The Power of Asking

I just came back from a work trip in Napa Valley, and it got me thinking about something simple but life-changing: the power of asking.

Almost every interesting experience I’ve had in the last few years happened because I dared to ask for something even when it felt awkward or out of place.

We all have that one event or opportunity we secretly wish we could be part of. Maybe we wait for an invitation that never comes, or tell ourselves it’s not our place to ask. Because asking feels risky. It opens the door to rejection and rejection stings.

But what if, behind that one uncomfortable question, is a “yes” that changes everything?

Yes Theory

Back in December 2023, I got to attend one of the wildest events of my life, Matt’s goodbye party and book launch. Matt, one of the founding members of Yes Theory, was leaving the YouTube channel to start over and live a simpler life.

I had no official invitation. I only heard about the event through a podcast and knew it would be hosted at the Yes House in Venice Beach, their final event before moving to Europe.

Around the same time, I pre-ordered Matt’s book, Talk to Strangers, and joined a live Q&A on Zoom. During the call, my heart was racing. I raised my virtual hand, somehow got picked, and before I knew it, my face was on the big screen in front of Matt, Ammar, and hundreds of fans.

I asked about friendship and moving to a new country… and then, nervously, if I could attend the event.

As soon as the words left my mouth, I regretted them. They muted their mics for a second, and I thought, That’s it. I just embarrassed myself in front of so many people.

Then, they unmuted.

Matt smiled and said, “Even though it’s a private event… we decided to invite you.”

I froze. I thanked them, logged off, and celebrated all over the house.

The next day, I was at the Yes House meeting multiple members who inspired me for years, attending the final gathering in that iconic space. All because I asked.

A huge Yes Theory sign at the Yes House

Even two years later, I still can’t believe it happened. That one tiny moment of courage led to one of the most surreal experiences of my life.

Creator Economy Summit

I took that same spirit into my job.

My company hosts a yearly Creator Economy Summit in Los Angeles, a big event for creators and media executives. As a software engineer, I had no reason to be there. But I wanted to experience it, to learn, to see the world I quietly admired up close.

So, I asked if I could volunteer.

To my surprise, my manager said yes.

I helped with registration, passed mics during Q&As, and met creators I’d followed online for years.

Meeting multiple creators, including Samir from Colin & Samir Youtube channel

The following year, I volunteered again. And these experiences ultimately inspired me to start creating content myself.

All of that started with one question: Can I help?

Women in Tech and Finance

Fast-forward to this month.

My company hosted its Women in Tech and Finance event or “WTF” as we call it — in Napa Valley. I had asked to attend before but got turned down due to budget. This time, I didn’t ask. I assumed it was another no.

Then, out of nowhere, I got a personal invitation.

That event turned out to be unforgettable. I met some of the brightest women in the industry, including Paris Hilton, one of the guest speakers. But beyond the glamour, it reminded me of something deeper: how powerful it feels to be surrounded by people who inspire you, especially as a remote worker who often feels disconnected.

Meeting Paris Hilton

And maybe, that invitation came because I’d asked in the past. Because I had shown interest. Because someone remembered.

The Lesson

Looking back, I can connect the dots: each of these experiences — the Yes Theory party, the summit, the Napa Valley trip — happened because of one simple thing. I asked.

Not because I was fearless, but because I chose to act despite the fear of rejection.

We often underestimate how close we are to the experiences we dream about. Sometimes, they’re just one question away.

So ask. Ask even if your voice shakes. Ask even if you expect a no.

Because the worst that can happen is hearing no.

And the best? You might just find yourself living a story you’ll tell for years.