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A middle-aged man with glasses sits at a wooden table, looking thoughtfully at his laptop while researching the differences between original medicare vs medicare advantage. His focused expression and open notebook suggest he is carefully weighing his healthcare options alongside his Social Security retirement strategy. Medicare and Health Insurance

Social Security and Medicare Decisions That Can Cost You for Life

Original Medicare vs. Medicare Advantage, Social Security timing, and the enrollment mistakes that follow you permanently.

April 15, 2026
A group of happy friends cheers with coffee mugs during a bright brunch, embodying the freedom and social connection that successful DIY retirement planning can provide. Retirement Planning

DIY Retirement Planning Works Better With People You Trust

Most people do DIY retirement planning on their own. Here’s why a small peer group and tools you control can change everything.

April 14, 2026
Hiro Finance Financial Wellness

Hiro Finance Is Shutting Down: Here Are the Best Alternatives for Users Looking for a Smarter Financial Planning Tool

Hiro Finance is gone. Compare the best alternatives, including a powerful AI tool built for smarter financial planning.

April 13, 2026
paying taxes in retirement Retirement Income

How to Pay Taxes in Retirement and Avoid IRS Penalties

Paying taxes in retirement means managing income streams, quarterly deadlines, and the IRS safe harbor, without an employer doing it for you.

April 9, 2026
retirement planning strategies Planning

5 High-Impact Retirement Planning Strategies Most People Never Use

Most people skip retirement planning strategies with the highest payoff. Here are 5 of them, including one that’s essentially free money.

April 8, 2026
A young man with glasses sits on a couch, reviewing financial documents in front of his laptop with a pensive expression as he considers using ChatGPT for retirement planning. Planning

ChatGPT for Retirement Planning: Does It Work?

Using ChatGPT for retirement planning? We asked ChatGPT and Boldin AI the same question: “Can I retire?” This is how they replied.

April 7, 2026
A smiling couple wearing aprons stands proudly in their lush plant shop, representing the small business owners and employees who can benefit from retirement savings programs like CalSavers to secure their financial future. Retirement Planning

How CalSavers Works: What California Workers and Employers Need to Know

Learn how CalSavers applies to California workers and employers, including automatic Roth IRA enrollment, payroll deductions, and benefits.

April 6, 2026
contribution order for retirement accounts Financial Wellness

The Retirement Account Contribution Order: How to Get More From Every Dollar

The contribution order for retirement accounts can affect how much your money compounds tax-free. Here’s how to prioritize for tax efficiency.

April 2, 2026
emotionally intelligent investor Financial Wellness

Emotional Intelligence and Money: Are You Making the Right Decisions With Your Investments?

Money is not all about numbers and analysis. Emotions can help and hurt your financial security. Learn how to be an emotionally intelligent investor.

April 2, 2026
A hand reaching in to stop a row of falling colorful dominoes, symbolizing a strategic intervention to protect assets and mitigate the impact of a heavy capital gains tax on investment returns. Planning

Capital Gains Tax Brackets: How Income Pushes Your Rate Higher

Think you qualify for the 0% capital gains tax rate? Your other income may have already eaten that space. Here’s why, plus the 2026 brackets.

April 1, 2026
strength to strength Lifestyle

From Strength to Strength: The Smart Case for Retiring Earlier Than You Think

Arthur C. Brooks argues that staying in your career too long is a real risk, and that most successful people retire later than they should.

March 31, 2026
Planning

Podcast 109: Social Security & Medicare: What’s Changing and What It Means for You with Mark Miller

Steve Chen sits down with Mark Miller to unpack the biggest changes hitting Social Security and Medicare right now.

March 26, 2026
Roth conversion down market Planning

Roth Conversions in a Down Market: The Tax Window Many Miss

A market drop lowers what you’ll owe on a Roth conversion. Learn how to turn a portfolio pullback into a long-term tax win.

March 26, 2026
When do you have enough to retire Happy Retirement

‘Do We Have Enough?’ How This Couple Knew When to Retire

Leslie and Thomas Martin stress-tested their portfolio and gained the confidence to retire with a personalized financial strategy.

March 25, 2026
How much to invest in stocks Planning

How Much in Stocks? A Yale Formula Rethinks Allocation Rules

James Choi’s investing model suggests your stock allocation should depend on income, savings, and future earnings, not just age.

March 24, 2026
The odyssey plan Happy Retirement

The Odyssey Plan: Design 3 Futures Before You Lock in Your Retirement

The Odyssey Plan helps you explore bigger possibilities, test tradeoffs, and choose with real confidence.

March 20, 2026
Mutual fund fees Retirement Savings and Investments

Fees and Expenses on Mutual Funds and ETFs: A Complete Guide to the Often Misunderstood and Hidden Costs of Investments

Are you aware of just how much investing is costing you? Explore all the fees associated with your mutual funds and ETFs.

March 19, 2026
best state for retirement Housing and Home Equity

Where Should You Retire? A 9-Factor Framework to Get It Right

Explore 10 things to think about – lifestyle and financial factors – when considering the best state for retirement.

March 19, 2026
Planning

Video: Taxes in Retirement Office Hours

Planning for the future should involve strategizing to minimize taxes. Explore 25 tips to help you plan, do retirement tax filings, and save money.

March 13, 2026
market volatility Retirement Savings and Investments

10 Questions to Ask Yourself During Market Volatility

When markets feel uncertain, asking the right questions matters. These 10 questions can help you review your financial plan and make smarter decisions during volatility.

March 13, 2026
Stock market goes up Planning

The One Chart to Review Every Time the Markets Get Unsteady

Review the long term trajectory of the S&P 500, see how long historic recoveries have taken, and learn how to protect your financial security.

March 13, 2026
tax season checklist Taxes

Tax Season Checklist: 10 Essential Considerations to Review for Your 2025 Return

Are you “lucky” enough to have to worry about #3? Did you remember #5? Explore all 10 tips on this tax season checklist.

March 4, 2026
state taxes Housing and Home Equity

Which Are the Most Tax Friendly States for Retirees 2026?

Are you in a tax friendly state for retirees? Explore the best states for taxes and review the income and sales tax rates in all 50 states.

March 3, 2026
ikigai Aging Well

Blue Zones Report: 3 Okinawan Secrets to a Long Emotionally, Intellectually, and Physically Healthy Life

Want to live healthfully to 100? Learn the powerful and well researched Okinawan secrets to a long life: ikigai, moai, hara hachi bu and more.

February 26, 2026

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