Insights & Financial News | Oak Road Journal

Insights

How Long Do I Have to Roll Over My 401(k) After Leaving a Job?

There's no deadline to roll over your 401(k) — but waiting too long could still cost you. Find out what actually matters and when you need to act.

Can I Roll My 401(k) Into an IRA Without Penalty? Three eggs labeled "401K," "ROTH," and "IRA" resting on a bed of U.S. currency, illustrating the concept of a 401(k) to IRA rollover.

Can I Roll My 401(k) Into an IRA Without Penalty?

One wrong move on a 401(k) rollover can cost you 10% — gone before you even know it. Learn how to move your retirement savings to an IRA without triggering taxes or penalties, and why the method you choose makes all the difference.

Couple reviewing their financial plan together on a laptop at home

Is It Worth It to Pay for a Financial Advisor?

Is It Worth It to Pay for a Financial Advisor?

Welcome to Oak Road Wealth Management!

Welcome to Oak Road Wealth Management!

What football can teach us about diversification

What football can teach us about diversification

What REALLY matters when it comes to building wealth?

What REALLY matters when it comes to building wealth?

The truth about Social Security

The truth about Social Security

5 Ways to Use Your Tax Refund Wisely

5 Ways to Use Your Tax Refund Wisely

Accepting market cycles and focusing on the process

Accepting market cycles and focusing on the process

Choosing a Financial Advisor: Fee-Only vs Fee-Based

Choosing a Financial Advisor: Fee-Only vs Fee-Based

Where did we get this idea that we need to try to beat the market?

Where did we get this idea that we need to try to beat the market?

Roth IRA and 401(k) retirement account paperwork with a calculator and question mark note, representing the question: how can I avoid paying taxes on my retirement account

How Can I Avoid Paying Taxes on My Retirement Account?

How Can I Avoid Paying Taxes on My Retirement Account?

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?

How Much Do I Need to Retire?

Two professionals meeting at a desk for a free financial advisor consultation in Lee's Summit, Missouri

Can You Speak to a Financial Advisor for Free?

Can You Speak to a Financial Advisor for Free?

A $10 bill representing the importance of financial planning — Oak Road Wealth Management, fee-only fiduciary advisors in Lee's Summit, Missouri

Is $500,000 Enough to Work With a Financial Advisor?

Is $500,000 Enough to Work With a Financial Advisor?

Calendar with a pen highlighting a date, alongside text reading "Why Parents, Not Grandparents, Should Own 529 Savings Plans"

Why parents, not grandparents, should own 529 savings plans!

Why parents, not grandparents, should own 529 savings plans!

What’s Really Killing Your Credit Score?

What’s Really Killing Your Credit Score?

5 Questions You Must Ask Your Financial Advisor (To See If They Are A Fiduciary)

5 Questions You Must Ask Your Financial Advisor (To See If They Are A Fiduciary)

Top-down view of a fiduciary financial advisor reviewing financial documents and statements with a couple at a wooden table.

What Is a Fiduciary Financial Advisor?

What Is a Fiduciary Financial Advisor?

A flat-lay photograph of a leather briefcase, a notebook with the handwritten words "Roth IRA Conversions," a pair of glasses, and a leather journal on a wooden desk.

You Should Want to Pay More Taxes — Here’s Why Roth Conversions Can Save You a Fortune

You Should Want to Pay More Taxes — Here’s Why Roth Conversions Can Save You a Fortune

Social Security card with U.S. Capitol building, representing how Social Security works and federal retirement benefits

How Social Security Works: Benefits, Taxes & Timing

How Social Security Works: Benefits, Taxes & Timing

Tax rate schedules highlighted on IRS tax table, illustrating federal tax brackets for retirement income

What Tax Rate Do You Pay in Retirement?

What Tax Rate Do You Pay in Retirement?

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

How Is Social Security Taxed?

How Is Social Security Taxed?

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

How Is My Pension Taxed?

How Is My Pension Taxed?

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

Do I Have to Pay Federal Taxes on My Retirement?

Do I Have to Pay Federal Taxes on My Retirement?

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

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

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

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?

How Much Do I Need to Retire?

The truth about Social Security

The truth about Social Security

5 Financial Misconceptions About Retirement

5 Financial Misconceptions About Retirement

Accepting market cycles and focusing on the process

Accepting market cycles and focusing on the process

Who really benefits from complex financial products?

Who really benefits from complex financial products?

Physical gold Bitcoin coins scattered over a pile of US dollar bills, featuring a prominent green text box with the headline: "What Happens When Too Few Own Too Much? Bitcoin, Intrinsic Value, and a Warning for the Average Investor."

What Happens When Too Few Own Too Much Bitcoin?

What Happens When Too Few Own Too Much Bitcoin?

Why Simple, Disciplined Investing Builds Real Wealth

Why Simple, Disciplined Investing Builds Real Wealth

What shouldn't you put in a trust — living trust documents on a desk with a pen and glasses, illustrating estate planning decisions.

What Shouldn’t You Put in a Trust?

What Shouldn’t You Put in a Trust?

A well-lit suburban home at dusk representing estate planning and transferring a house to your children.

What Is the Best Way to Leave Your House to Your Children?

What Is the Best Way to Leave Your House to Your Children?

What are the Disadvantages of a QCD?

What are the Disadvantages of a QCD?

What are Common QCD Mistakes to Avoid?

What are Common QCD Mistakes to Avoid?

A checklist with a fountain pen titled "What qualifies as a qualified charitable distribution?" used to illustrate 2026 IRA tax donation rules.

What Qualifies as a Qualified Charitable Distribution?

What Qualifies as a Qualified Charitable Distribution?

Overhead photograph of a tax planning desk set with a 2021 Form 1040, glasses, wooden blocks spelling "TAX", a vintage orange alarm clock, and a stack of money. A green overlay box asks: "HOW DOES THE IRS KNOW YOU MADE A QCD?". Includes the Oak Road Wealth

How does the IRS know you made a QCD?

How does the IRS know you made a QCD?

Detailed photograph of a stack of office folders and a calculator on a desk. The spine of a blue folder clearly displays the word 'TAX'. Overlaid in a green banner is the text: 'Is it better to take a Qualified Charitable Distribution (QCD) or a charitable

Is it Better to Take a QCD or a Charitable Deduction?

Is it Better to Take a QCD or a Charitable Deduction?

Roth IRA and 401(k) retirement account paperwork with a calculator and question mark note, representing the question: how can I avoid paying taxes on my retirement account

How Can I Avoid Paying Taxes on My Retirement Account?

How Can I Avoid Paying Taxes on My Retirement Account?

Tax rate schedules highlighted on IRS tax table, illustrating federal tax brackets for retirement income

What Tax Rate Do You Pay in Retirement?

What Tax Rate Do You Pay in Retirement?

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

How Is Social Security Taxed?

How Is Social Security Taxed?

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

How Is My Pension Taxed?

How Is My Pension Taxed?

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

What Taxes Go Away When I Retire?

What Taxes Go Away When I Retire?

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?

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

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

Do I Have to Pay Federal Taxes on My Retirement?

Do I Have to Pay Federal Taxes on My Retirement?

A flat-lay photograph of a leather briefcase, a notebook with the handwritten words "Roth IRA Conversions," a pair of glasses, and a leather journal on a wooden desk.

You Should Want to Pay More Taxes — Here’s Why Roth Conversions Can Save You a Fortune

You Should Want to Pay More Taxes — Here’s Why Roth Conversions Can Save You a Fortune

2026 Backdoor Roth IRA: The "Loophole" for High Earners

2026 Backdoor Roth IRA: The "Loophole" for High Earners