Facing the Rest of the World with a Nontraditional Lifestyle

When I left my corporate career in early 2020, I didn’t fully understand the ways that I would, in later years, slowly become decoupled and desynchronized from a society that values hustle, status, and self-worth generated to a large degree around our career titles. You’ll read the same thing repeatedly on the internet: Ignore the haters, do your thing.

But when I actually sit down and talk with those who are living a similar nontraditional lifestyle, regardless of their financial position, I find that the tidy internet talking points leave many of us dissatisfied. After all, humans are one of the most social species on the planet. We shouldn’t be surprised by the difficulty in overriding instinct, to go against the grain of what the herd values most. My thinking has evolved dramatically on this subject in recent years, so let’s dig in.

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“The Rewards of Being in One Place for a While” (Meghan Walker and Callan Cooper)

By popular demand, I’ve decided to extend a travel series centered around the topic of building community or maintaining our need for social interactions when away from home. Community building is especially complicated when abroad, where cultures and languages vary considerably from our own. My guests today, veteran travelers with considerable expat experiences, are perfectly suited to discuss this topic.

Meghan Walker, a previous guest who writes at awaytofi.com, spent many of her formative years living abroad in Kenya and New Zealand. Her husband, Callan Cooper, is an expat living in the United States from New Zealand, where they met. Meghan and Callan joined me in my home in Colorado for a rare in-person interview, where we discussed in detail the beauty and challenges of international extended travel, careers, evolving travel philosophies, and financial tactics that can have you living a similar life much sooner than you think.

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Dr. Jim Dahle of the White Coat Investor on Building the Ideal Life

Jim Dahle is the founder of the White Coat Investor, a widely consumed personal finance and investing blog and podcast specifically designed for physicians and other high-income careers. What Jim created in 2011 as a simple blog has grown into a multi-media empire that now employs fifteen people and hosts content from a range of columnists.

Jim has cut back from his full-time (plus) emergency physician career and White Coat Investor responsibilities to focus on what makes life worth living, and that’s where I wanted to pick up this conversation. Jim is a climber, husband, and father of four. Today we discuss how he’s managed to step away, at least slightly, from his hard-charging career and blogging days to what he’s now describing as his ideal life.

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The Great American Student Loan Debt with Emma Crawford

In America, student loan debt has exploded over the last twenty years, with the average inflation-adjusted federal loan debt per student rising from under $29,000 in 2011 to nearly $40,000 in 2020. Students and their parents are paying an increasingly costly price for college education, outpacing growth in expected starting salaries.

After more than three years, loan payments are coming due again after the expiration of a Covid-era forbearance program put in place under President Trump and extended under President Biden. My guest today, Emma Crawford, is intimately familiar with student loans as both a borrower as well as a former university aid advisor, and now as a financial planner.

Emma Crawford is the former Director of Financial Wellness and Financial Aid Advising for the University of Wisconsin School of Medicine and Public Health. She holds the Certified Financial Planner (CFP) designation and is a fee-only financial planner for Perk Planning, based out of Madison, Wisconsin. Emma joins me on the show today to discuss the evolving and complicated world of student loans for the first two-thirds of the show. The final third of the interview is dedicated to discussing the equally convoluted world of financial planners and advisors. We discuss the nature of fee-only advising and who may find this type of service appropriate.

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QA11: Laying It Out in Simple Terms

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

For this week:

  • How has my lifestyle evolved since achieving financial independence and how do I spend my time?
  • Updated thoughts on money and markets
  • Are we putting too much faith in institutions like Vanguard?
  • Can and should life insurance policies be used for retirement savings?
  • Tax avoidance versus accepting higher tax rates
  • What is a Simple IRA and how does it differ from a 401(k)? Can I still do Roth conversions?
  • Savings rates are great! Should I pay less on my loans to maximize my savings?
  • Big picture: Where do I start on getting my financial life together?
  • Outreach and presentations
  • So much more!
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The One Time to Be Average with Dave Rosen

Dave Rosen is a climber and ophthalmologist in his final year of residency. And Dave grew up like so many of us: broadly exposed to the importance of money and taught a thing or two about saving, but investing was a foreign concept and his lack of knowledge was a source of shame.

While Dave skimmed over it, he’s no slouch as a climber. He has bagged a pile of double-digit boulder problems up to V12, sent 5.13c, and developed numerous boulder problems, particularly in the South Mountain area near Phoenix where he and his wife lived for medical school for four years. He is hard-working, analytical, and pragmatic in his career and life approach. 

In this conversation, we discuss how Dave found climbing from the world of canyoneering, his early exposure to money and how that has markedly changed in recent years, the constant pull of greener grass, working backward from an ideal lifestyle, and the ethical and moral dilemmas of early retirement.

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Mike Piper: Down To The Essence Of Smart Money Management

Mike Piper is a CPA and the creator of the Oblivious Investor blog, where he teaches a philosophy of simple and low-maintenance investing.

Mike’s simple philosophy distills down to three primary principles:

  1. Diversify your portfolio
  2. Minimize costs (commissions, fees, mutual fund expenses, taxes)
  3. Ignore the noise.

Mike began his career as a CPA before realizing he could support himself by writing books. Surprisingly, he left his secure job during the 2008 financial crisis. He has gone on to publish seventeen books and is widely considered an expert in social security, tax, and a number of other personal finance topics. His work has been featured in the Wall Street Journal, Forbes, and Morningstar, to name a few.

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Six Important Reasons to Reconsider Early Retirement

Today on episode 65 I’m revisiting a post published almost exactly two years ago. At the time of writing, I’d been away from my corporate job for eighteen months. I spent six months of that time living in a tiny A-frame camper with my wife and dog before resettling in the St. George, Utah area.

I was climbing a lot and working on this website, but I can now comfortably admit that I was in a bit of a low spot in terms of overall life satisfaction. The issue was one of expectations. In other words, I expected too much about a life without my career and I took for granted elements of my work life that enhanced life satisfaction. I was feeling stale with this project—I wouldn’t start the podcast until late summer—and despite having all the time in the world to dedicate to the craft of climbing, I was slowly coming to the realization that I’d used climbing as an attempt to fill a void that was not yet clearly defined or outlined.

Two years later, I’ve spent considerable time addressing each of the areas discussed in this post, to varying degrees of success. Stay tuned in the coming weeks and months for other changes still ongoing.

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