I have an off-site storage unit where I keep a classic Land Rover Defender and the assorted parts and tools required to keep it from transitioning into a haven for mice. I don’t get out there as often as I should, but, you know…life. If I find a few unscheduled hours on a Saturday I throw on old clothes, drive out there, and spend a few hours elbow-deep in something mechanical or electrical. It’s meditative in the way that only tasks with a clear endpoint can be—torque a bolt or two, rewire this switch, get covered in grease, feel accomplished.

A few weekends ago, I arrived to find the man in the unit next to mine settled into what looked like a perfectly reasonable Saturday: radio playing, beer in hand, a joint clearly smoldering somewhere. The music drifting through the thin walls was a collection of ‘90s soul, hip-hop, and rap that I hadn’t heard in years; the kind of playlist that makes repetitive work feel almost celebratory.

I thought: good for him. My mind immediately built a story. He was relaxing after a long week. Maybe he had a workshop in there, too. Maybe his apartment was too small, or his partner didn’t want the noise, or he just preferred the solitude. I thought of the Schrebergärten I’d seen in Berlin a decade ago—those clusters of tiny garden sheds where families who live in cramped urban apartments go on weekends to have a backyard, a grill, a few square meters of private green space. This man, I decided, was doing his version of that.

When I left that first day, I told him I’d enjoyed listening to his music while I worked. That it had made the afternoon better. He laughed a little—a kind laugh, not a corrective one—and I went home feeling good about the interaction.

I came back the next day. He was there again. Same setup. Same music, roughly. But this time my unit smelled faintly of urine and old cigarette smoke, and something in the back of my mind shifted without quite surfacing.

It wasn’t until the third day, when the pattern was undeniable, that I understood what I’d been looking at all along: he wasn’t hanging out. He lived there.

I’ve thought about this moment more than I’d like to admit. Not because it was dramatic, because it wasn’t. No confrontation occurred. But something about the quiet, three-day lag between what I saw and what was actually happening rattled me. Because the reason it took me three days to see the truth wasn’t a lack of information, but an excess of assumption.

My brain, operating from within a life where a storage unit is a luxury—a place to keep a hobby vehicle—could not immediately process the possibility that someone else’s storage unit was their home. The data was there from day one; I just couldn’t read it correctly, because my own experience was writing the caption.

This is what privilege does, not loudly nor maliciously. It writes the first draft of every story we encounter, and it does so before we’ve even decided to pay attention. We don’t notice the assumptions because they feel like observations. They feel like the world simply making sense.

If you work in wealth management, or if you’re part of a family that has benefited from significant resources, this pattern is worth examining—not as a moral failing, but as a perceptual one.

I’m fairly certain that advisors make assumptions about clients’ children all the time. We assume the 24-year-old who seems disengaged is lazy rather than overwhelmed. We assume the one who spends freely has no financial anxiety. We assume the quiet one in the meeting understands what’s happening because they’re nodding. We assume that access to resources translates to comfort with them—that growing up around wealth produces something like fluency, when it often produces something closer to performance.

Families do this too, in a different register. Parents assume their children see money the way they do; that the values are inherited along with the assets. They assume their kids understand the sacrifices behind the wealth because they were physically present during the building of it. They assume that because their child has never experienced financial hardship, financial anxiety must also be absent.

These assumptions aren’t born of carelessness; they’re born of a worldview so deeply lived-in that it becomes invisible. Which is precisely what makes them dangerous.

I don’t tell the storage unit story to perform humility, or to suggest I’ve solved this problem in myself. I tell it because the three-day delay is instructive: it shows how long a well-meaning, reasonably observant person can look directly at something and see only what their own life has prepared them to see.

In our work—whether we sit on the advisor side or the family side—the cost of that delay is real. It’s the client whose distress goes unnoticed because it doesn’t look like distress from where we’re standing. It’s the young adult whose silence gets interpreted as assent because we’ve never had reason to be silent in a room full of people managing our money. It’s the family conversation that never happens because everyone assumes everyone else is fine.

The fix isn’t guilt: guilt is self-referential, and ultimately useless here. The fix is developing the habit of noticing the story your mind writes before the facts have fully arrived—and then asking, with genuine curiosity, whether the story is yours or theirs.

The man next to me didn’t need my cheerful commentary about his music. He needed someone to see him clearly. And for three days, I couldn’t. Not because I didn’t care, but because my own life made it easy not to look.

That’s the blind spot. And the only way through it is to keep noticing.