The Tax Clarity Letter

Taxes are rarely just about taxes. They influence how we invest, retire, preserve wealth, and plan for the future. The Tax Clarity Letter explores the often-overlooked role taxes play in life's most important financial decisions.

Latest Insights

Investing

Why a 100% Monte Carlo Score Might Be a Warning Sign

Jun 21, 2026

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2 min read

Why a 100% Monte Carlo Score Might Be a Warning Sign

Financial success can create opportunities that are easy to overlook.

Mike Skolnick, CPA, PFS, RICP®

Taxes

The Hidden Cost of Letting the Tax Tail Wag the Dog

Jun 13, 2026

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2 min read

The Hidden Cost of Letting the Tax Tail Wag the Dog

Thoughtful financial decisions require balancing taxes with risk, flexibility, and long-term goals.

Mike Skolnick, CPA, PFS, RICP®

Investing

A Great Investment Can Still Be a Bad Decision

Jun 5, 2026

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2 min read

A Great Investment Can Still Be a Bad Decision

Why successful investments can create difficult decisions about concentration, diversification, and taxes.

Mike Skolnick, CPA, PFS, RICP®

Investing

May 30, 2026

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2 min read

The Paradox of Financial Success

Why building wealth often creates new decisions about risk, diversification, taxes, and long-term planning.

Mike Skolnick, CPA, PFS, RICP®

Investing

Why Selling Company Stock Can Feel So Difficult

May 24, 2026

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2 min read

Why Selling Company Stock Can Feel So Difficult

Exploring the tension between taxes, diversification, and the fear of missing future gains.

Mike Skolnick, CPA, PFS, RICP®

Withholding

Why Bonuses Often Trigger Surprise Tax Bills

May 16, 2026

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2 min read

Why Bonuses Often Trigger Surprise Tax Bills

Understanding the difference between withholding and your actual tax liability.