Thimble Island Private Wealth

10/15/2026

🏴‍☠️ Well, well, well… look who’s making a comeback. 👀
A familiar face. A legendary comeback. 💰⚓

Can you guess who’s returning?

10/15/2026

🚨 Social Security's largest increase in four years is coming.

Benefits are set to rise 3.6% in 2027, adding about $900 annually for the average retiree.

Check out this Wall Street Journal article for a closer look at what the increase means and why it's happening.

Amount of earnings subject to Social Security tax will rise to $192,300

10/15/2026

📣 Medicare Open Enrollment starts today.

From October 15 through December 7, Medicare beneficiaries can review and make changes to their coverage for the coming year.

If Medicare is part of your retirement planning picture, now is a good time to review your current coverage and evaluate whether it still aligns with your needs.

10/14/2026

The latest Weekly Market Commentary examines strong business lending, tighter credit spreads, and housing constrained by mortgage rate lock-in. Read it here: https://www.thimblepw.com/market-commentary

10/13/2026

Retiring within the next 5-10 years? Now is the time to start thinking through the decisions that can have the biggest impact on your future.

Join us this Friday as we discuss: ✔ Retirement income ✔ Social Security ✔ Healthcare costs ✔ Retirement readiness

📅 October 16
🕛 12:00 PM ET
📍 Virtual & Free

Reserve your spot today: https://lpl.zoom.us/webinar/register/WN_aQYOiI0VSvKGj1g7MKWfEw #/registration

10/12/2026

🚨 Many business owners revisit their marketing, technology, and growth strategies as their company evolves. But what about their retirement plan?

What worked for your business years ago may not be the best fit today. As your workforce, profitability, and long-term goals change, it may be worth revisiting your retirement plan design.

📖 Download our complimentary Business Owner Retirement Plan Guide to learn more: https://www.thimblepw.com/business-owner-services

10/08/2026

Retirement is about more than choosing a date.

How will Social Security fit into your income plan? What should you expect for healthcare costs? And most importantly, will your savings support the lifestyle you envision? We’ll cover these questions and more in our next Financial Fridays webinar.

📅 Friday, October 16
🕛 12:00 PM ET
✅ Free to attend

Register here: https://lpl.zoom.us/webinar/register/WN_aQYOiI0VSvKGj1g7MKWfEw #/registration

10/07/2026

The latest Weekly Market Commentary examines rising government debt costs, Treasury market stress, and what investors should watch as higher rates reshape the fiscal outlook. Read it here: https://www.thimblepw.com/market-commentary

10/06/2026

💭 Thinking about retirement?

Before you focus on a number, start with the questions.

Where will your income come from?
What will healthcare cost?
How will taxes affect your income?
When should you claim Social Security?
And perhaps most importantly: what kind of life do you want your retirement to support?

Retirement planning isn’t simply about accumulating enough money. It’s about creating a strategy that helps your resources support the life you’ve worked to build.

Save this post for your next planning conversation and join us for our next Financial Friday 10/16 as we discuss Preparing for Retirement.

10/05/2026

🍎 Let's give teachers the recognition they deserve.

Teacher Day is the perfect opportunity to thank the educators who challenged us, encouraged us, and helped shape who we are today.

Tag a teacher who made a difference in your life or share a favorite memory below. 👇