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Retire With Purpose – The Retirement Podcast

Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life.

Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial, discusses thoughts and ideas with some of today’s foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you’ve always imagined and deserve.

Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.

Latest Episodes:

306: Sharing Your Wisdom in Your Second Act with Chip Conley Aug 01, 2022

Show notes

Today, I'm talking to Chip Conley. Chip founded Joie de Vivre Hospitality at the age of 26, turned it into the second largest boutique hotel brand in America, and sold the business 24 years later. Soon after, the founders of Airbnb came to him for advice, and he joined them as their Head of Global Hospitality and Strategy before settling into a role as their Strategic Advisor for Hospitality and Leadership.

He's also the founder of Modern Elder Academy, the world's first "midlife wisdom school," with a campus in Baja California Sur and one soon to open in Santa Fe. In his most recent book, Wisdom at Work: The Making of a Modern Elder, Chip writes about the value of humility, emotional intelligence, and wisdom–and how companies like Airbnb benefit from skills that can only come with age.

In this conversation, Chip and I discuss the identity crises that come with exits of all sizes and the lessons he learned by joining Airbnb, how our calling evolves over the course of our lives, and how to find (and take advantage of) the incredible opportunities that life transitions give us.

GET A FREE COPY OF CHIP'S BOOK, WISDOM AT WORK!

Here's all you have to do...

Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
Step 2.) Text BOOK, that's B-O-O-K to 866-482-9559 for a link to our book request page, complete the form and we will ship you the book for free. It's that simple!

In this podcast interview, you'll learn:

What it means to be a modern elder.
The difference between calling, purpose, and meaning.
How Chip is working to teach wisdom at Modern Elder Academy.
What midlife is and isn't–and why Chip believes "midlife crisis" to be a misnomer.
The equations that can help us identify (and learn from) our emotions.
Chip's advice for anyone over the age of 50 who's thinking about taking a big leap.

Show Notes: Howardbailey.com/306

Rate & Review the Podcast: RetireWithPurpose.com/review

Weekly Retirement Newsletter: RetireWithPurpose.com/weekend-reading

305: Tax-Loss Harvesting in Down Markets: When You Should & When You Shouldn't Jul 29, 2022

Show notes

This week's retirement reading is from Kitces titled, Why Tax-Loss Harvesting During Down Markets Isn't Always A Good Idea. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/305.

Show Notes: Howardbailey.com/305

Rate & Review the Podcast: RetireWithPurpose.com/review

Sifting through the copious amount of conflicting financial advice and retirement information can be daunting - but it doesn't have to be! Each week, Casey makes it super easy. He hand-picks 4 of the most important articles you need to read, that are beneficial to you whether you're at, near, or in retirement! If you want them sent straight to your inbox, sign up by visiting RetireWithPurpose.com/weekend-reading

304: Calculating Your Retirement Spending Number: A Formula for Pinpointing Income Gaps Jul 22, 2022

Show notes

This week's retirement reading is from Kiplinger titled, An Easy Way to Find How Much You Will Spend in Retirement. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/304.

Show Notes: Howardbailey.com/304

Rate & Review the Podcast: RetireWithPurpose.com/review

303: Professor Jeremy Siegel's Advice for Managing Money and Emotions in a Recession Jul 18, 2022

Show notes

Today, I'm speaking with Professor Jeremy Siegel. Jeremy was the Russell E. Palmer Professor of Finance at the Wharton School of the University of Pennsylvania for many years and now is the Senior Investment Strategy Advisor to WisdomTree. He makes regular appearances to share his expertise on the state of our economy and financial markets. You've likely seen him on CNN and CNBC, or perhaps you've read his columns for Kiplinger's Personal Finance or Yahoo! Finance.

Jeremy Siegel has been called one of the best stock watchers alive. With interest rates and inflation seemingly out of control right now, Jeremy's expertise has been in great demand, and I'm thrilled to have the opportunity to have the man who identified what we now know as Siegel's paradox on the podcast.

In this episode, you'll hear his thoughts on how we should be consuming the information that we see on TV and read online to make better decisions, the circumstances that have put us in what he defines as a "mild recession," and the moves he's making at WisdomTree, where he's been managing funds for almost twenty years and so much more!

In this podcast interview, you'll learn:

Why Jeremy doesn't believe the markets are anywhere near as overvalued as they were at the height of the 2000-era dot com bubble.
How to consume information about the markets to make better investment decisions.
Why markets overreact to both upturns and downturns in our economy.
Why so many mutual funds underperform against the index–and how to seek out passive and low-cost growth opportunities.
Why real estate has historically been much more volatile than it looks right now and may be a poor choice for diversification.

Show Notes: Howardbailey.com/303

Rate & Review the Podcast: RetireWithPurpose.com/review

Weekly Retirement Newsletter: RetireWithPurpose.com/weekend-reading

302: Bear Markets and Recession Risk: 3 Ways to Get Through Tumultuous Times Jul 15, 2022

Show notes

This week's retirement reading is from A Wealth of Common Sense titled, What's Priced Into the Stock Market? Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/302.

Show Notes: Howardbailey.com/302

Rate & Review the Podcast: RetireWithPurpose.com/review

301: Volatility and Wealth Loss: How to Make Sense of Today's Market Headlines Jul 08, 2022

Show notes

This week's retirement reading is from Noahpinion titled, Where does the wealth go when asset prices go down? Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/301.

Show Notes: Howardbailey.com/301

Rate & Review the Podcast: RetireWithPurpose.com/review

300: The Power of Financial Therapy: How to Improve Your Money Management Skills with Bari Tessler Jul 04, 2022

Show notes

My guest today is Bari Tessler. Bari is a Financial Therapist and the Founder of The Art of Money. She's a pioneer in the financial therapy field and the author of The Art of Money: A Life-Changing Guide to Financial Happiness.

Bari's mission is to merge emotional literacy with financial literacy, to help her clients understand the role money plays in careers, romance, parenting, creativity, spirituality, health, self-worth, and how we show up in the world. This work gives people the power to "unshame" their money stories, whether they're struggling as individuals, couples, or creative entrepreneurs.

In our conversation, Bari and I discuss how her unique practice helps her clients work through so many of the problems that arise around money, the three phases of her financial therapy methodology, and why it's so important that we do away with the taboos around talking about money.

GET A FREE COPY OF BARI'S BOOK, THE ART OF MONEY: A LIFE-CHANGING GUIDE TO FINANCIAL HAPPINESS

Here's all you have to do...

Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
Step 2.) Text BOOK, that's B-O-O-K to 866-482-9559 for a link to our book request page, complete the form and we will ship you the book for free. It's that simple!

In this podcast interview, you'll learn:

What financial therapy is, and why almost everyone could benefit from it.
Techniques you can use right now to check in with yourself as you make important decisions, financial or otherwise.
The three phases of Bari's financial therapy methodology.
How something as simple as renaming our debt gives us the freedom to create a plan to pay it off and forgive ourselves.
The three tiers that make up Bari's financial map of intention–and why she doesn't call it a budget.

Show Notes: Howardbailey.com/300

Rate & Review the Podcast: RetireWithPurpose.com/review

Weekly Retirement Newsletter: RetireWithPurpose.com/weekend-reading

299: You Need to Avoid These 5 Retirement Planning Mishaps. Here's How Jul 01, 2022

Show notes

This week's retirement reading is from Kiplinger titled, The 5 Biggest Regrets People Have About Retirement. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/299.

Show Notes: Howardbailey.com/299

Rate & Review the Podcast: RetireWithPurpose.com/review

298: Bear Markets and Your Emotions: How Retirees Should Handle Today's Volatility Jun 24, 2022

Show notes

This week's retirement reading is from Compound Advisors titled, The Greatest Paradox in Markets. Listen in as Casey Weade breaks down the article and shares what he thinks! Today's episode can also be accessed by visiting Howardbailey.com/298.

Show Notes: Howardbailey.com/298

Rate & Review the Podcast: RetireWithPurpose.com/review

297: Retirement Living: How to Find Your Happy Place with Ryan Frederick Jun 20, 2022

Show notes

Today, I'm talking to Ryan Frederick. He's the founder of SmartLiving 360, where he helps people answer the tough questions that come with living in an age where everyone is living longer. He believes that while retirees can thrive, their lifestyle choices will have more impact than ever before on just how healthy and satisfying their retirement will be.

Ryan has been focused on the challenges facing people who relocate in retirement for much of his life. In fact, he lived in a senior housing community in his twenties! With over 15 years of experience, he's become an innovator, developer, and strategy consultant in aging and longevity. His work has been cited in Forbes, The Washington Post, and several other outlets.

In this episode, Ryan and I dig into many great topics, including the age segregation that has unfortunately come to define the senior living industry. We'll also discuss how empty nesters and retirees can find a happier and healthier place in retirement when looking to make a move and how to take the principles of Blue Zones and apply them to your own life, even if relocating to Greece isn't in the cards.

GET A FREE COPY OF RYAN'S BOOK, RIGHT PLACE, RIGHT TIME: THE ULTIMATE GUIDE TO CHOOSING A HOME FOR THE SECOND HALF OF LIFE

Here's all you have to do...

Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
Step 2.) Text BOOK, that's B-O-O-K to 866-482-9559 for a link to our book request page, complete the form and we will ship you the book for free. It's that simple!

In this podcast interview, you'll learn:

What Ryan learned from residing in a senior living facility in his twenties.
Why Ryan says "place" instead of "home" – and how the pandemic has made it so much harder for people to find real connection.
How to use the SmartLiving 360 assessment to determine if you're thriving in place–and what to do if you're not.
Why people are least happy in their 40s and 50s and often find happiness again later in life.
How to conquer your fears when you know you need to make a change, but don't yet know what that change should be.
The apps Ryan and his wife use to track their activities and ensure they're spending their time wisely

Show Notes: Howardbailey.com/297

Rate & Review the Podcast: RetireWithPurpose.com/review

Weekly Retirement Newsletter: RetireWithPurpose.com/weekend-reading

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