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Simplified Financial Planning in Greater Boston

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Recognizing and Resolving Financial Infidelity

Recognizing and Resolving Financial Infidelity

Posted on February 9, 2026

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How Credit Cards Can Support Financial Flexibility

How Credit Cards Can Support Financial Flexibility

Posted on February 2, 2026

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Don’t Leave Retirement Money Behind: How to Track Down Old 401(k)s

Don’t Leave Retirement Money Behind: How to Track Down Old 401(k)s

Posted on January 12, 2026

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Retirement Dress Rehearsal: Testing Your Financial Plan Before You Retire

Retirement Dress Rehearsal: Testing Your Financial Plan Before You Retire

Posted on January 2, 2026

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Caring for a Loved One? Here’s How to Ease the Financial and Emotional Burden of Caregiving

Caring for a Loved One? Here’s How to Ease the Financial and Emotional Burden of Caregiving

Posted on December 8, 2025

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OBBBA Brings Big Changes to 529 Plans and New Opportunities for Families

OBBBA Brings Big Changes to 529 Plans and New Opportunities for Families

Posted on December 1, 2025

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How to Make Holiday Giving a Meaningful Family Tradition

How to Make Holiday Giving a Meaningful Family Tradition

Posted on November 10, 2025

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Winter Wellness Strategies to Boost Energy, Mood, and Resilience

Winter Wellness Strategies to Boost Energy, Mood, and Resilience

Posted on November 3, 2025

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2025 Estate Planning Checklist: Key Documents to Review Now

2025 Estate Planning Checklist: Key Documents to Review Now

Posted on October 13, 2025

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Medicare Open Enrollment: What to Know Before You Choose

Medicare Open Enrollment: What to Know Before You Choose

Posted on October 6, 2025

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The Tradesperson

DISCLAIMER: This is a hypothetical situation and is not based on real-life examples or actual results. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investments or strategies may be appropriate for you, consult your financial advisor prior to investing. Carl didn’t have to go to college to carve out a solid career. He’s skilled at what he does, puts in hard work every day, and has the callouses to show for it. That competence and reliability have paid off in making him an asset to his employers, so the income he brought in over the years coupled with a commitment to living beneath his means has allowed him to create a nice nest egg. He shared that he was starting to feel the years. That’s the tradeoff for doing work you enjoy, I guess. He was looking forward to another ten years on the job, but his body might have other ideas. Carl confessed that his back was starting to feel stiff some days. He wasn’t in pain or injured, but it was taking him a little longer to loosen up in the morning, and he was ready to hit the couch when he got home at night. He wanted to make sure he was protected. He expressed that he would've rathered have a stiff back from wiring a building than sitting at a desk all day. But he wanted to make sure his family would be okay in case he would have to hang up his gear earlier than planned. With a son in college to become an engineer and a teenage daughter who planned to follow in her father’s footsteps by learning a trade, he and his wife, an RN, had tuition and child-rearing expenses to cover. But they’d be empty nesters soon, and he wondered if downsizing their lifestyle could leave them with more options in the long run. Besides regularly setting money aside, he wasn't familiar with investing or tax strategies, so he didn't know where to start. He shared that they were not extravagant people but chose a good school district and mortgage to go with it. When the kids were gone, they were thinking it might be easier on the budget and more enjoyable to move out of the suburbs into a smaller house with some land.

Primary Concerns

  • Are they set up for retirement, whether they choose to stay on schedule or retire early?
  • Will they be able to cover their son’s college tuition and help their daughter establish her career?
  • Will his wife be taken care of should something happen to him?

Next Steps

  • Review their investment and savings accounts and how each one contributes towards taxation of retirement income
  • Create an alternative retirement plan, considering possible early retirement
  • Explore the idea of selling their home, purchasing land, and building a smaller home

Overcoming Negativity Bias in Your Personal Finance Journey

Overcoming Negativity Bias in Your Personal Finance Journey

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Essential Questions to Ask Your CPA for Smart Financial Management

Essential Questions to Ask Your CPA for Smart Financial Management

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Wellness and Wealth: Investing in Your Long-Term Health

Wellness and Wealth: Investing in Your Long-Term Health

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How to Prepare for Growing Healthcare Costs in Retirement

How to Prepare for Growing Healthcare Costs in Retirement

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How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

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5 Questions to Ask Yourself 5 Years Before Retirement

5 Questions to Ask Yourself 5 Years Before Retirement

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Creating a Shared Financial Vision: Having the Money Talk with Your Partner

Creating a Shared Financial Vision: Having the Money Talk with Your Partner

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Strategies to Mortgage Freedom

Strategies to Mortgage Freedom

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Beyond the Mortgage: Is Buying a Home Right for You?

Beyond the Mortgage: Is Buying a Home Right for You?

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The Emotional Side of Retirement: How to Face Your Fears and Find Fulfillment

The Emotional Side of Retirement: How to Face Your Fears and Find Fulfillment

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How Understanding Your Money Personality Can Shape Your Financial Journey

How Understanding Your Money Personality Can Shape Your Financial Journey

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Year-End Financial Checkup: Charting a Healthy 2024

Year-End Financial Checkup: Charting a Healthy 2024

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Rethinking Retirement: Your Bucket List Awaits

Rethinking Retirement: Your Bucket List Awaits

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From Stock Options to PTO: Factors to Evaluate Before Changing Jobs

From Stock Options to PTO: Factors to Evaluate Before Changing Jobs

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Taming the Money Monster: Strategies for Addressing Financial Anxiety

Taming the Money Monster: Strategies for Addressing Financial Anxiety

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How to Make Your Staycation Feel Like a Vacation

How to Make Your Staycation Feel Like a Vacation

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Opportunity Costs of Early and Late Retirement

Opportunity Costs of Early and Late Retirement

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Financial Planning in the Face of a Terminal Illness

Financial Planning in the Face of a Terminal Illness

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How to Negotiate a Raise at Work

How to Negotiate a Raise at Work

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Should you join the FIRE movement?

Should you join the FIRE movement?

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How to Avoid Repeating the Money Mistakes of the Past

How to Avoid Repeating the Money Mistakes of the Past

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Parents’ Guide to Financial Aid: Scholarships, Grants, and Student Loans

Parents’ Guide to Financial Aid: Scholarships, Grants, and Student Loans

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10 Home Improvements That May Increase Your Home’s Value

10 Home Improvements That May Increase Your Home’s Value

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8 Financial Health Tips for 2022

8 Financial Health Tips for 2022

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Life Skills College Students Should Know Before Leaving Home

Life Skills College Students Should Know Before Leaving Home

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Factors to Consider When Buying Life Insurance

Factors to Consider When Buying Life Insurance

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A Quick Guide to Building an Emergency Fund

A Quick Guide to Building an Emergency Fund

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Your Adult Child and Money Management

Your Adult Child and Money Management

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It’s Never Too Late for College Financial Planning

It’s Never Too Late for College Financial Planning

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It’s Never Too Early for College Financial Planning

It’s Never Too Early for College Financial Planning

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7 Ways to Reduce Financial Stress

7 Ways to Reduce Financial Stress

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How to Teach Your Children Good Financial Literacy Skills

How to Teach Your Children Good Financial Literacy Skills

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Financially Savvy Ways to Travel

Financially Savvy Ways to Travel

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The Widow

DISCLAIMER: This is a hypothetical situation and is not based on real-life examples or actual results. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investments or strategies may be appropriate for you, consult your financial advisor prior to investing. After the loss of a spouse, widows often find themselves dealing with both grief and pressing financial concerns at the same time. That’s why there’s no time like the present to meet with an attorney and get your documents updated to make sure they are in good order. The eventual (if not immediate) need for a power of attorney and health care proxy to be filed is of the utmost importance. Heart disease is one of the leading causes of death in America. And although we know this to be true, it seems that dementia is right up there with the clients we help. The onset is often young (late 50’s, early 60’s), and to date, there is no cure, no surgery to be done. Laura and her husband came to see me, and I was given a heads up that he was having some memory issues and was having some testing done. She urged me not to mention the ‘D’ word in front of him as it was early in the process for him, and he knew what it meant and what the outcomes were. We had a conversation, the three of us. His comprehension was good, but there were differences. I checked my notes as to the last time their wills were updated… it had been a while. On a subsequent visit, Laura let me know she had difficulty grasping the enormity of the potential expense of caring for him. By choice, long-term care insurance had not been part of their plan. She projected the harsh realities around the cost of care, not to mention the taxes on their IRAs to access those funds. She shared that he has life insurance, but it expires in 5 years. She couldn't stop feeling awful, but she counted on that being there for her, assuming she would have to use their retirement assets to pay for care. I reminded her that it’s not selfish; it’s survival. Her goal was to provide him great care while he was alive. His goal was for the two of them to enjoy their lives together. He would be upset if, after 40 years of professional work, she spent all of it on him. By the end of our conversation, she understood that the death benefit is for the survivor, not the person whom the policy is on. As to the timing of it, my experience is that spouses who survive their loved ones have already mourned the very essence of their being well before their bodies have given up. The willingness to do what is right for him now will somehow be balanced out later.

Primary Concerns

  • Will she have enough money to live off of as it is being depleted by medical expenses and long-term care?
  • How should she handle finances on her own? Where should she start?
  • What if she runs out of money?

Next Steps

  • Update estate plan and documents
  • Create a comprehensive financial plan that takes personal circumstances into account
  • Provide resources and guidance to help her fully understand the household finances, so she feels comfortable managing them on her own

Overcoming Negativity Bias in Your Personal Finance Journey

Overcoming Negativity Bias in Your Personal Finance Journey

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Essential Questions to Ask Your CPA for Smart Financial Management

Essential Questions to Ask Your CPA for Smart Financial Management

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Navigating Tax Season Scams: How to Protect Yourself from Fraud

Navigating Tax Season Scams: How to Protect Yourself from Fraud

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How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

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Year-End Financial Checkup: Charting a Healthy 2024

Year-End Financial Checkup: Charting a Healthy 2024

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Rethinking Retirement: Your Bucket List Awaits

Rethinking Retirement: Your Bucket List Awaits

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Is Semi-Retirement the Perfect Compromise?

Is Semi-Retirement the Perfect Compromise?

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Taming the Money Monster: Strategies for Addressing Financial Anxiety

Taming the Money Monster: Strategies for Addressing Financial Anxiety

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Planning for the Costs of Alzheimer’s and Dementia Care

Planning for the Costs of Alzheimer’s and Dementia Care

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5 Benefits to Consolidating Your Investment Accounts with a Financial Advisor

5 Benefits to Consolidating Your Investment Accounts with a Financial Advisor

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A Windfall of Opportunities: How to Make Smart Choices with Sudden Money

A Windfall of Opportunities: How to Make Smart Choices with Sudden Money

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How to Know if It’s Time to Downsize Your Home

How to Know if It’s Time to Downsize Your Home

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Flying Solo in Retirement: 6 Financial Strategies for Women

Flying Solo in Retirement: 6 Financial Strategies for Women

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Digital Estate Planning: 5 Steps to Protect Your Digital Assets

Digital Estate Planning: 5 Steps to Protect Your Digital Assets

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5 Steps to Protect Your Finances from Cognitive Decline

5 Steps to Protect Your Finances from Cognitive Decline

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Pet Ownership Can Be Costly But the Benefits Are Priceless

Pet Ownership Can Be Costly But the Benefits Are Priceless

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Preparing to Retire Single

Preparing to Retire Single

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Checklist for What to Do When a Spouse or Parent Dies

Checklist for What to Do When a Spouse or Parent Dies

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Unique Issues Women Face When Planning for Retirement

Unique Issues Women Face When Planning for Retirement

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9 Common Questions About Social Security Benefits Answered

9 Common Questions About Social Security Benefits Answered

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The Single Mom

DISCLAIMER: This is a hypothetical situation and is not based on real-life examples or actual results. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investments or strategies may be appropriate for you, consult your financial advisor prior to investing. Life doesn’t always go as planned, but the more dedicated, disciplined, and prepared we are, the better financial future we can enjoy—no matter the circumstances. Paige had been to a presentation I did about her workplace benefits. The company was having on-again, off-again “reduction-in-force” offers to take an early retirement, or to simply leave. When I answered the phone, the caller sounded a little nervous. She had never met with an advisor before, but after attending the presentation, she thought I might be able to help her. She started working at the phone company right out of high school. A few years later, she was married, and soon after that, well, you know those newlyweds! By the time her daughter was five, her husband had left. It turned out, fatherhood wasn’t for him… nor was consistently making child-support payments. That didn’t stop Paige from working and raising her daughter to become a healthy, productive adult, or from making her 401(k) contributions. As the years went by, she had questions like “Is she saving enough? Do the investments make sense? How is she going to pay for college? Can she afford to buy a new car when she retires? Should she pay off her mortgage? Her dream trip to Tuscany… is it doable?” She looked to me for advice and guidance. I admired (and still do) her commitment to providing for her daughter and her consistent resolve to save and invest for her future retirement. Paige accomplished a lot—a whole lot, really. But the best offer yet from her company came in her mid-50s. She had been saving, waiting, for this moment for over 30 years. It was scary—no, intimidating—for her to really contemplate not having that paycheck, paid vacation, and benefits. So how does she evaluate the early retirement offer? How will she live? Where will she get money from? Will she pay taxes on her retirement? What about the company stock? I reminded her that we’ve talked about this many times. She did some great prep work with me, but I understand that big decisions like this can be stressful, especially with the deadlines. I was able to explain it to her again so she could be confident in her decisions. Paige did take that offer. She works part-time now and spends one to two days a week caring for her parents. “Do they have health care proxies, powers of attorney, and wills?” I asked. She laughed as she knows it's a never-ending conversation with me. As long as time marches on and the world keeps changing, it never really ends. The topics of conversation and how I am trying to help keeps our relationship fresh.

Primary Concerns

  • How can she know that she is making the best financial decisions for her children's and her future?
  • How does she prepare for retirement when she's juggling so many other expenses?
  • How can she ensure that she will have funds available should an emergency arise?

Next Steps

  • Offer financial advice and guidance along the road to retirement
  • Create a customized, comprehensive retirement plan
  • Establish a new household budget that prioritizes what matters to her most

Overcoming Negativity Bias in Your Personal Finance Journey

Overcoming Negativity Bias in Your Personal Finance Journey

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Essential Questions to Ask Your CPA for Smart Financial Management

Essential Questions to Ask Your CPA for Smart Financial Management

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Relocating for Family: A Parent’s Guide to Making the Right Choice

Relocating for Family: A Parent’s Guide to Making the Right Choice

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How to Prepare for Growing Healthcare Costs in Retirement

How to Prepare for Growing Healthcare Costs in Retirement

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How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

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How to Raise Financially Savvy Kids: Budgeting, Saving & Money Talks

How to Raise Financially Savvy Kids: Budgeting, Saving & Money Talks

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Strategies to Mortgage Freedom

Strategies to Mortgage Freedom

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Beyond the Mortgage: Is Buying a Home Right for You?

Beyond the Mortgage: Is Buying a Home Right for You?

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How Understanding Your Money Personality Can Shape Your Financial Journey

How Understanding Your Money Personality Can Shape Your Financial Journey

Read Post

Year-End Financial Checkup: Charting a Healthy 2024

Year-End Financial Checkup: Charting a Healthy 2024

Read Post

Investing in Your Child’s Future: Exploring Your Options for Your Child’s K-12 Education

Investing in Your Child’s Future: Exploring Your Options for Your Child’s K-12 Education

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Taming the Money Monster: Strategies for Addressing Financial Anxiety

Taming the Money Monster: Strategies for Addressing Financial Anxiety

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How to Make Your Staycation Feel Like a Vacation

How to Make Your Staycation Feel Like a Vacation

Read Post

How to Negotiate a Raise at Work

How to Negotiate a Raise at Work

Read Post

How to Avoid Repeating the Money Mistakes of the Past

How to Avoid Repeating the Money Mistakes of the Past

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Parents’ Guide to Financial Aid: Scholarships, Grants, and Student Loans

Parents’ Guide to Financial Aid: Scholarships, Grants, and Student Loans

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6 Tips to Avoid Overspending on Your Summer Vacation

6 Tips to Avoid Overspending on Your Summer Vacation

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How to Budget for the Holidays

How to Budget for the Holidays

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Life Skills College Students Should Know Before Leaving Home

Life Skills College Students Should Know Before Leaving Home

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A Quick Guide to Building an Emergency Fund

A Quick Guide to Building an Emergency Fund

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Unique Issues Women Face When Planning for Retirement

Unique Issues Women Face When Planning for Retirement

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It’s Never Too Late for College Financial Planning

It’s Never Too Late for College Financial Planning

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It’s Never Too Early for College Financial Planning

It’s Never Too Early for College Financial Planning

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How to Teach Your Children Good Financial Literacy Skills

How to Teach Your Children Good Financial Literacy Skills

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Financially Savvy Ways to Travel

Financially Savvy Ways to Travel

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The Married Couple

DISCLAIMER: This is a hypothetical situation and is not based on real-life examples or actual results. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investments or strategies may be appropriate for you, consult your financial advisor prior to investing. Corrine retired first. One of the largest razor blade companies was headquartered in Boston, and they treated their employees well. A pension combined with a 401(k) match in the form of a stock that did very well gave her a comfortable nest egg and monthly income…not to mention a Medical ESOP plan. Her husband Ed retired many years later. An employee of the federal government, he wanted to work longer to increase his pension benefit. He too did well with his Thrift Savings Plan (TSP). But he had some credit card debt, so we devised a strategy to pay it off over two tax years, using vacation buyout money at retirement and TSP funds the following tax year. The couple had been clients of mine for several years, and he had put off retiring more than once. When I saw them call in, I figured he was calling to let me know he had finally decided to retire. Unfortunately, he was calling to let me know that his son died very prematurely. They came in, still reeling from grief, to discuss what they wanted to do next. Corrine and Ed come from a small island nation where family customs favor the eldest son. At the time of his death, he had two young children, the older of whom was two and the other only months old. They want to provide for their grandchildren to make sure they can be educated when the time comes. Neither Ed nor Corrine had attended college, but they made sure their sons did, and now, in their son’s absence, they will provide for his children. Given their young age, I suggested they speak with a local estate planning attorney to see if she thought setting up some type of trust to put assets in (and to name as a beneficiary) would help them accomplish their goals. She agreed, drafted the relevant documents, and they are now comforted by having a plan in place. Their son’s death triggered Ed to retire immediately. He and his wife now care for their grandchildren daily when their mother goes off to work. Their involvement in the grandchildren’s lives helps to ease their pain, pass on family values, and keep the legacy of their son alive.

Primary Concerns

  • Are they getting the most from their retirement plans and benefits?
  • What if something unexpected arises?
  • How can they help support their grandchildren now and in the future?

Next Steps

  • Work together to maximize their retirement benefits
  • Adjust their retirement plan to accommodate for unexpected circumstances and expenses
  • Refer them to an attorney in their community who will help them accomplish their goals to benefit their grandchildren

Overcoming Negativity Bias in Your Personal Finance Journey

Overcoming Negativity Bias in Your Personal Finance Journey

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Essential Questions to Ask Your CPA for Smart Financial Management

Essential Questions to Ask Your CPA for Smart Financial Management

Read Post

Relocating for Family: A Parent’s Guide to Making the Right Choice

Relocating for Family: A Parent’s Guide to Making the Right Choice

Read Post

Wellness and Wealth: Investing in Your Long-Term Health

Wellness and Wealth: Investing in Your Long-Term Health

Read Post

How to Prepare for Growing Healthcare Costs in Retirement

How to Prepare for Growing Healthcare Costs in Retirement

Read Post

How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

How to Wrap Up Your Taxes With Confidence and Prepare for Next Year

Read Post

5 Questions to Ask Yourself 5 Years Before Retirement

5 Questions to Ask Yourself 5 Years Before Retirement

Read Post

Creating a Shared Financial Vision: Having the Money Talk with Your Partner

Creating a Shared Financial Vision: Having the Money Talk with Your Partner

Read Post

Strategies to Mortgage Freedom

Strategies to Mortgage Freedom

Read Post

The Emotional Side of Retirement: How to Face Your Fears and Find Fulfillment

The Emotional Side of Retirement: How to Face Your Fears and Find Fulfillment

Read Post

How Understanding Your Money Personality Can Shape Your Financial Journey

How Understanding Your Money Personality Can Shape Your Financial Journey

Read Post

Year-End Financial Checkup: Charting a Healthy 2024

Year-End Financial Checkup: Charting a Healthy 2024

Read Post

Rethinking Retirement: Your Bucket List Awaits

Rethinking Retirement: Your Bucket List Awaits

Read Post

From Stock Options to PTO: Factors to Evaluate Before Changing Jobs

From Stock Options to PTO: Factors to Evaluate Before Changing Jobs

Read Post

Investing in Your Child’s Future: Exploring Your Options for Your Child’s K-12 Education

Investing in Your Child’s Future: Exploring Your Options for Your Child’s K-12 Education

Read Post

Taming the Money Monster: Strategies for Addressing Financial Anxiety

Taming the Money Monster: Strategies for Addressing Financial Anxiety

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Retirement Income: Thinking Beyond Retirement Savings and Investing

Retirement Income: Thinking Beyond Retirement Savings and Investing

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Planning for the Costs of Alzheimer’s and Dementia Care

Planning for the Costs of Alzheimer’s and Dementia Care

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5 Benefits to Consolidating Your Investment Accounts with a Financial Advisor

5 Benefits to Consolidating Your Investment Accounts with a Financial Advisor

Read Post

Financial Planning in the Face of a Terminal Illness

Financial Planning in the Face of a Terminal Illness

Read Post

How to Know if It’s Time to Downsize Your Home

How to Know if It’s Time to Downsize Your Home

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Digital Estate Planning: 5 Steps to Protect Your Digital Assets

Digital Estate Planning: 5 Steps to Protect Your Digital Assets

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10 Home Improvements That May Increase Your Home’s Value

10 Home Improvements That May Increase Your Home’s Value

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Why It’s Important to Designate a Power of Attorney

Why It’s Important to Designate a Power of Attorney

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5 Things to Consider Before Buying a Vacation Home

5 Things to Consider Before Buying a Vacation Home

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Your Credit Score and Retirement: What You Need to Know

Your Credit Score and Retirement: What You Need to Know

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Tips For a Healthy and Happy Retirement

Tips For a Healthy and Happy Retirement

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How to Invest for Your Grandchildren’s Future

How to Invest for Your Grandchildren’s Future

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Living Your Best Retirement

Living Your Best Retirement

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6 Essential Health Tips for Seniors

6 Essential Health Tips for Seniors

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9 Common Questions About Social Security Benefits Answered

9 Common Questions About Social Security Benefits Answered

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Social Security Benefits: 5 Important Facts

Social Security Benefits: 5 Important Facts

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Maximize Social Security Benefits

Maximize Social Security Benefits

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