The Encore Phase

Terry Castelli

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Self-Improvement
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Explorations of navigating retirement---the Encore phase of life.

Aug 12

Letting Go Of Old Habits

In this episode of The Encore Phase, Terry and Justin welcome a special guest — Justin's son, Silas — to help kick off a conversation about learning to relax into unscheduled time. Building on their last episode's discussion of the "encore mindset," Terry and Justin dig into a bad habit many carry from their working years: staying tethered to schedules and measuring the day by what gets accomplished rather than simply being present. Silas offers a kid's-eye view of what a truly relaxed day looks like, and the conversation moves through letting go of old identities tied to titles and achievement, reframing "bad habits" as simply old habits that no longer serve, and finding the balance between boundaries and support as external pressures shift with age. Terry and Justin close with a simple reminder: don't hold on too tightly. Letting go of old habits and rediscovering the freedom of "before we knew better" is its own kind of progress.
Jun 30

The Encore Mindset

In this episode of The Encore Phase, Terry and Justin dig into something they've circled around before but never fully unpacked: what does it actually mean to build an "encore mindset"? They start from Bob Buford's Halftime — the idea that life has two halves, with a pivotal "halftime" in between. The first half is about building infrastructure: career, security, identity. But the second half isn't about what you want your life to be — it's about how you want it to feel. Terry walks through why this phase calls for something more spiritual, more self-examined, and frankly more willing to fail than the first half ever allowed. They talk about the fear of losing identity once the job title disappears, why exploration looks different across generations, and why so many retirees default back to structure instead of leaning into the freedom they finally have. They also get into purpose, legacy, and the quiet fear of fading into the background once you're no longer "needed" in the way you used to be — and why your value never actually goes away, even when the external reinforcement does. It's a more reflective conversation than usual, with a couple of favorite quotes from Marcus Aurelius and Nietzsche woven in. For anyone approaching this phase of life — or already in it — this one offers plenty to sit with.
May 5

The Curiosity To Continue Exploring

It's Episode 25 — the silver jubilee! Terry and Justin celebrate the milestone by sitting down for a conversation that hits differently: do we settle for who we are when we reach retirement, or is this actually the greatest invitation to get curious again? They dig into the real difference between comfort and contentment, why curiosity isn't just a nice idea but a high-vibration force that literally changes your life, and what it means to become a beginner again — ego and all — in the encore phase. Plus: Justin shares the origin story of how one blog led to a podcast led to a business, his experiment becoming a hip hop producer (yes, really), and a coaching story about a client who nearly quit right before his $50K breakthrough. Topics covered: Comfort vs. contentment — why one kills growth and the other doesn't The power of staying curious at every age Dropping the ego to become a beginner again Regret, identity, and what to do with 164 free hours a month Why the darkest moment often comes right before the breakthrough Energy, vibration, and why curiosity raises your frequency
Mar 20

Is The Encore Phase Also A Reset?

In this episode of The Encore Phase, Terry and Justin sit down for one of those honest, unhurried conversations about what retirement actually feels like from the inside — not the highlight reel version, but the quiet moments when things start to feel a little flat. They dig into what Terry calls the "gentle reset"—the natural drift that happens when the anchors of work, routine, and responsibility are suddenly gone. It's not failure. It's not regret. It's a signal. And they talk about how to listen to it. Terry and Justin cover a lot of ground in this one, including the difference between a reset and an evolution, how to stay in what my dad describes as a "perpetual state of recalibrating," why comfort can be more dangerous than discomfort, and how the people around you — your social circle, your energy, your community — may need to shift too. Terry also shares something Justin has been nudging him toward for a while: he's completed a retirement life coaching certification and is in the early stages of launching a coaching practice to help others navigate exactly these kinds of transitions. If you or someone you know is approaching or already in the encore phase and feeling that sense of "is this really it?" — he may be just the guide you need. This conversation is for anyone in the encore phase — or any phase — who's wondering whether what they're feeling is normal. It is. And there's something meaningful waiting on the other side of it.
11/28/2025

Is It Authenticity Or Being Best Version Of Your Self?

Can you live your best life without being your authentic Self?
10/08/2025

What Is Success?

Society has given us a definition of success, but who says you have to subscribe to that definition for your life?
09/04/2025

Enjoy The Life You've Built

In this episode, Terry and Justin talk about the importance of enjoying the life that you've built.
07/29/2025

The Encore Phase Shouldn't Be A Permanent Vacation

In this episode, Terry discusses lessons learned in the first few years of his Encore Phase. Videos mentioned by Justin: The Story Behind Santiago: https://youtu.be/LyIzIM8azFo?si=X9t-nlw7qWltbnsE Santiago The Brand: https://youtu.be/UWVbCZG5iNM?si=lWZatA_IUrAM8Vum Santiago Website: https://youtu.be/5QjO66pzrjQ?si=YbDZqbG4iHYbwbq8 The Keep Pursuing Series Playlist: https://youtube.com/playlist?

Explorations of navigating retirement---the Encore phase of life.

Creator

Terry Castelli
Years Active

2025 - 2026
Episodes

25
Rating

Clean
Copyright

© 2025
Show Website

The Encore Phase