John McCaffery

06/19/2026

An HSA is more than a way to pay for current healthcare costs. It can play a critical role in long term retirement planning when paired with a 401(k). The average 65-year-old today may need more than $172,000 for healthcare expenses in retirement, yet many employees have not accounted for this in their savings strategy.
By using both an HSA and a 401(k), employees can strengthen their financial future. Those who take advantage of this combination tend to save more, feel more confident about retirement, and are less likely to tap into their savings early. Together, these benefits create a more complete approach to preparing for both everyday needs and future healthcare costs.

fidelityworkplace.com

06/18/2026

How much of one stock is too much? See how concentrated equity positions could influence your finances and how you can strategize to manage their impact:

raymondjames.com

06/17/2026

For business owners, stepping away from your business and entering retirement can be a significant shift.
After years of building, leading, and creating value, stepping away can leave a gap in both structure and purpose. This shift in identity makes it even more important to intentionally build a lifestyle that supports your health, passions, and sense of meaning. Whether it's starting an encore venture, mentoring others, giving back, or focusing on relationships, there are many ways to create fulfillment in this next phase.
I'm sharing a Thrive Guide with ideas and inspiration—and if you'd like help turning those ideas into a plan that fits your life and aligns with your finances, I'd be happy to connect.
https://www.raymondjamesconnect.com/f7hz0V

06/05/2026

Retirement planning isn’t just about hitting a number. Many people save consistently for decades and still feel uncertain once income changes. That uncertainty often comes from trying to make decisions in isolation, wondering how spending, taxes, Social Security, and risk actually work together over time.
In this video, we walk through our planning process and how we start by understanding the person first, not just the balance sheet. From there, we help bring all the pieces together into one clear framework, so decisions are made in context rather than guesswork.

If you’re approaching retirement or already there and want to better understand how planning can provide structure and clarity, this video is a good place to start.

If someone you know could benefit from this conversation, feel free to share it.

06/01/2026

Finding purpose later in life – through service, creativity or connection – can be transformative. Becoming a docent is one way to do just that while making a meaningful impact on your community.

raymondjames.com

05/29/2026

Reaching an eight-week streak of positive growth, the S&P 500 was on a roll in May. Strong earnings in the tech sector helped lead the way as the market pushed ahead through inflationary pressures. Get the details in the May market recap:

raymondjames.com

05/29/2026

To help create an effective retirement income plan, you should know these six things about Social Security survivor benefits:

raymondjames.com

05/28/2026

As prenuptial agreements are rebranded for the app era, we explore how these often-aligned documents can actually work in favor of the long haul:

raymondjames.com

05/22/2026

We remember with gratitude those who made the ultimate sacrifice. Their legacy lives on.

05/21/2026

yahoo.com