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Blog

Jack Cuddihy | Feb 11, 2026

Tax Planning vs. Tax Preparation: They're Not the Same Thing

Tax Planning
Finance
Retirement
Investments

Many people think about taxes once a year — when April rolls around and it's time to file.

By then, the year is already in the rearview mirror. The decisions

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Jack Cuddihy | Jan 30, 2026

Tax Planning vs. Tax Preparation: They're Not the Same Thing

Tax Planning
Retirement
Finance

Many people think about taxes once a year — when April rolls around and it's time to file.

By then, the year is already in the rearview mirror. The decisions

Read More
Jack Cuddihy | Jan 6, 2026

5 Financial Crossroads That Could Reshape Your Future

Finance
Retirement
Family
Tax Planning
Risk Management

You know how life tends to throw in a few plot twists?

They don't ask if you're ready. They just show up—with potential financial consequences tagging along.

A

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Jack Cuddihy | Dec 11, 2025

What 2025 Taught Us About Staying the Course

Investments
Finance
Risk Management
Retirement

Some years pass quietly. 2025 wasn't one of them.

Between market swings, geopolitical shocks, and a news cycle that never seemed to pause, this year tested

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Jack Cuddihy | Dec 9, 2025

Common Retirement Regrets—And Proactive Moves to Consider

Retirement
Finance
Savings
Risk Management
Insurance
Health
Family
Estate Planning

Many people don’t regret being retired. They regret how they got there.1

“I wish I had saved earlier.”

“I didn’t think long-term care would matter.”

“I should’ve

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Jack Cuddihy | Nov 19, 2025

One Economy, Two Realities: Understanding Today's Economic Divide

Finance
Investments
Savings
Credit
Risk Management
Retirement

It’s possible for one economy to tell two different stories. One of growth, opportunity, and abundance. Another of constraint, anxiety, and scarcity.

This isn't

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Jack Cuddihy | Nov 8, 2025

How to Talk to Your Aging Parents About Estate Planning (Without Making It Tense)

Estate Planning
Family
Health
Disability
Insurance
Risk Management

These conversations aren’t easy.

Bringing up long-term care or estate planning with aging parents can feel like stepping on a landmine—awkward, emotional, maybe

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Jack Cuddihy | Oct 31, 2025

What Recent Inflation Signals Mean for Financial Planning

Finance
Savings
Investments
Retirement
Tax Planning
Credit
Risk Management

Inflation has been the boogeyman of the economy for months.

Sticky prices. Rising gas costs. A looming rate hike.

The latest report provided useful data for

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Jack Cuddihy | Oct 14, 2025

Rethinking Retirement: Why True Wealth Is More Than Money

Retirement
Lifestyle
Health
Family

Rethinking Retirement: Why True Wealth Is More Than Money

You’ve mapped out your dream retirement. Maybe it’s a cozy beach town, golf twice a week, time with

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Jack Cuddihy | Sep 11, 2025

Overlooked Retirement Expenses (And How to Plan for Them)

Retirement
Finance
Health
Tax Planning
Family
Real Estate

A comfortable retirement doesn’t come with a fixed price tag.

Expenses can change over time, and some of the most important ones are easy to overlook.

That’s one

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Jack Cuddihy | Aug 13, 2025

Why Your Brain Sabotages Your Investment Plan (No Matter What the Market Does)

Investments
Finance
Savings
Risk Management

The Dow crosses 45,000. Your brain whispers: "This has to be the top."

The market drops 15%. Your brain screams: "Get out before it gets worse!"

Different

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Jack Cuddihy | Jul 10, 2025

Why Patience Beats Perfection: The Long-Term Investor's Guide to Market Timing

Finance
Investments

Over the course of your investing life, you’ll encounter market lows and highs. Headlines often spotlight the extremes, especially when markets reach record

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