If you haven’t noticed, every Wednesday for a little over a month now, I’ve posted a short lesson about what I do. Sometimes they’re anecdotes or How To’s or links but they all relate to a collection of ideas that are slowly creating a new industry. An industry that it’s not quite too late to get on the ground floor of. I guess for now we have to call that new media.

When Seth Godin wrote about two simple web businesses that he thought might be lucrative, I laughed because I get paid to do both of them by multiple companies. Or if that’s not enough, Fred Wilson just tried to hire someone who likes to comment on blogs. That’s what I’m talking about.

Last month, literally as I walking into a meeting a total stranger emailed me an article about the person I was about to meet with. It had been published for like 20 minutes. The meeting was a total secret so they could have had no idea. I was blown away. I can’t even put a number on how much that email was worth.

But then I remembered, for the last year and a half I’ve been publishing every good thing I’ve come across for free. God knows how many times I’ve emailed writers that I like with pieces I figured they would like. It was only a matter of time before somebody returned the favor.

I sort of fell into it and got really lucky. Tucker sat down and taught me everything. But if he hadn’t, I would have kept doing it anyway, slowly figuring it out by trial and error. I would have had to do it without the benefit of somebody else’s toys.

So every Wednesday for the foreseeable future, I’m going to try and talk about the things I’ve learned and am learning. It’s helpful to me because I finally get to articulate them and hopefully, it can be helpful to everyone else. Later on down the road, it will all make more sense when the official announcement about this is made. If you want to get a jump on it, start with all the books in the Internet/Strategy section of my reading list.

“Nothing appeared to make my poor mistress more angry than seeing me, seated in some nook or corner quietly reading a book or a newspaper. I have had her rush at me, with the utmost fury, and snatch from my hand a newspaper or a book, with something of the wrath and consternation which a traitor might supposed to feel on being discovered in a plot by some dangerous spy.” My Bondage and My Freedom, Frederick Douglass

If you can for a second, think that the world is much like that mistress. The more you learn and the more initiative you show, the less power it holds over you. That is a very scary thought. A threat. Subversive. Not ‘totally subversive, man‘ but real, undermining, ‘tell me what you know about [name]’ kind of shit.

My relationship with a major Hollywood player – a guy whose clients and companies you know – was irrevocably shattered by the books I read. The ones that piled up on my desk. The new one I carried when I went to eat. The research papers I print on the copy machine. An Amazon package, twice a week.

I was not supposed to know that stuff. What was I doing? What was I planning? Who the fuck did I think I was?

If you can understand that every bit you steal, every word you sneak, is part of a larger struggle. Each one makes you just a little more free. It’s light penetrating the dungeon, Douglass said. They show you the whip and the chain. And then eventually, the revelations weigh you down so heavily that you have to make a choice. Are you a Slave For Life or are you a Free Man Now?

They know that. They know whether you’ve been informed of it or not. So you might as well start to take the thing seriously. It’s the only job that matters.

And if you don’t like the story or the analogy, let’s put it another way: Douglass risked violence and death to read whenever he could, what excuse do you have?

A really well meaning kid emailed me yesterday. He just failed out of his first year of college. He was talking passion and philosophy. His email signature was one of those lines about mission statements in Jerry Maguire and when I replied, he hit me with the Tim Ferriss autoresponder (that he’s had for several months).

“Due to a heavy workload…I’m only checking email once daily.”

Alright dude, where do you get off? I know how hard it is to fail out of college. If you’re sentient it’s nearly impossible. It’s not about passion and direction and working a 4-hour workweek. It’s about accomplishing the basic tasks that you were assigned at a satisfactory level. Then you can start to talk about the other stuff.

School sucks. There’s tons of bullshit and busy work. That’s the point. You need to be able to master that. And succeed past it to the point where you can handle it on autopilot as you focus on the things that matter. What you don’t get to do, especially as a young person, is just pretend that you’re better than doing it. Seth Godin had a cool line about this a few months ago. If you don’t have an extraordinary resume, where do you get off masquerading as an extraordinary applicant?

I always try to think: Do I deserve this? Did I put enough credit in to comfortably debit out? That’s partially the reason for this. I’m a little masochistic but that’s me. It’s arbitrary standard but I feel like the way to stay grounded is to institutionalize the idea of questioning yourself and your status.

Hard work is not fun. It’s hard, actually. And without that as a backbone or a given, moving forward is impossible. Failing out of school, getting fired, constantly being passed up, not finding a break, etc. If I can’t get the basics right, where do I get off (deserve) talking about anything else?

Just a question I tried to keep running at all times.