I’ve been reflecting on just how many of you are currently navigating meaningful changes—retirements, relocations, career shifts, liquidity events, family dynamics, and personal milestones. These transitions don’t just happen on a calendar. They unfold in real life, often with layers of emotion, complexity, and opportunity. And through it all, financial planning plays a quiet but essential role in helping you turn uncertainty into direction, intention, and progress.

In this edition of The Affinity Insider, you’ll find insights and tools designed to support you through moments of change—big or small. Here’s a look at what’s to come:

📌 Your Finances in Focus — Real-life transitions and how smart planning helps keep things in sync.

📈 Market & Investing Commentary — A look at global strength, U.S. resilience, and what’s driving returns in 2025.

🎯 Featured Article — The Three-Bucket Strategy: a structured way to turn your retirement savings into lasting income.

📚 What I’m Reading, Watching & Listening To — Thought-provoking ideas at the intersection of wealth and well-being.

🌊 Behind the Scenes — Turning 40 and building with intention, personally and professionally.

Whether you’re coasting or climbing right now, I hope this month’s edition offers a moment to reconnect with your goals, and a reminder that you don’t have to navigate any of it alone.

Let’s dive in.

💸Your Finances in Focus

Life in Motion. Planning in Sync.

Life rarely unfolds in a straight line, and neither does financial planning. This month, we’re highlighting some of the life transitions and decisions we’re actively helping clients navigate. From exciting milestones to unexpected challenges, each one brings new financial considerations and opportunities.

Some clients are stepping into retirement, while others are starting families or managing equity events. A few are relocating, navigating a loss, or simply trying to make smart decisions with cash flow, taxes, and investments. In every case, our focus is on aligning financial choices with personal values and long-term goals.

Here are just a few of the transitions we’re currently supporting:

Family and Lifestyle

• Growing families, new marriages, and caring for loved ones
• Home moves, renovations, or downsizing
• Inheritance planning and estate transitions

Career and Wealth

• Job changes, sabbaticals, and downshifting
• Law firm partner planning and equity compensation
• Retirement transitions and early planning

Financial Decisions

• Liquidity events and private stock sales
• Investment property strategies
• Navigating health challenges with financial clarity

If any of these sound familiar, or if you’re facing something not listed here, we are here to help. Schedule time to connect.

📈Market & Investing Commentary

In May, the market was largely buoyed by easing trade tensions as well as strong fundamental earnings growth. Looking to the future, while risks remain — as well as bouts of volatility and uncertainty — there are also potential tailwinds with more favorable fiscal policies (lower taxes) and monetary policies (lower interest rates) in the second half of the year and beyond.

In terms of recent developments, here are some key market drivers to keep in mind:

1. Jobs Above Expectations: Despite fears of tariffs and government efficiency policies, non-farm payrolls increased above expectations at a healthy 139,000 for May, as reported by the U.S. Bureau of Labor Statistics. Furthermore, unemployment remained unchanged for the third straight month at a relatively low 4.2%. Overall, the employment report highlights the resilience of the U.S. economy.
2. Corporate Earnings Above Expectations: Despite fears of a weakening consumer, S&P 500 companies delivered strong results in the first quarter with an earnings growth rate of over 13%. According to FactSet, 78% of companies reported positive earnings surprises and 64% had positive revenue surprises in the first quarter. Overall, earnings reports have highlighted the resilience of the U.S. consumer.
3. Global Returns Above Expectations: Despite fears of disputes around the world, the MSCI All Country World Index (a benchmark for the global stock market) reached an all-time high this week, with a year-to-date return of nearly 17% (through June 10, 2025). The performance has largely been driven by developed markets, particularly Europe, although emerging markets such as Latin America have returned double digits in 2025. Overall, diversified portfolios continue to benefit as global markets rally and support relatively weaker returns in the U.S.

There are always reasons to fear the market and the economy, however, recent activity highlights the resilience and strength we are seeing across the globe.

As always, we’re here to help you cut through the noise and stay aligned with your goals—calmly, clearly, and with conviction.

🎁Featured Article

The Three-Bucket Strategy: An Organized Approach to Making Your Retirement Savings Last

Reaching retirement is a major milestone—but it also marks the beginning of a new kind of financial planning. For many retirees, the real challenge isn’t just how much they’ve saved, but how to use those savings to generate steady income, protect their lifestyle, and feel confident through changing markets.

This month’s article introduces the Three-Bucket Strategy—a clear, time-tested approach to organizing your retirement savings by purpose and timeline. It’s designed to help you navigate both short-term needs and long-term goals without getting caught up in market noise or emotional decision-making.

If you’re wondering how to make the most of what you’ve worked so hard to build, this framework offers a way to do just that—with structure, clarity, and peace of mind.

👉 Read: “The Three-Bucket Strategy: An Organized Approach to Making Your Retirement Savings Last”

Did You Know? 👇

Against the backdrop of heightened political uncertainty, potential trade wars, and lower consumer sentiment, investors may have concerns about whether the US could tip into a recession. The National Bureau of Economic Research identifies recessions using backward-looking data, so we won’t know we’re in recession until after it’s begun.

Luckily for investors, markets are forward-looking and generally react before we see slower economic growth show up in the macroeconomic data. This also means that expected stock returns are positive, even when the economic outlook is weak. This is borne out in the historical data. One dollar invested at the start of a recession saw positive returns after three years in 11 out of 12 past recessions. The average of the three-year returns after the start of a recession was 43.2%, which is nearly identical to the 41.8% average return of all three-year periods from 1947 to 2024.

📰🎧🍿What I’m Reading, Listening To, and Watching

WEALTH

🦾 The 17 Elements Shaping the 21st Century – and Who Controls Them (First Trust)

🏡 US Housing Outlook (Apollo)

🔒Bill Gurley – The Gift and the Curse of Staying Private (Invest Like the Best)

WELL-BEING

🎹 Practice First, Then Optimize (Meaningful Money)

⏳ The Small Actions that Become Your Legacy (Harvard Business Review)

🎓 We Have to Really Rethink the Purpose of Education (The Ezra Klein Show)

🏡Behind the Scenes

The View from 40: Chasing Less, Building More

In May, I celebrated my 40th birthday, a personal milestone that invited a mix of reflection, gratitude, and curiosity about what’s next.

At age 30, I was constantly chasing markers of progress —running races, earning certifications, advancing my career. Life was filled with movement and momentum: domestic and international travels, adult league hockey games at nights, scuba instruction on weekends, and a steady pursuit of mental and physical challenges. I leaned into learning more about the world and about myself.

Now, at 40, life looks different, but the desire to grow hasn’t gone anywhere. The challenges are no longer measured by medals or miles, but by presence, responsibility, and the effort to build something meaningful over time. I’m almost five years married, the father of a joyful and curious toddler, and the founder of a business that reflects my values. The focus has shifted from personal exploration to building something lasting, for my family, my clients, and my future self.

To mark the occasion, my wife, son, and I spent a long weekend in Santa Barbara. There were no international flights or tightly packed itineraries, just sandcastles on the beach, museums filled with dinosaurs and oversized guitars, and time spent searching for crabs and waving at trains. Slower moments. Lasting memories.

Looking back on the past decade, I’m grateful for the foundation laid by putting in much of the work early. The time invested in personal growth, professional development, and financial planning has created a sense of freedom — not just for me, but for the people who depend on me. I trusted in the compounding power of effort, skill, and intention, and I’m beginning to see the returns.

What hasn’t changed is a core belief: wherever you are in life, there’s an opportunity to make the most of it: to reflect, to connect, to build, and to keep showing up with purpose.

I don’t know exactly what this next decade will bring, but I’m entering it with a deep sense of appreciation. I feel fortunate to have more financial freedom than I did at 30, even as I carry more responsibility for others. Both are a gift, and both add meaning to this chapter of life. I’m excited for what’s to come.

Thanks for being part of the journey.

P.S. ~ Whether it’s a new chapter or a quiet shift, I’d love to know — what moment lately has made you pause and reflect?