meta_pixel
Tapesearch Logo
Log in
Retire With Purpose - The Retirement Podcast

339: Winning the Retirement Game: How to Avoid Uncertainty and Boredom with Joe Casey

Retire With Purpose - The Retirement Podcast

Casey Weade

Education, Self-improvement, Business, Investing

4.7564 Ratings

🗓️ 9 January 2023

⏱️ 57 minutes

🧾️ Download transcript

Summary

Today, I'm thrilled to welcome Joe Casey back to the podcast. Joe is an Executive Coach at PEC and a Managing Partner at Retirement Wisdom, who helps people design their lives following their corporate careers to successfully navigate their transition to retirement.

In this new book titled, Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy, he walks retirees through the obstacles they're most likely to face in the next chapter of their lives. Tackling issues such as boredom, uncertainty, and drifting by helping them craft specific strategies to tackle these problems head-on.

In today's episode, we dig into what Joe's learned from working with people from all walks of life. We talk about the difference between left-brain financial planning and right-brain life planning and why so many advisors end up having to unwind what should have been "perfect" retirement plans.

We'll also talk about how to cast off pre-retirement mindsets that won't serve you once you've transitioned out of your primary career and much more!

GET A FREE COPY OF JOE'S BOOK, WIN THE RETIREMENT GAME: HOW TO OUTSMART THE 9 FORCES TRYING TO STEAL YOUR JOY

 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!

PS: If you'd like a free copy of Joe's book, all you need to do is leave us an honest review over on Apple Podcasts, then send your email and your username to info@howardbailey.com, and we'll get it out to you!

In this podcast interview, you'll learn:

  • Why Joe sees retirement as a game–and why most retirees don't actually want to kick back, relax, and withdraw.
  • Why so many people find themselves in a state of shock or identity crisis when they retire–and how "soft" conversations about retirement make this transition less uncomfortable.
  • How boredom paralyzes, scares, and frustrates us as we approach retirement–and what happens when we discover newfound passions.
  • What to do in the meantime as you wait for an opportunity to recharge your energy or artistic juices between career and retirement.
  • How to get retirees out of the habit of consuming 40+ hours a week of television.
  • Why retirement communities are rarely diverse and don't always encourage us to be at our best.
  • How to make a concrete list of your killjoys and start working through them.

Show Notes: Howardbailey.com/339

Rate & Review the Podcast: RetireWithPurpose.com/review

Sign Up to Casey's Weekend Reading Email!

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

Transcript

Click on a timestamp to play from that location

0:00.0

Welcome to the Retire with Purpose podcast, a show designed to help retirees and free retirees

0:11.7

maximize their financial confidence. Casey Weed is the CEO and founder of Howard Bailey Financial.

0:18.3

With office locations in Indiana and Ohio and serving clients all across

0:23.0

the United States virtually, Howard Bailey was voted first place, best financial advisor in 2020,

0:29.2

2021 and 2022. Casey is a certified financial planner and Wall Street Journal bestselling author.

0:36.2

He's your host on Retire with Purpose.

0:39.2

Hey, I'm Casey and I believe in retirement strategies that are driven by meaning and purpose.

0:46.1

Join me this week and every week as we discuss thoughts and ideas with some of today's

0:51.8

foremost experts in the field of finance and retirement, as well as

0:56.3

discussing trending topics that could impact your bottom line. These discussions can help you make

1:01.4

better financial decisions so you can live the lifestyle you've always imagined and deserve.

1:07.3

Welcome to the show. Today, I'm thrilled to welcome Joe Casey back to the podcast again.

1:15.2

If you're not sure who Joe Casey is, I'd encourage you to check out episode number

1:18.4

231 of the podcast before we even get started.

1:22.0

This is a great episode, but I really enjoyed our first conversation too, and I think they

1:26.8

tie in really well together.

1:28.4

If you didn't catch that, just as a reminder, Joe is an executive coach and a managing partner

1:33.5

at retirement wisdom, helping people design their lives, following their corporate careers

1:38.5

to successfully navigate their transition into retirement.

1:42.7

His new book is why we brought him on.

1:44.7

So his new book is titled,

1:46.3

Win the Retirement Game,

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from Casey Weade, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Casey Weade and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.