Retirement ReadinessConfidently Answer: Am I Ready to Retire?
Retirement isn't a single decision — it's a sequence of them. We help you get the order right.
How We Helped Clients Prepare for and Retire Earlier Than Planned
“With a public education pension of my own, and my husband having none, we're heading into a fall planning meeting to figure out what retirement really looks like for us, given how much the landscape has changed. It's exactly the kind of complexity I trust this team to help me navigate — like they always have.”
— Anne C.
“I'd made a career change that wasn't working out the way I'd hoped, and decided the better path was to retire early at 57. Right around that time, we got the call that our advisor, who had counseled me on retiring, had passed away. He'd already put a succession plan in place with Greg. Greg took up the ball and provided the advice and stability I needed during that time. During our conversations back then, and to this day, Greg leaves no doubt that he genuinely cares about his clients. Years later, we're happily retired, our portfolio continues to grow, and the whole experience has honestly been fantastic.”
— Kevin & Marian B.
“I spent nearly forty years with the same company, and as it was going through changes, I needed to understand my pension and healthcare benefits and how the timing of my retirement would affect our future. Our biggest fear back then was running out of money. As we interviewed advisors, Greg was the only one who told us, with real confidence, that we wouldn't have to go back to work. He built a plan around what we were comfortable with, and thirteen years later, we have more money than we did when we retired. Right after I moved everything over to him, the market took a turn while we were away on vacation, and Greg reached out to every client with a message that was calm and reassuring. That's just who he is — steady, no matter what's going on. I consider him a friend, and we trust him completely.”
— Bob G.
“My husband John did his research before he retired, and Greg was who he chose. More than twenty years later, Greg still manages our trust and my IRA and makes even taxes simple and easy. They know their business, and I have every confidence in them managing my estate and finances. They're fantastic people — they do the best for you, and you won't be disappointed.”
— Joan M
"At the time, we'd been with a broker-dealer model that always felt like it was trying to sell us something. What we wanted instead was real financial guidance — and that's exactly what we found. Greg simplified the whole process: where to put our money, how to manage it for the future, and a long-term plan that could absorb the day-to-day bumps in the road without throwing everything off course. Now that we're not working, Greg wants us to enjoy retirement, not just get through it. He models out different scenarios for us so we can feel comfortable saying yes to travel and the things we want to do, instead of second-guessing ourselves."
— Brett & Dana V
“After a career change, I worked at a nonprofit for four years and retired from it in 2024, then went back into the insurance industry to run commercial sales — an encore career, not a full stop. Through all of it, there's been a sense of consistent, stable advice that's given me real comfort making financial decisions, without the burden of worrying about the outlook. My family and I feel comfortable that I could retire whenever the time is right. Now we're looking ahead to my wife's retirement in a couple of years, and to Greg's guidance with Social Security timing and next steps.”
— Len R.
Additional Resources
More Ways to Get Informed
● The Pre-Retirement Checklist
● Financial Strategies for Women
● Insurance Needs Assessment: For Empty Nesters and Retirees
● How Will Working Affect Social Security Benefits?
● Understanding the Basics of Medigap Policies
● Follow Cambridge Cape Cod Advisors on social for ongoing insight
as you get closerThe Decisions in Front of You
Retirement readiness is really a set of interlocking decisions. Here's what deserves attention first:
● Current Social Security claiming age range (62–70)
● Medicare enrollment window requirements
● Withdrawal order considerations across taxable, tax-deferred, and Roth accounts
● Current Required Minimum Distribution age and Qualified Charitable Distribution options
● Healthcare bridge strategy considerations before Medicare eligibility
These are general considerations — specific ages, thresholds, and deadlines change over time and can vary by situation. We'll walk through exactly what applies to you.
our commitment to youGuided by What Matters Most
Strategies built around you. Values you can count on.
We create strategies tailored to your specific needs and goals. Years of experience have prepared us to guide you through life's transitions, and we do it with trust, honesty, and integrity. We believe values matter, and we live ours every day.
Get you personalized Retirement Readiness assessment.
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Fifteen minutes is enough to know whether we are the right fit. Reach out and we will find a time.