Insights & Financial News | Oak Road Journal

Insights

Torn hole in brown paper revealing the word “REGRET,” representing the #1 regret of retirees

What Is the #1 Regret of Retirees?

The #1 regret of retirees? Often, it's working too long. See why it happens and how a financial plan helps you retire with confidence.

Glowing incandescent light bulb on a soft gray background, symbolizing smart retirement planning ideas for 60-year-olds

What Is Good Retirement Advice for 60-Year-Olds?

Retirement considerations for 60-year-olds: 3 decisions to make now. Cover healthcare before Medicare, Social Security timing, and the income valley.

Paper cutout of a human head in light blue with a white jigsaw puzzle brain, representing mentally adjusting to retirement

How Do You Mentally Adjust to Retirement?

Your savings may be ready for retirement, but are you? Learn how to mentally adjust to retirement and build a life beyond work.

Smiling retired couple meeting with a virtual financial advisor on a laptop at home

Virtual Financial Advisor: How Oak Road Wealth Management Works With You Online

Work with a virtual financial advisor from anywhere in the U.S. See how Oak Road's fee-only fiduciaries plan, invest, and meet with you by video.

Golden bull and silver bear figurines face off before a stock chart, illustrating a Roth conversion in an up or down market

Is It Better to Do a Roth Conversion When the Market Is Up or Down?

Roth conversion when the market is up or down? A dip moves more shares for the same tax bill, but no one can time it. Here's what to do instead.

Person standing on pavement surrounded by arrows pointing in different directions, representing Roth conversion decisions

How Many Times Can You Do a Roth Conversion in a Year?

How many times can you do a Roth conversion in a year? No limit, but doing too many can backfire. See the smarter way to plan yours.

Four-panel image of one tree in spring, fall, winter, and bare branches, representing the best time of year for a Roth conversion

What Time of Year Is Best to Do a Roth Conversion?

What time of year is best to do a Roth conversion? Early can mean more tax-free growth. Late can mean fewer surprises. Here's how to choose.

Wooden blocks spelling the word PENALTY, illustrating whether a Roth conversion without penalty is possible

Can I Do a Roth Conversion Without Penalty?

Roth conversion without penalty? Yes, at any age. But one withholding mistake can trigger a 10% penalty. Here's how to convert the right way.

Torn paper scrap labeled "Roth IRA" on a textured surface, illustrating the sweet spot for Roth conversions

What Is the Sweet Spot for Roth Conversions?

Convert too little and you leave savings behind. Too much and you overpay. Find the sweet spot for Roth conversions: the right year and the right amount.