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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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.

How to Build a DIY Retirement Plan Without Going It Alone

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
books about retirement and aging

Best Books on Retirement 2026: 27 Picks for Planning and Purpose

Books on retirement planning, purpose, and healthy aging that Boldin readers keep recommending, plus top picks for gifts.

April 12, 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
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.

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.

CalSavers: 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
social security strategies

Social Security Optimization Strategies: 15 Tips to Maximize Your Benefits

Delaying Social Security to 70 can add $100,000+ in lifetime benefits. These are the planning strategies that make the biggest difference.

April 5, 2026
A smiling, confident older Black man with a white beard stands outdoors, radiating the happiness and freedom that come with the decision to retire at 62.

Retire at 62: What It Takes to Make It Work

At 62, Social Security is up to 30% smaller and Medicare is 3 years away. Here’s how to plan for both and know if your portfolio is ready.

April 4, 2026
A multi-generational Black family laughing together in a sunny field, highlighting the importance of legacy and financial planning beyond just the value of an average inheritance.

Average Inheritance From Parents Is $46,200. Most Get Less.

See figures by trust, education, and wealth tier, from $6,100 for the least wealthy to $2.7 million for the top 1%, plus what it means for your plan.

April 4, 2026
contribution order for retirement accounts

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
A smiling man with glasses and an orange sweater sits at his office desk while holding a smartphone, reflecting the convenience of tracking your investments and executing smart retirement tax planning.

Retirement Tax Planning: How to Keep More of Your Money

Retirees often pay more in taxes than they expect. Here’s how to plan withdrawal sequencing, Roth conversions, and RMDs for a lower bill.

March 27, 2026

Podcast 108: 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 Cost Less When Markets Are Down

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
A serene woman is relaxing and gazing at a beautiful sunset from her perch on a large, twisted tree limb. She reflects on her results from life expectancy calculators and how to best enjoy her remaining years.

10 Most Accurate Life Expectancy Calculators for Retirement

Compare the most accurate life expectancy calculators: Living to 100, Blue Zones, SSA and Wharton tools, and more. See who each is best for.

March 26, 2026
A smiling middle-aged woman with curly hair and a warm sweater on a coastal balcony, illustrating a happy lifestyle as she considers options for health insurance at 62.

Health Insurance Age 62 to 65: Average Cost Before Medicare

Average health insurance cost from 62 to 65 often tops $1,000 a month without a subsidy. See real cost ranges and how to plan for it.

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

James Choi’s Formula: How Much Should You Invest in Stocks?

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
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

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