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I’m embarrassed to admit I waited in line at a nightclub for 9 hours.

And I never got in. When I was 18, there was a club everyone wanted to go to. I got there nice and early when they opened. It was a chilly night. I wore a massive puffer jacket. Honestly, it was cruel to make people wait outside in the Antarctic conditions.

But people like me were suckers.

We had to be seen at this nightclub to inflate our fragile egos. I went with two of my friends. At the start of the night, we thought it was a given we’d get in. The wait was long. After 2 hours, we got to the front of the line. We were pumped.

Then the doorman Jason said “Sorry, guys, without a guest list, there’s going to be a bit of a wait.” We didn’t mind. We would wait. Every hour after that, I’d check with Jason about the wait. He kept telling me “Not long now buddy.”

At 6AM the nightclub closed. We were still outside waiting to get in.

Jason said “Sorry, guys, maybe next time.” I crossed the road and just stood there. I saw Jason and the security guards laughing. I assumed they were laughing at us.

I was pissed. I felt betrayed.

The two friends I was with thought I overreacted. A few weeks later, we weren’t friends anymore. I never quite got over what Jason did to us. It was cruel. He had no intention of ever letting us into the club. It was a game.

The 9 hours we waited in line to get in taught me a lot. I saw one guy give a $50 note to the security guard and go from the back of the line straight in. I saw hot girls walk to the front of the line and be let straight in.

We were in the general admission line. On the other side was the guest list. Those people didn’t wait. And right at the front was a VIP entrance. They didn’t line up or talk to anyone at all. They went straight in.

The next day I realized this is how life works. There are three entrances to every opportunity and most people choose the general admission line.

The story doesn’t end there.

About a year later, I found out that my dad had met the nightclub’s owner. My dad introduced us. The owner said, “Timbo, if you ever want to come to my club for free, let me know.”

So I did. The next weekend I went with the owner to his nightclub. I saw Jason. His whole vibe changed. He looked surprised. It didn’t end there. I ended up working for the owner. That meant I could use the staff entrance.

I could walk into the club whenever I wanted and do whatever I wanted. Jason saw. He watched. Then it went even further. I became a DJ at that nightclub.

Jason now saw me walking in with bags of vinyl records and a small crew. He saw me get handed stacks of drink cards for free alcohol.

On my birthday the owner threw a party for me. All my friends and I drank for free. Jason saw that too. Then one night, someone handed Jason one of my demo CDs of a mix I’d done. He walked up to me later that night and said “Man, that mix you did is one of the best DJ sets I’ve ever heard.”

He was blown away.

I never forgot what happened at that nightclub. It taught me you can settle for the general admission line in life, or you can find a way to skip the line altogether.

Stay the hell away from the front door

The front door for any opportunity is where you ask for permission.

“Please, sir, can I come in tonight?” The crazy thing is most people choose the front door. They choose the traditional path. They get told what to do.

Right now what makes me emotional is seeing so many people being laid off, then applying for jobs on websites or LinkedIn. It’s sad because they use AI to write their resume, and then the employer uses AI to read their resume and screen them out.

Humans are removed from the process.

And so many job ads are fake. They’re posted for compliance reasons, to test the market, or to build a pipeline of people for a possible future opportunity.

If you apply for a job and ask for permission, you either get ghosted, put through endless interviews, or low-balled on the job offer because everyone is getting laid off.

The front door sucks.

Same with dating. If you go through the front door and end up on some dating app, you’ll be put in touch with predators, people looking for free or paid s*x, and blatantly rude people who treat you like a doormat they wipe their dog sh*t filled feet on.

Starting a business is another area where the front door sucks. You go it alone through trial and error. You ask the bank for a loan to buy a business. Or you buy a McDonald’s franchise where they dictate the rules and take a huge chunk of revenue.

Either way, you’re asking for permission and being treated badly.

If someone stands in between you and your freedom, it’s a trap. And that’s every front door in existence.

You’ve got to be bold as hell to skip the line

Skipping the line sounds simple. Like anyone can do it.

I disagree. To skip the line you have to reject everything you’ve ever been taught. You have to reject what 99% of society does. But most of all, skipping the line is deeply psychological.

When you decide to skip the line you’re becoming a rebel. You’re being bold, courageous, and dangerous. When Freddy McBasic finds out what you’re doing, you’ve got to be strong enough to ignore him when he tries to talk you out of it.

But most people don’t act boldly. In fact, they don’t act at all. They just sit there in fear for most of their life and fantasize about what they could do without doing anything.

That’s your opportunity.

The high-profile job that didn’t exist

Early in my finance career, I was stuck in a call center. I couldn’t break out.

One afternoon a manager asked our team if one of us could process the paperwork for a small startup. No one wanted extra unpaid work. I said yes.

I’d never heard of the company. They were called Braintree, founded by the “don’t die” guy Bryan Johnson.

I did their paperwork as fast as I could. And I emailed them every day to keep them up to date. I didn’t think much of it. But they thought I was a hero. They told everyone at the bank I worked at how much of an asset I was to the company.

Eventually, I got a secondment to work with this manager directly. He taught me everything he knew. At the end of the secondment, he promised me a job. But there wasn’t one. I waited a year. Then the manager came back to me with an open position. It was at least 3x more senior than my current role.

He told me I already had the gig but to pretend I didn’t. I did fake interviews and acted humble. Then I g