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October 24, 2025 • 9 minutes
The Fall season is made for putting your feet up by the fire and diving into a great book. If you’re looking for a spark of insight, we found 6 new releases that will expand how you think about money, markets, and life.
We’ve included quick takeaways so you can capture the key lessons — even if you don’t have time to read every page.
Morgan Housel has done it again. Following his acclaimed best sellers The Psychology of Money and Same as Ever, his new book, The Art of Spending Money: Simple Choices for a Richer Life, explores the art (and emotion) of spending well. Rather than offering another list of financial “rules,” Housel helps you understand why you spend the way you do — and how your choices reveal what you truly value.
He reminds readers that wealth is not just what you save, but how intentionally you use what you have to create meaning and joy.
1) Money is Emotion and Identity, Not Math: We like to believe we make money choices logically, but much of what we do with our money reflects how we see ourselves — capable, generous, successful, secure. The sooner you understand the emotional story behind your spending and saving, the easier it becomes to make choices that actually serve you.
2) You Need to Define Your “Enough?”: Without a clear sense of what “enough” means, it’s easy to chase more — a bigger house, a newer car, or one more year of work. Defining your version of enough anchors your financial goals to contentment instead of comparison.
3) The Richest Life is Aligned with Your Values, Not Your Balance Sheet: Money is just a tool — a powerful one, but still a tool. A meaningful financial plan isn’t about maximizing wealth; it’s about directing your resources toward what matters most, so you can live in alignment with your purpose and priorities every day.
Your future budget is the best way to align your financial plan with your values and identity. Within the Boldin Retirement Planner, you can use the Basic Budgeter and define how your overall spending will shift over different phases of your life.
However, we really recommend that you use the Detailed Budgeter in the Boldin Planner to think through your spending. With the tool, you can define your expenses as “must spend” and “like to spend” in over 75 different categories. And, you can add all of your projected one-time expenses over your lifetime.
Don’t think of this as a budgeting exercise; it’s more like planning your dreams. And, how you define your future expenses is the foundation of your retirement success, both financial and emotional.
In 1929, Andrew Ross Sorkin brings history alive — and uncomfortably close to the present. He revisits the stock-market boom of the roaring ’20s and the crash that followed, showing how easy credit, speculative fervor, and overconfidence among investors and policymakers led to one of the most devastating financial collapses in U.S. history.
Through vivid and harrowing storytelling, Sorkin draws parallels between 1929 and today: innovation hype, leverage, and a collective belief that “this time is different.”
1) Market Euphora Hides Fragility: The moments that feel safest are often when investors take the biggest risks, fueled by optimism and blind spots. Understanding this cycle helps you avoid getting swept up when the crowd forgets that downturns are part of every market story.
2) Crashes Are About Human Behavior: Greed, fear, and overconfidence have been driving markets for over a century, and they still do today. Recognizing these patterns can help you stay steady when others react emotionally.
3) Resilience Comes from Preparation, not Prediction: No one can time the next downturn perfectly, but everyone can build flexibility into their plan. By stress-testing your finances before the storm, you’ll feel more confident and won’t need to panic if a crash occurs.
Boldin’s new Market Risk Explorer lets you test how your plan might hold up in different downturn scenarios — from mild corrections to a repeat of 1929. You can model what happens if markets fall 30%, inflation spikes, or interest rates change — and see how resilient your income and goals really are.
Planning isn’t about avoiding risk; it’s about understanding how much flexibility you need to build into your plans so that you can still sleep well at night.
William Bengen, best known as the creator of the “4% rule,” returns with a thoughtful new take on what it really means to retire well. In A Richer Retirement, he moves beyond the mechanics of withdrawal rates and delves into how people can achieve emotional and experiential wealth in retirement — not just financial security.
There are actually many pros and cons to using a fixed withdrawal method, like Bengen recommends. However, this book has many other key lessons:
1) Retirement planning is not a math problem — it’s a life design challenge: The numbers matter, but they’re only useful when they support a vision for your life. Start with what makes life meaningful, then build the numbers around that.
2) Spending flexibility is more powerful than any fixed “rule”: Bengen now emphasizes that retirees who adapt their spending to market and life conditions tend to feel wealthier and worry less.
3) The richest retirements come from aligning money with meaning: Bengen’s research shows that the happiest retirees don’t just have more, they use their resources with intention.
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The Boldin Planner enables you to test any “what if,” including many of the ideas Bengen covers in A Richer Retirement:
In Lucky by Design: The Hidden Economics You Need to Get More of What You Want, Wharton economist Judd Kessler invites us into the often invisible systems and “markets” that influence how opportunities are distributed in life — who gets the job, who wins the bid, who has access. It’s a great book for anyone who enjoyed Freakonomics, people who like economic concepts applied to everyday life, and explained in plain English.
Key Lessons
1) Markets are Everywhere: Understand that markets don’t just exist for stocks or houses — they exist for jobs, schools, relationships, and more. If you know how the game is structured, you can navigate toward “luck” rather than leaving it to chance.
2) There are Winners and Losers: The design of systems often favors some and disfavors others — identifying the rules lets you play smarter, not just harder.
In your Boldin plan, map out not just savings/investment flows but also opportunity flows (career changes, side-ventures, geographic moves). Then ask: what “market design” factors am I overlooking (network, timing, structural bias)?
In The Compass Within: A Little Story About the Values that Guide Us, Glazer tells a fictional parable about a rising manager, Jamie Hynes, who confronts misalignment between his ambitions, his values and the environments he’s in.
Core Values: Authenticity in work and life comes when you operate from your core values, not from external expectations.
Avoid Misalignment: When you’re misaligned with your values, you drain energy — when aligned, you gain clarity, courage, and better decisions.
For retirement planning: it’s not just “how much will I need?” but “how do I want to live?” If your plan flows from values, your spending, saving, and freedom choices align with your identity.
Jillian Johnsrud challenges the conventional single-exit retirement model and proposes a rhythm of “mini-retirements” throughout one’s career — breaks for adventure, rest, or reinvention. Retire Often: How Anyone Can Take Multiple Career Breaks to Unlock Adventure, Advance Their Career, and Find Financial Freedom is a total rethinking of the time scale of work-life balance.
Why not retire multiple times throughout your life? Learn more: Podcast: Jillian Johnsrud — Are Mini-Retirements Worth It?
Think in Life Chapters: Josnsrud suggests that retirement isn’t a one-time event. She advocates embedding smaller chapters of freedom and purpose throughout your life.
You’re Not Quitting: These breaks don’t require quitting — they require planning, financial flexibility, and intention.
Continue to Plan for the Ultimate Retirement: Think of your career as a multi-stage journey. You may want to plan for deliberate pauses to your savings, but everything needs to be mapped out over the long haul.
Use the Boldin Planner to model “breaks” in your working years: maybe a 3-month sabbatical aged 50, a 6-month global trip aged 55. Evaluate how those breaks affect savings, portfolio drawdown, reinvestment, and later retirement age.
Then build in resilience margins so the plan does not break if one of those breaks expands or shifts.
Boldin is democratizing access to high-quality financial planning. We empower people to manage a retirement plan that they can understand and trust. Our Retirement Planning software puts you in control of your future—while our coaching, classes, and access to expert advice from CFP® professionals at Boldin Advisors ensure you don’t have to do it alone. Whether you’re planning for retirement, navigating life transitions, or just trying to make smarter financial decisions, Boldin combines clarity, confidence, and affordability to help you move forward with purpose.
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Personal finance, investments and much more. Find fiction and many books on achieving a meaningful, happy, healthy and successful retirement.
Episode 44 of the Boldin podcast is an interview with Morgan Housel — a writer, former columnist at The Motley Fool and the Wall Street Journal, and a partner at the Collaborative Fund. He and Steve discuss Housel’s new book, The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness, and his perspective on […]
In podcast episode 39, Steve Chen and Jillian Johnsrud discuss mini-retirements and passive income.
