to deed the property into the trust after the fact. It’s usually easier to have the trust created first so the Tennessee property can be deeded directly into the trust at closing, but that’s not always practical given moving timelines.

Bank and Investment Accounts

For bank and investment accounts (excluding retirement accounts, which we’ll discuss separately), you’ll need to contact each financial institution and complete its specific forms to retitle. Instead of your account being in “John Smith’s” name, it becomes “John Smith, Trustee of the John Smith Revocable Living Trust.”

Different institutions have different processes. Some make it easy with simple forms. Others have more complex requirements. Some want to see a copy of your entire trust document. Others accept a certificate of trust, a shorter document that proves the trust exists without disclosing all the private details of your beneficiaries and distributions.

Here’s what you absolutely cannot do: you cannot retitle retirement accounts into your trust. IRAs, 401(k)s, 403(b)s, and other qualified retirement accounts have specific tax rules. If you transfer ownership of these accounts into a trust, it triggers immediate taxation on the entire account balance.

Instead, you name beneficiaries directly on retirement accounts. Typically, your spouse is the primary beneficiary, and your trust or your children are contingent beneficiaries, depending on your specific situation and tax planning goals.

The same applies to life insurance policies. You don’t retitle life insurance into your trust (though there are specialized irrevocable life insurance trusts for advanced estate tax planning). Instead, you update the beneficiary designation to name your trust if that’s appropriate for your situation.

Follow Through

The challenge with trust funding is that it requires follow-through. You can’t just sign the trust document and assume you’re done. You have to contact each financial institution, complete their paperwork, and follow up to ensure the retitling happens. Many people create trusts in Tennessee and then never complete the funding process. Years later, when they pass away, their families discover the trust is empty. All the assets are still in the individual’s name, which means they all go through Tennessee probate anyway—exactly what the trust was supposed to prevent.

As a new Tennessee resident, you also need to think about ongoing funding. When you open new Tennessee bank accounts, make sure they’re opened in your trust’s name from the beginning. If you buy additional Tennessee real estate, make sure it’s deeded to your trust. If you receive an inheritance or sell a business, make sure those assets flow into your trust. Estate planning isn’t a one-time event—it requires ongoing attention as your assets change.

Beneficiary Designations: The Most Powerful Estate Planning Tool You Probably Don’t Think About

Here’s something that surprises almost everyone: beneficiary designations on your retirement accounts, life insurance policies, and certain other accounts override everything else in your estate plan. Your will doesn’t matter. Your trust doesn’t matter. The beneficiary designation controls.

This is one of the most important aspects of estate planning, especially in Tennessee, where many retirees are moving with significant retirement account balances. Understanding how beneficiary designations work and keeping them updated can be the difference between your assets going to the people you intend or going to someone you haven’t thought about in decades.

The way property passes in Tennessee after you die depends on how that property is titled. Joint property with right of survivorship passes automatically to the surviving owner. Real estate titled solely in your name goes through probate unless it’s in a trust. But assets with beneficiary designations—retirement accounts, life insurance, bank accounts with payable on death designations, investment accounts with transfer on death designations—all pass directly to whoever is named as beneficiary, regardless of what your will says.

The Importance of Keeping Beneficiaries Updated

This creates major problems when people don’t keep their beneficiary designations up to date. The most common and most devastating scenario happens after divorce. Someone gets divorced, updates their will and trust to remove their ex-spouse, but forgets about the beneficiary designation on their old 401(k) from a previous employer. When they die, that 401(k) goes to the ex-spouse, regardless of what the will says, what the person’s intentions were, or how long ago the divorce happened.

This isn’t theoretical. It happens regularly.

Example

A divorced woman with two children gets sick. Her financial advisor reviews her accounts and mentions that her ex-husband is still listed as the beneficiary on her retirement accounts. She says she’ll change it. But she’s dealing with medical treatment; she’s not feeling well, she’s busy, and she never gets around to filing the paperwork. When she passes away, her ex-husband inherits two million dollars in retirement accounts intended for her children.

Sometimes the ex-spouse does the right thing and gives the money to the children anyway. But they’re not legally required to. And even when intentions are good, it creates complications and potential conflicts.

Primary and Contingent Beneficiaries

For Tennessee retirees, beneficiary designations are also critical tools for probate avoidance. Assets with properly designated beneficiaries pass directly to those beneficiaries without going through the Tennessee probate process. This is why it’s essential to not only name primary beneficiaries but also contingent beneficiaries.

Your primary beneficiary is who receives the asset first. For most married people, that’s their spouse. But what if your spouse passes away before you do? What if you die together in an accident? That’s where contingent beneficiaries become critical. They’re next in line if your primary beneficiary can’t inherit.

For contingent beneficiaries, you need to think carefully about your specific situation. If you have adult children who are financially responsible, you can often list them directly as contingent beneficiaries.

Minor Children

If you have minor children, you don’t want to list them as direct beneficiaries on large accounts. Minors can’t inherit significant sums outright. Someone would have to petition a Tennessee court, and the court would oversee administration of those assets until the children reach adulthood—exactly the kind of court involvement you’re trying to avoid.

Instead, for minor children, you typically name your trust as the contingent beneficiary. Your trust contains detailed instructions about how assets should be managed for your children, at what age they should receive distributions, who will serve as trustee, and how the money can be used for their benefit in the meantime.

The Exception

There’s one important exception: retirement accounts. For retirement accounts specifically, if you have adult children who are responsible, it’s often better to list them directly as contingent beneficiaries rather than listing your trust. This is due to tax implications under the SECURE Act, which dramatically changed the rules for inheriting retirement accounts in 2020.

The SECURE Act implemented what’s called the 10-year rule for most non-spouse beneficiaries. Previously, beneficiaries could “stretch” inherited retirement account distributions over their lifetime, minimizing the tax impact. Now, most beneficiaries must withdraw the entire account balance within 10 years of the original owner’s death.

How this interacts with trusts is complex. If a trust is named as beneficiary, the tax consequences can be significantly worse than if an individual is named directly, depending on how the trust is structured. Trusts have compressed tax brackets—they hit the highest tax rate at around $14,000 of income, whereas individuals don’t hit that rate until much higher income levels.

This is an area where you need both an estate planning attorney and a financial advisor working together. The right answer depends on your specific situation, your account balances, your beneficiaries’ circumstances, and your overall goals. But it’s critical to understand that what made sense before the SECURE Act may no longer apply. Tennessee residents moving from other states should have their beneficiary designations reviewed in light of these rule changes.

Blended Families and Second Marriages in Tennessee

Tennessee sees many retirees in second marriages or with children from previous relationships. These blended family situations require careful estate planning to protect everyone’s interests and prevent future conflict.

The challenge is balancing two important goals: taking care of your current spouse while ensuring your children from your first marriage eventually inherit. A simple will that leaves everything to your spouse creates significant risks. Your spouse could remarry after your death, and your assets could end up going to their new spouse and eventually to that person’s family. Or your surviving spouse might simply decide that since the assets are now theirs, they want to leave everything to their own children from their previous marriage. Without proper planning, your children could end up with nothing.

QTIP Trust

Tennessee trust law offers solutions through specialized trusts designed specifically for blended family situations. The most common is a QTIP trust (Qualified Terminable Interest Property trust). With a QTIP trust, when you pass away, your assets go into a trust that provides income for your spouse during their lifetime. The trust can also make distributions for your spouse’s health, education, maintenance, and support—everything needed to ensure they’re comfortable.

But your spouse doesn’t own the assets outright. They can’t change the beneficiaries. When your spouse eventually passes away, the remaining trust assets go to your children from your first marriage. This structure protects both your spouse and your children.

These arrangements require honest, sometimes uncomfortable conversations. You’re essentially telling your current spouse that you want to make sure your kids from your previous marriage inherit eventually. Some spouses understand and appreciate the clarity. Others might feel hurt or insulted. An experienced Tennessee estate planning attorney can facilitate these discussions and help you find solutions that work for everyone.

Other Complex Situations

Beyond blended families, many Tennessee retirees face another complex situation: adult children with different levels of responsibility or different life circumstances. Maybe you have three children, and two are financially responsible while one struggles with addiction, gambling problems, or simply isn’t good with money.

Tennessee trust law allows you to structure your estate plan so that responsible children inherit their shares outright while the share for the child with challenges remains in trust. A trustee manages that trust share, providing for the child’s health, education, maintenance, and support without giving them direct access to large sums of money that might contribute to their problems.

You can even build incentives into Tennessee trusts. For a child struggling with addiction, the trust could specify that they need to complete treatment, maintain sobriety for a certain period (verified through drug testing), attend a certain number of recovery meetings, or meet other milestones before receiving distributions. The goal isn’t punishment—it’s protection and encouragement for positive change.

The question often comes up: who should serve as trustee for a sibling’s share? This requires careful thought. Naming one sibling as trustee over another sibling’s inheritance can create family tension. One option is to use a corporate trustee—a bank or trust company that serves as a neutral third party. Corporate trustees are experienced, professional, and won’t be swayed by family dynamics. The drawback is the cost and the fact that they don’t know your family personally.

Another option is to name a family member as co-trustee alongside a corporate trustee. This creates a “good cop, bad cop” dynamic in which the family member remains involved in decisions but has the corporate trustee to help enforce boundaries and make difficult calls when needed.

Estate Planning for Single Individuals Retiring to Tennessee

Single people sometimes think estate planning isn’t as important for them. But for single individuals retiring to Tennessee, estate planning is absolutely critical—perhaps even more so than for married couples.

If you don’t have a Tennessee will or trust, Tennessee’s intestacy laws will determine who inherits your assets. These laws try to approximate what a typical person would want, but they often miss the mark for single individuals.

Under Tennessee law, if you’re single with no children and no will, your assets typically go to your parents if they’re living. If your parents have passed away, assets go to your siblings. If you don’t have siblings, it goes to more distant relatives. But what if you’re estranged from your family? What if you’d rather leave your assets to close friends, a long-term partner you’re not married to, or charitable causes you care about? Without proper estate planning documents, your wishes don’t matter—Tennessee’s default plan takes over.

Incapacity Planning

Incapacity planning becomes even more critical for single Tennessee residents. If you’re married, your spouse can often make decisions for you if you become incapacitated (though having formal documents is still important). If you’re single, there’s no automatic decision-maker. Without a financial power of attorney and healthcare power of attorney, your family or friends would have to petition a Tennessee court to start a conservatorship proceeding. They’d have to prove your incapacity in court, which is expensive, time-consuming, and stressful.

Think carefully about who you’d want making decisions for you in Tennessee.

  • A sibling who still lives in your previous state
  • Maybe a close friend here in Tennessee
  • An adult child from a previous relationship

Whoever it is, you need to formally name them in your Tennessee incapacity planning documents. Don’t assume the court will choose the person you would have chosen.

Single individuals also need to think about who will handle their affairs after they pass away. Who will be the executor of your Tennessee will or the successor trustee of your Tennessee trust? This person will need to:

  • Gather your assets
  • Pay your debts and Tennessee taxes (if any)
  • File your final tax returns
  • Distribute your estate according to your wishes

Choose someone organized, responsible, and willing to take on this role. And make sure you have successor options in case your first choice is unable or unwilling to serve.

Tennessee Estate and Inheritance Taxes: The Good News

Here’s one piece of genuinely good news for retirees moving to Tennessee: the state has no estate tax and no inheritance tax. Tennessee eliminated its estate tax in 2016 and had already eliminated its inheritance tax previously.

This makes Tennessee particularly attractive for retirees with significant assets. States like New York, Massachusetts, and several others have state estate taxes with exemption amounts much lower than the federal exemption. If you were planning your estate in one of those states, you might have been implementing sophisticated strategies to minimize state estate tax.

In Tennessee, you don’t have to worry about that. The only estate tax consideration for Tennessee residents is the federal estate tax, and the current federal exemption in 2026 is $15 million per individual ($30 million for a married couple). For most people, federal estate tax isn’t a concern.

That said, these rules are always subject to change.  If you have significant assets that might approach these thresholds, you should be working with an estate planning attorney who stays current on tax law changes and can implement appropriate strategies if needed.

For most Tennessee retirees, though, the lack of state-level estate and inheritance taxes is simply a welcome benefit that makes estate planning more straightforward.

The Tennessee Difference: What You Need to Update Now

If you’re retiring to Tennessee from another state, here’s your action checklist for estate planning documents that need immediate attention:

  1. Advance Care Directive (Healthcare Planning)
    This is Tennessee’s specific document that combines a healthcare power of attorney and a living will. Even if you have similar documents from your previous state, having a Tennessee advanced care directive ensures Tennessee hospitals and medical providers will immediately recognize and honor it.
  2. Financial Power of Attorney
    Get a Tennessee financial power of attorney that follows Tennessee law and meets Tennessee execution requirements. This prevents problems when your designated person tries to use it at Tennessee banks and financial institutions.
  3. Will or Trust
    If you own Tennessee real estate, you need Tennessee-specific estate planning, likely including a trust, since Tennessee doesn’t offer transfer-on-death deeds. Your out-of-state will might still be valid, but having Tennessee documents prepared by a Tennessee attorney ensures compliance with Tennessee law and smooth administration in Tennessee probate courts if needed.
  4. Trust Funding
    If you have a trust from another state, work with a Tennessee attorney to ensure it’s properly funded with your Tennessee assets. This includes deeding Tennessee real estate into the trust and retitling Tennessee bank and investment accounts.
  5. Beneficiary Designations
    Review all beneficiary designations on retirement accounts, life insurance policies, and other accounts. While these don’t need to be “Tennessee-specific,” moving to a new state is a perfect trigger to review and update them. Make sure they align with your current wishes and your overall estate plan.
  6. Digital Asset Planning
    While not Tennessee-specific, make sure your estate plan addresses digital assets, including cryptocurrency, online accounts, and password-protected information. Provide clear instructions about what you want to happen to these assets and ensure your loved ones can access important accounts.

Finding the Right Tennessee Estate Planning Attorney

Not all estate planning attorneys are created equal, and finding the right one makes a significant difference in the quality of your plan and the experience of creating it.

What to Look For

For Tennessee retirees, especially those new to the state, look for an attorney who:

  1. Focuses exclusively on estate planning. Estate planning is complex and constantly evolving. An attorney who dedicates their practice to estate planning stays current on law changes, understands planning nuances, and has deep experience with the issues you’re facing.
  2. Understands Tennessee-specific rules and procedures. Estate planning is highly state-specific. You need an attorney licensed in Tennessee who knows Tennessee probate procedures, Tennessee trust law, Tennessee execution requirements for documents, and how local institutions handle these documents.
  3. Offers both in-person and virtual options. Technology makes estate planning more convenient, but certain steps must be completed in person in Tennessee. Look for an attorney who offers flexibility. Initial consultations and planning discussions can often take place via Zoom, but document signing must be done in person with proper witnesses and notarization.
  4. Has a financial planning background or works closely with financial advisors. Estate planning intersects heavily with financial, tax, and retirement planning. An attorney who understands these connections—or who actively coordinates with your financial advisor—can create a more comprehensive and effective plan.
  5. Takes time to understand your unique situation. Cookie-cutter estate plans created from templates don’t work for most people. Your family situation, assets, goals, and concerns are unique. You need an attorney who asks the right questions, listens to your answers, and creates customized solutions.
  6. Communicates clearly. Estate planning involves legal terminology and complex concepts, but a good attorney can explain things in plain English. You should feel like you understand your documents and the decisions you’re making.

A Note on Online Estate Planning Templates

Online estate planning templates are tempting because they’re cheaper and more convenient. Estate planning is one area where trying to save money up front often ends up costing your family much more in the long run. Tennessee has specific requirements for valid documents. It has unique rules about probate, trust administration, and powers of attorney. An online template created for general use across all states won’t address Tennessee-specific considerations and might not hold up when your family actually needs to use it.

The cost of working with a Tennessee estate planning attorney is an investment in protecting your family and ensuring your wishes are followed. When you consider the potential costs of Tennessee probate, family conflict, or documents that don’t work as intended, professional guidance is worth every penny.

Taking Action: Your Tennessee Estate Planning Next Steps

If you’ve recently moved to Tennessee or you’re planning to retire here, don’t wait to address your estate planning. Here’s what to do right now:

Review Your Current Estate Planning Documents

Read through them. When were they created? What state were you living in? Who did you name in various roles? Are those people still the right choices? Do the documents still reflect your wishes?

Schedule a Review with a Tennessee Estate Planning Attorney

Even if you think your documents are fine, have them reviewed by someone licensed in Tennessee who can identify potential issues and ensure they’ll work smoothly in Tennessee courts and financial institutions.

Review Your Beneficiary Designations

Pull statements for every retirement account, life insurance policy, annuity, and other account with beneficiary options. Check who you’ve named as primary and contingent beneficiaries. Update anything that’s no longer correct.

Verify How Your Tennessee Real Estate Is Titled

Is it in your individual name? Your trust’s name? Jointly with your spouse? Understanding the current title is the first step toward ensuring it’s titled correctly for your goals.

Have the Difficult Conversations

Talk with the people you’ve named as executors, trustees, and powers of attorney. Make sure they’re willing to serve in these roles. Tell them where your important documents are located. Give them your attorney’s contact information.

Create a Comprehensive Asset List

Document all your accounts, insurance policies, real estate, business interests, and other assets. Include account numbers, institutions, and approximate values. Make sure this list includes online accounts and digital assets. Store it securely, but ensure your trusted people know where to find it.

Consider Your Family Dynamics

If you have a blended family, adult children with different circumstances, or other complex situations, don’t try to handle it with simple online forms. Work with an attorney who can create customized solutions.

Plan for Ongoing Review

Put a reminder in your calendar to review your estate plan every three years. Also plan to review whenever you have a major life change—marriage, divorce, birth or adoption of children, death of someone named in your plan, significant change in assets, or health changes.

Estate planning isn’t just about documents—it’s about protecting the people you love and ensuring your wishes are honored. Moving to Tennessee gives you a fresh start and an opportunity to make sure everything is in order. Take advantage of that opportunity.

Legacy is more than what you leave behind. It’s also how you leave it. Taking the time to create a proper Tennessee estate plan, keeping it updated, and making sure it’s properly executed and funded is one of the most important things you can do for your family.

At Imagine Financial Security, we help individuals over 50 with at least $1 million saved navigate these complex retirement decisions. If you are looking to

  • Maximize your retirement spending
  • Minimize your lifetime tax bill
  • Worry less about money

You can start by taking our Retirement Readiness Questionnaire on our website at www.imaginefinancialsecurity.com, so we can learn more about how we can help you on your journey to and through retirement.

Not quite ready to take the questionnaire, but want helpful tips and resources? Sign up for our monthly newsletter and/or subscribe to our YouTube channel.

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep.135: Retirement Tax Planning Should Start Now! Tax Planning vs. Tax Preparation in 2026

Most people think about taxes once a year, when it’s time to file their return. But tax preparation and tax planning are two very different things. Tax preparation looks backward. Tax planning looks forward. And when you’re approaching retirement, that distinction can have a major impact on how much of your money you actually get to keep.

In this episode, I share a story from earlier in my career that changed the way I thought about taxes and financial advice. Then I’ll breaks down some of the biggest tax-planning opportunities retirees and those approaching retirement should be thinking about throughout the year, not just during tax season.

We’ll discuss capital gain and tax-loss harvesting, Social Security taxation, ACA premium tax credits, Medicare IRMAA surcharges, charitable giving strategies, qualified charitable distributions, Roth conversions, inherited IRAs, and more.

More importantly, we’ll look at how all of these decisions interact.

Because good retirement tax planning isn’t simply about paying the least amount of tax this year. It’s about making intentional decisions today that could help you better manage your lifetime tax bill.

If you’re approaching retirement with significant savings and wondering whether you’re being proactive enough about taxes, this episode will give you a framework for what to be thinking about before year-end.

⁠⁠ -Kevin

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Retirement Planning Beyond Finances: Finding Purpose in Your Third Act

Most people don’t struggle in retirement because they didn’t save enough money. They struggle because retirement isn’t just a financial transition. It’s an identity transition. After decades of defining yourself by what you do, suddenly that answer disappears. You’ve planned for the numbers, but have you planned for who you’ll become?

The baby boomer generation is set to be the longest-living generation in history. Your third act (those 25 to 30 years after your traditional career ends) could span longer than many people’s entire careers. That’s not time to wind down. That’s time to decide what you want to be remembered for. But getting there requires more than a solid investment portfolio.

The Retirement Identity Crisis: When ‘What Do You Do?’ No Longer Fits

Picture yourself on an airplane. A friendly stranger strikes up a conversation and asks that quintessentially American question: “So, what do you do?”

If you’re recently retired, you might freeze. What do you do? After a long, uncomfortable pause, you might blurt out: “I’m retired.” It sounds like an achievement, maybe even a rite of passage. But the moment the words leave your mouth, something feels off. What does that even say about you? The only thing it communicates is that you don’t do something anymore. It’s a negative definition—an absence rather than a presence.

This is the retirement identity crisis, and it catches high achievers especially off guard. For decades, our roles and titles define us. I’m a financial planner, manager, teacher, engineer, etc. Those are what we do, not who we are. Who are you? That’s a much bigger, much harder question.

When Sandy Vecchi faced this exact moment on a flight to visit her daughter, the experience shook her. After three decades in financial services helping others prepare for retirement, she’d done everything “right” herself. She’d built savings, created a plan, even retired and moved to a beautiful property with her husband. But when a stranger asked what she did, she had no answer that felt authentic.

The emotional aspects of retirement often center on this identity shift. When you wake up in the morning, there’s no clear purpose pulling you out of bed. The structure that organized your life for 30 or 40 years is gone. Most people’s connections come from colleagues at work. Suddenly, those are missing too.

Research shows that humans are wired to need structure, connection, and challenge. Remove all three at once, and psychological well-being suffers. Often, physical well-being follows. Many retirees gain significant weight in their first two years. It’s not about the food; something deeper is missing.

The Retirement Honeymoon Phase: When Paradise Isn’t Enough

At first, retirement feels like everything it’s supposed to be.

  • You turn off the alarm clocks.
  • You sit on the porch with your morning coffee.
  • You read all those books on your “when I retire” list.
  • You travel.
  • You play golf.
  • You finally have time for hobbies you’ve put off for decades.

The retirement honeymoon phase is real, and it’s wonderful. You’ve earned this freedom. Every day feels like a gift. But here’s what financial planners rarely tell you: the honeymoon phase doesn’t last forever. For most people, it lasts about two years.

Then the cracks start showing. That complete lack of structure, which seemed so appealing at first, starts feeling directionless. The travel that was exciting begins to feel empty. You think, “We’re going on another trip?” and realize something’s missing. The endless leisure that looked perfect in the planning stages doesn’t fill the space left by decades of purpose-driven work.

When Sandy built a brand new home on 20-plus acres, bought chickens, and watched her husband get his Kubota tractor, it felt like paradise. They traveled. They enjoyed life. It was exactly what retirement brochures promise. About two years in, though, she started asking bigger questions: If I live to 100, what will I do with all those years? It definitely wasn’t going to be sitting on the porch doom-scrolling through Facebook.

Understanding retirement transition challenges means recognizing that the honeymoon phase is normal, and so is what comes after. The key is planning for both.

The Wake-Up Call: Mortality and Meaning

Sometimes it takes a crisis to clarify what matters. When Sandy’s husband received a devastating cancer diagnosis—a rare mutated form of the leukemia he’d already survived in his twenties—everything changed. They sold their forever home almost immediately. They moved into a small apartment near the hospital where he’d receive treatment. His only hope was a bone marrow transplant.

Sitting in hospital waiting rooms for months, watching a vibrant man fight for his life, forced a reckoning: If he’s fighting so hard to live, why am I not fully living mine?

You might not face something this dramatic. But at some point in your third act, mortality becomes real in a way it never was during your working years. Maybe it’s a health scare for you or someone close to you, or you find yourself attending too many funerals. Maybe it’s just looking in the mirror and realizing you have more years behind you than ahead of you.

That awareness can be terrifying or clarifying. Ideally, it’s both. It forces you to ask:

  1. What do I want to do with the time I have?
  2. What have I always wanted to do but put on hold?
  3. Who have I always wanted to become?

Beginning With the End in Mind

Stephen Covey’s principle of “beginning with the end in mind” becomes especially powerful in the third act. If you were on your deathbed, what would you hope people say about you? Nobody’s going to say they wish you’d worked more or had more screen time.

Here’s the harder question: What regrets do you have? Those things you kept saying would happen “someday.” You told yourself, “I’m too old,” or “I’m not good enough.” Those are the ones that haunt people.

Bronnie Ware wrote a book on the top five regrets of the dying. The number one regret?

People didn’t do what they wanted to do. They spent their lives doing what everyone else wanted them to do.

You can eventually make peace with your mistakes. You can learn from them, grow from them, and forgive yourself for them. Sidney J. Harris, an American journalist, put it perfectly:

“Regret for the things that we did can be tempered with time. Regret for the things we didn’t do is inconsolable.”

In your first two acts of life (childhood and career), you’re heavily influenced by parents, society, and expectations. You had to be practical because you had bills to pay, responsibilities to manage, and mouths to feed. There’s a little part of you that’s always been back there hanging on, asking: “Are you ever gonna give me a chance?”

The third act is when you finally can.

Purpose After Career Ends: More Than a Job

The word “purpose” gets thrown around a lot. It can feel cliché. But finding purpose in retirement is something you know in your heart you were meant to do with the talents you were given.

Purpose is bigger than a job. As Cicero said, as you get older, your goal is to mentor, to teach. Og Mandino, in “The Greatest Salesman in the World,” asks: What are you going to do that leaves traces on the world?

It doesn’t have to be grandiose, like your name on a building. More important is this: Did you touch anybody and change something for them? Maya Angelou said, “People won’t remember what you said or what you did, but they’ll remember how you made them feel.” That’s a legacy in itself.

Purpose in retirement might look like:

  • Starting a business you’ve always dreamed about
  • Volunteering at the library reading to kids
  • Mentoring young people in your former industry
  • Finally writing that book
  • Learning that instrument you put aside at age 12
  • Teaching classes in your area of expertise

The key is that it challenges you mentally and physically. Research consistently shows that you need to find something to challenge both, or you’ll decline rapidly. Our ancestors retired at 65 and passed away at 68. We’re not doing that anymore. We get a lot more years if we keep ourselves engaged.

When Sandy realized that little girl who used to twirl in the backyard pretending to be Maria von Trapp had disappeared when her parents divorced, she understood something powerful. That girl had dreams: unrealistic, creative, joyful dreams. But watching her mother struggle financially after divorce taught her that dreaming wasn’t safe. Security was everything.

Sandy spent decades building security by:

  • Getting an MBA (when very few women did)
  • Building a successful career
  • Helping countless clients prepare financially for retirement

She did everything “right.” But in doing so, she’d buried that dreaming girl completely.

The third act? That’s when the little girl gets to twirl again.

Practical Steps for Post-Retirement Life Planning

Understanding all this intellectually is one thing. Actually planning for it is another. Here’s how to approach retirement planning beyond finances:

Take a Sabbatical First

There’s nothing wrong with traditional retirement. You worked hard to get there. Take time to enjoy life, do some traveling, sleep in, play golf. Give yourself permission to have that honeymoon phase.

When you start thinking, “We’re going on another trip?” or the leisure starts feeling empty, that’s when you know it’s time to look at the bigger picture. For most people, this happens around the two-year mark. Don’t fight it. That restlessness is a signal, not a problem.

Get in the Best Shape of Your Life

Nothing else matters if you’re not healthy. You can have millions in the bank, but you can’t buy health. Physical wellness is the foundation for everything else in your third act.

Many retirees gain significant weight in their first couple of years. The lack of structure, the social eating while traveling, and the loss of purpose all contribute. Making physical health a priority isn’t vanity. It’s about giving yourself the energy and longevity to actually live your third act.

If you’re planning on centenarian status (and research suggests many baby boomers will reach it), you need to start treating your body like it needs to last that long. Start walking. Join a gym. Find physical activities you genuinely enjoy, whether that’s fly fishing in Montana or dancing or hiking.

Read Intentionally

Read books that challenge you to think about who you want to become. Not business books about maximizing productivity. Books about life, purpose, legacy, and growth.

Suggested reading includes:

  • “Who Do I Want to Be When I Grow Old?” by Leider
  • “From Strength to Strength” by Arthur C. Brooks (especially for high achievers)
  • Stephen Covey’s work (it’s much more than business advice—it’s life advice)

Reading isn’t just entertainment in the third act. It’s how you expose yourself to new ideas and reimagine what’s possible.

Make Actual Plans

Don’t just think about what you want to do. Put it on your calendar. If you don’t, it turns into “someday,” which vanishes into the sky.

  • Want to start a new business? Write a business plan with definitive deadlines.
  • Want to volunteer? Schedule the first day.
  • Want to learn something new? Register for the class.
  • Want to write a book? Block out writing time starting next week.

Your third act needs some structure. Not the rigid structure of your working years, but intentional structure. Even in retirement, having plans and dates keeps you moving forward.

Act (This Is the Hardest Part)

Acting is where most people get stuck. The first action is scary. Your first day volunteering. That first business meeting. Starting a class where you’re a beginner at age 65. We tend to think about it, get nervous, and say, “Okay, forget that, I’ll do it someday.”

Often, someday never comes.

The things you want to do in your third act will probably be awkward and embarrassing and not really good the first time around. That’s okay. If you’re not growing, you’re dying. That doesn’t stop being true just because you’ve retired. In fact, it becomes more important.

Focus on Quality Over Quantity

People need less quantity and more quality in their retirement years. It’s not about filling every day with activities. The goal is to fill your days with meaning.

The happiest retirees aren’t trying to stay busy for the sake of staying busy. They’re living intentionally, knowing what they want to do with their lives. If they were taken tomorrow, they’d know they were doing what mattered.

This might mean saying no to things that don’t align with your purpose. It might mean disappointing people who expect you to be available for every request now that you’re retired. It might mean setting boundaries that feel uncomfortable at first.

But living intentionally means making choices, not just going along with whatever comes your way.

Legacy Is More Than What You Leave—It’s How You Live

Yes, work with your estate planning attorney to set up trusts, update your will, and think about what you’ll leave your children financially. That’s important. Many people believe in gifting children while they’re alive so they can watch them enjoy it.

But the legacy you truly want to leave is for your children and loved ones to say: “They were incredible. They stepped out of their comfort zone to take chances on things that were awkward and embarrassing and probably not really good the first time around. They lived fully.”

When you’re on your deathbed, what will bring you peace isn’t the size of your estate. It’s knowing you touched people and changed something for them. You mentored, taught something valuable, and left traces on the world even if that world was just your community, family, or neighborhood.

It’s knowing you gave the dreamer in you a chance.

It’s Not Too Late (Even If You’re Already Retired)

Maybe you’re reading this and thinking: I’m already five years into retirement. I missed my chance. I should have thought about this before.

You haven’t missed anything. Sandy “unretired” after already being retired. She started a podcast, a blog, speaking engagements—all in her mid-60s. She’s learning new technology, putting herself out there in ways that would have terrified her younger self.

Her husband survived his bone marrow transplant. They went fly fishing in Montana, something they weren’t sure they’d ever do. He’s planning a halibut fishing trip to Alaska. They both realized they have more years behind them than in front of them. That clarity is a gift, not a curse.

Their kids are raised and doing well. Nobody’s living with them. This is the time to be selfish. For women especially, that permission is crucial. It’s okay to put yourself first and ask: What’s been on my list that I put on the back burner because I had to be an adult with responsibilities?

The Question That Changes Everything

There’s one question that cuts through all the planning and philosophy:

If you’re fortunate enough and healthy enough to live another 25 or 30 years, what do you plan on doing with all that time?

Really sit with that question. Not what will you do next month or next year? What will you do with potentially three decades?

The answer probably shouldn’t be “travel and play golf.” Those can be part of it. But for 30 years? That’s why so many retirees struggle after the honeymoon phase ends. They planned for leisure, not for purpose.

Take quiet time, not time filled with TV or social media, and look at yourself.

  1. What do you still want from your life?
  2. What do you want to do?
  3. How do you see yourself separate from all the roles and titles you’ve held?
  4. Who, or what, do you want to be?

These aren’t easy questions. They require sitting with discomfort and being honest about dreams you buried decades ago. They require admitting that maybe the life you planned isn’t the life that will actually fulfill you.

These are the questions that transform retirement from an ending into a beginning.

Your Third Act Starts Now

You don’t have to be retired to think about this. In fact, if you’re in your fifties and still working, now is the perfect time to start planning. Not just planning your finances (though that’s important), but planning who you want to become.

Look at your life and ask: Is there something I still want to do? Take that quiet time. Make those plans. Put dates on your calendar. Most importantly, start acting on them.

Will you

  • Retire early and take a sabbatical?
  • Never fully retire, but shift to consulting?
  • Work part-time doing something completely different?
  • Volunteer more?
  • Learn something new?

The third act doesn’t have a script. That’s the whole point.

Your third act does require intention. Challenging yourself, mentally and physically, is part of the deal. So is connection, structure, and purpose. You have to be willing to try things that might not work, to be embarrassed, to be a beginner again.

And that version of yourself who used to dream—before life taught you to be practical—finally gets to have a voice.

Because regret for the things you didn’t do? That’s inconsolable.

But regret for the things you’re about to do? That’s not regret at all. That’s living.

Retirement planning beyond finances means preparing for the identity transition, not just the financial one. Your third act could span 25-30 years, which is longer than many careers. The question isn’t whether you have time. The question is: What will you do with the time you have?

How We Help

At Imagine Financial Security, we help individuals over 50 who have at least $1 million saved navigate these complex retirement decisions. If you are looking to

  • Maximize your retirement spending
  • Minimize your lifetime tax bill
  • Worry less about money and live more

You can start by taking our Retirement Readiness Questionnaire on our website at www.imaginefinancialsecurity.com, so we can learn more about how we can help you on your journey to and through retirement.

Not quite ready to take the questionnaire, but want helpful tips and resources? Sign up for our monthly newsletter and/or subscribe to our YouTube channel.

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 134: What Every Retiree Needs To Know About Wills, Trusts, Probate, and Overall Estate Planning, As You Transition To Retirement (w/ Ryan Smith)

Thousands of retirees relocate every year looking for lower taxes, a lower cost of living, better weather, or to be closer to family.

In this episode, I’m sitting down with estate planning attorney and financial advisor Ryan Smith to discuss the estate planning issues that many retirees overlook after relocating. From wills and trusts to powers of attorney, healthcare directives, probate laws, and beneficiary designations, we’ll explain what should be reviewed when you establish residency in a new state.

While this conversation focuses on retirees relocating during retirement, the same planning considerations will apply to just about any retiree.

In this episode, you’ll learn:

  • Why moving to another state can impact your estate plan
  • Which legal documents should be reviewed after relocating
  • Tennessee-specific estate planning considerations
  • Common mistakes retirees make when changing residency
  • Practical steps to protect your family and your legacy
  • Making life easier for your fiduciary relationships and beneficiaries

Whether you’re moving for family, lower taxes, or a better retirement lifestyle, this episode will help you avoid costly planning mistakes before they’re discovered when it’s too late.

Connect with Ryan Smith here:

Next Frontier Estate Planning

👍 If you found this helpful: Hit Like, subscribe, and I’ll see you next week with more retirement planning content designed for people over 50 who want to make work optional.

~ Kevin

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 133: Will Social Security Benefits Get Cut By 22%? Or Will “The PROMISE Act” Save The Social Security Shortfall?

Will Social Security really be cut by more than 20%?Should you claim early before the rules change? Or is the media exaggerating what’s actually happening?

In this episode, I will break down the latest Social Security Trustees Report, explain what the 2032 Trust Fund projection actually means, and discuss the newly introduced PROMISE Act designed to begin addressing the program’s long-term funding shortfall.

You’ll learn:

  • What the Social Security Trust Fund actually is
  • Why the Trust Fund is projected to be depleted around 2032
  • Why Social Security isn’t expected to “go bankrupt”
  • Whether claiming benefits early is a smart strategy
  • How a potential 22% benefit reduction could affect a retirement plan
  • What the new PROMISE Act does (and doesn’t do)
  • The most likely changes Congress could make to strengthen Social Security
  • Practical planning steps you can take today without overreacting to the headlines

If you’re approaching retirement or already retired, this episode will help you separate fact from fear and make more informed decisions about one of the most important income sources in your retirement plan.

~ Kevin

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

 

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Retirement Planning for Singles

I was recently reviewing retirement plans for two long-term clients with remarkably similar situations. Both had saved a little more than $3 million and paid off their homes. Both delayed Social Security until 70. They had a lot going for them. But their retirement strategies looked completely different. Why? One client was married, the other was single.

That realization hit me hard. So much retirement content out there—ours included—focuses on married couples, joint life expectancies, and strategies built for two. But millions of retirees aren’t married. They’re divorced, widowed, or maybe they were never married in the first place. When it comes to retirement planning for singles, the strategy looks completely different than planning for married couples.

Let’s talk about what changes when you are single and planning for retirement.

Retirement Planning for One

Obviously, when retiring alone, you’re only planning for one life expectancy. According to IRS life expectancy tables, if you’ve reached age 60, your remaining life expectancy as a male is about 20 years. As a female, it’s about 23 years and some change.

For married couples, this can be complex, especially if one spouse is healthy with great genes and longevity on their side, while the other faces more uncertainty. You need to figure out different strategies, such as Social Security benefits and survivor benefit planning. The reality of retiring alone means you have complete control over your retirement vision and spending, which makes this equation simpler to address.

How Much Money Does a Single Person Need to Retire?

If longevity is stacked in your favor, it’s probably beneficial to delay your Social Security benefit until 70. Married couples have the option of delaying the larger of the two benefits while starting the smaller benefit earlier. When you’re single, you don’t have to compromise on your retirement lifestyle choices, but you must have adequate savings during that bridge period—the time from your retirement start date until you begin taking Social Security.

If you retire at 60, that bridge period could potentially be 10 years. A lot can happen in 10 years to your health, the markets, and ultimately your portfolio. How much money a single person needs to retire depends heavily on their Social Security claiming strategy. While retirement planning for singles simplifies life expectancy to some extent, it makes the Social Security timing decision extremely important. If you run into a bear market during that bridge period, it can be quite damaging, so you must have a bear market withdrawal strategy to hedge against that risk.   

Tax Planning Becomes More Complex

This is a big one. Tax brackets work differently in retirement for singles compared to married couples filing jointly. Singles cannot spread their taxable income across a joint return. Couples can—their brackets are basically doubled throughout all tax brackets until you hit that 37% top bracket.

Roth Conversion Opportunities

The Roth conversion window becomes smaller when you’re single. If you’re trying to fill up the 22% bracket, you have a lot less room to do so than if you were filing a joint return. You also need to be careful about IRMAA thresholds if you’re on Medicare.  These surcharges are hidden taxes on your Medicare Part B and Part D. If you’re doing Roth conversions, not only do you have less room in the income tax brackets, but you also have less room for error with those IRMAA thresholds.

The RMD Tax Trap

Once required minimum distributions kick in, they dramatically impact the single tax filer more than the joint filer. Let’s use that example I mentioned earlier: Client A, a joint filer with $3 million saved, versus Client B, a single filer also with $3 million saved. When those required minimum distributions kick in, they’re going to have a much bigger tax impact on the single filer.

Projecting out your lifetime tax bracket over time becomes critical because the tax trap of those required minimum distributions is more severe for single filers than married filers.

Investment Strategy

Here’s something I don’t see talked about enough: the investment strategy changes substantially when retirement planning for singles versus joint retirees. I have several couples I work with where one spouse has an aggressive risk tolerance, and the other has a very conservative risk tolerance. They sort of balance each other out.  One advantage from an investment perspective for singles is the simplified decision-making process.

On the surface, that can mean a more straightforward investment strategy in retirement. But I’ve noticed something interesting: during downturns, I hear from some of those single clients a little more. Maybe that’s just my imagination, but I think behavioral finance becomes much more important.

I was referred to a client about three years ago. She had been widowed for eight years and had been working with Fidelity.  She told me when I first met with her that she was checking her accounts every single day. Yes, every single day. It was giving her extreme anxiety, especially when markets were volatile back in 2022. She didn’t have that trusted partner to ride those ups and downs with. She was kind of panicking alone, and sometimes that can lead to bad investment decisions when you’re reacting emotionally to market volatility, especially when you’re retired. What you have is what you have; you’re not adding more to the portfolio.

I’m happy to report that I met with her a couple of months ago and she shared that she literally never checks her accounts anymore. That didn’t happen overnight. Early on when we were working together, she was still in that habit. But after thoughtful planning and strategic implementation, she gradually became more comfortable with the strategy and began worrying less about her portfolio each day. The investment strategy and planning around it become simpler because we aren’t battling different personalities, but the management can become more challenging when you’re in your own head with nobody to bounce ideas off of.

Housing Decisions: A Critical Component

On the surface, a single person may not need as much space. You could probably get away with a smaller single-family home or maybe even a condo. But the more challenging issue is aging in place. Should you move near family? Should you move near better healthcare? Statistics show that retirement planning for single women often accounts for longer life expectancies, making these decisions even more critical.

One solution that has been rapidly gaining popularity among retirees—and definitely within my client base—is moving into a CCRC, a continuing care retirement community. Think of a CCRC as buying into a retirement ecosystem instead of just buying a home. They typically have multiple stages of living:

  1. Independent living
  2. Assisted living
  3. Skilled nursing
  4. Memory care.

One of my clients who lives in Florida is in a very nice one in the Jacksonville area and absolutely loves it. All of her friends are there, her activities are there, her dining is there, her workout facilities are there, and even transportation to certain events is there. It’s basically maintenance-free living. After losing her husband more than a decade ago, she’s dating her neighbor two doors down. It’s hilarious and cute at the same time.

While there are many perks, the cost can be extremely high. Entrance fees can sometimes be $200,000, $500,000, or even a million dollars or more if they’re really upscale. Then you have monthly fees on top of that. Granted, a lot of your lifestyle will be covered by those monthly fees, but the upfront cost is massive. And unfortunately, your beneficiaries won’t receive that asset when you pass away like they would if you were to pass on a single-family home or a condo. 

Given their popularity, waiting lists can be long—sometimes five years or even 10 years. You need to decide on the right facility, get on the waitlist, and then make that financial commitment later.

Long-term Care Planning

Long-term care is a critical component for anyone’s retirement, but for singles it does create some complexity.  For starters, there is no spouse around to help with caregiving or coordinating caregiving as they age.  70% of caregiving today is provided by unpaid caregivers, most of whom are spouses. For singles:

  • Who will be the caregiver?
  • Who will be the caregiving coordinator?
  • Where would the funds come from to pay for that care?
  • Who is managing the financial affairs during all of this? 

One thing I hear time and time again from the folks I work with is that they do not want to be a burden on their family members. They don’t want to be a burden on their children or siblings. Maybe you don’t have that trusted family member who lives near you.  These long-term care planning decisions can be a bit more complicated, so make sure to speak with your advisor about your options and whether or not looking into Long-term Care Insurance might be a viable solution. 

Estate Planning

Singles face some built-in challenges in their estate planning.  There’s no automatic spousal direction where your spouse steps in to be your executor or manages the finances if you are unable to.

The question that a lot of single retirees I work with have difficulty answering is: Who will be that individual to step in on your behalf to make those financial decisions if you’re unable to? And furthermore, how familiar are those individuals with your plan?

If it’s a sibling or even an adult child, they may know they’re in charge of making those decisions, but they may not know your financial situation. They may not know your balance sheet. I work with an older client in her 80s who lost her husband about six years ago. She has tapped her two adult children into the planning process, and I work with them as much as I do with her directly.  This is how it should be done!

She wasn’t what I would call the CFO of the household. Her husband made a lot of those decisions on their behalf. She’s very fortunate to have her two daughters, who are both local, responsible, and involved in the process. Otherwise, this would be crippling for her. She would be so afraid of making the wrong decision. But some of you may not have that situation. Perhaps you don’t have children, or perhaps they’re not in a position to help due to proximity or fiscal responsibility.

Interestingly, this is a big reason single retirees and pre-retirees hire our firm. Having that trusted third party who knows your plan and can help your trusted contacts follow through on your wishes provides significant peace of mind. 

Lifestyle and Spending Patterns

There’s no research or data backing this—just my observation working with retirees over the last 18 years. Lifestyle changes are a bit more subtle for a single retiree than for a married couple. With married couples, I often see that as they age, travel slows down and going out to eat becomes less frequent. Life just becomes a little quieter.

But for a lot of the singles I work with, their spending is their community. It’s the golf league, the church trips, the travel groups, dinners out with friends. Those spending stages I often talk about—the go-go years, slow-go years, and no-go years—can be more subtle for single retirees versus married couples.

I’m sure many of you who are married and reading this are thinking, “We’re doing all those things too.” There’s no hard-and-fast rule on this one. But when you’re planning as a single, the lifestyle you want to build often becomes a core part of your social interactions. Keeping those in place as long as possible is important for your mental health.

The Good News About Retirement Planning for Singles

After reading this, you might think retirement seems more complicated if you’re single. I don’t actually think that’s true. There’s a simpler planning process in many ways.

  • One vision
  • One spending style
  • One retirement start date
  • One risk tolerance
  • One Social Security decision

Effective retirement planning for singles requires addressing unique challenges that married couples don’t face, but it also offers unique advantages.

At the end of the day, being single doesn’t mean retirement is better or worse. The strategy and the playbook simply change. Tax planning will be different. Your Social Security strategy will be different. Your housing decisions change. Long-term care planning becomes critical. Estate planning becomes more complicated. But with good, thoughtful planning, there’s no reason a single retiree cannot enjoy an incredible retirement.

In fact, some of the happiest retirees I’ve worked with are single because they’ve built retirement around the life they want, not the life someone else expected them to have. Many people worry about retiring alone, but with proper planning, it can lead to an incredibly fulfilling retirement.

Take Action Now

If this article made you pause and think about areas you haven’t thought through yet, I encourage you to start those conversations now. Whether it’s with your family members, an estate planning attorney, or a trusted financial planner, don’t wait until a health event or life change forces you into those conversations. Have them proactively, not reactively.

If you are approaching or already in retirement and don’t have a trusted partner, consider working with a financial planner who understands the unique challenges and opportunities of retirement planning for singles.

At Imagine Financial Security, we help individuals over 50 with at least $1 million saved navigate these complex retirement decisions. If you are looking to

  • Maximize your retirement spending
  • Minimize your lifetime tax bill
  • Worry less about money

You can start by taking our Retirement Readiness Questionnaire on our website at www.imaginefinancialsecurity.com, so we can learn more about how we can help you on your journey to and through retirement.

Not quite ready to take the questionnaire, but want helpful tips and resources? Sign up for our monthly newsletter and/or subscribe to our YouTube channel.

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 132: Unretired and Making the Most of Your “Third Act” (w/ Sandy Vecchi)

Planning for retirement isn’t just about building an investment portfolio. For many people, the hardest part of retirement is feeling that loss of identity their careers provided.

I’m very excited to have Sandy Vecchi on for this episode to discuss one of the most overlooked aspects of retirement planning: purpose, identity, and building a meaningful “third act.”

After spending decades in financial services, Sandy discovered that many retirees struggle not because they risk running out of money, but because they lose the structure, relationships, and identity that work once provided. Following a deeply personal family health crisis in her retirement, she completely redefined what retirement could look like and now helps others do the same.

In this episode you’ll learn:

• Why retirement is an identity transition, not just a financial one
• The “honeymoon phase” many retirees experience
• How to discover purpose after leaving your career
• Why financial independence creates freedom, but not fulfillment
• The biggest regrets people have later in life
• Practical ways to prepare emotionally before retirement
• How to build a meaningful legacy beyond money

If you’re within a few years of retirement, or have already retired, this conversation may change how you think about your next chapter.

If you enjoyed this episode, please like, subscribe, and share it with someone preparing for retirement.

~Kevin

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

📌 Connect with Sandy Vecchi:

Website:  https://www.sandyvecchi.com

YouTube:  https://www.youtube.com/@sandyvecchi9814

LinkedIn:  https://www.linkedin.com/in/sandy-vecchi-mba-a2a528378/

Instagram:  https://www.instagram.com/sandyvecchispeaking

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 131: Why I’m Telling This 59-Year-Old to Stop Saving for Retirement (Case Study)

What if the smartest retirement move isn’t retiring at all? In this episode, I walk through a case study of a 59-year-old professional with more than $3 million saved who could retire tomorrow, but isn’t sure he should. Instead of asking whether he can retire, we explore a different question: What if he simply stopped saving for retirement? By redirecting tens of thousands of dollars each year toward travel, family, hobbies, and experiences while continuing to work a few more years, he may actually improve both his financial confidence and his quality of life. In this episode we discuss:

• What “coasting to retirement” really means
• When saving more stops meaningfully improving your retirement
• How delaying retirement changes your odds of success
• How many high-income professionals oversave
• How to know if you’ve already “won the game”
• The emotional side of retirement planning

Every retirement plan is different, but if you’re approaching retirement with $1 million, $2 million, or more saved, this may be one of the most important mindset shifts you’ll ever hear.

⛳ PFR Nation (Who This Is For)If you’re over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the community!

-Kevin

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

7 Retirement Expenses That Consistently Catch Pre-Retirees by Surprise

When I launched Imagine Financial Security back in 2021, I thought I had everything figured out. I created detailed spreadsheets with revenue projections for years one, two, and three. I mapped out my expense projections carefully. But here’s what I discovered: the revenue I thought I needed to support my family was 50% lower than reality.

Part of that gap stemmed from inflation, which hit 9.1% in 2022. But a bigger part? My wife and I went from zero to three children in just 16 months (yes, twins surprised us with pregnancy number two). I’d never owned a business before. I’d never been a dad before. I didn’t know what I didn’t know.

You’re facing a similar challenge as you approach retirement. One of the biggest mistakes pre-retirees make is underestimating their retirement expenses. I’ve had people sit down with me and confidently say they need $8,000 a month to retire. Then we start talking about travel plans, golf trips, gifting to children and grandchildren, replacing vehicles, and home repairs. Suddenly, that $8,000 becomes $10,000, $11,000, or even $12,000 a month.

This doesn’t happen because people are lying or fudging their budget. It happens because they kind of forgot how life really works. Understanding your retirement expenses is critical to building a plan that actually works. If we’re off by $10,000, $15,000, or $20,000 annually, that could mean the difference between retiring at 55 versus waiting until 59 or 60.

Today, I’m sharing seven retirement expenses that consistently catch people by surprise. These aren’t theoretical concerns. These are real issues I’ve observed over 18 years of helping people plan for and execute successful retirements.

Why Estimating Retirement Expenses Is More Challenging Than You Think

Estimating retirement expenses requires thinking through scenarios you’ve never experienced yet. You’re trying to predict costs for a lifestyle you’ve never actually lived, potentially spanning 25, 30, or even 35 years. The challenge with estimating retirement expenses is that most people are overly optimistic. They envision the retirement they need rather than the retirement they really want.

If you’re married or have a partner, this gets even more complicated. You’re probably the chief financial officer of your household, but your spouse or partner probably isn’t. They may be more inclined to spend on things you’re not thinking about. Having open communication and honest dialogue about these expenses is critical.

A retirement plan is only as good as the inputs that go into it. If our investment return assumptions are wrong, that’s a problem. If inflation projections are off, that’s a problem. But as long as we’re directionally right on those factors and we get the budget assumptions right, we should be in good shape.

Nobody’s going to dial in every single expense 100% accurately—that’s impossible. But if we underestimate spending assumptions, that can dramatically impact your entire plan.

Expense #1: The Go-Go Years – When Living Expenses in Retirement Peak

I like to break retirement into three distinct phases.

  1. First, you have the go-go years—the honeymoon phase of retirement.
  2. Then come the slow-go years, when you start to slow down because physically you don’t have the health you had in your 50s and 60s.
  3. Finally, there are the no-go years later in life, when your family is probably visiting you rather than you visiting them.

Your living expenses in retirement will likely be higher in the early years than you expect. I recently had someone tell me, “Kevin, retirement is great, but every day is Saturday. The things I loved doing on Saturday when I was working, now I can do every single day.”

If I were retired today, I’d be playing golf, fishing, traveling, and going out to eat far more often than I do now. If you’re a golfer, you know exactly what I’m talking about. I’d be booking trips to Bandon Dunes, Royal Port Rush, Streamsong, and Pinehurst. I’d rather take those trips when I’m physically able to swing the club properly, not when I’m 75 or 80 and can barely hit the ball 200 yards.

Maybe you’re not a golfer. Maybe you’re thinking about bucket-list travel or cycling trips. Whatever your passion, you’re going to pursue it heavily during your go-go years because this is the honeymoon phase of your retirement.

Planning for the Go-Go Years

Here’s something important to remember: no one has a crystal ball. You can’t tell me exactly how long your go-go years will last. I once had a client who had big plans for retirement at 65. She passed away right before retirement at 64. That story always hits home for me because it reminds me that we never know what may happen. One diagnosis can change everything.

Even if you plan to work another three, four, or five years, nothing stops you from thinking about bucket-list trips today. Many of you listening have already saved seven figures or multiple seven figures for retirement. The impact of your additional savings contributions today isn’t as meaningful as contributions you made 25 or 30 years ago—that’s the compounding effect at work.

If you’re only working two or three more years and you’re maxing out 401(k)s and Roth accounts, you may actually be oversaving. You might be able to carve out $15,000 or $20,000 to take some of those bucket-list trips today instead of waiting. Because again, we never know what may happen.

People often assume retirement spending will match their pre-retirement spending. Not so fast. In the go-go years, I consistently see people spending more in that early phase because there’s pent-up demand. Think about the pandemic—everyone was stuck at home, and then when restrictions lifted, there was massive pent-up demand for travel and experiences. Early retirement works the same way. You’ve got all these things you want to do, and suddenly you have the time to check them off your list.

Expense #2: Home Repairs and Renovations You’ll Actually Want

We need to build home repairs into the budget. I’ve seen rules of thumb suggesting you budget 1% of your home value annually. That’s a good starting point, but here’s what I’ve noticed: when you retire, you start noticing things like:

  • I kind of want to renovate the kitchen
  • Let’s redo the basement
  • I want to create a better man cave
  • We should throw in a pool or redo the deck

Life slows down a little, and you’re spending more time at home. You start thinking, “I’ve worked hard to reach financial independence. I love my house, but I want to make it the house I want to stay in for the next 20 to 30 years.”

If you’ve been in your home for 10, 15, or 20 years, there are probably projects you’ve been putting off. Just because the mortgage is paid off doesn’t mean housing expenses disappear. Principal and interest payments go away, sure, but taxes and insurance continue—and they’ll probably increase over time.

Build in not only recurring unexpected repairs but also those big-ticket items on your wish list. I’ve seen people spend six figures or multiple six figures in the first couple years of retirement just getting their house “retirement ready.” They’re making it a place they’re proud of and want to spend time in over the next 10, 15, or 20 years.

Expense #3: Taxes – The Most Underestimated Retirement Expense

If you’ve been following my podcast or YouTube channel, you know I’m passionate about tax planning and minimizing your lifetime tax bill. Taxes are an overlooked expense that pre-retirees commonly underestimate.

Many people think, “Well, when I’m working, taxes just get withheld. I max out my 401(k), but there’s not much else I can do.” In retirement, you get to choose your tax strategy. You get to choose your tax bracket to a certain degree, especially in that early phase of retirement.

The Golden Window for Tax Planning

I call the period from retirement until required minimum distribution age (73 or 75) the golden window for tax planning—the Roth conversion window. After that window closes, there’s not much you can do. You really need to be intentional before you retire and during early retirement about minimizing your lifetime tax bill.

These strategies could save you six figures, or even multiple six figures, in lifetime taxes paid. On top of that, you can maximize the tax efficiency of your legacy. This is a big reason why many clients hire us.

Think about it: once you retire, your tax situation often simplifies. You might have some consulting income or part-time income, but most of your income comes from retirement distributions, dividends, and interest. Pretty straightforward. But your tax preparer isn’t looking at your lifetime tax bill—that’s what we focus on.

There are so many opportunities here:

  • Planning for Social Security taxation
  • Planning for required minimum distributions
  • Optimizing capital gains
  • Tax loss harvesting
  • Minimizing IRMAA surcharges
  • Maximizing ACA tax subsidies before Medicare

For many of you, especially those who’ve built sizable wealth in tax-deferred accounts, taxes could actually be your top one, two, or three expenses in retirement.

What’s underestimated isn’t just the tax amount—it’s the lack of planning for taxes. Being intentional about the timing of those taxes, when to execute conversions, when to harvest gains at 0%, when to focus on ACA subsidies versus minimizing your long-term tax bill—these are all things you need to consider as you approach retirement and go through that early Roth conversion window phase.

If you miss that window, there’s not much you can do later on.

Expense #4: Adult Children May Still Be on the Payroll

This is tough for some of you, but it’s reality: adult children might still be on the payroll. I’m not talking about an 18, 19, or 20-year-old. I’m talking about an adult child who’s 30, 35, or even 40 years old.

I see this firsthand. I’ve been an advisor for 18 years, and I’m fortunate to have great relationships with the clients we serve. People tell me things they probably don’t even tell their therapist. It’s tough. You want to help your kids and grandkids, but there’s a fine line between helping out and enabling.

Enabling

I’ve seen what enabling does, and it’s not pretty. If you’re an enabler, you often don’t even see it yourself. You almost need a third party to step in and say, “You need to stop this.”

I had a client who admitted she was enabling her adult daughter. Her late husband, who was this daughter’s stepfather, stepped in and said, “No, we’re not doing this anymore.” He put his foot down and cut her off. Unfortunately, that fractured the relationship, but it was what was best for both parties—mom and daughter. I pray that one day they can reunite and work out their differences, but it hasn’t happened yet.

I’ve also seen the other side, where enabling continues. You’re not doing them a favor.

Short-Term Help

That said, there are times when you genuinely need to step in and help your adult child.

  • Are they going through a divorce
  • Maybe they lost a spouse
  • Is there a large expense coming up like a wedding or a down payment

If they’re good stewards of money and grateful for the gifts you give them, that’s entirely different.

These situations will come up. How do you quantify that? I really don’t know. It’s hard to say. You know your family best. You know what goals might arise and how to potentially budget for them.

This surprises many pre-retirees. They think, “The kids are off the payroll. They’re out of college. They’re on their own.” Not so fast. In today’s world, housing costs have skyrocketed, childcare is expensive, and raising a family is hard.

How to Budget for Assisting Adult Children

I don’t have a perfect answer for how to budget for these things, other than:

  1. Try not to enable your adult children.
  2. Help when you can—many of you can easily help financially.
  3. Pick the areas you are willing to help with.
  4. Come up with a plan.
  5. Communicate why you want to help them.
  6. Make sure it doesn’t become something they expect every time something big comes up.

This is also a great opportunity to revisit your estate plan given the financial dynamics with your beneficiaries and how they are navigating their own finances. 

Expense #5: Delegating Tasks You Used to Do Yourself

You’re going to start delegating things you used to do yourself. This can even happen pre-retirement. It happens to me to a certain degree. There are things I used to DIY that I’d rather delegate now. My time is limited. If I were DIYing everything, I’d have no time for my podcast or to spend with my kids.

Over time, you’ll find you start to delegate more. Lawn care, landscaping, cleaning your home—all these things. You’re thinking, “I’d rather travel. I’d rather go on this golf trip than spend my Saturday mowing the lawn.”

The older you get and the closer you get to retirement, think through what’s realistic. What tasks will you probably delegate over the long term? What do those things cost? Build that into your budget.

Talk to your neighbors who are in their 70s and 80s. Are they mowing their own lawns? Are they doing all their gardening? Maybe some of them are, but probably many are delegating at this point.

Think through what expenses could become part of your annual recurring budget and build them into your retirement plan.

Expense #6: Vehicle Replacement – A Typical Expense in Retirement People Forget

When planning for typical retirement expenses, don’t forget to account for the cost of replacing your car every 7-10 years. Vehicle replacement may seem like a small issue because it doesn’t happen every year, but if you do the math, the numbers add up quickly.

If you have a 30-year retirement and you’re replacing your car every seven years, that’s three new cars per person. If you have two people in your household, that’s potentially six or seven new cars during retirement.

Look at vehicle prices today. I’ve been driving this Honda for 12 years now. I can afford a new car—I just had other things I wanted to spend my money on. But we’re getting to that point. The car has some mileage on it, and my wife wants something bigger and safer for road trips.

I haven’t replaced a car in six years. The last vehicle we bought was my wife’s minivan. Prices have gone up astronomically. It’s unbelievable. I see some of these SUVs people are driving—and I’m not judging—but people are spending $110,000 or $120,000 on vehicles.

Many of you listening could easily afford that, but you’re still not doing it. You’re comfortable buying used vehicles. That’s fine—I value experiences over vehicles. I’m not a big car guy. But if you like to replace your vehicle every three to five years, you need to factor that in. If you’re doing the bare minimum—once every seven, 10, or 12 years—you still need to budget for it.

Vehicle Replacement Planning

Regardless of your vehicle plan, put it on paper. Put it into your retirement budget. Figure out how you’ll finance it. Will you pay cash? Where will that money come from?

  • Brokerage accounts
  • Traditional IRA
  • Required minimum distributions
  • Roth account

Have a plan and be intentional. This isn’t like an unexpected home repair. This will come up regularly, and it can dramatically impact your long-term plan if you don’t budget for it.

Expense #7: Healthcare and Aging Costs Throughout Retirement

Healthcare in the US is expensive—we all know this. It’s a racket, frankly, no matter how you slice it. Once you go on Medicare, things get a little easier, but many of you will retire before Medicare eligibility.

You don’t realize how much your employer subsidizes your insurance until you retire. Then you see the sticker price on a private policy: $1,000, $2,000, or even $6,000 a month if you’re living in California. These are expenses you need to budget for.

If you’re strategic and listen to my advice about minimizing premiums through ACA premium tax credits, that’s a different conversation. That goes hand in hand with tax planning in retirement. But there’s that bridge to Medicare you need to plan for.

Once you’re on Medicare, the game isn’t over. You still have out-of-pocket expenses: vision, dental, supplemental insurance, Medigap. All of these can add up significantly more than you planned for.

Maybe you’re fortunate enough to have high income in retirement, and you’re subject to IRMAA. You could be paying another $10,000 a year in medical costs because of your modified adjusted gross income. You need to factor that in post-Medicare.

Aging and Long-Term Care

Then later on, we’ve got aging in place and long-term care. These are things we need to think about when building a retirement budget. Statistics show 70% of you will need some kind of care later in life. We don’t know how long that will last or the extent of care needed.

Most of you would probably prefer to age in place at home rather than move into a nursing home. Think about how to modify your home to make it livable throughout your 70s, 80s, 90s, and potentially into your 100s.

At the very end of life, what if you’re part of that 70% who needs long-term care? How will you pay for it?

  1. Will you fund it out of pocket?
  2. Will you have long-term care insurance?
  3. Will you use your traditional IRA, an HSA, or a Roth account?

Think through that long-term care plan, so you’re not a burden on your beneficiaries and adult children.

Retirement Spending Isn’t Linear—And That’s Why Planning Matters

The biggest lesson I want you to take away is this: retirement spending is not linear. You don’t spend the same amount at 62 as you do at 82. The challenge is that the most expensive years are often the early years for your lifestyle, but later in retirement, healthcare costs spike. Things flip. Healthcare may be lower on the front end and higher on the back end. Travel and golf are higher on the front end, lower on the back end.

Think about checking off those big bucket-list experiences early in retirement, then adjust your spending as you move through different retirement phases. Retirement planning isn’t about figuring out one spending number—it’s about understanding how expenses change over time.

Most retirement issues don’t happen because someone earned 7.5% versus 7.2% on their investments. They happen because the assumptions were way off, particularly on the expense side.

If you’re approaching retirement and want help stress testing your plan—figuring out how taxes, spending, and financial optimization all tie together—this is exactly the type of work we do at Imagine Financial Security.

How We Can Help

Our firm helps individuals over 50 who have at least $1 million saved navigate these complex retirement decisions. If you are looking to

  • Maximize your retirement spending
  • Minimize your lifetime tax bill
  • Worry less about money

You can start by taking our Retirement Readiness Questionnaire on our website at www.imaginefinancialsecurity.com, so we can learn more about how we can help you on your journey to and through retirement.

Not quite ready to take the questionnaire, but want helpful tips and resources? Sign up for our monthly newsletter and/or subscribe to our YouTube channel.

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 130: The Retirement Playbook Changes When You’re Single (Here’s What Nobody Talks About)

Retirement planning looks very different when you’re single. Whether you’re divorced, widowed, or intentionally single, the financial decisions you face in retirement aren’t the same as they are for married couples.

In this video, I’ll discuss the unique retirement planning challenges facing single retirees, including Social Security claiming strategies, Roth conversions, tax brackets, Medicare IRMAA surcharges, estate planning, long-term care, investment strategy, housing decisions, and why retirement spending may look different when you’re planning for one instead of two.

Topics Covered:

• How retirement planning changes when you’re single
• Social Security strategies for single retirees
• Roth conversions and tax planning
• Medicare IRMAA and RMD planning
• Estate planning essentials
• Housing and Continuing Care Retirement Communities (CCRCs)
• Long-term care considerations
• Retirement spending for single retirees
• Advantages of retiring single

Whether you’re already retired or preparing for retirement, understanding these differences can help you better prepare as you plan for and execute a successful retirement.

-Kevin

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.