Insights & Guides
Perspectives on disciplined investing
Educational articles on retirement planning, risk management, and the principles behind thoughtful, long-term portfolio stewardship.
Filed an Extension? October 15 Is Your Last Chance to Fund a 2025 SEP IRA
Self-employed and filed for an extension? You can still open and fund a SEP IRA for 2025 until October 15 — and deduct it on last year's return. Here's how the rules work.
Married? Your Social Security Claiming Decision Is Really Two Decisions
Spousal benefits, survivor benefits, deemed filing, and the earnings test — the Social Security rules couples most often miss when deciding who claims when.
Trump Accounts Are Open: What Parents and Grandparents Need to Know
Trump Accounts opened for funding on July 4, 2026, with a $1,000 federal contribution for eligible children. Here's how the new accounts work, per IRS guidance.
The Roth IRA Five-Year Rules: Why There Are Two Clocks, and Which One Applies to You
The Roth IRA has two separate five-year rules — one for earnings, one for each conversion. Here's how each clock works, when it starts, and why it matters less after 59½.
Which Account Should You Draw From First in Retirement? Taxable, IRA, or Roth
The standard advice is taxable first, IRA second, Roth last. Here's why that order is only a starting point — and why the years before RMDs can change the answer.
Market Notes: What SpaceX, AMD, Palantir, and Lilly's Earnings Told Long-Term Investors
The first week of August 2026 in plain English — SpaceX's debut quarter as a public company, AMD's record that got sold, Palantir's 93% growth, and Lilly's price-versus-volume story.
Your First RMD at 73: Timing, the April Deadline, and the Two-RMD Trap
Turning 73 means required minimum distributions begin. Here's how the first-year April deadline works and why delaying it can push two taxable RMDs into one year.
Market Notes: What Microsoft, Meta, Apple, and Amazon's Earnings Told Long-Term Investors
Big Tech's July 2026 earnings week in plain English — the numbers Microsoft, Meta, Apple, and Amazon reported, the one-time items behind the headlines, and lessons for long-term investors.
The Inherited IRA 10-Year Rule: What Heirs Need to Know
If you inherited an IRA from someone who died in 2020 or later, the 10-year rule may require annual withdrawals. Here's what to understand before year-end.
Market Notes: What Alphabet, Tesla, IBM, and Intel's Earnings Told Long-Term Investors This Week
A look at what Alphabet, Tesla, IBM, and Intel actually reported in late July 2026 — the numbers, the one-time items that distorted them, and what durable-business investors can learn.
Qualified Charitable Distributions: Give From Your IRA and Skip the Tax on Your RMD
A QCD lets IRA owners 70½ and older give directly to charity, count it toward the RMD, and keep it out of taxable income. Here's how the 2026 rules work.
Social Security's Trust Fund Date Moved Up to 2032: What It Actually Means for Your Benefits
The 2026 Trustees Report projects the retirement trust fund depletes in late 2032, with 78% of benefits still payable. What that does — and doesn't — mean.
Market Notes: What the Banks, the Chipmakers, and UnitedHealth Told Long-Term Investors This Week
A look at what JPMorgan, Goldman Sachs, TSMC, ASML, and UnitedHealth actually reported in mid-July 2026 — the numbers, the caveats, and what durable-business investors can learn.
Earn Over $150,000? Your 401(k) Catch-Up Contributions Are Now Roth-Only
Starting in 2026, higher earners age 50+ must make 401(k) catch-up contributions as Roth. Who's affected, how the $150,000 test works, and what to check.
A Mid-Year Tax Checkup for Retirees: Withholding, Estimated Taxes, and the December RMD Move
July is the right time for retirees to catch under-withholding. Safe harbor rules, the Sept. 15 estimated tax deadline, and a year-end RMD technique.
The SALT Cap Just Quadrupled: What the $40,400 Deduction Means for New York Homeowners in 2026
The SALT deduction cap rises to $40,400 in 2026 — but phases back down above $505,000 of income. What NY-area homeowners should know before year-end.
New York's Estate Tax Cliff: Why Going Just Over the Line Can Cost a Fortune
New York taxes estates above $7.35 million in 2026 — and a quirk called the cliff can tax the entire estate, not just the excess, if you go a little over.
The New $6,000 Senior Deduction: Who Qualifies and How It Works
A new federal deduction lets many people 65 and older deduct an extra $6,000 for tax years 2025 through 2028. Here's who qualifies and the income limits.
New York Capital Gains Tax: What NY-Area Investors Should Know
New York taxes capital gains as ordinary income — with no preferential rate. Here's how the state, city, and federal layers stack up for NY-area investors, and why it matters for planning.
Roth Conversions: When They Make Sense — and When They Don't
A Roth conversion can be a powerful tax-planning tool or an expensive mistake. The difference comes down to your tax rate now versus later, and a few details most people overlook.
2026 IRA & 401(k) Contribution Limits: What Changed and How to Use It
The IRS raised retirement contribution limits for 2026. Here are the new 401(k), IRA, and catch-up figures — and the planning ideas worth acting on.
AI vs. Your Advisor: What Technology Can — and Cannot — Do For Your Retirement
AI-powered financial tools are genuinely useful. They are also genuinely limited. Understanding the difference could save you from an expensive mistake.
Concentrated Stock: Managing Employer Stock Risk Before Retirement
Having too much of your net worth in a single company's stock is one of the most common — and most preventable — wealth risks facing pre-retirees today.
7 Questions to Ask Your Financial Advisor Before You Hand Over Your Portfolio
Most investors never ask these seven questions. The ones who do make significantly better decisions about who manages their money.