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      IRA Beneficiary Designations and Your Estate Plan

      Too often an overlooked yet important element of your estate plan is your 401(k) and [...]

      09
      Apr
      What Your Estate Plan Should Consider in a Low Yield Environment

      In many ways your estate plan intersects with a variety of disciplines. Legal and tax [...]

      01
      Apr
      Income Tax Planning for Trust Beneficiaries

      In a recent column I discussed the benefits of embedding continuing testamentary trusts for your [...]

      26
      Mar
      Are Beneficiary Trusts Too Restrictive?

      To protect loved ones’ inheritances from predators, creditors, divorcing spouses and even from estate taxes [...]

      19
      Mar
      Common Missing Elements in Estate Plans

      I’ve reviewed many estate plans in my 30+ years of practice. It is not uncommon [...]

      12
      Mar
      Should Your Estate Plan Factor Unrepaid Loans to Your Children?

      Lucy loaned her son money over the years. First, it was $75,000 for a down [...]

      05
      Mar
      Should I Pay Dad’s Credit Cards?

      When a parent dies one of the first questions their adult children ask me is [...]

      26
      Feb
      Between Liberty and License

      John Locke, a British Enlightenment figure of the late 17th century, is credited with some [...]

      19
      Feb
      Call an Attorney

      Call an Attorney When a Loved One Dies – Even When You Have a Revocable [...]

      12
      Feb
      Joint Accounts Don’t Count Towards Bequests

      Robert created a trust that first distributed the first $2 million to his wife, Linda [...]

      05
      Feb
      Family Fishing
      Be Careful Naming Trust as IRA Beneficiary

      I’ve had several new clients come to me with an existing estate plan that includes [...]

      22
      Jan
      US Dollar Stamp
      Why Now is a Good Time for Advanced Estate Planning

      Recently I’ve fielded many calls about advanced estate planning strategies, most likely brought on since [...]

      15
      Jan
      You Can't Get Everything Online
      You Can’t Get Everything Online

      A friend of mine officiated at another friend’s wedding some time before the pandemic. I [...]

      08
      Jan
      Washington DC capitol
      How Might a Biden Administration Affect Taxes?

      It appears that Joe Biden will take the oath of office on January 20th as [...]

      18
      Nov
      Dead Fish Go with the Flow
      Dead Fish Go with the Flow

      After the Holocaust, social scientists were haunted by the question of why so many people [...]

      12
      Nov
      Election and Market Returns
      Elections and Market Returns

      This column is scheduled to run on November 6th, but I’m writing it a week [...]

      06
      Nov
      Letter to You
      In My Letter to You

      I recently watched a television interview of Bruce Springsteen, a favorite of mine. He released [...]

      28
      Oct
      Locked Up
      Locked Up Until Age 35?

      Rob, a well-mannered, intelligent 25-year-old beneficiary to his grandfather’s trust came to me with a [...]

      28
      Oct
      Who Should Own Your Life Insurance Policy
      Who Should Own Your Life Insurance Policy?

      Several years ago, you took out a life insurance policy on your life and named [...]

      28
      Oct
      Health Education Maintenance and Support
      Health, Education, Maintenance and Support

      For those of you who have wills and trusts that contain testamentary (post-death) trusts that [...]

      28
      Oct
      Disney Castle
      Now is the Time

      When I was growing up in Indianapolis, we would visit my grandparents in Clearwater every [...]

      28
      Oct
      Who Can Serve as Your Personal Representative
      Who Can Serve as Your Personal Representative?

      “James,” a widower, sat in my office as we prepared his will together. “My sons [...]

      17
      Oct
      9 Tips for Meaningful Last Words
      9 Tips for Meaningful Last Words

      My client, let’s call him Pascal, complained to me recently while reading over his estate [...]

      14
      Oct
      Can We Tax Our Way Out of Inequality
      Can We Tax Our Way Out of Inequality?

      Our national conversation over inequality has, to me, foundational issues that have largely gone unaddressed. [...]

      12
      Oct
      Retaining Your Trusted Financial Advisor
      Retaining Your Trusted Financial Advisor

      What many clients don’t realize is that they may lose their trusted financial advisor when [...]

      07
      Oct
      Are Our Children Equal?

      Any parent of more than one child knows how different our kids are – even [...]

      05
      Oct
      A Valuable Law School Lesson

      I was 18 years old when my dad dropped me off as a freshman on the front [...]

      05
      Oct
      Covid Opportunity
      The Opportunity COVID Provides Your Family

      I’m happy to announce that my oldest daughter Gabi became engaged recently to her longtime [...]

      05
      Oct
      Black Sheep
      What to Do with the Black Sheep Beneficiary

      Most families have black sheep. You know what I’m talking about. There might be three siblings, but [...]

      05
      Oct
      Why Israel Lacks Statues
      Why Israel Lacks Statues

      I’m going off topic today, choosing to address the controversy surrounding the removal of statues [...]

      06
      Jul
      When You Don’t Avoid Probate with a Trust
      When You Don’t Avoid Probate with a Trust

      A couple of years ago, a very nice couple visited with me in my office. [...]

      06
      Jul
      Four Different Methods of Charitable Giving from Your Estate
      Four Different Methods of Charitable Giving from Your Estate

      Many individuals have charitable intent that they would like to incorporate into their estate plans, [...]

      06
      Jul
      Google U
      Google U

      Several years ago, when my mother was first diagnosed with acute myelodysplastic leukemia, the first thing [...]

      06
      Jul
      On George Floyd and Black Lives Matter
      On George Floyd and Black Lives Matter

      As a somewhat public figure simply by writing this column for over twenty years, I [...]

      16
      Jun
      How The Crusades Created Estate Planning
      How The Crusades Created Estate Planning

      We take for granted that the tool of a revocable living trust is available to us. We [...]

      16
      Jun
      Salesman vs. Estate Planners
      Salesman vs. Estate Planners

      There’s a big difference between a counselor and a salesman. This became evident to me [...]

      16
      Jun
      Oh No! Don’t Do It!
      Oh No! Don’t Do It!

      In recent weeks I’ve encountered calls from clients who, unbeknownst to me, took on the [...]

      16
      Jun
      The Irony of Keeping It Simple
      The Irony of Keeping It Simple

      When a new client first visits with me to update their estate plan, it isn’t unusual for them [...]

      16
      Jun
      VUCA Now More Than Ever
      VUCA Now More Than Ever

      Some time ago I discussed the concept of VUCA (volatile, uncertain, complex and ambiguous), and [...]

      16
      Jun
      Revealing Vulnerabilities Necessary to Create Appropriate Estate Plan
      Revealing Vulnerabilities Necessary to Create Appropriate Estate Plan

      I often begin my initial consultations with a simple question. “What do we hope to accomplish today?” I intend [...]

      16
      Jun
      Resume vs. Eulogy Virtues
      Resume vs. Eulogy Virtues

      A few years ago, New York Times columnist David Brooks wrote about two different sets [...]

      06
      May
      Gratitude
      Gratitude

      The next time that you feel depressed, angry, envious, unhappy, or are simply having a [...]

      14
      Sep
      Spoiling the Grandchildren
      Spoiling the Grandchildren

      Having just sent my youngest off to Elon University in North Carolina, I’ve been reflecting [...]

      07
      Sep
      Looking at the Prenuptial Agreement
      Looking at the Prenuptial Agreement

      Albert and Victoria were interested in marrying as they had cohabitated for many years, but [...]

      24
      Aug
      It’s All in a Name
      It’s All in a Name

      Names are important. A little boy named Wilfred today, compared to in the past, may [...]

      17
      Aug
      Trust and Love
      Trust and Love

      My favorite definition of love is ‘giving someone the power to destroy us and trusting [...]

      10
      Aug
      When Everyone is Thinking the Same Thing
      When Everyone is Thinking the Same Thing

      General Patton was once famously quoted “When everyone is thinking the same thing, then somebody’s [...]

      03
      Aug
      A Digital World
      A Digital World

      So much of our lives are electronic and digital now, we don’t even realize it. [...]

      27
      Jul
      The Importance of Communication
      The Importance of Communication

      While communication with your team of legal, tax and financial professionals is important to put [...]

      21
      Jul
      Should You Title Your Car In Trust?
      Should You Title Your Car In Trust?

      Clients frequently ask whether one should transfer the title to their automobile into their revocable [...]

      14
      Jul
      Creating Education Trusts
      Creating Education Trusts

      Over the years clients have asked me how to provide for educational gifts within their [...]

      07
      Jul
      Asset Alignment
      Asset Alignment

      Did you know, however, that you can have the best estate planning documents ever drafted [...]

      15
      Jun
      Acting in Concert
      Acting in Concert

      Did you ever wonder where the phrase “acting in concert” comes from? It may have [...]

      08
      Jun
      Does Your Dog Bite?
      Does Your Dog Bite?

      One of my all-time favorite movie scenes is from The Pink Panther Strikes Again where [...]

      25
      May
      The Vultures
      The Vultures

      Those ugly turkey vultures are quite ubiquitous throughout Southwest Florida. You see packs of them [...]

      11
      May
      An Apprenticeship in Reality
      An Apprenticeship in Reality

      According to Peterson, a significant number of parents today fail to socialize their children. They [...]

      04
      May
      Island Residence Dreams Shattered
      Island Residence Dreams Shattered

      Many of my clients who live on the islands dream of leaving their beloved residence [...]

      30
      Mar
      Heavy Lifting and the Do-it-Yourselfer
      Heavy Lifting and the Do-it-Yourselfer

      Twice a week I train with a personal trainer to help keep myself physically fit. [...]

      10
      Mar
      Contract or a Covenant?
      Contract or a Covenant?

      When considering your estate plan, I ask this question: do you consider it a contract [...]

      09
      Mar
      The Perils of Joint Accounts
      The Perils of Joint Accounts

      I hear this question all too often.  A client will come in, thinking they have [...]

      23
      Feb
      Tax Law Provides Opportunities
      Tax Law Provides Opportunities

      You may be aware that the Tax Cuts & Jobs Act was enacted at the [...]

      16
      Feb
      State & Local Tax Deduction Slashed
      State & Local Tax Deduction Slashed

      Many of you have heard that the Tax Cuts & Jobs Act of 2017 that [...]

      09
      Feb
      Secret Trusts
      Secret Trusts

      Many clients have expressed a desire to create trusts for loved ones, but to not [...]

      26
      Jan
      Myths About Estrangement
      Myths About Estrangement

      From time to time a client will not tell me about a child because they [...]

      26
      Jan
      Never Go Into Retail
      Never Go Into Retail

      Growing up in Indianapolis, my family was close to my maternal grandparents who owned retail [...]

      19
      Jan
      5 Signs a Caregiver is Stealing
      5 Signs a Caregiver is Stealing

      What do you do when an heirloom bracelet goes missing? How about when a bank [...]

      12
      Jan
      When You Don’t Avoid Probate with a Trust
      When You Don’t Avoid Probate with a Trust

      A couple of years ago, a very nice couple visited with me in my office. [...]

      22
      Dec
      Son Abusing Father's Trust?
      Son Abusing Father’s Trust?

      When you’re named as a trustee to a trust, especially a trust in which you [...]

      22
      Dec
      Rings in Peanut Butter and Buried Treasures
      Rings in Peanut Butter and Buried Treasures

      Children of a recently deceased client learned an expensive lesson not too long ago after [...]

      22
      Dec
      Homebrewed Amendments
      Homebrewed Amendments

      What happens when a man dies with a will or a revocable trust that was [...]

      22
      Dec
      Escaping Your Former State’s Taxing Authority
      Escaping Your Former State’s Taxing Authority

      Regular readers of this column know that I like to educate on the importance of [...]

      22
      Dec
      Where Are You From?
      Where Are You From?

      So where are you from? And if you own a residence in Florida and haven’t [...]

      06
      Nov
      When an IRA Distribution Causes a Probate
      When an IRA Distribution Causes a Probate

      Most clients who have revocable trusts believe that there won’t be a probate opened upon [...]

      06
      Nov
      Deductions for Hurricane Related Casualty Losses
      Deductions for Hurricane Related Casualty Losses

      Many Florida residents, particularly those in Southwest Florida, suffered casualty losses from Hurricane Irma recently. [...]

      22
      Sep
      When to Throw it Away
      When to Throw it Away

      My father-in-law, Ronald, is a pack rat.  He and my mother-in-law can’t park their cars [...]

      15
      Sep
      Trustee Liability
      Trustee Liability

      When naming spouses, children or other loved ones to serve as trustees in your testamentary [...]

      01
      Sep
      Adapting: Technology and Wealth
      Adapting: Technology and Wealth

      As an estate planner, it is fascinating to me to see how some have acquired [...]

      18
      Aug
      The Story of Uncle Benny
      The Story of Uncle Benny

      In my wife’s family lore they tell the story from many years ago about Uncle [...]

      04
      Aug
      The Money-Making Power of Imagination
      The Money-Making Power of Imagination

      As Freeform (formerly ABC Family) is wont to do, a Harry Potter marathon aired this [...]

      03
      Aug
      Never Go Out Without an Umbrella
      Never Go Out Without an Umbrella

      Many retirees figure that once they move past the stage in their lives where they [...]

      25
      Jul
      Back-Up Your Brain
      Back-Up Your Brain

      Like many professional offices, ours has gone electronic and mostly paperless – at least as [...]

      21
      Jul
      Home Is Where Rover Lives
      Home Is Where Rover Lives

      Many who own residences both here in Florida and in some northern states often consider [...]

      21
      Jul
      What?
      What?

      A new client, Theresa, who recently relocated from a northern state, brought me her trust [...]

      20
      Jul
      Rescuing a Child with the Family Business?
      Rescuing a Child with the Family Business?

      You may be surprised to learn that more than 90% of American businesses are family [...]

      20
      Jul
      Deeds, Warranties and Title Policies
      Deeds, Warranties and Title Policies

      Many don’t completely understand the different types of deeds that might be used when transferring [...]

      18
      Jul
      The Third Rail
      The Third Rail

      I recently visited New York, Boston and Chicago, and in each location I used public [...]

      18
      Jul
      I Didn’t Say You Were Beautiful
      I Didn’t Say You Were Beautiful

      It’s amazing to me how the written word is often misconstrued. I believe this happens [...]

      17
      Jul
      The In-Laws
      The In-Laws

      When drafting up wills and trusts, I sometimes have a client tell me that they [...]

      12
      May
      Setting Expectations
      Setting Expectations

      Like many of you, over the past few weeks we entertained guests from northern locales [...]

      04
      May
      Don’t Write in the Margins
      Don’t Write in the Margins

      While attending law school, I used to take a yellow highlighter and pen, writing in [...]

      28
      Apr
      Two Hats
      Two Hats

      When my children were young, I used to read Dr. Seuss books to them. One [...]

      21
      Apr
      Right Hand Left Hand
      Right Hand Left Hand

      It’s frustrating when we receive conflicting advice about a particular topic, and that is as [...]

      07
      Apr
      Art or Science?
      Recalculating

      I’m always looking for shortcuts when driving, especially during busy season. Most long-time Sanibel residents [...]

      31
      Mar
      Health, Education, Maintenance and Support
      Health, Education, Maintenance and Support

      For those of you who have wills and trusts that contain testamentary (post-death) trusts that [...]

      24
      Mar
      No Split Residency to Retain Dual Homesteads
      No Split Residency to Retain Dual Homesteads

      At the conclusion of our recently held client workshops we open the floor for questions. [...]

      28
      Feb
      Will vs Revocable Living Trust
      Will vs Revocable Living Trust

      Occasionally I am asked a basic estate planning question that I will review today, and [...]

      24
      Feb
      Retaining Your Trusted Financial Advisor
      Retaining Your Trusted Financial Advisor

      What many clients don’t realize is that they may lose their trusted financial advisor when [...]

      10
      Feb
      Changes When Becoming a Florida Resident
      Changes When Becoming a Florida Resident

      Many people move to Florida or establish residency here not only for the sunshine but [...]

      03
      Feb
      5 Reasons for Baby Boomers to Update
      5 Reasons for Baby Boomers to Update

      I was born at the tail end of the baby boomer generation – which is [...]

      13
      Jan
      Different Baskets
      Different Baskets

      When choosing how to approach your estate plan, it’s important to realize that the different [...]

      09
      Jan
      A History of Trusts
      A History of Trusts

      We take for granted that the tool of a revocable living trust is available to [...]

      09
      Dec
      Jeopardizing Creditor Proof Life Insurance
      Jeopardizing Creditor Proof Life Insurance

      Under Florida law, life insurance is exempt from the claims of creditors. The exemption is [...]

      28
      Nov
      Don't Name Minor Children as Beneficiaries
      Don’t Name Minor Children as Beneficiaries

      A common mistake, particularly with young parents who come into my office, is the naming [...]

      16
      Nov
      Promissory Notes are Part of Your Estate
      Promissory Notes are Part of Your Estate

      Ken and Barb have a joint trust that provides for one another and upon the [...]

      07
      Oct
      It's Not The Money or Property They Fight Over
      It’s Not The Money or Property They Fight Over

      I was very close to my great grandmother, whom I called “Bubby.” A framed picture [...]

      06
      Oct
      Durable Power of Attorney vs Trustee
      Durable Power of Attorney vs Trustee

      Many clients become confused between the difference of the duties and responsibilities of the person [...]

      23
      Sep
      Removing and Replacing Successor Trustees
      Removing and Replacing Successor Trustees

      When you have a revocable living trust, you typically serve as your own trustee. Upon [...]

      16
      Sep
      Same Sex Couples Estate Planning
      Same Sex Couples Estate Planning

      The last few years have brought several favorable developments for same sex couples in the [...]

      26
      Aug
      Who Qualifies as Your Personal Representative?
      Who Qualifies as Your Personal Representative?

      “James,” a widower, sat in my office as we prepared his will together. “My sons [...]

      19
      Aug
      Trust Decanting
      Trust Decanting

      I’ve written in the past about a variety of ways to modify problem trusts. I [...]

      01
      Jul
      Open Discussions with Your Adult Children
      Open Discussions with Your Adult Children

      An adult child of a client who recently passed away contacted me to discuss what [...]

      17
      Jun
      Spendthrift or Risk Tolerance?
      Spendthrift or Risk Tolerance?

      A client, “Alec” discussed imposing a third party trustee on his son “Terrance’s” inheritance, while [...]

      20
      May
      Art or Science?
      Art or Science?

      “Calvin” visited with me recently, armed with spreadsheets describing the distributions he wanted his revocable [...]

      08
      Apr
      Problems with Trusts
      Problems with Trusts

      “I know that you’re big on revocable trusts,” Jennifer began during our initial client consultation, [...]

      01
      Apr
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      Becoming a Florida resident is easy, the hard part is escaping your former state’s taxing authorities. Discover the advantages to Florida residency and strategies to create your best estate plan. This book addresses whether your will, revocable living trust, durable power of attorney, health care surrogate and living will documents from up north remain valid, the important issues you should consider when updating your documents to Florida law, and whether you can achieve tax savings by becoming a Florida resident.

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      This website has been prepared by Sheppard Law Firm for informational purposes only and does not constitute legal advice. The information is not provided in the course of an attorney-client relationship and is not intended to substitute for legal advice from an attorney licensed in your jurisdiction.

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