I found myself with 48 hours alone in Osaka recently before meeting up with friends. Solo time in a new city always sparks a desire for adventure, but this time, I had a specific mission, inspired by something I’d just read in the Almanack of Naval Ravikant. He mentioned that maybe 90% of our decisions are driven by fear, and only 10% by true desire.
That hit me hard. How many things do I not do because of some underlying fear? Fear of rejection, fear of judgment, fear of looking stupid?
So, I decided to run an experiment for those 48 hours: Actively identify fear in every decision, and then consciously choose what I would do without that fear.
Step 1: Spotting the Fear Monster
The first step was just awareness. Before making a choice – big or small – I’d pause and ask: “Is fear playing a role here? Am I holding back because I’m afraid of something?”
Step 2: Calling It Out (The Chris Voss Hack)
Here’s where it got interesting. The moment I mentally pinpointed the fear (“Okay, I’m afraid of looking awkward if I approach that group,” or “I’m afraid she’ll say no”), something shifted. It reminded me of Chris Voss’s negotiation technique of “labeling” emotions. By simply naming the fear, acknowledging its presence, its power seemed to diminish significantly. It was still there, maybe, but it felt less controlling, less paralyzing. Paradoxically, seeing the fear made it less scary.
The Testing Ground: Osaka Nightlife
Dinner led to deciding to check out a club – the perfect laboratory for this experiment. Clubs can be high-stakes environments for social fear.
Armed with my fear-labeling technique, I decided to operate with zero fear as my default. If I felt a flicker of hesitation about talking to someone, I’d label it (“Ah, fear of rejection”) and then act anyway, as if the fear wasn’t a factor.
I ended up talking to tons of people. I chatted with a cool Japanese DJ named Yui and, pushing past my usual hesitation, asked direct questions I normally wouldn’t. Did it lead anywhere? No, but that wasn’t the point! The point was I acted despite the potential for awkwardness or rejection, simply because I’d decided fear wasn’t going to be the driver.
I also had an interaction with a girl from Laos. In a moment of wanting to push my boundaries of acceptable conversation (after labeling the fear of being perceived negatively), I asked a very direct, perhaps unconventional question about her appearance, making sure my tone was genuinely curious and non-creepy. It was purely an experiment in acting without the usual social filters dictated by fear. And guess what? The world didn’t end. She wasn’t offended; we just continued chatting.
The Revelation: The World is Kinder Than Your Fear
Across these interactions, the biggest takeaway was this: The negative consequences my fear usually predicts rarely happen. Or if they do, they’re far less dramatic than imagined. People are generally more accepting and resilient than our fearful minds give them credit for. Acting authentically, even a bit boldly (while still being respectful, of course!), didn’t lead to disaster. It led to interesting conversations and a profound sense of liberation.
Living Free from Expectation
This experiment connected deeply with another idea from Naval’s book: We have such a short time here, and we’re not obligated to live up to anyone else’s expectations. Worrying about disappointing people or fitting into their mold is a burden, often rooted in fear. Their expectations are theirs, not yours.
True freedom comes from shedding that fear – fear of judgment, fear of not meeting expectations, fear of failure. When you operate from desire, from authenticity, from a place of “What would I do if I weren’t afraid?”, you become incredibly powerful.
My 48-hour experiment was just a glimpse, but it was potent. Imagine consistently identifying fear, labeling it, and choosing to act from desire instead. Keep doing that, and yeah, you might just become unstoppable.