retire early Archives - Page 2 of 3

February 20, 2023February 19, 2023

Darrow Kirkpatrick: Beyond Doubt on the Colorado Trail

Today on episode 55 I’m honored to welcome Darrow Kirkpatrick, former engineer, climber, investor, author, and the creator of the popular blog CanIRetireYet.com. Darrow began serious saving and investing in his mid-30s and retired at age 50 in 2011 from a career in software engineering.

In this wide-ranging interview, we explore why Darrow stepped away from personal finance writing after creating a popular blog, his adventures on the Colorado Trail and the inspiration for a memoir, and the journey and struggle to finding meaning and purpose at any stage in life.

December 19, 2022December 18, 2022

QA9: What Is the Point of Financial Optimization?

We’re back to the digital mailbag to answer your questions!

For this week:

Hot Seat Questions: My favorite blogs, podcasts, articles, and books. Musings on my biggest financial mistakes and the advice I’d give my younger self.
How do my wife and I keep meaning and purpose in our lives without traditional careers?
To sell or not to sell a home that was purchased in 2021
How to sell investments and minimize taxes
The proper hierarchy of investment accounts
Roth vs Traditional 401(k): Which is better?
I-Bonds: Should we be buying more?
Saving strategies for a home down payment
Receiving inheritance in a foreign currency
Critical nuance on withdrawal strategies in a high inflation/poor market return environment
So much more!

October 31, 2022October 30, 2022

It’s Not All Hard Luck with Shay Skinner

In her late teens and early twenties, Shay Skinner was disowned from her family. She struggled with crushing mental illness, which ultimately culminated in a suicide attempt that left her in financial ruin. From this dismal situation, Shay filed for bankruptcy and began a long and fruitful climb toward being whole again. How can we summon the courage to take such measures of personal accountability?

October 17, 2022October 31, 2022

Can The 4% Rule Actually Work For Early Retirement?

The 4% rule suggests that a retiree who withdraws no more than 4% of their portfolio each year could have provided for a 30-year retirement window during most historical retirement windows. And that is true! The problem is that the FIRE community, however, perpetuates at least two misconceptions when discussing the 4% rule. Today, we address those common misconceptions about utilizing investment income. And, most importantly, we discuss how to use a flexible withdrawal strategy to weather bear markets and/or reduced future returns.

September 19, 2022September 18, 2022

Earning to Buy Time with Meghan and Jeff (A Way to FI)

Today’s guests on episode 44 are Meghan and Jeff, two Colorado climbers who are at very different positions on the spectrum of financial independence. Jeff achieved financial independence along with his wife, Rose, over four years ago. Meghan, along with her husband, were inspired to get serious about their personal finances after meeting and learning from Jeff and Rose. Jeff and Meghan now write about their experiences and learnings at awaytofi.com.

Today we discuss their different origin stories, long-term goals, and shed some light on the fraught balance between work, money, family, and the seemingly elusive control of our time.

March 21, 2022March 20, 2022

EP 26: How to Spend Retirement Money Early

This week on episode 26, we revisit the Roth conversion ladder, a method used to spend retirement money early without penalty and with little to no tax burden.

February 28, 2022March 13, 2022

EP 24: Bitches Get Riches: What Do We Really Value?

Today on episode 24 I’m thrilled to host Piggy and Kitty of Bitches Get Riches. Yes, you heard that right. These ladies have generously self-applied the “B” word, offering me cover from the internet masses for using it in this case. You’ll hear it soon: I’m cancel-proof on this one. Piggy and Kitty write and host their own podcast dedicated to imparting “funny lessons about the adulting skills we were never taught, yet mysteriously expected to know.” Sound familiar?

December 20, 2021December 19, 2021

EP 18: Kenzie King: Hiking the Pacific Crest Trail

Today on episode 18 I want to welcome Kenzie King. If you listened to last week’s interview with Michael Langer you will recognize Kenzie as Michael’s girlfriend. Kenzie and Michael walked away from lucrative engineering careers in Houston, Texas and moved into a van. Only months later, seemingly on a whim, they smashed the Pacific Crest Trail, hiking over 2,600 miles across California, Oregon, and Washington.

I promise that this is not a retelling of last week’s story. Kenzie has a very unique perspective on their journey. And regardless of your thoughts on the backpacking or thru-hiking, Kenzie shares a number of insightful opinions on the evolving dynamics of workplace culture, relationships in trying environments, and levels of financial or emotional security necessary to make bold and truly lasting changes in our lives. Hang on all the way to the end for some of the best moments of this conversation.

December 6, 2021December 5, 2021

EP 16: (Part 1) The Boring Guide to Successful Investing

This week on episode 16 I want to revisit a two-part series on the nuts and bolts of our very simple investing strategy. I wrote these posts early in the history of this website, back in late 2018. We felt an investing strategy needed to be simple and lasting, so you might be surprised to learn how boring it all seems. But in this case, boring is good.

And like a simple investing strategy should be, it really hasn’t changed much. However, once we achieved financial independence and left our traditional jobs, we have made some minor changes to our plan. And I’ll share those changes with you today.

November 29, 2021November 28, 2021

EP 15: Craig Faulhaber: Near-Death Experiences and Early Retirement

My guest this week is climber, math professor, and real-deal van lifer, Craig Faulhaber. On September 19, 2021 Craig was involved in a very serious climbing accident. This is the sort of accident that can end a life at worst, and dramatically alter its course at best. But, as you will hear in this conversation, Craig has an amazing sense of optimism in the face of very difficult life events.

To add to my shock at his accident, I was surprised to learn that Craig was on the cusp of retiring early just before his accident. Please enjoy this special conversation where we discuss the delicate nature of life, unconventional living, home ownership, relationships and marriage, and even the ethics of investing. Plus so much more!