Designing Your Next Chapter
Welcome to this week’s Get Ready Newsletter.
This week, I’ve been thinking about the second half of life and how much of it depends on our preparation for this transition.
Retirement, aging parents, health, end-of-life planning, purpose, identity, cognitive decline, and financial security are often treated as separate conversations. In reality, they are deeply connected.
The next chapter of life often begins gradually: a health change, a parent needing help, a career shift, a spouse passing away or a phased retirement.
I’ve seen how powerful it is when people prepare for both the money part of retirement and the life part. That is where financial readiness matters.
A good plan helps the numbers support the life you are preparing for, including your health, relationships, documents, purpose, and support system.
The Question to Ask Before Life Happens
What kind of life are you actually preparing for?
A second question may matter just as much:
Who needs to be part of that conversation before decisions become urgent?
From the Get Ready Before Life Happens Podcast
This week, I’m featuring four conversations about designing a strong next chapter with intention, preparation and support.
Your Health Is Your Greatest Asset
Stevyn Guinnip, author of Grow Wellthy, joined me to talk about health net worth, the compounding effect of daily habits, and why retirement planning should focus on health span, not just life span.
The key takeaway: your health is an asset that directly impacts your financial life.
Small health habits compound just like financial investments. Identifying your health assets helps you protect your energy, expand your options, and support your long-term well-being.
Tony’s Take: If we treat health as an asset and invest in it early, we give our future selves more options, more energy, and fewer regrets.
🎙️Watch or listen (here)
Rethinking Retirement Through a Portfolio Life
Maria Dastur, founder of Second Half Community, joined me to talk about designing a portfolio life that blends purpose, contribution and financial security.
The key takeaway: retirement can become a phase of flexibility and impact.
A portfolio life diversifies streams of meaning, purpose, and income. Strong networks provide support during career transitions. Knowing your numbers allows you to pivot with more confidence.
Tony’s Take: A fulfilling life after mid-career comes from curiosity, community, and knowing your numbers. When we stay open to learning and surround ourselves with people who believe in us, we create more freedom to design the next chapter with purpose.
🎙️Watch or listen (here)
Why Your Financial Plan Should Be as Unique as Your Life
Mike Milligan, CFP® and author of The One of a Kind Financial Plan Book, joined me to talk about building a personalized financial plan and retirement strategy that aligns money, values, relationships, and purpose.
The key takeaway: one-of-a-kind lives deserve one-of-a-kind financial plans.
A clear retirement vision includes health, community, impact, and an understanding of how past money experiences shape future decisions. Diversification applies to life purpose as much as financial risk.
Tony’s Take: Financial planning becomes more meaningful when it starts with purpose, defining what matters and aligning money with our values. It becomes a guide for living with intention.
🎙️Watch or listen (here)
Why End-of-Life Planning Is the Ultimate Gift to Your Family
Greg Barnsdale, death doula and author of Do Not Ignore Your Mortality, joined me to talk about why end-of-life planning is one of the most meaningful acts of preparation we can make for our families.
The key takeaway: planning ahead reduces stress and confusion for loved ones.
Clear wishes, organized documents, family communication, and thoughtful preparation can help prevent conflict during difficult times. End-of-life planning supports emotional resilience, financial stability, and meaningful legacy.
Tony’s Take: End-of-life planning is an act of love. When we organize our wishes and prepare our affairs, we leave our families with direction, resilience, and the space to focus on what matters most.
🎙️Watch or listen (here)
Recommended This Week
3 Big Questions to Ask Your Aging Parents
Amy Arnott shares three practical questions to ask aging parents about finances, estate planning, and living arrangements. The questions are direct and useful:
• How healthy are your finances?
• Do you have end-of-life plans and documents?
• Is your home still safe and comfortable for you?
Tony’s Take: Though these conversations can be uncomfortable, they are a gift. Asking gently, early, and over time helps families prepare before decisions become urgent.
📖 Amy Arnott for Morningstar (read)
Your Next Edit: Reinvention, Retirement and What Comes Next
Andrea Maizes and Judy Hoberman explore the emotional, practical, and personal side of leaving one season of life and stepping into another. This episode is for every woman who knows there’s more ahead…and wants to step into it thoughtfully, confidently, and fully.
Tony’s Take: Reinvention is not only a financial transition. It is a life transition. The real question is what you want to build next, and how your money can support that next chapter.
🎙️ Andrea Maizes and Judy Hoberman on The Trailblazer Chronicles (Spotify)
Permission to Prosper
Dr. Preston Cherry writes that the most important financial decisions are often life decisions. Strong planning starts with the life someone is trying to live, then turns that life into strategy and action.
Tony’s Take: When the plan reflects the life you are preparing for, financial decisions become more intentional, personal, and actionable.
📖 Dr. Preston Cherry for Financial Harmony (read)
Mind, Body, and Wallet 2026
Guardian Life explores explores how the choices we make today can help shape our health, happiness, and financial confidence for years to come.
📊 Guardian Life (here)
When Work Becomes Optional: Redefining Retirement
Bernadette Joy and Eric Blake discuss debt, financial independence, financial fluency, and redefining retirement as work becoming optional rather than obligatory.
Tony’s Take: Financial fluency gives people the language to make choices, create freedom, and advocate for themselves.
🎙️ Bernadette Joy and Eric Blake on The Simply Retirement Podcast (watch or listen)
What You Will Lose When You Retire
Dan Haylett writes about the five steps to thrive in retirement: name the losses out loud; build a self that isn’t your job title; find new tribes, on purpose; learn the skill of spending and invent your own nexts.
Tony’s Take: Retirement planning can help people name what is changing and build something meaningful for the next chapter.
📖 Dan Haylett for Humans vs. Retirement (read)
This Week’s Readiness Step
Choose one next-chapter conversation to start.
It could be about health, work, retirement, caregiving, housing, documents, end-of-life wishes, or how you want to spend your time.
Ask yourself: What would help the people I care about feel more prepared for this transition?
Your Financial Readiness System
Readiness grows when your information, people, wishes, decisions, and next steps are organized before they are needed. It also grows when your financial life reflects the health, relationships, purpose, and support system you want for the next chapter.
Final Thought
Life rarely changes in only one area at a time. Health, work, family, purpose, care, and money often move together. Financial readiness gives us a way to connect those pieces before decisions become urgent.
Curiosity is where financial readiness begins.
Ask better questions, and the path forward becomes clearer.
Because when life happens, the way you think about money matters.
Tony
P.S. Have a new podcast episode, book, article, research report, tool, or project that helps people think differently about money or prepare before life happens? Send it my way. I’m always looking for thoughtful resources to consider sharing in a future Get Ready Newsletter.
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