On Love & Money

“What the issue comes down to for me is this:

I believe that life happens on two levels. The body-level tells us to go commercial. The soul-level tells us to follow our hearts.

If you’re lucky, you’re like Bruce Springsteen. You live on the heart level and you never have to leave it. You ignore every concept of “what will sell.” Instead you dive deep into your own world and your own passions. You go from Born to Run to Darkness on the Edge of Town to The River to Born in the USA and you keep going.

If you’re the Boss, you don’t have to sell out. You don’t have to pander to your audience. Instead you lead them. They want you to. You tell your story, follow your obsessions—and, holy Asbury Park, your secret, inner, crazy life turns out to be their secret inner crazy life too.”

Stephen Pressfield


I’ve got friends on both sides of this argument.

Most of the ones on the “for love” side do that for a living—they tell people how to do what you love for a living.

Most of the ones on the “for money” side seem to say so just to spite the guys on the love side.

Pressfield helps me to cut through the platitudes and go to my story: what’s been my experience?

I’ve been in safe and profitable jobs. For one reason or another I’ve quit every one.

I’ve been enthusiastic about lots of stuff — been in love a lot — and most of those haven’t made me much money.

But I seem to make better friends through the love stuff. (Most of the friends that I mentioned above, in fact. Except for one, whom I met when I was in one of those jobs I quit).

And doing the love stuff has led me to where I am now, creating a learning community for online entrepreneurs. I can’t tell if this one’s more for the love or for the money. I’m hoping it’ll do both nicely.

And it should be said, of all the love stuff I’ve done, I never really went all in on any of them. This is the first time I’ve had enough experience, stones and muscles to focus and dedicate myself to anything.

So that’s my new answer to the question: what does your own experience tell you?

Don Miller on “Changing the Rules”

“I know you read a Seth Godin book convincing you you could be a billionaire by creating a tribe. And you read a Timothy Ferris book convincing you you could work four hours a week and be rich. Guess what? Both of those guys work as tirelessly as depression-era farmers. They do this because the laws of the universe haven’t changed. You have to work to eat. And you have to work hard.

And let me add this. Sell out. Scrub a toilet. Nothing is beneath you.

I’ve watched scores of twenty-somethings quit their jobs and start businesses based on books written by people who sell fantasies. These writers tell one story about a guy who bought an island because he created some online business and convinced people they could do it too.

Don’t be fooled. The chances of that happening to you are about the same as winning the lottery. Writers are making millions by convincing people they can win the lottery too.”

Donald Miller

The Function of the Majority of Your Art

“The function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars.”

Art & Fear


This is from a book about making art. I don’t know who these authors are but they really nailed something for me.

I’ll only make a few pieces of truly good stuff over the course of my life.

That’s the reality.

I could break my head over trying to epic-ize everything I make. I could reach for celebrity and recognition through lots of truly great things, getting broody, moody and horribly not fun in the process.

Or I can make this thing the best I can right now. It’s not me. I’m not it. There’s some sort of exchange going on between me and it, but neither of us are each other. So let’s keep it casual.

Because any sane person knows that the best you can do right now is the best you can do right now.

This is embarrassing to admit, but when I read this I first thought about my tweets.

Before pushing “publish” on a tweet I typically have a moment of, “c’mon. Nobody cares about this. This isn’t funny. Make something funny and post that. Is this the kind of thing Merlin would post?”

But I’ve been wondering recently if I won’t look back and wish I shared more. If 20 years from now I’ll read through the archives and wished I just tried more stuff.

This quote hits me with reality, balances me. I might make a few good tweets over the course of my life. The shitty ones will help me get there.

I mean, these are fucking tweets we’re talking about.

Oh, and art. We’re also talking about art. Which is kinda like business to me. So that too.

Henry Rollins on The Iron

The Iron never lies to you. You can walk outside and listen to all kinds of talk, get told that you’re a god or a total bastard. The Iron will always kick you the real deal. The Iron is the great reference point, the all-knowing perspective giver. Always there like a beacon in the pitch black. I have found the Iron to be my greatest friend. It never freaks out on me, never runs.

Friends may come and go. But two hundred pounds is always two hundred pounds.”

Henry Rollins


I continue to come back to this article and the idea that the things which are hard for us are teaching us — like a sensei.

I’ve experienced this most with lifting weights, so I’ll stick to that illustration, but I’ve also sensed it with growing a business, raising a son and staying married.

When I approach the weight asking, “what lessons do you have for me today?” my whole mental posture changes. It’s no longer a contest, no longer about my ego, a thing for me to win or lose. It’s a relationship between a master and an apprentice.

When I’m in that posture the workout is better, it works out more of me. Also, I do less stupid shit.

In business it helps me not be crushed by a piece of bad news, gets me in the posture where my reaction is more, “ok, what do we learn from this and what’s the right thing to do?” and less, “fuck, my ideas are shit, the world is shit, i’m going to die alone and I have a small penis.”

If you haven’t read this full article from Henry Rollins, I highly recommend it: The Iron & The Soul by Henry Rollins.

Frank Chimero on How vs. Why

“A complex world has made us over-emphasize How-based thinking and education. Once the tools are understood, grasping why to do certain things becomes more valuable than how to do them. How is recipes, but learning a craft is more than following instructions.

How is important for new practitioners learning to avoid common mistakes. Why is for those who wish to push, are not risk-averse, and seek to improve. How is coulda, Why is shoulda. How is finishing tasks, Why is fulfilling objectives. How results in more, Why yields better.”

Frank Chimero