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Win the Retirement Game – Now Available

Saving and investing for retirement takes discipline and sacrifice. But Sam Dogen, creator of the Financial Samurai website, points out that you also need to spend money to make money. He’s taught over 90 million readers how to invest wisely, not just financially, but in all facets of life. He joins us to discuss his Wall Street Journal bestseller, Buy This, Not That, and his lessons from more than a decade into a very early retirement.

San Dogen joins us from San Francisco.

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Bio

Sam Dogen is the author of Buy This, Not That: How to Spend Your Way to Wealth & Freedom  and the mastermind behind FinancialSamurai.com, one of the largest independently-run personal finance sites with roughly one million organic visitors a month. He launched Financial Samurai in 2009 when the world was falling apart and his net worth was taking a beating. His inspiration was to help himself and others make sense of the chaos. As a finance veteran since 1999, Dogen writes from firsthand experience to provide the most helpful insights possible. He spent 13 years working at Goldman Sachs and Credit Suisse, holds a BA in Economics from The College of William & Mary, and an MBA from UC Berkeley. In 2012, he left his day job in finance at age 34 to be permanently free and pursue being a writer. He has lived in seven countries and has traveled to over 60 countries so far.

Dogen’s writing delves deeper into investing, real estate, retirement planning, career strategies, and more, so we can all achieve financial independence sooner, rather than later. Financial Samurai is also proud to be one of the pioneers of the modern-day FIRE movement. Since the financial crisis, more than 80 million visitors have stopped by FinancialSamurai.com to learn, share, and grow. In addition, Dogen’s work has been highlighted in major publications such as CNBC, MarketWatch, Forbes, The Consumerist, The Chicago Tribune, The Los Angeles Times, and many more.

Dogen is also known for The Financial Samurai Podcast and the one-of-a-kind eBook, How To Engineer Your Layoff, which teaches employees how to negotiate a severance package and be free. When not writing or podcasting, Sam can often be found on the playground taking care of his two young children or on the softball field or tennis court.

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For More on Sam Dogen

Buy This, Not That: How to Spend Your Way to Wealth & Freedom

Financial Samurai website

Weekly Newsletter

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Wise Quotes

On Purpose and Meaning in Retirement 

“It’s definitely a learning process because you don’t know how you will feel in retirement until you get there, until you no longer have that steady paycheck. And so for the first year, I thought ‘Ok, I want to play a lot of tennis golf and travel the world.’ So, that’s what I did. I went to 20 countries. [I] saw nine Gothic churches. But after about the fifth church, they all started looking the same. And after about eight months, I started getting really bored of this early retirement lifestyle.

So in my mind I stopped saying I’m an early retiree. I just said I’m a writer, because I wanted to spend time writing on Financial Samurai which was, and still is, my passion hobby, the thing that I love to do every single day. And I found that the ideal amount of work – purposeful work – to do is about 20 hours a week. Now if you think about it, before in the olden days, when we had to go to the office for work, maybe let’s say we’re there for 9 hours. We would spend maybe three or four hours doing, at least for me, deep work and then three or four hours of so-so work, and then one to two hours of  lunch – and then just water cooler and chitchat. And so, I felt that if I could do deep work before my family woke up it would provide me enough meaning and purpose. And then after that, I could spend time playing tennis, softball and spend time with family. And so that is what I learned over the years: that you have to find a really meaningful thing to do post your day job, because that journey is what is most rewarding. Having a goal and working towards it every single day, seeing progress in whatever you’re doing. That is what brings so much purpose after retirement.”

On Fear

“The fear in your head is often worse than reality. If I could rewind time twenty-five years, I would say Sam, invite more people out to drinks, lunch and dinner. Ask that person. You just never know what might happen. The fear in your head is greater than the reality, because at the end of the day, you can just start over and try again if you fail. But just keep on failing because eventually you’re going to find your success.”

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Podcast Episodes You May Like

How to Retire Early and Live Your Life Fully – Leif Dahleen

You Can Learn a Lot from the Principles of FIRE – Chris Mamula

What Are The Keys To A Successful Retirement? Fritz Gilbert

Retirement Stepping Stones – Tony Hixon

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About Retirement Wisdom

Planning for retirement goes well beyond your 401k or IRA. How will you invest your time after your full-time working years?

You’ll need another portfolio.

I help people create an active multipurpose retirement, with the right mix of interests, activities and pursuits to invest your time wisely. And for many, like me, it includes a new version of work – redefined on your own terms.

Schedule a call to see if a 1-on-1 coaching program or a small group Designing Your New Life program can give you an edge in your next chapter.

Visit retirementwisdom.com for tools and resources to help you retire smarter.

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About Your Host

Joe Casey is an executive coach who also helps people design their next life after their primary career. He created his own next chapter after a twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.
If you’re thinking about retirement, you’ll also need to be planning for longevity. That’s why Joe returned to school, earning a Masters in Gerontology from the University of Southern California. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1.5 % globally in popularity by Listen Notes. Business Insider has recognized him as one of 23 innovative coaches who are making a difference.

Joe is the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

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Intro and Outro voiceovers by Ross Huguet.

Announcement: I’m thrilled to share that my book Win the Retirement Game launches on August 9th.

Take advantage of the special Kindle price available for a few days. I’m practically giving it away so you, our podcast listeners, can get ready to win your own retirement game.

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Missed some episodes of our retirement podcast? You won’t want to miss these.

In Part 2 of the Best of The Retirement Wisdom Podcast so far in 2022, we discuss a diverse mix of topics:

  • Many people are working longer. How do you navigate the evolving world of work?
  • How a retired police chief is making his early retirement a masterpiece
  • The emotional aspects of retiring
  • Why how you think about aging affects how you actually age
  • How to downsize and declutter like a pro
  • Why mindfulness is a key asset in grandparenting
  • How retirement can come abruptly and earlier than you planned

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Listen to the full conversations:

Kerry Hannon – In Control at 50+

John P. Weiss  – An Artful Life

Kate Schroeder – The Emotional Side of Retiring

Becca Levy – Breaking the Age Code

Matt Paxton – Keep the Memories, Lose the Stuff

Shirley Showalter – The Mindful Grandparent

Jim Kerr – The Long Walk Home

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About The Retirement Wisdom Podcast

Planning for retirement goes well beyond your 401k or IRA. How will you invest your time after your full-time working years?

You’ll need another portfolio.

I help people create an active multipurpose retirement, with the right mix of interests, activities and pursuits to invest your time wisely. And for many, like me, it includes a new version of work – redefined on your own terms.

Schedule a call to see if a 1-on-1 coaching program or a small group Designing Your New Life program can give you an edge in your next chapter.

Visit retirementwisdom.com for tools and resources to help you retire smarter.

__________________________

About Your Host

Joe Casey is an executive coach who also helps people design their next life after their primary career. He created his own next chapter after a twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.
If you’re thinking about retirement, you’ll also need to be planning for longevity. That’s why Joe returned to school, earning a Masters in Gerontology from the University of Southern California. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1.5 % globally in popularity by Listen Notes. Business Insider has recognized him as one of 23 innovative coaches who are making a difference.

Joe is the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

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Intro and Outro voiceovers by Ross Huguet.

Win the Retirement Game – Now Available

Adjusting to life in retirement isn’t easy. You don’t get a playbook when you retire. You need to develop your own – one that’s right for you, and for your unique circumstances and interests. And retiring isn’t your next chapter. It’s the next in a series of new chapters. When my clients take time to look back at their lives so far, they often discover more interests and pursuits than they recall at first. The diversity of your experiences and skills over time can offer a menu of choices to re-engage with in these next chapters of life. Author Anne Montgomery shares reflections on her career and life experiences, her observations on retirement, and notes that we have to learn to be retired.

Anne Montgomery joins us from Arizona.

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Bio

Anne Butler Montgomery has worked as a television sportscaster, newspaper and magazine writer, teacher, and amateur sports official. Her first TV job came at WRBL-TV in Columbus, Georgia, and led to positions at WROC-TV in Rochester, New York, KTSP-TV in Phoenix, Arizona, and ESPN in Bristol, Connecticut, where she anchored the Emmy and ACE award-winning SportsCenter.

She finished her on-camera broadcasting career with a two-year stint as the studio host for the NBA’s Phoenix Suns. Montgomery was a freelance and/or staff reporter for six publications, writing sports, features, movie reviews, and archeological pieces.

Her novels include Wolf Catcher, The Castle, The Scent of Rain, A Light in the Desert, and Wild Horses on the Salt.

Montgomery taught high school journalism for 20 years and was an amateur sports official for four decades, a time during which she called baseball, ice hockey, soccer, and basketball games and served as a high school football referee and crew chief. Montgomery is a foster mom to three sons. When she can, she indulges in her passions: rock collecting, musical theater, scuba diving, and playing her guitar.

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For More on Anne Montgomery

The Road to a Happy Retirement Can Be Slippery

Wolf Catcher

Other Books by Anne Montgomery

Website and Blog

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Podcast Episodes You May Like

The Emotional Side of Retiring – Kate Schroeder

Figure It Out – Mike Westhoff

Solo and Smart – Carol Marak

Everyday Vitality – Dr. Samantha Boardman

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Wise Quotes

On Identity

“I’m used to filling up with my days with a whole bunch of things that I think are important – and suddenly I don’t have those things. The other problem is that I had this belief that what I did was who I was. Instead of just being me, Annie Montgomery, I’m an umpire, I’m a referee, I’m a teacher, I’m a reporter. That’s who I am – and that’s not true. Those are things I did. So it’s that idea that I think we have to consider that our jobs are not actually who we are. They’re just things we do.”

On Learning to Retire

“What’s going to make you feel better in retirement is looking forward to something. Whereas people that can’t, don’t have anything to look forward to, I think it gets depressing. So I would say, don’t be too hard on yourself. Understand you worked your entire life, and this is not a transition that’s going to go away in a day. We have to learn how to be retired. And maybe there should be lessons for this. I know when I was a teacher, they kept having meetings about what happened in retirement, but it never focused on the social aspects of it or how do you deal with your time, this extra time? It was all about the financial end of things. So I don’t think enough people talk about this end of it.”

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About Retirement Wisdom

Planning for retirement goes well beyond your 401k or IRA. How will you invest your time after your full-time working years?

You’ll need another portfolio.

I help people create an active multipurpose retirement, with the right mix of interests, activities and pursuits to invest your time wisely. And for many, like me, it includes a new version of work – redefined on your own terms.

Schedule a call to see if a 1-on-1 coaching program or a small group Designing Your New Life program can give you an edge in your next chapter.

Visit retirementwisdom.com for tools and resources to help you retire smarter.

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Intro and Outro voiceovers by Ross Huguet.

Win the Retirement Game – Now Available

Mike Westhoff spent 32 years in the NFL, mainly with the Dolphins, Jets and Saints, as an exceptionally creative and highly effective coach. Now 74 and retired, he joins us to discuss his book Figure It Out. We discuss his decision to retire and pivot to a second career – and his decision to unretire in 2017 to join Sean Payton and the New Orleans Saints. But there’s more than football to Mike Westhoff. His book is also a compelling story of resilience and perseverance, battling cancer, enduring multiple highly complex surgeries, and overcoming a series of devastating setbacks. His experiences and observations offer valuable insights for those who are also in the midst of figuring out this phase of life we call retirement.

(And if you love football, as I do, stick around as we chat about some  interesting NFL topics.)

Mike Westhoff joins us from Florida.

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Bio

Simply put, Mike Westhoff is the greatest special teams coach in National Football League history.

Roger Goodell, NFL commissioner, said of him: “We called Mike Westhoff the mad scientist. He changed the game.

Sharp-witted, creative, and intensely focused, Westhoff spent thirty-two years working alongside and learning from some of the legends of the sport—including Don Shula, Dan Marino, Bear Bryant, and Woody Hayes—while revolutionizing the most misunderstood phase of the game.

Over the course of 657 games, primarily with the New York Jets and the Miami Dolphins, Westhoff was a relentless innovator—constantly figuring out new ways to help the individual skills of hundreds of players surface and develop.

But his story isn’t just about football. Mike Westhoff also has waged multiple battles with cancer. In his new book Figure It Out, he presents his one-of-a-kind experiences and unfiltered views in his trademark style—a refreshing blend of honest (sometimes brutally so), funny, and poignant. His deep insights into the workings of special teams—illustrated by 27 detailed original diagrams—and timely commentary on the current state of pro football reveal a critical side of the sport that very few truly understand.

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For More on Mike Westhoff

Figure It Out 

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Podcast Episodes You May Like

From the NBA Hardwood to the Altar – Steve Javie

Believe In Yourself & Try Something New – Carol Cooke

The Skill Set for Life’s Transitions – Bruce Feiler

Ready to ROAR? – Michael Clinton

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Wise Quotes

On Resilience

“One of the things I learned, and I learned this from Dr. Mankin: don’t let the illness define who you are, fight through it. You’re still the same person. You may not look perfect. You sure don’t feel perfect. You know you’re not, but you’re still the same. Go out to dinner, just go. You don’t look great, but just go. All of a sudden I couldn’t walk the way I had to, and I had to wear a big leg brace, and I had to use a cane. And so, here I’m coaching in the National Football League with a cane. And I was a guy that when I first started, I could throw the receiver drills at the Combine, and now I’m walking around with a cane, like some old grouch. But what I realized is that, okay, I have a cane, but I can do this job better than anybody ever did it. And that was my goal. And that’s the only goal I ever had.”

On His Decision to Unretire and Jump Back into the Fray

“That part with the New Orleans Saints takes on a separate meaning for me. I did not want to go to the New Orleans Saints. I didn’t know anybody. I got a call from a guy that I knew that asked about the New Orleans Saints wanting to talk about coming back to work. I said, no, I’ve got a TV show tomorrow. I’m done. So, and make a long story short, I agreed to talk with Sean Payton, who I had tremendous respect for, but I had never met him. I never said hello to him in my life. I knew who Drew Brees was, but I didn’t know one person in the building. I didn’t know anybody. Okay, so I talked with him, and he said: look, we’re really a good football team, but this part of our game, it’s just not clicking. Can you help? We need you to see if you can put it together.  I said: Well, you can’t fire anybody. If you fire someone, I won’t come. He said, Okay, I’m not gonna fire anyone. I’m not going to do that, but you’re going to have to run the whole thing. So the next thing I know, two days later, I’m on a plane going to New Orleans, and I’m going to coach practice before a game with the Atlanta Falcons on a Wednesday afternoon. And I didn’t know one player.”

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About Retirement Wisdom

Take charge of your future.

Your life in retirement will be multidimensional, and so your planning should be as well.

Schedule a call to find how how the Designing Your Life process (developed by Bill Burnett & Dave Evans at Stanford) can help you unlock a new direction – on your own terms.

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About Your Host 
Joe Casey is an executive coach who also helps people design their next life after their primary career. He created his own next chapter after a twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.
If you’re thinking about retirement, you’ll also need to be planning for longevity. That’s why Joe returned to school, earning a Masters in Gerontology from the University of Southern California. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1.5 % globally in popularity by Listen Notes. Business Insider has recognized him as one of 23 innovative coaches who are making a difference.

Joe is the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy launching on August 9th.

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Intro and Outro voiceovers by Ross Huguet.

We’ve been cooking more at home since the pandemic. Is it time to expand our menus? In his second act, Chef Dennis Littley shows people how to cook restaurant quality meals at home. He’s a good example of how you can take the skills and experience from your primary career and spin them in a new direction.

Dennis Littley joins us from the Garden State.

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Bio

Dennis Littley is a retired chef and culinary instructor who is now living the dream working on his second career as a food and travel blogger, brand promoter and LiveStreaming show host and producer. Through his blog, Ask Chef Dennis – A Culinary Journey, as well as his social media channels, Dennis has amassed an impressive combined following of over 1.8  million.

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For More on Dennis Littley

Ask Chef Dennis – A Culinary Journey

Recipes

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Podcast Episodes You May Like

A Tapas Life – Andy Robin

Stupid Things I’ll Never Do When I Get Old – Steven Petrow

A Rock Star’s Second Act – Brett Anderson

Reclaim What You Love – Stephanie Raffelock

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About Retirement Wisdom

Take charge of your future.

Your life in retirement will be multidimensional, and so your planning should be as well.

Schedule a call to find how how the Designing Your Life process (developed by Bill Burnett & Dave Evans at Stanford) can help you unlock a new direction – on your own terms.

___________________________

About Your Host 
Joe Casey is an executive coach who also helps people design their next life after their primary career. He created his own next chapter after a twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.
If you’re thinking about retirement, you’ll also need to be planning for longevity. That’s why Joe returned to school, earning a Masters in Gerontology from the University of Southern California. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1.5 % globally in popularity by Listen Notes. Business Insider has recognized him as one of 23 innovative coaches who are making a difference.

Joe is the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy launching on August 9th.

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Intro and Outro voiceovers by Ross Huguet.

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