Showing 50 results of 203
I'm not a camping guy, and I'm not really a hiking guy. Why, then, did I go on a two-week backpacking trip? And what lessons did I learn? The post What I Learned About Myself, Finance, and Adventuring...
No matter how experienced you are with money, there's always room to grow and learn. It's a characteristic you'll find in the most successful people, including one of the greatest investors of all tim...
Losing $70,000 during the 2008-09 Global Financial Crisis was the majority of our life savings. Here's what I learned from that bear market. The post What It Feels Like to Lose Money appeared first on...
Aging loved ones' care needs put pressure on financial plans and caregivers. It's important to talk openly about options before a crisis happens.
Skip the crowded cobblestones of the 13 Colonies. These four regional routes prove America’s history is best learned on the open road.
I need to run some different scenarios, as I’ve recently learned about the potential benefits of waiting to collect social security, using various other income streams in the meantime and all the vari...
I enjoy continued financial education. While this is generally good, there is a zone where you know enough to be dangerous but not prudent. The post Lessons Learned by a Moderate-Income Physician from...
I got an email yesterday, and I suspect all of you who use Vanguard received the same. It’s rare for me to write within one day of something happening, but […] The post Vanguard’s Security Audit – Wha...
I recently got an e-mail from a reader who’s on the fence about having kids, wondering why we decided to have a kid, and how they can make the decision. I told him while I couldn’t give them the answe...
Three hundred episodes into the Retire Today podcast, the microphone is turned around as author and business strategist Nicole Gebhardt interviews Jeremy Keil about the journey that shaped his retirem...
I’ve made nearly two dozen investments across special purpose vehicles and angel checks in healthcare startups. Here's what I've learned. The post What I Learned Making 22 Healthcare Startup Investmen...
Did you set a budget that matched your planned retirement income and live on that for a period of time before you retired? If you have a partner was it difficult to get on the same page? Wife and I ar...
Healthcare is one of the biggest expenses retirees face, yet few people understand how the system behind their care actually works. Jeremy Keil welcomes physician, hospice doctor, and author Dr. Jorda...
My parents usually have their budget meeting at the kitchen table on a Sunday afternoon for a few hours. Here's what they've taught me. The post What I’ve Learned as a Teen While Watching My Parents i...
For those who are between 59 1/2 and 65, do look into doing (some) Roth conversions within your IRA/401K accounts. If you don't, you may end up in a bind in the future. I did not do any Roth conversio...
David Conti has spent decades writing about retirement, Social Security, Medicare, and personal finance. After helping others prepare for retirement throughout his career—including his time at Fidelit...
Is your portfolio as well built and diversified as you think? If you're worried it won't help keep you safe in retirement, it could be time to renovate.
This past Father's Day, June 21, 2026, I had a choice to make. I could play pickleball from 9am to 12noon at an indoor club called Flyte, a 30-minute drive north. Or I could take my kids 30 minutes so...
Tuesday, June 02 - Monday, June 08, 2026 Most Commented score comments title & link 39 127 comments Type A retired folks - How big was the change for you? And did it hurt? 365 110 comments Grocery sho...
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...
Most of us focus on how much to save for retirement, but what you'll spend is just as important, and your spending habits might change more than you expect.
Tuesday, May 19 - Monday, May 25, 2026 Most Commented score comments title & link 583 558 comments Whoopsies - learnings from regrettable decisions in retirement 94 181 comments Any retirees who plan ...
A few days ago, I learned that there is a regulation that the federal government is proposing that would allow private equity companies to access funds in retirement accounts. Public comment on the pr...
I've been playing poker for money since I was a kid. Here are all the lessons learned that I can apply to my investment life. The post Financial Lessons Learned from Playing Poker appeared first on Th...
If The Pitt’s chief attending has you rethinking the daily grind, it might be time to plan a strategic career pause — before you call it quits for good.
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...
Joe Schmitz Jr. and Jeremy Keil explore the 2% Club of retirees and the unique challenges that come with significant retirement savings and a pension. https://youtu.be/G04JKpKyLJ0 Most retirement conv...
While critics complain that economists are always at odds, there are plenty of areas of agreement that contain valuable lessons for our working lives and more.
What do retirees on Medicare do about dental and vision coverage? Are there programs you can sign up for? I just learned that these are not covered by Medicare, which seems crazy. (61 year old plannin...
One of the most fortunate events of my life was my first job after college at the Center for Retirement Research at Boston College (CRR). Not because of the salary — I think I earned less than $40K. W...
Jesse Cramer and Jeremy Keil detail 7 real world lessons learned from working with hundreds of retirees. There’s a big difference between studying retirement… …and actually sitting across the table fr...
I'm hanging out with my four-year-old grandson, he's on my lap talking away, but my mind was elsewhere. I was thinking about the future. I wasn't focused on him at all, but rather an important convers...
As of today, I’ve published 500 blog posts online since January 2017. That’s slightly more than 1 per week. Given ... Read more
The first quarter of 2026 brought a whirlwind of market events—geopolitical shocks, surging energy prices, and a notable shift away from mega-cap US growth stocks. Despite the turbulence, the markets ...
Advisors acting as financial planning sherpas can guide clients up tricky terrain to reach retirement peaks.
“May the Fourth be with you.” A long time ago, in a galaxy far, far away, a kid sat too ... Read more
Using ‘Atomic Habits’ to reach your financial goals — James Clear's habit framework applied to wealth building and long-lasting confidence. The post ‘Atomic Habits’ and Your Money: 6 Lessons for a Wea...
After decades writing about retirement — first at Fidelity Investments and now as an independent writer and coach — an expert turns 65 and reflects on what he's learned.
We've published more than 50 profiles of regular people sharing how they made their first $1 million. Their stories are rich with helpful insights.
I’m just not a sit-around-the-house kind of guy, never have been. I also think it’s a blast to learn something new, especially under the eye of someone who really knows what they’re doing. And so I kn...
Played competitive tennis for about 30 years. Stopped two years ago, not by choice. The knees made the decision for me. I thought retirement would at least mean I could sleep through the night. It has...
I recently attended a financial advisor conference focused on artificial intelligence. Drawing on what I learned, this post summarizes my thoughts on how AI may reshape financial planning for retireme...
They say too much TV will rot your brain. I spent many hours watching television, and my brain is fine—and I learned plenty about finance. The post The Financial Lessons I’ve Learned from Watching My ...
Holding too much company stock can be disastrous — as Silicon Valley Bank and Kodak employees learned the hard way. The key is to diversify as soon as you can.
No matter what you think about previous generations, they just might have legit financial advice that can help you reach your goals. The post 5 Financial Lessons That Boomers Taught This Millennial Th...
From a surprise hip surgery to your stories of reinvention, I’m looking back at a year of navigating retirement alongside you.
Lessons from ERISA Expert Witness Eric Dyson on how to reduce fiduciary risk and be better prepared if the Department of Labor comes calling.
As a semi-retired physician, here's how I handled a huge bull run and the tariff fears in 2025. I definitely made some investing mistakes. The post What’s Your ‘Sleep Well’ Number? Lessons from a Mark...
One thing I’ve learned from 30 years of investing and DIY money management is that there is always another way — and often the other way is more “optimized” than the current way. I put optimized in qu...
January 10th, 2026 is the 1 year anniversary of my retirement! I can’t believe how fast the year flew by. I was 61.5F when I finally had the courage to let go of my career & paycheck. I have finally l...