Sensible Money

10/29/2026

What does a retirement plan’s “probability of success” actually tell you?

In this free webinar, Dana Anspach, CFP®, RMA®, walks through three ways to check a retirement plan: fundedness, a historical audit, and Monte Carlo analysis. You’ll learn what each one shows, what the numbers don’t tell you, and what to consider if your plan falls off track. She’ll also cover the Critical Path®, a number worth checking each year.

📅 Thursday, January 21, 2027
🕘 9:00–10:30 AM PT

Save your spot: https://buff.ly/cdbbLF1

10/15/2026

Better projections aren’t the missing piece in retirement income. Better alignment is.

In her new feature in Investments & Wealth Review, “The Missing Piece in Retirement Income,” Dana Anspach, CFP®, RMA®, explores how advisors can align risk management, spending assumptions, and success metrics with the four phases of retirement: pre-go, go-go, slow-go, and no-go.

She covers matching assets to the specific risks they’re meant to address, modeling spending the way retirement tends to unfold, using a funded ratio as a planning metric, and preparing for risks that fall outside the portfolio, such as fraud, cognitive decline, and underinsurance.

Read the full article: https://buff.ly/Kybx0q8

10/13/2026

Using AI for retirement questions? Dana Anspach has some thoughts. 🪄

After attending an AI course at Stanford, Dana shares in her latest blog post why she now treats AI tools like a capable intern: helpful with guidance and feedback, but worth double-checking. She covers where AI has helped her, where it’s fallen short, and four practices she uses to get more out of it.

Read it here: https://buff.ly/Z04YGhR

How are you using AI? Tell us in the comments!

AI Tools may seem like a magic wand, but only if you know how to use it. I attended an AI course at Stanford, and here's what I learned.

10/09/2026

Retirement planning often focuses on one question: when can I retire? But what comes after matters just as much.

Dana Anspach, CFP®, RMA®, recently joined Joe Saul-Sehy on the Stacking Benjamins podcast to talk through the four phases of retirement: Pre-Go, Go-Go, Slow-Go, and No-Go. They discuss how spending and priorities can shift over time, why building flexibility into a plan matters, how sequence of returns can affect retirement income, and what to consider around taxes and long-term care.

Watch the full conversation:

Most retirement plans focus on one big question: When can I retire?...

10/07/2026

⏳ Last chance to register! "How to Plan for Long Term Care Costs" with Dana Anspach and Stefan Cherneski is happening tomorrow, Thursday, October 8th, 10:00–11:30am PT.

🗓️ Thursday, October 8, 2026 | 10:00–11:30am PT
Save your spot: https://buff.ly/RlJuFmd

10/02/2026

Only a few days left to sign up! 📅 Join Dana Anspach and Stefan Cherneski this Thursday, October 8th at 10am PT for a free webinar on planning for long-term care costs.

Whether it's for yourself or a loved one, this is a great opportunity to get ahead of the tough questions before they become urgent. Reserve your spot:

Health care needs in our 80’s and beyond. Will Medicare cover your needs? What options are available? In this webinar, retirement expert Dana Anspach is joined by insurance professional Stefan Cherneski to cover health care needs in later life.

10/02/2026

Proud to share that our founder, Dana Anspach, was featured on Michael Kitces' Financial Advisor Success podcast — episode 509!

In the conversation, Dana walks through how Sensible Money has built a differentiated retirement planning process, including the three distinct "retirement readiness tests" she uses with clients (Monte Carlo analysis, a fundedness ratio, and historical stress testing) and how she aligns client portfolios directly to their cash flow needs through an asset-liability matching approach.

It's a deep, practical look at what true retirement-income specialization looks like in practice.

🎧 Listen to the full episode: https://buff.ly/L0gSWeT

Kitces.com

09/30/2026

Proud to see Dana Anspach's book "Living Off Your Acorns" featured in Morningstar's roundup of top retirement and investing reads!

Morningstar's Christine Benz spotlights Dana's idea of the "pre-go" years — the stretch before retirement when it's worth thinking through not just your finances, but how you'll find meaning and structure once you stop working. Benz also notes how Dana's real stories help bring the ideas to life.

Check out the full list of recommended books: https://buff.ly/sWX5dym

09/29/2026

Have you thought about how you'd cover the cost of long-term care if you or a loved one needed it someday? It's a question a lot of families wait too long to ask.

Dana Anspach and Stefan Cherneski from Sensible Money are hosting a free webinar to walk through the planning side of long-term care — what to consider, what questions to ask, and how it fits into your bigger financial picture.

🗓️ Thursday, October 8, 2026 | 10:00–11:30am PT
Save your spot: https://buff.ly/RlJuFmd

09/25/2026

Dana Anspach, founder of Sensible Money, recently joined The Motley Fool's Hidden Gems Investing podcast to talk about the years right before retirement — often called the "pre-go" years.

She and host Robert Brokamp covered how to de-risk your portfolio as retirement nears, when to actually pull the trigger on retiring, and strategies to lower taxes throughout retirement. They also discussed the "arrival fallacy"—why reaching retirement doesn't automatically mean fulfillment, and what to do about it.

🎧 Give it a listen: https://buff.ly/TOdfRuM