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  • A Dovetail Financial Insights banner introducing educational articles about retirement decisions and how life and wealth connect.

Retirement Planning Articles

A bright dressing room table with a jewelry box, travel pouch, and nearby accessories, suggesting that moving something to a simpler place may still leave certain features tied to where it started.
Ross Marino | Apr 21, 2026

Rollover or Stay Put? What This Decision Really Protects

Investments
Tax Planning
Retirement Income
Risk Management
IRA
401(k)
Rolling over an old 401(k) can reduce account clutter. Before moving it, review whether the plan still holds an option you may need later.
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A circle of miniature presentation easels surrounding a central stand, illustrating that a retirement date should be reviewed alongside Social Security, healthcare, taxes, and portfolio withdrawals rather than as a single decision.
Ross Marino | Apr 13, 2026

Before You Pick a Retirement Date, Make the Pieces Work Together

Retirement Timing
Social Security
Medicare
Tax Planning
Retirement Income
Retirement is not one lever. See how Social Security, taxes, Medicare, and withdrawals interact so one choice does not create pressure somewhere else.
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A woman in her 60s stands on a covered porch with a mug, looking out at the rain before responding to what has changed.
Ross Marino | Apr 1, 2026

A steadier way to think about market highs and lows

Investments
Risk Management
Retirement Income
Headlines move fast. Your decisions don’t have to. Use a plan that shows what to rebalance, what to review, and what can wait.
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Three wooden markers along a garden path read “Pause,” “Verify,” and “Protect,” showing a simple response routine before acting on a suspicious message.
Ross Marino | Mar 19, 2026

The New Phishing: How AI Imitates Trust and What to Do Next

Scams & Digital Security
AI can make a phishing message sound polished, familiar, and urgent. A simple pause, verify, protect routine can help you check what is real before money or
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Bound paper records tied together beside a blank sheet and pencil on a wooden worktable, representing tax preparation as documenting what has already happened.
Ross Marino | Mar 4, 2026

The Real Difference Between Tax Preparation and Tax Planning

Tax Planning
Retirement Income
Roth Conversions
Charitable Giving
Tax preparation reports last year. Tax planning shapes this year while choices still exist. Here is how they connect without becoming the same.
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Brightly colored pottery labeled Conversion, Gain, RMD, and Gift sits on a shelf marked “This year,” above pottery on a shelf marked “Later premiums.”
Ross Marino | Feb 14, 2026

NIIT, IRMAA, RMDs: Why Tax Decisions Need a Multi-year Plan

Tax Planning
Investments
Medicare
Retirement Income
Roth Conversions
RMD
IRA
A tax move that looks helpful this year can affect what happens later. A multi-year view can reveal consequences that a one-year tax review may miss.
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A small connected tabletop model sits in a calm sunlit room, suggesting how one tax decision can touch several review points.
Ross Marino | Feb 4, 2026

Before You Convert, Give, or Sell: See How the Tax Decisions Connect

Roth Conversions
Tax Planning
Charitable Giving
Investments
Before a Roth conversion, gift, or sale, review what else may change in the same year or later.
Read More
A biracial couple sits together in a sunlit room, studying a decision tray as they think through connected retirement choices.
Ross Marino | Jan 10, 2026

When Retirement Decisions Connect, the Weight You Feel Starts To Make Sense

Retirement Income
Social Security
Investments
Tax Planning
Retirement stress often stems from interconnected questions, not a single issue. See how one answer can change another.
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A calm living room scene shows a mixed pile of papers being separated among a protective document box, a scanner, and a secure discard container to show that records are easier to sort when each one’s job is clear.
Ross Marino | Jan 8, 2026

Keep, Scan, or Shred? A Simple Path to Paper Control in Retirement

Recordkeeping
Tax Planning
Estate Planning & Legacy
Scams & Digital Security
When every paper feels important, a cleanup can stall. Start with what the document still needs to prove.
Read More
A wooden organizer separates retirement spending into essential costs, flexible choices, healthcare, taxes, and income sources, showing why one percentage cannot capture a household’s needs.
Ross Marino | Jan 4, 2026

The Problem With 70 to 80%: What Retirees Really Need to See

Retirement Spending
Retirement Income
Social Security
Medicare
Tax Planning
A retirement income percentage can serve as a starting point. A household plan becomes more useful when it shows the spending that must continue. It should also
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Woman in her 60s with light brown skin stands in a bright artisan studio, her left hand resting on a counter with no ring visible.
Ross Marino | Dec 12, 2025

Succession Is Not One Decision: How the Pieces Fit Together Near Retirement

Business Succession
Tax Planning
Estate Planning & Legacy
Retirement Income
Succession can involve timing, taxes, and people. See how the pieces fit before treating the sale as the only decision.
Read More
Connected glass vessels with water flowing between them, illustrating how retirement income decisions influence one another over time.
Ross Marino | Dec 3, 2025

Social Security at a Crossroads: Start Now or Build a Bigger Lifetime Benefit?

Retirement Income
Social Security
Tax Planning
Family Support
A Social Security start date affects current cash flow, future monthly income, and sometimes survivor protection. Review what each path is meant to protect
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Dovetail Financial helps people nearing or living in retirement connect decisions about income, taxes, investments, Medicare, healthcare, family support, and life changes. Dovetail Financial Group LLC is a fee-only Registered Investment Adviser headquartered in Wilmington, NC. Advisory services are offered through Dovetail Financial Group LLC. Our team includes CFP® professionals. CRD #311298. Information presented on this site is for informational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any product or security. Investments involve risk and, unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed here. The information being provided is strictly as a courtesy. When you link to any of the websites provided here, you are leaving this website. We make no representation as to the completeness or accuracy of the information provided on these websites.
 

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