When the High-Water Mark Becomes the Trap

In our recent Capitalize Your Fridays podcast, Taylor and I discussed a simple but powerful investing problem: once people see a new high in their portfolio, that number quietly becomes the new emotional baseline. Then a normal pullback starts to feel like something is wrong—even when the portfolio may still be well above what was actually invested in the first place. 

That disconnect is where trouble starts.

We anchor to the peak. We mentally “own” it. And when markets inevitably pull back—as they always do—the decline feels like a real loss, even if the long-term progress remains intact. The chart here illustrates this dynamic: a rising portfolio, a clear high-water mark, and then a meaningful drop that feels worse than it actually is because of where we’re measuring from.  That would be challenging enough but today, the backdrop makes it more difficult.

The inflation chart below is hard to ignore. I’m not suggesting we are reliving the late 1970s. History doesn’t repeat that neatly. But the resemblance is close enough to make a serious point: inflation can be persistent, uneven, and frustratingly slow to resolve. It doesn’t glide back to target just because we expect it to.