Gilbert Wealth Articles

Holding Gain vs. Tax Loss: How You Can “Lose” and Still Be Ahead

You’re looking over your quarterly performance review. There it is—one of your investments is proudly showing a healthy gain. You feel good about it.Later, you pull up your brokerage statement. Same investment… but this time it’s showing a loss. Not just a tiny dip—an actual negative number in the gain/loss column.You stare at it for a moment. Which one is right? How can the same holding be up in one place and down in another?Here’s the twist: both are right. Two Different Ways to Measure the Same Investment What’s happening comes down to two ways of looking at investment results:…
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Should You Aim for 100% Success in Monte Carlo Retirement Simulations?

Monte Carlo simulations are a staple in retirement planning. They run thousands of potential future market scenarios to estimate how likely your portfolio is to last throughout retirement.Monte Carlo projections can generate a number of outputs but one of the most commonly discussed is the Probability of Success. It goes like this: "Based on our assumptions, you have a 90% Probability of Success". One question often comes up next: What about the other 10%?This portion of the projection has been dubbed the "Probability of Failure" and can be a confusing or scary thing to see.  But what exactly does “failure” mean? And is it really bad…
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Three Core Ways to Project Retirement Success — and How They Compare

If you’ve ever asked, “Will I run out of money in retirement?” — you’re not alone. It’s one of the most common (and most important) questions people ask.To answer it, financial planners and DIY'ers use different types of retirement projections. Each method takes a slightly different approach, and depending on which one you use, your results — and your peace of mind — can look very different.In this guide, we’ll walk you through the three main ways to project retirement success: Straight-Line Projections (The Spreadsheet Method) This is the classic retirement projection and often people start here. Straight-Line Projection can be…
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How to Get Promoted: A Roadmap to Career Advancement

Growing your income has more potential to increase your wealth over time. While cutting expenses can be an important piece, expenses can only be so low whereas income can grow to levels where regular expenses are nearly irrelevant. While there are many ways to grow your income, the easiest and most applicable for most people is getting promoted. Getting promoted isn’t just about working hard—it’s about working strategically. Promotions go to those who consistently deliver value, make their contributions visible, and position themselves as ready for the next level. Whether you’re aiming for your first leadership role or the next rung in your…
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The Different Ideologies Surrounding Social Security Claiming

When people talk about when to claim Social Security, they often sound like they’re debating politics, barbecue styles, or the best way to make coffee. Opinions are strong. Camps are divided. And the “right” answer depends heavily on what you value most.Over the years, I’ve seen five main ideologies emerge. They’re not just financial strategies—they’re reflections of personality, risk tolerance, and even life philosophy. The "Cash It In Crew" These folks see Social Security as a lifetime tab they’ve been paying into—and they’re ready to cash out as soon as the window opens at age 62.They argue that no one…
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Beyond Longevity: The True Goal of Aging Well

As a financial advisor, I’ve had countless conversations with clients about longevity. The topic often comes up when we talk about retirement planning, Social Security timing, or healthcare costs.When I mention that a healthy 65-year-old today has a good chance of living into their 90s, the most common response is:“I don’t want to live that long.”When I ask why, the answers are strikingly similar. They’ve seen parents, grandparents, or neighbors live out their final years in poor health—bedridden, in pain, or battling multiple chronic conditions. They’re imagining those final years as nothing but decline. A burden. And I get it. No…
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The Six Habits of Highly Successful Retirees

Retirement isn’t the finish line. It’s a doorway. Beyond it lies a chapter that can be rich with meaning, connection, and joy—if you choose to live it with intention.The transition to retirement is not easy for everyone as moving from decades of work centric life to the unstructured life of retirement can be challenging.Over the years, I’ve seen people step into retirement and flourish, while others lose their way. The difference rarely comes down to wealth alone. It comes down to habits—daily ways of living that keep life vibrant and dreams alive.Here are six habits that seem to shine through…
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The Economic Value of Social Security: A Critical Piece of Lifetime Net Worth

Social Security is often seen as a government benefit—something earned over a lifetime of work but not fully appreciated until retirement. However, when evaluated economically, Social Security represents one of the most valuable assets many retirees possess. Its true value becomes even clearer when viewed through the lens of a comprehensive lifetime net worth statement, which accounts for both current assets and the present value of future income and expenses. The Economic Value of Social Security At its core, the economic value of Social Security lies in its stream of guaranteed, inflation-adjusted payments that continue for life. These payments often rival…
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The Most Common Surprises in Retirement Planning

If you’ve ever pictured retirement as a smooth glide into sunny days, long lunches, and more time for the things you love, you’re not alone. Most of us imagine this next chapter as simpler, easier, and free from the worries of our working years. And while much of that can be true, retirement often comes with its own set of surprises—some welcome, others… not so much.People who’ve worked hard, saved diligently, and thought they’d covered every base, often find themselves blindsided by taxes they didn’t expect, expenses they didn’t plan for, or emotional adjustments they never saw coming. It’s not that…
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What Is Financial Independence?

For many, the concept of financial independence sparks visions of early retirement, tropical beaches, and never having to work again. But financial independence (FI) is more than a fantasy—it’s a measurable, achievable financial state. At its core, financial independence means you no longer need to earn a paycheck to cover your living expenses. Instead, your investments, passive income, or other resources provide enough income to support the lifestyle you choose.Imagine that - having enough income from your assets that you are able to sustain your lifestyle safely for the rest of your life without having to work another day in your…
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