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Post-Memorial Day Check-In: Are You on Track for Summer Goals?

Post-Memorial Day Check-In: Are You on Track for Summer Goals?

June 02, 2025

As we step into summer, here in Newtown, Fairfield County, Connecticut, I’m Tony Leonardi, a CFP® professional guiding retirees toward confident financial futures. Memorial Day just passed on May 26, and it was a weekend of reflection for me—raising a new American flag, honoring veterans like my friend with over 20 years in the Air Force Special Forces, and enjoying a family barbecue. Despite the wet weather, I fired up my outdoor pizza oven, harvested wine cap mushrooms from my garden for a sausage and mushroom pizza, and savored lobster rolls, ribs, hot dogs, and salads—Italian-style, of course! This got me thinking: How are your summer goals shaping up, financially and personally? Let’s check in.


Reflecting on the First Half of 2025

Memorial Day is more than a holiday—it’s a chance to honor sacrifices and assess our progress. With 2025 nearly halfway done, let’s look at Q1 and Q2. Have you stuck to your budget? Rising costs, like healthcare or travel, and higher grocery bills reported by clients in Fairfield County, can derail even the best plans. Now, the markets: The S&P 500 has been a rollercoaster. As of May 27, it closed at 5,921.54, up 2.05% from the previous day, snapping a four-day losing streak. Last week, it hit 5,900 on May 21, a 23% gain from its early April low of 4,800, though it’s flat year-to-date compared to January’s start.

Last week brought volatility: a 1.6% drop on May 21 (Dow down 800 points) due to Trump’s tax-cut bill fears adding to the $37 trillion US debt, and a 2%+ weekly loss by May 23 after tariff threats on the EU (delayed to July 9). The Moody’s downgrade on May 16 triggered a 1.2% futures dip, while 30-year mortgage rates hit 6.86%—the highest in three months—affecting bonds. Yet, yesterday’s rally came from a tariff reprieve on the EU, boosting trade hopes, and an unexpected consumer confidence jump, signaling resilience. All 11 S&P 500 sectors rose, led by tech.

If your portfolio leans on the market, are you on track? Have you adjusted spending or added downside protection? Reflect: Do your investments match your long-term risk tolerance, or is it time to reassess amid this volatility?


Setting Summer Goals for Retirement

Summer is for enjoyment—maybe a trip like my son Tony’s recent France adventure, where he returned engaged to Maddie (congratulations!), or my niece Alexa’s new son, Baker Calo Beger, born 5/25/25, adding joy to our family. Or perhaps it’s gardening, which I’ve tackled despite Connecticut’s wet spring. But summer can strain your retirement if unchecked—overspending or neglecting health can hit your budget hard.

Set realistic goals. Financially, allocate a “fun budget”—say, $100-$500 daily for a beach trip—and use rewards points or mid-week travel (e.g., a client saved thousands on Cape Cod in June) to save. If you lack a budget or plan, I’d love to help at LeonardiFamilyWealthcare.com. For health, staying active cuts future costs. Try a 20-minute daily walk or join a local walking group—pickleball’s big here too. More active years mean more time enjoying savings, not medical bills. We’ll explore this health-wealth link more in an upcoming episode with a special guest.


Actionable Steps to Stay on Track

Here are three steps for a balanced summer:

  1. Review Your Plan: Check your probability of success meter (a tool for my clients) to see if market swings or spending shifts affect you. Need one? Let’s build it together.
  2. Adjust Spending: Can $200 cover a weekend getaway without touching your emergency fund? If not, opt for day trips—small tweaks avoid big issues.
  3. Prioritize Health: Commit to three 20-minute walks weekly or cook two to three veggie-rich meals using Newtown’s farmers’ market produce. It’s fresh veggie season—seize it!

These steps align your finances and health for a fulfilling summer.


Stay Steady This Summer

From Memorial Day reflections to the S&P 500’s 23% trough-to-peak gain (now 5,921.54), your progress matters. Yesterday’s 2.05% rally shows resilience, but volatility persists. Stay focused on long-term goals, not short-term headlines.

For more, visit LeonardiFamilyWealthcare.com. Listen on Spotify or Apple Podcasts, watch on YouTube, and download the 2025 Retirement Reset Checklist. Rate us on Apple if you’d like! Whether in Fairfield County or beyond, let’s build a smarter retirement. Enjoy your summer!