Meet Your Guide
About Keith
A practical educator helping people navigate retirement with confidence and clarity.
Keith Callahan, NSSA®
Retirement Educator • Founder, Secure Retirement Solutions
Keith Callahan helps people approaching retirement understand the decisions that matter most — when to claim Social Security, whether Roth conversions make sense, how to build reliable income, and how to protect what they've spent a lifetime building.
As a National Social Security Advisor (NSSA®) and licensed life and annuity professional, Keith brings his retirement education directly into the community, hosting free workshops at local libraries and community centers throughout Massachusetts.
He is the author of Claiming Social Security: How to Get the Most From Your Guaranteed Lifetime Income Check, a practical guide that explains in simple language how to avoid the common mistakes people make when filing for Social Security. Copies are available at his workshops and seminars.
Keith lives in Sherborn, Massachusetts, with his wife Amy and their six children.
Background & Credentials
- National Social Security Advisor (NSSA®)
- Licensed life and annuity professional
- Published author on Social Security
- 20+ years of leadership, entrepreneurship, and education experience
- Community workshop educator throughout Massachusetts
- Focus areas: Social Security, Roth conversions, retirement income
Why This Work Matters to Me
I wasn't always the person teaching others how to protect what they've built. For a period of my life, I was the cautionary tale.
By age 29, I had bought, renovated, and sold more than 50 homes. I was making more money than I knew what to do with. Then the housing market collapsed in 2007.
I was left holding eleven homes I could not sell — all underwater, all with mortgages I could not cover — along with friends and family who had invested alongside me.
It was one of the most humbling experiences of my life.
I made sure every person who invested with me got their money back. Every one of them. It took time, but I kept my word. I am proud of that. But the experience of losing everything stayed with me — not just as a regret, but as a lesson.
At the same time, millions of retirees were watching the 2008 market crash devastate their 401(k)s and IRAs. Decades of hard work were suddenly exposed to forces they could not control.
That reality changed the way I think about money.
From that point on, I became deeply focused — not just on how to grow wealth, but on how to protect it. How to create security. How to help make sure one market crash, one stretch of bad timing, or one unexpected event does not undo a lifetime of work.
That became the heart of my work.
People spend decades building wealth, but very few are ever shown how to protect it, how to create reliable income from it, and how to make it last.
That is the gap I care about helping people close.
You have spent years building what you have. My role is to help you protect it, create dependable retirement income, and move forward with greater clarity and confidence.
— Keith Callahan
Our Mission
Secure Retirement Solutions exists to bridge the gap between what people need to know about retirement and the clear, honest education that helps them act with confidence.
We're not trying to manage everything for you. We're trying to make sure you understand your options so well that you can make decisions you feel good about — today and for years to come.
Let's Start a Conversation
Whether you attend a workshop first or want to jump straight to a consultation, Keith is here to help.