I got tickets to see Paolo Nutini. Then I messaged everyone I could find who works at the venue and asked if I could come backstage to say hi. It happened.
I was in Thailand and saw a plane fly overhead. I decided I wanted to learn to fly. I emailed every airport nearby, found a pilot, and proposed a deal: I'd cover all costs if he taught me. He did.
My first real job was my dream job. MTV was running an event about video games and I walked up to every man from the show, talked to them about what I knew, and asked if they had a job opening. They hired me.
I had dinner with Ludovico Einaudi because I messaged everyone at his record label until someone responded.
My first business got a $1,000-per-hour consultant for free. I told him how much I admired his work and asked if he'd be willing to help me. He was.
I was vegan, sitting in a high-end restaurant with nothing on the menu I could eat. I went up to the manager and said so. The head chef came out, asked what I loved to eat, and made me 3 courses. I paid nothing. The next week I came back and all 3 dishes were on the menu.
None of this happened because I'm lucky, well-connected, or charming. It happened because I asked. Every time, there was a real chance of rejection, and I have had plenty of those.
Every time, I asked anyway.
Most people wait until conditions are perfect. The conditions are never perfect. The window you're waiting for is not coming.
You have nothing to lose.
Ask.
