Insights & Financial News | Oak Road Journal

Insights

IRS Form 1040 tax documents — understanding federal taxes on retirement income

Do I Have to Pay Federal Taxes on My Retirement?

Yes — and the wrong withdrawal strategy could cost you thousands. Discover how the three tax buckets work and why sequence of withdrawals matters more than most retirees realize.

401(k) label on hundred dollar bills — Oak Road Wealth Management

What Is a Good 401(k) Balance at Age 65?

A "good" 401(k) balance at 65 is one that funds your retirement goals—but it depends on Social Security, pensions, and other income. Oak Road Wealth Management explains what really matters.

A ceramic jar labeled "Retirement Fund" surrounded by coins, dollar bills, and dice — illustrating the uncertainty and planning involved in retirement savings.

How Much Do I Need to Retire?

Wondering how much you need to retire? The real answer depends on what you plan to spend — not a magic number. Here's how to think about it clearly.

Medicare cards and dollar bills illustrating how Medicare checks your income every year through IRMAA surcharges

Does Medicare Check Your Income Every Year?

Yes — Medicare checks your income every year to determine if you owe an IRMAA surcharge. Learn how it works, the 2026 thresholds, and how to control it in retirement.

Medicare clipboard showing Part A hospital coverage, Part B medical coverage, Part C Medicare Advantage, and Part D prescription drugs, with a stethoscope

Can I Drop My Medicare Advantage Plan and Go Back to Original Medicare?

Wondering if you can drop your Medicare Advantage plan and switch back to Original Medicare? Yes — but timing and health status matter. Oak Road Wealth Management in Lee's Summit, MO explains exactly how.

Typewriter with the word "Premium" typed on paper — illustrating Medicare premium costs for wealthy retirees

Do Wealthy People Pay More for Medicare?

Do wealthy people pay more for Medicare? Learn how IRMAA surcharges raise premiums for high earners — and why a Roth IRA can mean lower Medicare costs, even with millions saved. Oak Road Wealth Management, Lee's Summit, MO.

Medicare Part A and Part B checklist on clipboard with stethoscope — Oak Road Wealth Management

How Much Does Medicare Cost Me Monthly?

Wondering how much Medicare costs per month in 2026? Oak Road Wealth Management walks through Part A, Part B, and Part D premiums, deductibles, and IRMAA surcharges — so you can plan with confidence.

Welcome to Oak Road Wealth Management!

I’m Dan Shepard, Founder and President of Oak Road Wealth Management. Welcome to my new blog! I started Oak Road because I wanted to provide a better experience for investors. There’s a lot of bad information out there about what it takes to build wealth and create Financial Independence.

What football can teach us about diversification

What a great weekend of football, turkey, family and friends! I hope you had a great one! Football has been on my mind and in honor of that time honored tradition, I wanted to relate our nation’s favorite pastime to investing.