There’s a moment many of us reach — in our work, our finances, our health, and/or physical activities — when things have become so habitual, that we stop asking questions.

At first, that familiarity feels like confidence. But over time it can harden into something else, the sense that we already know and understand everything — a faint hint of arrogance. And when that happens, we gradually live on autopilot paying less attention, listening less to other perspectives.

This kind of confidence can shift into rigidity when we start to expect certain outcomes as guaranteed — that our knees will last forever, that a client relationship will stay the same, that the way we've always done things will keep working. But life doesn’t hold still. AI is changing how we work, our clients and bosses change, our finances change, we change.

Emptying Your Cup

A core Buddhist teaching is to invite humility — not as a means to put ourselves down, but as a way of keeping the mind malleable, young, and open. It’s the willingness to admit that things are always changing and that we don’t ever see the whole picture.

There’s a Buddhist story about a teacher who pours tea into a student’s cup until it spills over. The student protests, and the teacher replies, “Just like your mind — there’s no room for anything new.”

 Emptying your cup doesn’t erase experience — it lets experience keep unfolding.

What Humility Actually Looks Like

When we approach life with humility, we pause more. We ask for feedback. We don’t have to have all the answers — a relaxed and wise place to stand.

This kind of openness shapes how we respond to both success and setbacks. When something we did goes well, we can appreciate it without clinging to the idea that it was entirely our doing. We remember the teachers, friends, and the many causes and conditions that helped make it possible. And when something doesn’t go well, we’re less likely to collapse into blame or shame. Instead, we look with curiosity: What happened? What can I learn?

Something To Try This Week

1. Recall a time when you didn’t approach something with humility. For example, when I wanted to invest in a privately held tech company, I didn’t want to tell my friends or even my financial advisor because I felt this was a sure thing. I didn’t want them to shake-up my confidence. This was a tell-tale sign of arrogance. Five years later, I lost my entire investment. But I learned something valuable: Sharing is an act of courage and humility, not weakness.
2. Now, name a decision you want to make in the coming months. Could you commit to sharing this with people who will offer varying perspectives? Could you review the decision with the idea of a beginner’s mind?

Buddhism emphasizes the value of not knowing. That sounds strange, but there’s evidence that when we open to not knowing the answers – to humility – our intelligence and creativity burn brighter.

Practicing Humility With Your Next Financial Decision

Humility doesn’t mean doubting yourself or giving up control. It means recognizing that financial and other decisions are rarely best made alone.

It’s not about stepping back from your gifts. It’s about making space for an unexpected insight to arrive, and shifting from a habitual life to one that’s full of mystery.