Insights from Keith Cheverie

Tips from Keith

Practical guidance and straightforward tips for self-employed professionals navigating health coverage decisions.

September 18, 2026

Navigating the 2027 Health Insurance Rate Increase: A Practical Guide for Healthy Families

Prepare for the 2027 health insurance rate increase. Compare private health insurance vs ACA options to protect your budget during open enrollment.

September 7, 2026

The 90-Day Transition Plan: Going from Corporate to Independent

Planning to leave corporate for independent work? Here's the 90-day plan I walk clients through — protect first, structure second, optimize last.

August 19, 2026

The Healthy Family's Dilemma: Why ACA Plans May Not Be Your Best Option

If your family is healthy, you might be the one funding the ACA system instead of benefiting from it. Here's why private plans often make more sense for healthy families.

August 18, 2026

The Total Cost of Ownership Trap in Health Insurance

Your $450/month premium isn't what you actually pay. Here's why shopping for health insurance by monthly price alone is costing you thousands.

August 12, 2026

The HSA Triple Tax Advantage: The Only Account in America That Does This

The HSA is the only account in America with a triple tax advantage. Here's how it works, why most self-employed professionals aren't using it, and how to get started.

August 11, 2026

Health Coverage Is a Business Decision, Not a Utility Bill

A fractional CFO was overpaying by $6,000/year because he treated health insurance like a utility bill. Here's how your health plan affects your taxes, cash flow, and business structure.

August 10, 2026

The Benefits Cliff: What You Really Lose Going Independent

When you leave corporate to go independent, everyone talks about the salary gap. Nobody talks about the $20,000-$30,000 in benefits you just lost. Here's what disappeared — and how to replace it.

August 3, 2026

Why Your 2027 Health Insurance Rates Are Going Up — and What to Do About It

ACA Marketplace insurers are proposing a median premium increase of 14% for 2027, on top of a 58% jump in 2026. Here's why healthy individuals and families are bearing the cost — and what you can do about it.

July 29, 2026

Brace Yourself: Health Insurance Premiums Are Heading Up Again in 2027

Preliminary 2027 individual-market rate filings show a median proposed increase of about 14%. Here's what self-employed professionals should do now to prepare — starting with not auto-renewing their health plan.

July 20, 2026

Five Questions Every 1099 Worker Should Ask About Health Coverage

Before you choose a plan, these five questions can help you cut through the noise and focus on what actually matters for your situation.

July 15, 2026

COBRA vs. Individual Coverage: A Straightforward Comparison

COBRA is a bridge, not a destination. Here's how the two options stack up so you can decide with confidence.

July 10, 2026

Why Self-Employed Professionals Need a Different Coverage Strategy

You don't have an HR department sorting through options for you. Here's what to think about when you're your own benefit decision-maker.