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.
Would Your Retirement Survive the Great Depression?
Happy Friday Reader ☀️ Imagine retiring at age 65 with a $3 million portfolio... Then, within a few years, your portfolio falls to roughly $1 million. Would your retirement plan survive? Most people assume that if their portfolio lost two-thirds of its value, their retirement lifestyle would need to be cut by two-thirds as well. But that's not necessarily true. One of the biggest misconceptions in retirement planning is confusing a portfolio decline with an income decline. A retiree's...
We Have $1.5M Saved. Why Can We Only Spend $5,000/month?
Happy Friday Reader ☀️ This week, I shared a case study involving a 64-year-old couple with roughly $1.5 million saved for retirement. Their advisor recommended spending about $5,000/month from their portfolio. The recommendation was based on traditional retirement planning concepts like: ✅ The 4% Rule ✅ Monte Carlo Analysis ✅ Static spending assumptions None of these tools are inherently bad. But they often answer a very different question than retirees are actually asking. Most retirees...
Why Some Retirees Pay FAR More in Taxes Than Expected
Happy Friday Reader ☀️ Most retirees understand the power of compound growth. Invest early. Stay invested. Let time do the heavy lifting. But there’s another form of compounding that many people underestimate heading into retirement: Taxes. For decades, tax-deferred accounts like IRAs and 401(k)s can be incredibly effective wealth-building tools. Your investments grow tax-deferred, contributions may reduce taxable income, and compounding works in your favor during your working years. But...
How Better Income Planning Can Change Your Retirement Timeline
Happy Friday Reader ☀️ One of the biggest misconceptions in retirement planning is that the goal is simply to accumulate “enough” money. But in reality, the real goal is optionality. Because when income is structured properly, retirees often discover they have far more flexibility than they realized: ✅ The ability to spend more confidently ✅ Greater protection from market volatility ✅ More flexibility with investments ✅ Or even the option to retire earlier than planned This week, I worked...
Why $2 Million Still Doesn’t Feel Safe in Retirement
Happy Friday Reader ☀️ One of the biggest surprises in retirement is that hitting a “magic number” often doesn’t create the financial confidence people expected it would. I’ve talked to retirees with $2 million, $3 million, and sometimes far more… yet many still feel uneasy about spending. Because deep down, retirement was never really about the size of the portfolio. It was about whether the income could actually hold up for the rest of their life. That’s what makes retirement so...
How much can you actually spend in retirement?
Happy Friday Reader ☀️ Most people think retirement success comes down to one number: “Do I have enough saved?” $1M… $2M… maybe more. But after everything I shared this week, here’s the reality: 👉 Retirement isn’t funded by your net worth👉 It’s funded by your income More specifically… 👉 How much you can safely spend without running out? Because portfolios don’t create peace of mind—income does. The problem is, most plans are still built around accumulation: Save more. Invest more. Delay...
Why Timing Matters More Than You Think in Retirement
Happy Friday Reader ☀️ Most people think retirement success comes down to one number: “Do I have enough saved?” But there’s a factor that often matters just as much… Timing. Two retirees with the exact same portfolio can have completely different outcomes — simply based on when they retire. That’s because early market losses don’t just hurt… They can quietly derail an entire income plan. This week, I focused a lot on this idea — and more importantly, how to build a plan that isn’t dependent...
Can You Retire at 65 and Help Your Kids Financially?
Happy Friday Reader ☀️ Most people approaching retirement ask: “Do we have enough?” But this couple asked something better: “Can we retire comfortably… and still help our son get started in life?” That’s the kind of question that leads to a real plan. Meet Mark & Linda Both age 60, retiring at 65 $1.8M saved today ($1.2M in the market) Maxing out 401(k)s + Backdoor Roth IRAs Goals: $17,000/month retirement income $50,000 gift at 65 ~$15,000/year ongoing gifting Step 1: Build the Income Floor...
When should you take Social Security? (a better question to ask inside)
Happy Friday Reader ☀️ A different way to think about Social Security… One of the most common questions I get is: “When should I take Social Security?” And the honest answer is… it depends Most advice focuses on two options: Take it early Create immediate, guaranteed income Reduce pressure on your portfolio Tradeoff: lower lifetime income and reduced survivor benefits Delay it Increase your benefit ~7–8% per year Create a larger, inflation-adjusted income stream Tradeoff: more reliance on...
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...
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.