Matthew R. Harris
I help individuals and families transition from the accumulation phase of retirement to the income phase through structured income planning and tax-smart withdrawal strategies.
The 10-year Window That Can Make or Break Your Retirement
Happy Friday Reader ☀️ There’s a 10-year window that can make or break your retirement plan.And most people don’t even know it exists. I refer to it as the “critical window”—the 5 years leading into retirement, and the first 5 years of retirement. This is the period where your plan is most vulnerable to poor market returns… and where a few bad years can have a lasting impact on your income, flexibility, and long-term results. If you experience poor market returns during this window, it can...
How to Navigate Market Volatility in Retirement (without overreacting)
Happy Friday Reader ☀️ Over the past couple of weeks, I’ve been having a lot of very similar conversations. Clients feeling uneasy about the market.People wondering if they should be making changes.And a growing sense of uncertainty around what actually matters right now. And honestly, that’s usually what drives the content I put out each week. It’s not random.It’s a direct response to what I’m seeing, hearing, and being asked in real time. Right now, one theme keeps coming up again and...
The Shift from Accumulation to Income
Happy Friday Reader ☀️ There’s an important mindset shift that happens as you transition from the accumulation phase to the income phase And most financial advice is centered around growing your portfolio (which is the ultimate goal of the accumulation phase) But eventually, the question changes It’s no longer: “How do we accumulate MORE money?” It becomes: 👉 “How do we effectively live on this portfolio we have built?” And that’s where everything changes The problem is… Most people never...
Two Retirees. Same $2M. Very Different Paychecks.
Happy Friday Reader ☀️ Stay tuned until the end of the email: I included a short overview of my Structured Roth Conversion Guide, which outlines a strategy for making Roth conversions more structured and tax-efficient. Most people approaching retirement focus on one question: “How much have we saved?” But a better question is: 👉 “How much income can our savings actually produce?” Because retirement doesn’t run on a portfolio balance. It runs on income. Two retirees could each have $2 million...
What happens to your health insurance if you retire before 65?
Happy Friday Reader ☀️ Most people assume they have to work until 65 because of one thing: Health insurance. But the reality is many retirees stop working years earlier — and there are several ways they bridge the gap before Medicare begins. One of the most common questions I hear from people considering retirement is this: “If I retire before 65… what do I do about health insurance?” Since Medicare doesn’t begin until age 65, it’s a legitimate concern. For many people, the fear of losing...
The 4 IRA Risks Most Retirees Overlook
Happy Friday Reader ☀️ Most retirees think their IRA is theirs. It’s not. It’s a tax-deferred partnership with the federal government. And if you don’t have a proactive strategy, the IRS decides: • When you withdraw• How much you withdraw• How much you pay Here’s what most people never see coming: 1️⃣ RMDs at 73 Forced withdrawals that can push you into higher brackets in your 70s. 2️⃣ IRMAA Surcharges One extra dollar of income can trigger thousands in higher Medicare premiums. 3️⃣ The...
How This 60-Year-Old Couple Increased Retirement Income by 28%
Happy Friday Reader ☀️ Over the past few months, I’ve received a lot of feedback from readers asking for more detailed case studies — real numbers, real scenarios, and a clearer look at how small planning decisions can materially impact retirement income. So today, I’m sharing one that may look very similar to your own situation. If you’re within a few years of retirement, this will likely feel familiar. Most couples assume their retirement income is “set” once they hit their number. Doug &...
They Did Everything Right for Retirement - Except for This
Most people approaching retirement quietly wonder the same thing: “Do we actually have enough — not just to retire — but to live the life we want?” For Ben and Jennifer, both 61, that question was no longer theoretical. Retirement was just five years away — and they didn’t want guesswork or hope. They wanted a plan. Their goals were clear: • $14,000 per month after taxes• Income that keeps pace with inflation• Strong legacy potential for their children• Confidence that a market downturn...
Safe Money Weekly - 2.6.26
Happy Friday Reader! Just a quick reminder — I quietly rolled out a brand-new website that I had built as a free, growing resource hub for smarter, more confident retirement decisions. It brings 300+ of my blogs into one place (no paywalls), lays out my retirement income philosophy in more detail, answers many of the FAQs I get every day, and includes real client stories, and resources I’ll keep expanding over time. 👉 Your New Retirement Resource Hub Now as usual, all of the new resources...
Safe Money Weekly - 1.23.26
Happy Friday Reader! Just a quick reminder from last week — I quietly rolled out a brand-new website that I had built as a free, growing resource hub for smarter, more confident retirement decisions. It brings 300+ of my blogs into one place (no paywalls), lays out my retirement income philosophy in more detail, answers many of the FAQs I get every day, and includes real client stories, and resources I’ll keep expanding over time. 👉 Your New Retirement Resource Hub Now as usual, all of the...
I help individuals and families transition from the accumulation phase of retirement to the income phase through structured income planning and tax-smart withdrawal strategies.