My first job out of college was at a Think Tank.

When I showed up to work, my new boss kicked his feet up on the table and said to me (in front of everyone):

"This will be your first job, and your last job. After this, you'll work for yourself."

Here's what he taught me

1/ "Don't be a glorified traffic conductor."

For years, I didn't have a formal job title.

He hated people who obsessed over titles but didn't actually produce anything.

He demanded that I learn ACTION is more valuable than whatever I call myself on a sheet of paper.

2/ "Freedom comes with a price."

I idolized my boss. I was 23. He was 32. Young, accomplished, wealthy.

He also worked 12 hours per day. Constantly stressed.

Everyone says they want freedom, but how you define "freedom" determines the price you have to pay to afford it.

3/ "The ROI of your reputation is measured over decades, not days."

Constantly, out of the blue, my boss would receive calls or emails from people he hadn't talked to in years.

They had landed a new job. New role at a new company.

They needed help & thought of him.

4/ "Start living AS IF."

I told my boss the reason I couldn't do X was because I hadn't yet achieved Y.

He said, "Everything you think you want now, you'll get in 5 years, and you'll say the same thing all over again."

"Live as if you're already 'there,'" he said.

5/ "I have 3 learning disabilities. If I can, so can you."

I wrote my bosses emails. I spell-checked his Tweets.

He had dyslexia. He was ADD and bipolar. He regularly drank coffee on top of taking Adderall.

"I know what I don't know," he'd say. "That's why I hired you."

5/ "Don't pay attention to how much it costs. If it's a good enough idea, someone will pay for it."

I watched him negotiate multimillion dollar deals.

I listened to him give pitches that turned into national campaigns.

"Money funds creativity, not the other way around."

6/ "If someone says 'That will never work,' I know I'm onto something."

He HATED if someone validated one of his ideas.

That meant it wasn't different enough.

The response he wanted was rejection.

"That means you're living in the future," he'd tell me.

7/ "Ask for forgiveness. Don't ask for permission."

I watched my boss take creative liberties that made everyone in the room feel uncomfortable.

But 99% of the time, he ended up being right.

"If I waited for permission," he'd say, "I'd never get anywhere."