#251: Do you love the idea of making money on your own -- without a boss?
Can you imagine deciding how you spend each day?
Are you bored and looking for a challenge? Do you love the thought of adventure?
Today’s guest, Chris Guillebeau, knows all about hustling, living an unconventional life, working towards seemingly impossible goals, and combining his interests into an epic lifestyle business that brings him freedom and joy.
Chris is the New York Times bestselling author of The Art of Non-Conformity, The $100 Startup, and The Pursuit of Happiness. He has traveled to 193 countries, served four years as a volunteer on a hospital ship in West Africa, and is a successful speaker, writer, and entrepreneur.
Oh yeah, and he’s a high school dropout. (A super accomplished high school dropout.)
How did Chris accomplish so much without a high school degree? How did he forge a path toward his goals despite depression and anxiety? What advice does he have for aspiring side hustlers and entrepreneurs? Find out in today’s episode.
For more information, visit the show notes at https://affordanything.com/episode251
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From High School Dropout to Successful Entrepreneur, Author and World Traveler -- with Chris Guillebeau

You can afford anything, but not everything. We make daily decisions about how to spend money, time, energy, focus and attention – and ultimately, our life.
How do we make smarter decisions? How do we think from first principles?
On the surface, Afford Anything seems like a podcast about money and investing.
But under the hood, this is a show about how to think critically, recognize our behavioral blind spots, and make smarter choices. We’re into the psychology of money, and we love metacognition: thinking about how to think.
In some episodes, we interview world-class experts: professors, researchers, scientists, authors. In other episodes, we answer your questions, talking through decision-making frameworks and mental models.
Want to learn more? Download our free book, Escape, at http://affordanything.com/escape. Hosted by Paula Pant.

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We delve into the world of Financial Independence (FI) with a pioneer -- Vicki Robin, the co-author of Your Money or Your Life.

In the 1970s, Vicki Robin and Joe Dominguez, from vastly different backgrounds, came together over a shared vision: FI as a life philosophy, not just a savings strategy. Their book, "Your Money or Your Life," which sold more than one million copies, outlined a three-dimensional approach to FI:

Financial Intelligence: Thinking clearly and objectively about money.
Financial Integrity: Aligning your spending and earning with your values.
Financial Independence: Breaking free from paycheck dependence and limiting beliefs about money.

In this podcast episode, Vicki will discuss a new dimension she's added:

Financial Interdependence: Recognizing the importance of giving and receiving within our communities and the world.

Vicki and I discuss how to move beyond "just the money" during the quest for financial freedom.

This episode originally aired in 2018.

We're sharing this as part of GREATEST HITS WEEK, a 5-day series in which we're sharing 5 episodes, across 5 days, that we produced during the earliest years of the Afford Anything podcast. You may have missed it then; enjoy it now.
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Vicki Robin: Financial Independence After 70 [GREATEST HITS WEEK]

Esquire Magazine editor-at-large and bestselling author A.J. Jacobs joins the show to discuss his experimental approach to life.
Jacobs, whose TED Talks have been viewed more than 3 million times, shares best practices around motivation, habits, confidence, boosting happiness, and optimizing creativity.
In this episode:
-- Discover the benefits that come from frequently changing your habits
-- Learn why "fake it 'til you become it" is A.J.'s secret weapon for habit development.
-- Explore how extreme gratitude can transform your mindset.
-- Hear a cautionary tale of healthy living gone wrong.
-- Learn how to make any career or business connection by unearthing the way in which you're distant cousins (as everyone on earth is, at most, roughly 70th cousins)
Plus, hear a hilarious story about Jacobs revealing his entire sexual history to actress Scarlett Johansson.
This episode originally aired in 2017. 
We're sharing this as part of GREATEST HITS WEEK, a 5-day series in which we're sharing 5 episodes, across 5 days, that we produced during the earliest years of the Afford Anything podcast. You may have missed it then; enjoy it now.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

A.J. Jacobs: Habits, Health, and Human Connection [GREATEST HITS WEEK]

Stocks or skills? How should you invest? Should you pour money into unlocking your income potential? Or should you pour money into the market?

Forget the motivational posters -- unlimited potential is real. But unlocking it takes investment. The question is: Do you invest in yourself or the market? Stocks, bonds, real estate offer clear returns. But what about investing in your skills, a side hustle, or education? 

Financial advisor Michael Kitces joins us to crack the code on maximizing your return on investment, both personal and financial. Learn how to make smarter choices about your future and unlock your true potential.

We're sharing this as part of GREATEST HITS WEEK, a 5-day series in which we're sharing 5 episodes, across 5 days, that we produced during the earliest years of the Afford Anything podcast. You may have missed it then; enjoy it now.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Michael Kitces: Investing in Stocks vs. Skills [GREATEST HITS WEEK]

JL Collins, the author of "The Simple Path to Wealth," achieved financial independence in 1989 with a surprisingly simple strategy: saving half his income and investing in index funds.

In this episode, JL breaks down his ultra-simple investing approach. He argues that keeping things uncomplicated leads to better results in the long run. "The less you mess with your investments," he says, "the more freedom you have to focus on what truly matters."

This episode is for anyone who feels overwhelmed by complex investment strategies. Learn how to set your finances on autopilot and get on with living your life.

We originally recorded and aired this episode in 2016.

We're sharing this as part of GREATEST HITS WEEK, a 5-day series in which we're sharing 5 episodes, across 5 days, that we produced during the earliest years of the Afford Anything podcast. You may have missed it then; enjoy it now.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

JL Collins: How to Beat Wall Street with a Boring Portfolio [GREATEST HITS WEEK]

Today’s guest is Jean Chatzky, financial editor for the TODAY Show, host of the HerMoney podcast and a frequent guest on TV shows like Oprah, Regis & Kelly, and The View.

We discuss six money rules to guide your spending, including:

#1: The more time you spend looking, the less happy you’ll be with what you find.
#2: Your retirement trumps their tuition.
#3: Losing money hurts more than it should.
#4: Big numbers make smart people do stupid things.
#5: Don’t lend money to friends & relatives, and don’t co-sign for loans.
#6: If it's 50% off, it’s still 50% on.

This leads us into discussing tactics to prevent wasteful spending, such as:

-- The 10/10/10 Rule: How will you feel about this purchase in 10 minutes? 10 months? 10 years?
-- The 24 Hour Rule: Delay the purchase by 24 hours. Do you still want it?
-- Only Pay Full Price: Paradoxically, avoiding sales – and ONLY buying items at full price – might help you save more money in the long run.

Finally, we chat about how to balance financial priorities when you and your spouse want different things. What if you want to retire early, but your spouse doesn’t? How do you handle this?

Jean shares her ideas on these topics in this episode, which we originally recorded and aired in 2016.

We're sharing this as part of GREATEST HITS WEEK, a 5-day series in which we're sharing 5 episodes, across 5 days, that we produced during the earliest years of the Afford Anything podcast. You may have missed it then; enjoy it now.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

From High School Dropout to Successful Entrepreneur, Author and World Traveler -- with Chris Guillebeau

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