Insights & Financial News | Oak Road Journal

Insights

Can a Market Crash Ruin Your Retirement? Understanding Sequence of Returns Risk

In the world of retirement planning, the order in which you earn your investment returns can be just as important as the average return itself. This phenomenon is known as sequence of returns risk.

The Conversation That Never Happened:

Last month, I lost one of my longest-standing clients. But what has stayed with me isn’t the end of her life. It’s what happened at the beginning of her retirement — years before she ever became my client.

Wills for Retirees with $1 Million: The 2026 Guide to a Simple, Secure Legacy

If you’ve reached retirement with $1 million in assets, you are the quintessential “Millionaire Next Door. You didn’t get here through luck; you got here through decades of 401(k) contributions, sensible home buying, and probably saying “no” to a few too many luxury SUVs.

Backdoor Roth IRA 2026: The Strategic Guide for High-Net-Worth Retirees

In the world of high-net-worth financial planning, the Roth IRA is often regarded as being very tax efficient. It offers tax-free growth, tax-free withdrawals, and a complete exemption from Required Minimum Distributions (RMDs) during the original owner’s lifetime.

Qualified Charitable Distribution: The Premier 2026 Tax Strategy for Retirees

In the current 2026 tax environment, retirees with significant Traditional IRAs face a growing challenge: “Required Minimum Distribution (RMD) creep.

Gifting Appreciated Stock: The 2026 Tax Strategy for High-Net-Worth Portfolios

In the current financial climate, high-net-worth investors face a unique set of challenges. With the S&P 500 having seen significant growth over the last five years and the 2026 tax rules now in full effect, your “winners” in your brokerage account might actually be a growing tax liability.

IRA Benefits Over 401(k)

For the average worker, a 401(k) is an excellent “set it and forget it” wealth-building tool. But for the retail investor who has successfully crossed the $1,000,000 threshold, the rules of the game change.

When Can I Retire?

It sounds like a simple question, but the answer is rarely just about hitting a certain age or reaching a round number in your investment accounts. Retirement readiness is a blend of math, planning, psychology, and risk management.

You Should Want to Pay More Taxes

Most people think taxes are the enemy. They’ll say things like, “I want to pay as little tax as possible” or “I’ll deal with taxes later. You should want to pay more taxes. Not today, necessarily — but strategically, intentionally, and at the right time.