How to Outlive Your Assets

Hi, Tom here.

Big thanks to everyone who joined our Wealth Workshop yesterday. We dove into some great topics—investing, retirement strategies, and estate planning. If you missed it, don’t worry: keep an eye out for our July session invite.

Today’s edition addresses a concern many of you shared: how to ensure your money lasts longer than you do.

Let’s dive in.

The storyline goes like this:

You’re driving to a dinner party with your spouse, radio quietly playing. A commercial from a local car dealership reminds you you're due for a new car soon. Immediately, your mind drifts to retirement, just a few years away, and the financial strain a new purchase might add.

You recall those pricey flights to Florida last winter, irritated by inflation and wondering if your 401(k) is ready.

As you pull into your friend’s neighborhood, you briefly notice other people’s landscaping and quickly move on.

This internal conversation lasted just 20 seconds—but it tapped into a deep fear we all share:

Will my assets provide the income and lifestyle I’ve worked so hard for?

It's perhaps the most fundamental financial worry—one that only grows louder as retirement approaches.

You’ve done well and built a strong portfolio. But retirement feels different. Without steady income, each dollar spent feels like it’s pulling you closer to zero.

Compounding this anxiety, many of us built wealth during a zero-interest-rate era—an environment very different from today’s. Earning safe interest feels simple yet oddly foreign.

The fear of misspending and facing tight cash flow later in retirement is real. Nobody wants financial stress in their 80s.

So, how do we ensure our assets outlive us?

Let’s learn from one of the greatest companies of all time: Microsoft.

In the late 90s, Microsoft had it all.

Windows ran on nearly every PC, and Office was the essential tool for businesses and schools worldwide. The digital future belonged to them.

Revenue soared, profits climbed. Microsoft seemed unstoppable.

Your financial life before retirement resembles Microsoft’s peak in the 90s: Your career and income at all-time highs. Your portfolio robust after weathering storms.

It feels like standing at a mountain summit. But mountains have two sides, and every ascent eventually faces descent—a reality Microsoft confronted.

In the wise words of a seasoned Mount Everest guide:
“You don’t pay me to get up the mountain, you pay me to get down.”

Right after Microsoft’s peak came two almost existential blows:

• A high-profile antitrust case that nearly split the company.

• A 60% crash in its stock price during the dot-com bust.

You guys can remember this. It was a one-two punch. Microsoft went from dominance to defense. From offense to survival.

This storyline of “when the good times end” plays out in the minds of every investor planning for their future. When planning for the ultimate financial move—retirement—the fear looks like this:

• A market drop right after you stop working

• A lifestyle that’s no longer funded by portfolio income

• A realization that what worked in the past might not work now

Microsoft could’ve coasted. Or panicked. Or faded away. But they didn’t.

Instead, they reinvented, playing the best game in business-the long game.

Microsoft didn’t disappear. They focused on what matters and made wise, deliberate moves:

• They focused relentlessly on cash flow. When companies hit turbulence, cash flow is king. Microsoft survived because they had ample reserves. Your liquidity serves the same purpose—it's leverage.

• They doubled down on core strengths. Office and Windows were still essential products for most companies. You possess unique strengths—your ability to invest, willingness to adapt, budgeting skills, or contentment. Whatever edge you have, that’s your focus.

• They slowly shifted toward new models. Over time, Microsoft evolved into a cloud-first company, embracing subscription revenue and changing the way they made money.

Today?

Microsoft is worth over $3 trillion.

You’re not a trillion-dollar company. You can’t raise capital or pivot into cloud computing. But you can build a financial plan mirroring the same principles.

Here’s how high-net-worth families stay wealthy in retirement—and make sure they never run out of money:

1. Don’t confuse peak income with peak security. Your current high earnings don’t guarantee future security. Without a solid retirement strategy, wealth can erode quickly—especially in the first five years of retirement.

2. Build durable cash flow. Retirement isn’t funded by hope; it’s funded by predictable income. Start with Social Security, then layer in dividends, interest, rental income, and carefully timed asset sales, structured using the bucket approach (cash for short-term, bonds for intermediate-term, equities for long-term growth).

3. Prioritize tax efficiency. Smart sequencing—taxable accounts first, then tax-deferred, finally Roth accounts—extends asset longevity by cutting your tax bill.

4. Liquidity buys control. Having cash or near-cash assets isn’t lazy—it’s powerful. Microsoft didn’t survive by being aggressive; they survived by having reserves. Your liquidity allows you to ride out volatility, fund surprises, and maintain control.

5. Know your burn rate—and its risks. Many underestimate monthly spending (e.g., thinking it's $15K when it's really $22K). You can't manage what you don't measure. Track spending precisely to sustain your lifestyle.

6. Understand longevity and health risks. Retirement could last 30+ years. Having conversations early in retirement on your unique exposure to these risks is the easiest way to manage them when they come. Get on this early.

7. Make the shift from accumulation to distribution. Retirement is a mind trip—you go from decades of wealth-building to wealth-preserving. Your plan must shift accordingly. Prioritize income, flexibility, tax efficiency, and ongoing adjustments through regular scenario planning.

8. Keep a margin. Always. Microsoft invested in R&D even during downturns. Maintain a financial margin for generosity, volatility, and life's unexpected events.

Retirement Isn’t the End—It’s a New Game

The goal is simple - live well, freely, and never question your ability to afford life's joys—whether it's a trip with grandkids, a lake home remodel, or helping family.

But achieving that freedom takes intentional planning and adaptability—just like Microsoft’s epic comeback.

If you’re 5–10 years from retirement or already there, we’d love to talk. We help families like yours design financial plans that outlive them—not the other way around.

If you're anything like me:

Before making a significant decision, you probably want clear information, a trusted relationship, and a straightforward next step.

Our full-service wealth management offering, Bergen, helps successful families ($1M+) turn wealth into lasting retirement security. My team and I have dedicated our professional careers to living, breathing, and practicing wealth management, serving our clients as trusted fiduciaries and advisors—and I'm confident we can support you not only today but for decades to come.

If my perspective on markets and wealth resonate, let’s talk.

In this brief, complimentary call, we'll quickly determine:

• If Bergen aligns with your financial goals.

• Immediate insights you can apply.

• Clear next steps toward financial clarity and confidence.

No hard pitches—just honest conversation.

Schedule Your Bergen Wealth Session Now →