Warning Signs Retirement Is Off Track

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What if the word retirement is setting us up for the wrong life?

After years in senior leadership roles, Cesar Aguirre discovered something most of us miss about retirement: the word itself matters more than we think. In English, we “retire” – we withdraw. In Portuguese, you become “aposentado” – left aside or left behind. But in Spanish-speaking cultures, retirement is called “jubilación” – which comes from the word for joy.

That distinction changed everything for Cesar. Because when he stepped away from his career, it wasn’t the loss of work that shocked him – it was the jarring shock of losing an identity. He realized retirement isn’t just a life transition, it’s an identity transition, offering an opportunity to redefine who you want to become, and retire with purpose.

Cesar joins us to share the framework he developed through his own transition – a ten-chapter roadmap for moving from “what I’m leaving” to “what I’m moving toward.” He’ll reveal why planning goes far beyond your finances, how to measure success when you’re no longer producing output, and the key warning signs that show up early when retirement first starts going wrong.

This is a conversation about why approaching retirement with more intention might just create the most fulfilling chapters of your life. How will you retire with purpose?

Cesar Aguirre joins us from Florida.

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Bio

César Aguirre is a seasoned HR executive with over 40 years of experience in global talent development. Now in active retirement, he embodies reinvention with passion as mentor, consultant, and author. In his book, Retirement with Purpose: The 10 Rs of Retirement, he shares his vibrant energy and insights to help readers rediscover purpose and embrace joyful living in their post-career lives. He currently resides in a lively 55+ community in Central Florida with his wife, inspiring others to design their authentic journeys for the second act of their lives.

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For More on Cesar Aguirre

Retirement with Purpose: The 10 Rs of Retirement

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Podcast Conversations You May Like

How to Prepare Mentally for Life After Work – Joseph Maugeri

Re-Visioning Retirement – Susan Reid, PhD

How to Retire – Christine Benz

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About The Retirement Wisdom Podcast

There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time.

About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.

Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University.

In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

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Wise Quotes

On The Power of Language

“Retirement becomes a celebration, not a retreat. I think the languages shape mindset. And mindsets shape behavior. So when retirement is framed as a joy, planning shifts from survival to flourishing become more natural.”

On Measuring Success in Retirement

“A good day is no longer about output, it’s no longer about how much you produce. It’s about action that is intended, an action that aligns with a master plan.”

On What He’d Do Differently

“I wish I had thought about it and prepared for my post-work identity a little sooner and more deliberately. In my job in HR, I helped many others plan careers, but I underestimated how much my own self-worth was tied to that job in that title. I think I did it humbly. I can say that I did a solid job planning financially, but probably not as good in preparing emotionally for the change. For a brief period of time, a few months, I underestimated that the identity shift that was occurring and the loss of a daily structure that I was so accustomed to.”

On What He’s Gained in Retirement

“Presence, the ability to not just having the time, but having the mindset of real presence, presence with my wife, which I neglected for a few years while I was traveling or working, presence with my kids, now with my grandkids, the rest of my friends, and new friends. I also gained a space and time for mastery, my hobbies. I enjoy cooking, well, time to do more and do a little better, exercising, riding the bike three or four times a week, playing pickleball. Retiring has given me time to go more in depth on my preferences instead of just speed, because in my working years, I was always rushing. Even when I was at home, I needed to accomplish, I needed to do things. I needed not to be idle. And retirement has now given me presence and bandwidth.”

On Warning Signs

“I think there are three main things that one needs to start paying attention to. Isolation. If you don’t have that network, social network, family network, and you become isolated. A loss of structure. Doing nothing without a structure or living in the past tense. When people stop connecting with others, when they drift through the days without an intentional plan, or when they only talk about what they used to be, that should be a warning, – a huge yellow flag for oneself and for loved ones that are looking after them.”