True Retirement Story: How a Plan Salvaged an Unexpected Early Retirement with Anthony Napolitano – Milwaukee Financial & Retirement Advisors

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Jeremy Keil interviews Anthony Napolitano about how he managed to adapt his retirement plan after an unexpected end to his career.

I often tell people that the majority of folks don’t get to choose the exact moment they retire. It’s a reality that’s hard to face, but it’s a truth I’ve seen play out time and again. That’s why I believe having a plan, even if you think you’re decades away from retirement, is the best kind of insurance you can have.

I recently had the pleasure of speaking with Anthony Napolitano on my podcast, Retire Today. Anthony’s story is a perfect example of why having a retirement plan is so crucial. He’s about 15 months into his retirement journey, and his story is a powerful reminder that while the road to retirement may be “somewhat planned, somewhat unplanned,” a solid foundation can make all the difference.

The “Aha!” Moment: From Saving to Planning

Anthony’s background is in finance, and he’s always been a “personal finance kind of nerd”. He consistently saved money throughout his working years, but he didn’t have an actual retirement plan until he was 47. His “aha!” moment came during a conversation with a colleague who asked him, “Do you actually have a retirement plan? Do you know where your income is going to come from?”. This question prompted Anthony to get serious about his future.

He worked with an advisor and created a plan that projected his income and expenses until age 95. This was the first time in his life he had such a detailed roadmap. His initial goal was to retire at 55, a full eight years away. But as often happens, life had other plans.

A Serendipitous Retirement

Anthony’s career path wasn’t a straight line to the finish. He was “downsized” from his company after 25 years. This unexpected break gave him a taste of what retirement might be like, and it really “steeled [his] nerves” and made him get serious about his plan. He eventually found another senior executive role, but two years later, he was retired again due to another “corporate restructuring”.

While the timing wasn’t his choice, Anthony was ready. He’d had the benefit of a financial plan and had spent the year leading up to his retirement focusing on the non-financial side of things. He had also started listening to personal finance podcasts during his daily walks, which reignited his love for the subject and gave him a ton of confidence.

Anthony’s story confirms what I’ve seen in my practice and what the data shows: on average, people retire about three years earlier than they plan. But having a plan in place gave Anthony the confidence to say, “I’m doing all right,” even when the decision was made for him.

Beyond the Numbers: The “Retirement Life Plan”

I was particularly impressed with Anthony’s “retirement life plan.” He’s a very structured person, and he’s applied that structure to his life in retirement. He didn’t want a generic “bucket list” but rather a framework for a balanced and purposeful life. He created four pillars for his plan:

Health: He maintains a routine of daily walks and strength training a few times a week.
Mindset/Hobbies: This was the area he had to work on the most, as he didn’t have many hobbies while working. Now, he enjoys hiking, cooking, traveling, off-roading, and gardening.
Purpose: Anthony found his purpose in combining his love of sports and personal finance with his desire to help kids. He coaches at a local high school and is developing a financial literacy program for students.
Relationships: Recognizing that relationships are crucial, especially for men who often struggle to maintain them, Anthony created a “friends project”. He has a weekly calendar reminder to reach out to friends, rekindling old connections and strengthening existing ones.

This structured approach allows him to constantly update and work on his life, ensuring he’s not just “floating around”. It also gives him a way to hold himself accountable and measure his progress.

A Journey of Self-Discovery

One of the most surprising things Anthony discovered was the challenge of being overcommitted, even to things he loved. He started coaching and working at a winery, two things he had always wanted to do. But the schedule and lack of freedom began to feel like a burden. He realized he needed to say “no” more often and find a better balance.

This realization is a testament to the fact that retirement is a journey, not a destination. It’s a time for trial and error, for exploring new things, and for continuously evolving. Anthony is grateful he can go through this process while he’s healthy and can fully enjoy it. His worst day in retirement is still better than his best day at work.

Anthony’s story is an inspiring example of how a thoughtful, proactive approach to both the financial and non-financial aspects of retirement can lead to a fulfilling and purposeful life. If you’re interested in sharing your own retirement story, please email me at podcast@keilfp.com. I’d love to hear it.

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