A Case Against Market Timing

Hi, Tom here.

Hope you’re all having a great week.

Tariffs, market volatility, rate cuts in Europe, tax cuts coming in the US—just a few things happening as you ponder your own financial life.

Let’s cut through the noise.

Last week was historic.

I mentioned it briefly at the start of last week’s edition, but it’s worth repeating—if you survived, great work. The week felt like the Super Bowl of personal finance. Markets moved with massive force. Emotion was everywhere.

There were likely thousands of articles written in just a few days, all trying to answer one question:

What should I do right now—buy or sell?

That was the gist. And based on the historic trading volume, people were doing both—big time. Some investors sold everything. Others doubled down. It was a moment of extreme conviction—or extreme fear.

What were people really trying to do?

They were trying to guess whether or not we were heading into a recession. If they believed we were, they sold. If they believed we weren’t, they bought. It was that simple.

I had conversations with people on both sides of the aisle. Interestingly, how someone saw the market last week often lined up with how they saw politics.

• Many on the left saw it as a clear policy failure.

• Many on the right saw it as just another step in a longer-term strategy.

• The center saw both sides.

Is that surprising, though? We live in a world that’s highly divided. It makes sense that those divisions would bleed into the way people invest. So it’s no wonder we saw record trading volumes.

Charged up. Emotional. People voted with their portfolios.

There will be plenty of stories told in the years ahead about what happened last week. Some will be about brilliant trades; others about painful losses. But what I want to focus on is the underlying risk that doesn’t get enough attention: the danger of market timing.

Don’t miss out.

For those with significant wealth, the temptation to protect assets by sidestepping volatility is real. But the data shows just how costly that can be. Consider the chart below:

This isn’t just a theoretical risk. For high-net-worth investors, missing out on the market’s best days can mean millions of dollars in lost opportunity. And here’s the kicker: the best days often come right after the worst days—when fear is at its peak and headlines are at their loudest.

But first, what even is market timing?

Market timing is when you make an investment decision—buying or selling—based on information presented to you in the moment. It might be a headline, a chart, a conversation, or just a gut feeling.

Here’s something most personal finance experts won’t say out loud:

Timing matters.

It matters a lot.

What you buy and when you buy it can make a huge difference in your long-term outcome. The same goes for selling.

Let’s be honest—some of the best investors in the world have made fortunes by getting the timing right.

• Warren Buffett has been sitting on a pile of cash for the last year. He hasn’t deployed it yet (as far as we know), but when he does, it will be with timing in mind.

• Mark Zuckerberg started Facebook at just the right moment—betting his time and his investors’ money on a massive shift happening online.

• Bill Ackman shorted the market during COVID and bought near the bottom. His timing was extraordinary.

But you don’t need to be on the Forbes list to benefit from good timing.

Think about the 40-year-olds who stuck with their investments during the Great Financial Crisis. They went on to enjoy one of the biggest bull markets in history. Many are now in their late 50s, earning more than ever, sitting on sizable portfolios, and wondering what all the panic was about.

Or take the families who moved to Phoenix or Nashville in 2018. They bought homes when it still felt risky to relocate—and now they’re sitting on massive equity gains thanks to soaring real estate prices in two of the fastest growing metros in the US.

In other words: timing is real—but it’s only obvious in hindsight, and nearly impossible to get right consistently.

• You want to work in great industries, at great companies, during the right cycles.

• You want to invest in the right asset classes—at the right times.

• And yes, you want to avoid selling when panic hits.

But here’s the nuance: timing only works when it’s part of a strategy—not when it’s a reaction. 

And last week?

That was a reaction.

What Really Happened Last Week

To understand what unfolded, you need to go back to the beginning.

President Trump initiated this trade war, and it was always going to be him who had to resolve it. His administration floated messages to the press, carefully choreographing their posturing. The idea, it seemed, was to announce tariffs after markets closed—giving investors time to process the news before Thursday’s open—and then roll out tax cuts over the weekend to soften the blow.

But the market didn’t wait. It panicked.

The narrative slipped away. Investors started pricing in a recession. Selling began.

In client meetings, I joked that my $25 Yeti mug could soon cost $60 if tariffs stick and brands pass those costs on to consumers. It was a light example, but it hit home. If consumer goods were doubling, what else might break?

The administration lost control of the message—and the markets ran with it.

It became clear that something drastic had to happen. And then, in true President Trump fashion, the president stepped back in with a 90-day truce. And just like that, the market moved nearly $10 trillion in a single day.

That’s how fragile sentiment is. That’s how quickly it can flip.

Savvy investors know when to move—and when to wait.

They zoom out. They tune out the noise. They wade through the emotion and focus on what actually matters. They move with purpose. They don't flinch because of a headline.

Last week was not the time to make life-altering portfolio decisions.

When red fills the screen…
When Good Morning America starts covering the market…
When Twitter feels like CNBC on steroids…

That’s when you need to pause. That’s when you need to ask yourself a hard question:

Is there enough information in front of me right now to justify a major change in my financial plan?

Most of the time, the answer will be no.

Market timing works for the lucky, the legendary, or the truly informed (think Hedge Funds that spend $30m a year on research).

But for most of us—especially in moments like last week—trying to time the market is a recipe for regret.

So instead of trying to outguess the economy or beat the headlines, focus on what’s always worked:

• A disciplined strategy

• Long-term thinking

• A portfolio aligned with your goals—not your fears

That’s how you build real wealth. Not by jumping in and out, but by staying in—and staying sane.

Because money doesn’t grow when you panic.

It grows over time.

Two more ways I can help you:

• BluePrint — Our flat-fee financial planning service for clarity and direction, no matter what’s going on in the world. Perfect if you want professional advice without full asset management, on-going advice and implementation. Let’s start with a quick conversation.

• Bergen — Our premium wealth management service for individuals and families with $500,000+ in liquid assets. We’ll optimize your financial plan, navigate markets, take financial stress off your plate, and provide ongoing support—regardless of what life brings your way. Let’s talk.

What a week it was.

Appreciate you,

Tom