Retirement Planning

Your retirement plan is a roadmap to your future, but like all plans, it is likely to evolve and change over time.

The economy will not behave exactly as you have anticipated and your own life and goals will also change over time.

And, the best retirement planning goes way beyond your savings and investments. Numerous other factors like Social Security, when you stop work, your longevity, home equity, debt, taxes, income sources, inflation, spending, healthcare costs, lifestyle choices, and more may actually represent greater value or be more important than your savings with regards to your overall financial wellness.

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diy 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
paying taxes in retirement

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

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
chatgpt retirement 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
CalSavers

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

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

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

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

‘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

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

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
best state for retirement

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

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
state taxes

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
create a retirement plan

19 Reasons to Create Your Own Retirement Plan (It’s A Lot More than Knowing, “When Can I Retire?”)

What can you learn by creating a retirement plan? Get inspired by 19 planning insights and discover your path to a secure future.

February 26, 2026

Understanding How Concepts of Time Impact Your Financial Plans

Explore how different philosophical and cultural definitions of time can provide insights into your financial decision-making process.

February 19, 2026
retirement manifesto

Write A Retirement Manifesto: A Declaration of What You Want Your Life to Be

The transition to retirement is an ideal time to write a manifesto. In retirement you are no longer defined by the work you do for money. You can be defined by you.

February 18, 2026

Podcast 107: What Happens Next for CalSavers? With Fiona Ma & David Teykaerts

CA State Treasurer Fiona Ma and CalSavers Director David Teykaerts break down how the state is improving retirement access.

February 5, 2026
work retirement savings

Still Working? Here Are 12 Ways to Supercharge Your Retirement Savings and Retire Earlier

Consider all the strategies for maximizing saving opportunities while you are working.

February 5, 2026
dirty little financial secrets

The 7 Dirty Little Financial Secrets People Don’t Tell Their Spouses — or Their Advisors

7 common financial secrets that quietly undermine goals — and how bringing them into the open leads to better decisions and more confidence.

February 5, 2026
no regret retirement

The No-Regret Retirement: 16 Ways to Plan for a Life of Freedom and Confidence

A no-regret retirement isn’t about timing or a big bank account. Learn how to plan with clarity and confidence for the life you want.

January 29, 2026
mandatory retirement age

Mandatory Retirement Ages: Pros, Cons, and Why Age Alone Falls Short for Planning

Explore why you should break from conventional thinking on retirement ages, particularly the idea of a mandatory retirement age.

January 23, 2026

Podcast 106: The Automatic Millionaire in an Automated World with David Bach

David Bach joins Steve Chen to discuss The Automatic Millionaire, his IRA Flat Tax idea, RMD delays, retirement spending, and AI in financial planning.

January 22, 2026
financial roadblocks

The 4 Mindset Shifts That Unlock Retirement Planning Progress

Here are 4 mindset shifts for overcoming the mental blocks that might be preventing you from retirement planning progress.

January 22, 2026

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