Retiring Into a Different World

Hi, Tom here.

Thanks to everyone who joined our Wealth Workshop yesterday on cash flow.
Our next one is June 11th at 11am—reply to this email and let me know what you’d like me to cover.

This week, I want to talk about a shift I’m seeing with a lot of people nearing retirement:

The world they built their wealth in is no longer the one they’re retiring into.

Let’s get into it.

You’ve built your wealth in a world you worked to create.

You’re probably planning your retirement—or already living it—in a world that feels more and more unfamiliar and uncertain.

I always tell people I’m a washed-up, greying millennial—and even as a somewhat young person, it’s getting harder to keep up with the direction and speed of tech.

Furthermore, never in my adult life can I recall a time when conflict felt so... normal.

• Multi-year wars in Ukraine and Gaza.

• Skirmishes in the Red Sea.

• Escalating border battles between India and Pakistan.

• And the not-so-hidden tariff wars the U.S. is fighting.

I heard a quote this week that summed things up well:

But this edition isn’t about geopolitics or political drama, nor a checklist for your portfolio.

It’s about the hard choices you’ll face as you approach retirement—and the quiet stories that will guide how you make them.

What you’re reading comes straight from my conversations with you.

I’ve spoken to many clients, friends, prospective clients, and family members over the past month and a half. When markets get volatile, these questions always rise to the surface.

This edition reflects what I’ve been hearing.
What you’ve been telling me.
What’s on your mind.

Yes, markets popped this week on news of easing tariff tensions. But the backdrop is still tough.

And if you were to sit down with me right now, at age 55, and walk through your retirement plan, I’d tell you this:

We’ve got four decades to plan for.

That’s a long runway—and a lot of unknowns.
And when the future feels this unclear, I know exactly where I go for direction—
for better or worse:

My memory bank.

What’s in your memory bank?

Your memory bank is made up of lived experiences—the moments that shaped how you see the world.

Some are consciously chosen. Others are welded in by the highlight reels of life—or by heartbreak, loss, and uncertainty.

Scientists still don’t fully understand how memory works. But one thing is clear:
Memories don’t just store facts—they shape beliefs. And those beliefs guide decisions.

When you return to those memories, you don’t just recall what happened—
you relive how it felt.

And those feelings? They can serve as a guide.

Here are two memories I return to often:

• North Dakota in January. -20°F and an arctic wind that whips my face and takes my breath away. And yet, when I feel that cold, I often think of stepping into my car in the intense heat August—the humid air burning my skin and the feeling that this experience evokes. Maybe that’s just how I cope with winter. But that contrast—cold and heat, discomfort and comfort—is welded into my memory.

• March 2020. I was working from a makeshift desk in my upstairs bedroom. Markets were swinging violently. Our client AUM was fluctuating by more than $10 million a day. I was on the phone with clients, trying to understand what a pandemic meant—for their portfolios, and their lives. I remember it like it was last week.

Those memories shape how I cope. They remind me what real stress feels like.

And your memory bank is full, too.

But here’s the catch:

Memory can mislead you—especially when it comes to money.

People absolutely draw from memory to navigate uncertainty. The most sacred memories often become internal compasses when things feel off course.

In many ways, your memory bank helped build your wealth.

But if you’re not careful, those same memories can quietly blind you—
especially when protecting your wealth matters most.

Here’s why:

The world you’re investing and planning in is changing—fast.

• At Shopify, managers must prove that AI can’t do the job before they’re allowed to hire a person.

• Job openings for once-venerated software engineers are plummeting.

• De-globalization is no longer hypothetical—it’s already underway.

• Markets are changing in response.

The world that helped you grow your wealth won’t be the world you retire in.

And as you step into retirement, you need to be painfully aware of the beliefs tucked away in your memory bank—so they don’t quietly steer you in the wrong direction.

Let me give you an example.

One day in 2010, you read an article on Yahoo about a new “hot stock.”

It was a small tech company with a product that promised to revolutionize how people worked. You took 25% of your IRA and—with a dash of courage—hit the buy button.

A year later, the stock was down by half.
Your courage landed you in the graveyard of bad investments.

You didn’t just lose money—you lost sleep. You questioned your judgment, internalized your mistake, and swore to never do that again.

This is a tale as old as time. Ask me sometime about my own greatest hits in this department.

A month later, you read an article on passive investing—the benefits of diversification, low fees, and staying the course.

It made sense.

You couldn’t afford another mistake, so you went all in. And for the last 15 years, you’ve been investing the same way.

Your strategy became a habit.
Your habit built your wealth.
Now there is a string of memories that say: passive investing—no matter what.

Okay, example over.

You have a memory of losing money that became the catalyst for a new investment strategy. That strategy turned into a habit. That habit created wealth.

And if you’re like many of the people I talk to, you’ve built most of your net worth over the last 15 years—in great markets, using a great strategy: passive investing.

This worked.
It still works.
But markets evolve—even if your strategy doesn’t.

Let me show you what I mean.

Take the AGG ETF—the iShares version of the Barclays Aggregate Bond Index. Think of it like the bond equivalent of VOO or QQQ: broad, passive, diversified, and cheap.

You’ve likely held it—or something like it—in your portfolio.

But over the last decade, three things inside AGG have changed:

• The maturity profile of the fund has lengthened.

• The allocation to U.S. Treasuries has grown from ~35% to 45%.

• And the bond market itself has structurally shifted due to new bank regulations.

In other words:
Your strategy didn’t change—but the thing you own did.

Which means the risk inside your portfolio today might not match what you want your money to actually do for you.

If you’re comfortable owning a growing chunk of long-dated government debt as you head into retirement, that’s your call.

But you should at least know that’s what’s happening under the hood.

Google once seemed unstoppable.

It had internet search cornered and built a trillion-dollar cash cow in the process.

Then came AI.
And just like that, people stopped searching for answers—
they started asking for them.

Google didn’t plan to change.
But the world changed anyway.
And by adapting, it’s now positioning itself for massive success in the AI era.

That’s how the world works—
it shifts, often quietly, until one day it’s unmistakably different.

And while memories are hard to forget,
your future—and your wealth—need more than what used to work.

Make sure your retirement plan is built for the world ahead—
not just the one you remember.

Two ways to turn preparation into peace of mind:

• BluePrint — Our flat-fee financial planning engagement. Designed for individuals and couples who want expert guidance without a long-term commitment. We’ll help you clarify your goals, assess your risk, and map out a plan to retire on your terms. If you’re looking for high-impact financial advice—fast—this is the place to start. Let’s start with a quick conversation.

• Bergen — Our flagship wealth management offering for those with $1M+ in investable assets. We work with financially successful families navigating retirement, transitions, and legacy decisions. Bergen is more than portfolio management and traditional advising—it’s about helping you reduce complexity, optimize income, minimize tax drag, and helping make sure your financial life fully supports your values, family, and goals. Let’s have a conversation.

Your memory bank holds the story of how you got here—every risk you took, every lesson you learned, every win that felt earned.

Every client we’ve had the privilege of serving has brought with them the scars of past battles and the stories of hard-won victories.

Our mission has always been the same: to help you turn your experience into lasting freedom—through thoughtful financial planning, intentional investing, and a partnership built on trust and respect.

If you’re ready to talk, we’re here for you.

Talk soon,
Tom