Seeking Retirement

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Retirement Toolkit: How Does Step Up in Cost Basis Work

This week Roger talks about one of the biggest challenges retirees face today: information overload. He explains why more information doesn't always lead to better decisions and why building a great r...

share.transistor.fm Jul 08 2026

ACA subsidy cliff state research

I ran the KFF calculator for a couple at $84,599 vs $84,601 across nine states. The two-dollar difference ....yikes. I wanted to know what it actually costs a pre-retiree couple to land on the wrong s...

reddit.com Jul 02 2026

How do I decide whether or not to work?

After working for 27 years for the same organization, I found out in late April that my job was being eliminated as of July 1st (a story for another post) I am 64, divorced with two grown children. My...

reddit.com Jun 29 2026

IRMAA: The Medicare Premium Surprise and How to Avoid It

This week Roger breaks down IRMAA Medicare surcharges and why retirees should understand them without letting them dominate retirement planning decisions. He explains how the income thresholds work, c...

share.transistor.fm Jun 24 2026

A contrarian Social Security strategy for the ultrawealthy

Claiming Social Security early might seem counterintuitive for the ultrawealthy, but one advisor says that when the benefits are used to fund life insurance in an irrevocable trust, the strategy could...

financial-planning.com Jun 23 2026

Preparing to downsize. Anyone downsize and regret it?

Wife and I (63) looking to downsize. 20 years in a two story, walk out, 4 bedroom, 3.5 bath that’s been an awesome home to raise two girls. Wife is retired and I’ll retire in next 2 years. Makes a lot...

reddit.com Jun 23 2026

“The 5 People You Meet Before Retirement”

It's important to have perspective throughout life. Preparing for and living in retirement is no exception. In this episode we have a little fun discussing the possible perspectives of “The 5 People Y...

retirementroadmappodcast.podbean.com Jun 19 2026

Know What You Pay: A Guide to Investment & Advice Costs

Roger Whitney explores the relationship between cost and value in retirement planning, focusing on how to better understand the fees associated with financial advice, investments, and insurance produc...

share.transistor.fm Jun 10 2026

Retirement Plan Post Analysis and What I Have Learned

Back story: - 2015 Spouse retired at 65 and receives SS. - 2021 I retired at 64.6 and receive a monthly pension and SS. - Prior to retirement, we were able to save ~300K in cash. ~400K in 401. In 2014...

reddit.com Jun 08 2026

What to do when a layoff gives you a new alternative

I planned to retire 3/30/2027. Today, I was told I am going to be laid off. However because I've been a great performer for so many years, I can choose whether I get laid off October 2026 or Feb 2027....

reddit.com Jun 04 2026

Retire Before Your Kids Leave Home, Not After

I recently received a great comment on my post, Why All Rich People I Know Still Have Life Insurance. It was the last line that stood out. Here's what Marc had to say. I had life insurance ($1M) throu...

financialsamurai.com Jun 03 2026

Teaching Financial Lessons In Graduation Season

Graduations mark the end and beginning of certain chapters in life. In this episode we explore ways of teaching financial lessons at these important junctures in life. Glenn is available for in person...

retirementroadmappodcast.podbean.com May 30 2026

Malpractice Tail Coverage in the Age of Nuclear Verdicts

Tail coverage is no longer a technical add-on for malpractice insurance when terminating a contract. It is long-term financial protection. The post Malpractice Tail Coverage in the Age of Nuclear Verd...

whitecoatinvestor.com May 29 2026

Our Medicare Advantage Experience

I have no affiliation with any health insurance companies and no particular ax to grind. I just want to share our experience because I see a lot of scary information out there about Medicare Advantage...

reddit.com May 28 2026

Why Every Rich Person I Know Still Has Life Insurance

Here's something I've noticed: the loudest voices arguing against life insurance after financial independence almost always come from people who aren't financially independent yet and don't have kids....

financialsamurai.com May 27 2026

17 Physician Disability Insurance Mistakes to Avoid

Many doctors are making critical errors when buying disability insurance. Here's what you need to know to protect yourself and loved ones. The post 17 Physician Disability Insurance Mistakes to Avoid ...

whitecoatinvestor.com May 23 2026

I pulled the trigger, July 3rd will be my last day.

I just informed my manager that I'll be retiring July 3rd. Pretty exciting. The plan has been afoot for a while now, but I needed to let them know. I've tested the numbers, I've created my fund for th...

reddit.com May 12 2026

Retirement “Side Gigs”

Often times retirees like to stay busy with a “Side Gig”. In this episode we delve into a number of ways retirees sometimes continue to work either part time or for a limited period of time in their e...

retirementroadmappodcast.podbean.com May 08 2026

What is Your “Sleep Well at Night” Funded Status?

In this post, we discuss how you can use the Actuarial Approach and its funded status metric to help you feel more confident about your spending plan in retirement. It is a follow-up to our post of Ja...

howmuchcaniaffordtospendinretirement.blogspot.com May 08 2026

Should I buy a car for my fresh College Grad daughter?

I received a severence check from my company for the VSP. Boldin says I have enough to spare a 15k car to my daughter which will help her through Grad School. She will be living with me and we have be...

reddit.com May 06 2026

67+10 months and started receiving my checks today!

I'm still working, born in 1959, and making more than I have in my top 35 years, so working still is going to be bonus additional money. Has anyone ever done this before? Everyone I know retired and s...

reddit.com Apr 24 2026

Retiring this summer, here's a story....

IDK how much I can share here. You never know if someone you know is also here. After 28 years, I'm done. If the work were not so horrible, and the company so greedy, I'd probably stay and make it a f...

reddit.com Apr 23 2026

Housing - Rent or Own during retirement?

Afternoon all - A few days ago, I saw a video from a fianancial consultant who was advocating that if you own a home you should consider selling it when you retire, take the proceeds from the sell and...

reddit.com Apr 20 2026

Unneeded life insurance policies?

Whole life policies purchased 35 years ago, very small and dwarfed by our current portfolio. But still paying for it every month. Really want to cash them out now so my kids have a couple things left ...

reddit.com Apr 18 2026

Health, Vision, Dental Insurance for people under 65

I am not yet retired but getting my ducks in order. I am a NYS teacher. If I retire at 62 I need to pay for my own insurance until Medicare at 65. The school’s health insurance for both my husband and...

reddit.com Apr 16 2026

Today is my first day of retirement

Yesterday was my last day of work. I just turned 61 on Easter. I have a full NYS retirement pension after working 30 years in public service. This feels weird. I am in the process of moving to be a bi...

reddit.com Apr 13 2026

Post Advisor Meeting - It's going to be okay

This is my first post in this group, so if this is out of place or out of line, I'm happy to remove it. I never had a plan for retirement, just, sock money away in a Vanguard account and hope for the ...

reddit.com Apr 12 2026

Graded vs. Level Premium Disability Insurance

Disability insurance is a must for a doctor, and plenty of options exist. Here's what to know about graded vs. level premium insurance. The post Graded vs. Level Premium Disability Insurance appeared ...

whitecoatinvestor.com Apr 04 2026

Die With Zero: Are You Giving Your Kids Too Much? - 575

Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to build your own retirement AND support your kids financially, today on Your Money, Your Wealth® podcast number 575. "Lloyd and Diane" in Mo...

purefinancial.com Apr 01 2026