Affinity Insider | May 2026

Lately, life has felt especially full in the best kinds of ways: balancing work, family routines, short-term progress, long-term planning, and the anticipation that often comes with entering a new season of life. Moments like these have a way of sharpening perspective around what matters most and reminding us how interconnected our financial decisions often are with the lives we’re trying to build.

This edition of the Affinity Insider is centered around thoughtfully meeting the moment, financially, personally, and emotionally, during seasons of growth, transition, and change. From preparing for a growing family to navigating market uncertainty and retirement planning decisions, many of this month’s themes revolve around building stronger foundations for the future while remaining grounded in the present.

Here’s what you’ll find inside:

💸 Your Finances in Focus — A practical framework for preparing financially for a growing family while balancing flexibility, protection, and evolving priorities.

📈 Market & Investing Commentary — A look at April’s strong market rebound, concentrated leadership, corporate earnings strength, and the continued AI investment cycle.

🎁Featured Article — How smart tax planning can help retirees create greater long-term confidence and  flexibility throughout retirement.

📊 Did You Know? — Why this quarter’s corporate earnings results continue reinforcing the importance of underlying business fundamentals beneath market headlines.

👶Behind the Scenes — A personal family update as we prepare for an exciting new chapter and watch our young son proudly embrace his role as future big brother.

Thank you, as always, for allowing me to be part of your financial life and long-term journey. Whether you’re navigating major transitions or simply trying to make thoughtful decisions during a busy season of life, I hope this month’s insights provide a bit more clarity, perspective, and encouragement along the way.

Let’s begin.

💸Your Finances in Focus

Preparing Financially for a Growing Family

Preparing financially for a child is rarely just about buying more “stuff.” More often, it’s about preparing your life to absorb change gracefully.

A growing family can reshape how you think about time, flexibility, career decisions, housing, savings, risk, and even what “enough” means. While many couples initially focus on the logistics, the most valuable conversations are often broader:

What kind of life are we trying to build together over the next few years?

For some families, the major question is childcare. For others, it’s whether their current home still works. Sometimes it’s navigating leave policies, one income temporarily carrying more weight, or simply creating more breathing room in an already busy life.

The good news is that most of these decisions do not need to be solved all at once.

At Affinity, we often encourage clients to think about this transition in phases rather than as one giant checklist.

What tends to matter first

During pregnancy, planning is often less about optimization and more about creating clarity, flexibility, and resilience.

That may include:

• Reviewing maternity/paternity leave policies and expected cash flow changes
• Strengthening emergency reserves
• Evaluating childcare expectations and future costs
• Reviewing health insurance and employer benefits
• Discussing housing and lifestyle priorities
• Beginning conversations around how you’d want your growing family cared for and protected

Many couples also discover that the financial decisions themselves become easier once they feel aligned on the bigger picture. Conversations around flexibility, support systems, commute, career goals, family rhythms, and lifestyle priorities often create more clarity than spreadsheets alone.

What changes after baby arrives

Once routines begin taking shape, planning often shifts toward implementation.

This may include:

• Updating insurance and beneficiary designations
• Revisiting monthly spending and savings systems
• Updating tax withholding and dependent-related planning
• Establishing education savings goals if desired

Importantly, these priorities are interconnected and often evolve dynamically. A home purchase may influence insurance needs and emergency reserve targets. Childcare decisions may impact career flexibility and savings goals. Protection planning may become more urgent as responsibilities grow.

The objective is not perfection. It’s building a thoughtful framework that allows your financial life to adapt confidently as your family grows. Many of the best decisions during this season are not perfect decisions. They’re simply thoughtful, flexible, and good enough for the stage of life you’re in.

To help simplify the process, I’m also sharing an interactive planning checklist that outlines many of the practical financial, tax, insurance, and estate planning considerations that commonly arise when preparing for the arrival of a child.

👶Interactive Child Planning Checklist

The arrival of a child rarely makes life feel more controllable. But thoughtful planning can create more clarity, flexibility, and confidence for the road ahead.

📈Market & Investing Commentary

A Strong Rebound

Markets rebounded sharply in April following a volatile first quarter, with the S&P 500 rallying more than 13% since March 31st and delivering its strongest monthly gain since late 2020.  Yet, beneath the headline recovery, market leadership remained relatively concentrated, with a smaller group of large-cap technology companies continuing to drive a disproportionate share of index performance.

Three Developments Shaping Markets:

1.📈 Corporate fundamentals remain supportive

Despite uncertainty in the headlines, corporate fundamentals remain relatively healthy. Earnings expectations for U.S. companies continue to hold up well, with profit margins expected to remain near historically elevated levels.

2. 🔄 Companies are resuming share buybacks

Another notable development has been the reopening of corporate share repurchase windows following earnings blackout periods. Many companies, particularly within technology and financial sectors, have authorized substantial buyback activity this year.

While buybacks are only one piece of the puzzle, they can provide an additional source of support for equity markets while also signaling confidence from corporate management teams in their businesses and future cash flows.

3. 🏗️ Investment in AI and infrastructure continues accelerating

Large technology companies also continue investing heavily in artificial intelligence infrastructure, data centers, and long-term technology modernization initiatives. Importantly, these investments are occurring alongside continued shareholder returns rather than replacing them.

While AI-related enthusiasm has contributed to periods of concentrated market leadership, ongoing investment also reflects how businesses continue positioning for long-term productivity gains and future growth opportunities.

The Bottom Line

Markets will continue responding to familiar forces: economic growth, inflation trends, interest-rate policy, corporate earnings, and global events. While headlines can shift quickly, recent market activity is another reminder of the importance of looking beyond short-term noise and staying focused on long-term fundamentals.

As always, we remain focused on helping clients stay disciplined, diversified, and aligned with their long-term goals amid short-term market moves.

🎁Featured Article

How Retirees Turn Tax Planning Into Long-Term Financial Confidence

Retirement often brings more flexibility with time, but also more complexity around taxes, income decisions, and long-term planning. Withdrawals, Social Security timing, Medicare considerations, and investment income can all interact in ways that meaningfully affect financial outcomes over time.

In this month’s featured article, we explore how thoughtful tax planning can help retirees create greater confidence, flexibility, and clarity by coordinating decisions across multiple years rather than reacting one year at a time.

Inside the article, you’ll learn:

• Why retirement can create unique tax planning opportunities
• How thoughtful withdrawal strategies may help improve after-tax outcomes over time
• Where Social Security, Medicare, and investment income decisions often overlap
• Why multi-year tax planning matters more than isolated annual decisions
• How proactive planning can support greater flexibility and confidence throughout retirement

Whether you’re already retired, preparing for the transition, or helping family members navigate these decisions, this article offers a calm framework for thinking about taxes as an important part of long-term financial confidence.

Click here to read the full article.

Did You Know? 👇

This quarter’s S&P 500 Index earnings results have been remarkable, with an above-average number of Index constituents (84.0%) reporting earnings above estimates in Q1’26.

A few notable trends beneath the surface:

• The recent average earnings beat rate has been closer to 78%, making this quarter notably stronger than normal
• S&P 500 earnings growth approached 28% year-over-year as of early May, the strongest pace since the post-COVID rebound period in late 2021
• If sustained, this would mark the sixth consecutive quarter of double-digit earnings growth for the index
• Revenue growth has now remained positive for 22 consecutive quarters
• Technology and Communication Services continued to lead earnings growth, reflecting ongoing AI-related market strength

Financial takeaway: While headlines often focus on uncertainty surrounding inflation, interest rates, and geopolitics, corporate earnings remain one of the primary long-term drivers of stock market returns. This is a helpful reminder that markets can continue advancing even during periods of elevated uncertainty when underlying business fundamentals remain resilient.

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

📉 The Fallacy of Concentration (Financial Analysts Journal)
A research-driven challenge to the idea that concentrated portfolios reliably create superior outcomes, highlighting how survivorship bias often shapes the stories investors remember.

🤖 Can Nvidia Double From Here? (Josh Brown)
A nuanced look at how extraordinary companies can still justify lofty valuations when earnings growth, market dominance, and investor expectations continue compounding together.

🧠 The Impact of AI on SaaS: A Risk Framework for Investors (Research Affiliates)
A framework for evaluating which software businesses may benefit from AI adoption and which may see competitive advantages erode as AI lowers barriers to entry.

🛢️ Oil Price Uncertainty (Dimensional Fund Advisors)
A helpful perspective on why sudden oil price movements tend to create short-term uncertainty while markets and economies gradually adapt over time.

🏡 Where Should We Live? (Modern Husbands)
A practical framework for couples navigating where to live by balancing finances, career opportunities, relationships, lifestyle preferences, and long-term goals together.

🌅 The Most Overlooked Retirement Decision… It’s Not Your Portfolio (The Stay Wealthy Retirement Show)
An insightful conversation on how where you live in retirement can have an even greater impact on fulfillment, relationships, and daily life than investment performance itself.

🏡Behind the Scenes

The Big Bro Club

Over the past few months, our family has been preparing for an exciting new chapter: Stephanie and I are expecting our second child, a daughter, arriving in early October (or perhaps a little sooner if she decides she’s ready).

One of the best parts of the experience so far has been watching Caleb step into his future role as big brother.

Like many three-year-olds, he absolutely loves opening gifts and packages. So when it came time to share the news with him, we gave him a package containing a “Big Bro Club” shirt.

The moment he opened it, his eyes lit up.

He immediately wanted to put the shirt on and proudly started talking about his new baby sister.

There was just one small problem: at that point, we didn’t actually know if the baby was a boy or a girl.

We tried explaining this to him, but he confidently dismissed us. In his mind, the logic was obvious: moms make girls, dads make boys.

(Reasonable logic… although it does leave a few unanswered questions about how he arrived.)

A few weeks later, during a family gathering, Caleb wore the same shirt while running around with the grandparents. Everyone was so focused on playing with him, joking around, and taking pictures that it took some of them nearly twenty minutes to actually read what the shirt said. Once they did, the reactions were filled with excitement, hugs, and plenty of happy disbelief.

Then came the gender reveal.

Naturally, this also involved another package for Caleb to open.

Inside the box was a balloon. Blue or pink?

He bounced around the room with complete focus and anticipation before finally opening it to reveal a pink balloon floating into the air.

“A baby sister!”

Then, without missing a beat, he looked at us confidently and said:

“I told you. I knew it.”

One thing that has stood out to Stephanie and me during this pregnancy is how different the experience feels the second time around. Emotionally, there has been a greater sense of calm and familiarity. Life doesn’t fully pause the second time — there are still daycare drop-offs, work schedules, playground trips, bedtime routines, and a young one who wants to wear superhero shirts nearly every day.

At the same time, the physical demands on Stephanie have certainly been greater this pregnancy, which has made Caleb’s kindness and excitement even more meaningful to watch. He regularly checks in on the baby, talks about becoming a big brother, and has approached the entire experience with an incredible sense of gentleness and joy.

As many of our clients know firsthand, seasons like these have a way of bringing both excitement and perspective. They remind us that some of the most meaningful parts of life are not built around perfect timing or perfect plans, but around growing families, shared anticipation, and the people we get to experience life alongside.

We’re incredibly grateful and excited for this next chapter, and we look forward to welcoming our daughter to the Pantele family this fall.

P.S. ~ Many of our conversations with clients lately have centered around growing families, changing routines, and very full calendars. These seasons can feel demanding, but they’re often the ones we later remember most fondly.