Insights & Financial News | Oak Road Journal

Insights

Social Security cards representing how Social Security benefits are taxed in 2026

How Is Social Security Taxed?

Wondering how is Social Security taxed in 2026? See the exact combined-income thresholds, a step-by-step calculation, and 3 fiduciary-approved ways to keep more of your benefit.

Hand dropping a coin into a glass jar labeled "Pension," illustrating how pension income is taxed

How Is My Pension Taxed?

Federal rules, state-by-state differences, and public vs. private pension treatment — explained by a Lee's Summit fiduciary advisor.

Wooden dice spelling "TAXES" stacked on rising piles of coins, representing retirement tax planning

What Taxes Go Away When I Retire?

Think retirement means tax-free living? Not quite. Here's exactly which taxes disappear when you retire — and which ones follow you anyway.

Person reviewing tax documents and using a calculator to calculate the new $6,000 senior tax deduction

What Is the New $6,000 Tax Break for Seniors?

You may qualify for a new $6,000 tax deduction — but one IRA withdrawal or capital gain could wipe it out. Here's what retirees need to know before year-end.

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.