#409: Liz and her husband are planning to retire in 5 to 10 years. They have rental income properties, but Liz is bored of managing these, and she’s intrigued by the idea of buying stocks at a discount when the market is low. Should she sell her rental properties and use the money to buy stocks instead?
Rebecca is a high income earner and thinking about investing in a Roth 401k … but she’s scared of how much she’ll have to pay in taxes. Should she do it anyway?
Anonymous made big changes last year: she got a new career AND sold a house! Now she needs help figuring out capital gains and lowering how much she’ll have to pay in taxes … and she won’t have access to her company’s 401K for most of the year.
Kyle and his wife are moving into their dream home! What should they do with their current place?
Former financial planner Joe Saul-Sehy and I tackle these four questions in today’s episode.
Enjoy!
P.S. Got a question? Leave it here
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Ask Paula: Should I Sell My Rentals to Buy More Stocks?

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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Enjoy Part 1 of our two-part Episode 500 special, recorded live at a comedy club in Brooklyn.
Brad Barrett, host of the ChooseFI podcast, joins us on stage to talk about what financial independence ideas and practices have changed … and what ideas and practices have remained consistent, universal and time-tested throughout the years.
For more information, visit the show notes at https://affordanything.com/episode500
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LIVE FROM BROOKLYN: Episode 500 with ChooseFI’s Brad Barrett

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.
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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.
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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.
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Ask Paula: Should I Sell My Rentals to Buy More Stocks?

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