I wrote not too long ago about being lazy. Then, I got praise for talking about being lazy, and now, today, I had this idea to write about spending time and money on stuff just because it feels good, and so it kind of looks like I’m moving in the direction of being a feel-good, let’s-do-nothing guru, so maybe soon I’ll just start soliciting donations, trying to expand into the lucrative hedonism market, or perhaps trying to appeal to the shiftless hippie market. (Although, the hippie market is largely penniless, so maybe not.)

Perhaps. Let’s see where this goes.

For now, I’ll just say that I’m embarking on an experiment that I think Tim Ferriss would be proud of, with his whole “let’s work less and Tango more” way of doing things. Tim Ferriss and maybe the folks at Zen Habits, who kindly linked to me two days ago.

Specifically…

I’m asking: How can I radically increase my productivity — not so that I can do more in the time I currently spend, but so that I can do the same amount of stuff in far less time?

I’m asking: How much of this STUFF in my life (tasks, loose ends, mental clutter, paperwork, what-have-you) do I really need?

I’m asking: How much of what I really want out of life in the moment — primarily the emotional states of relaxation, satisfaction, happiness, etc — can I create NOW instead of stressing out now so that I can apparently create them in the future?

There’s posts upon posts upon posts I could (and likely will) write about those three questions and what I’m doing about them, but the last has been on my mind lately because it’s something anybody can do right now, without waiting for permission, and without any training.

Right now, you could decompress and feel better.

Right now, you could have more of what you’re really looking for. Not everything, and not even most things. Not the private yacht, and maybe not the freedom from your job if that’s what you’re after. But you can have some of it, right now.

And that’s a way cool thing to realize.

What I mean

Last year, my well-documented real estate woes were dragging this household down. On average, we had to find $2500 on top of our regular living expenses each month simply to stay afloat. That was the shortfall between what the real estate cost to maintain and what it brought in in revenue.

I wasn’t making tons of money, so this was tough to say the least. Even when my income started to increase, it was nearly impossible to find that much money to throw down a hole, never to see it again.

Imagine being required to take twenty-five $100 bills out of your wallet each month and burn them, and you’ll get the picture.

It was nearly impossible to do that month in, month out, for the better part of two years. But here’s the thing: It was possible. We had to beg, borrow, (but not actually steal) to find that money, but what seemed impossible had to be possible in fact… because we did it.

Interestingly, although we could find that impossible $2500 to throw away, much smaller expenses were far, far harder to afford.

For instance. In the midst of mind-numbing stress, we’d want something fun, like a Wii. But we couldn’t get it, because we couldn’t afford it. How could we? They cost a couple hundred dollars. We didn’t have that to spare.

Robin would get a gift certificate for Christmas to go to a nice place and get her hair done and would say, “I wish I could do that more often”… but of course we couldn’t afford stuff like that, because we had to trim everywhere we could.

I would skip going to Starbucks. Not buy DVDs. We’d watch every penny, because we needed that money to piss away on real estate debt.

Then it hit me. That was fucking idiotic.

How to be totally irresponsible

Each and every month, we were throwing away $2500 on average. THROWING IT AWAY. These investments weren’t recovering; the money was literally going bye-bye, never to appear in our lives again.

We could find money to do that with, but couldn’t free up a measly $150 for a Wii system.

We could burn $18,000 over the course of a year, but couldn’t find $85 for a nice salon job, or $15 for a fucking DVD. Or $4 for a latte.

We had all this pressure to generate money for something we hated, but wouldn’t allow ourselves even the smallest things we enjoyed if it meant laying out cash.

That was bullshit. Taking care of obligations is all fine and well, but refusing to take care of ourselves in order to do it was criminal. We were worth more than a slave’s existence. We were better than simple indentured labor.

When this dawned on us, we slowly began doing things that were really irresponsible. Bit by bit, we pushed. We bought the latte. I’d badger Robin until she’d make an expensive hair appointment. We bought the Wii.

Interestingly, no bad things happened. We were already past red-line, so finding $2600 we didn’t have wasn’t much different from finding $2500 we didn’t have.

And on the flip side, we found that allowing these small comforts made us feel better. Made us a bit more clear-headed. Made us more confident. And at around the same time, I was developing my new “fuck you” attitude. Better moods led to me being able to better tap my resources, to show up more on a day-to-day basis, to come up with solutions to problems that had simply always felt depressing and hopeless. And eventually, with hard work, things started to change for the better.

Coincidence? Maybe. There were a lot of factors at play. But making the mental shift that said, “I’m worth more than this shit” was part of what allowed things to change, in my not-so-humble opinion.

I don’t know how to finish this post

There’s not a huge moral here, and a ton of gray area. If your financial situation is shit, I don’t suppose it’s blanket good advice for everyone to shirk responsibility and buy fun stuff — especially when you consider that a lot of shitty financial situations were created by behaviors like buying the big screen HDTV when you couldn’t afford it.

But I do know that life can beat you up plenty. There can be a lot of people and circumstances on the other side of the fight, struggling against you. If you insist on joining their efforts to destroy you instead of ever fighting on your own side — never pushing back, never opposing those people who are beating you up — then things just get that much harder.

Maybe you shouldn’t buy the Wii. But maybe you should blow off work for the afternoon and go for a walk, because it feels nice and allows you to clear your head.

If you’re in the grocery store and they have cheap floral arrangements and you like flowers, maybe you should spend five bucks to buy a bouquet because it makes you feel good.

If your house is dirty and you really should clean it, maybe you don’t, and maybe you read a book instead.

I can’t tell anyone what to do, and everyone will have to find their own line between “being reasonably responsible” and “stupidly pretending to be responsible while actually crapping on your own head.” And there’s a difference between “giving yourself a break in order to recharge and fight a better fight” and “sticking your head in the sand without actually improving things.”

I can only tell you what I’d do, and what I’ve done. And I’ll tell you here and now, honestly, that if I was still in that $2500 monthly mess and had an opportunity to take a $200 weekend trip that I knew would get me out of my head and improve my mental state, I’d do it even if it meant paying my “responsible” bills late. I’d make “what I have to do” wait until after I’d satisfied at least a little bit of “what I want to do.”

Use this advice with caution, but know this: Life can be an asshole to you sometimes. When it is, don’t insist on always being an asshole to yourself too.

—————————-

P.S: In the spirt of The Interactive Offer, about which I had a rollicking good webinar with Clay Collins on Wednesday (you can still get the recording here), I’ve been considering creating a product centering on some way-cool ways I’ve been answering those three “I’m asking” questions near the top of this post. Ways that have reduced the amount of time I’m required to work by 30-40% already, and have drastically reduced my stress levels and cleaned up my mental and physical clutter at the same time.

Would anyone be into me creating a new product or course around that? Any ideas or suggestions, any interest, any what-have-you? Let me know in the comments if so.

The thing is, if I do this (it’s not a sure thing, but feels pretty likely), it would be a virginal moment. I have no other tattoos. This would be my first (and second, technically; what I have in mind would appear on both arms), and it wouldn’t be something small that people might miss. I’d go from being “a guy with no tattoos” to “a guy who’s definitely sporting some ink.” That’s a fundamental change in the minds of a lot of people — like the folks who grew up with me, and who I’ll see at my next high school reunion.

If I do it, I have no doubt it’s going to make people look at me a bit differently. And I guess that’s kind of the point, because I’m definitely a different person now.

This is not a tattoo post. This is a change post.

It seems to me that in life, we’re given certain trials, certain tests. If there’s a lesson we’re supposed to learn, we’ll be given as many chances as it takes to pass that test. If we pass, we grow and become more. And if we resist, we stay where we are and repeat that lesson again and again.

Me, I’ve never liked change. I’d find a moment in time that felt good and I’d hang on to it. When something fundamental in my life threatened to become something else, I’d fight against it. I’d end up panicky, nervous, or miserable. This was true regardless of the nature of the change. Even “good change” was scary.

But the world seems to have willfully beaten the acceptance of change into me lately.

The past two or three years have been filled with upheaval. We had a second kid; the economy took a nose dive; I lost all of my clients; my family situation changed in a few other fundamental ways; I regained new clients and a totally new business; I took on investments and lost them; I made a lot of money and went through over a year of a past-redline, we’ve-borrowed-all-we-can-including-from-both-of-our-parents existence; I made more money; I starved in a dearth of work; I fought for new work; I became downright overwhelmed with an excess of work.

I got mad as hell. I lost faith. I found faith. I finally accepted that there is no spoon.

And when it dawned on me that what held me back was fear of doing something arbitrarily “wrong” in the eyes of the world, I learned to break the rules.

You go through that much change and you become immune to it. You go through that many downs with your ups, and you start to get an attitude. You start to feel like you’ve gotten your stripes, like you’ve paid your dues. You get to the point where you’re like, “Fuck you if you have a problem with what I’m doing. I earned this.”

You start to consider advice, but ignore mandates and requirements.

And if people start to question your questioning of the rules, their opinion completely stops mattering.

You start to entertain a new world of possibilities. To grow.

You realize that you’ve changed so fundamentally that you’re no longer the same person in many ways. Maybe it’s true that you weren’t the kind of person who would ever do A, B, or C. But if you’ve changed, maybe you are that kind of person now. The only pigeonhole that can hold you is one you make for yourself, and that you continue to believe truly exists.

You leave the illusion of a “safe” existence. You take your bumps and bruises, and you get stronger because of it.

Maybe you start to realize that you don’t want to die without any scars.

I have a scar on my left forearm. It’s from the time I missed an Olympic clean and broke my arm. That scar will always be there, and I’m glad. Every time I look at it, I remember how I never quit. I remember how I went to the gym after surgery, in a brace, and used the other arm, or did heavy squats, or ran. I remember how my doctor told me to take it easy, and how I did not. I remember how I was given adversity and rose above it.

I want a tattoo because I’ve encountered some adversity over the past few years and have fought successfully through it. That adversity left scars — very cool, very large scars with a story behind them. Only, they’re scars you can’t see. I kind of want the tattoos because I want people to be able to see those scars — and to be able to see them myself, so I’ll always remember what I’ve learned.

Always believe. Question the judgments of others. Fight like hell.

Those lessons can’t be learned intellectually. They can’t be learned other than through experience, through trauma. Without the kind of psychic injury that leaves a scar.

So I can say the following without hesitation:

If you’re in the middle of some shit, don’t let it get you. If there’s one thing I’ve learned above all else, it’s that the best things in my life have grown out of the most terrible and traumatic experiences of my life. It’s hard to keep your chin up while life is crapping on you, but that’s what you have to try to do. You have to trust that there’s a personally evolutionary outcome in the works, and keep telling yourself that if you don’t give up, it’ll work out. It might not work out in the way you expect or even want… but it will work out.

If you’re breaking out and doing something crazy and new, it can’t be done safely. Great things cannot be idiot-proofed.

And if you’re not breaking out, maybe the world is forcing you to do just that. Maybe you’re being kicked in the ass for your own good. If that’s true, you have two choices: you can go under, or you can rise to the challenge.

Keep fighting. Always keep fighting.

All you’re doing right now is earning your scars.

—-
This is the first part of a long-ass post that I guess I’ll have to split off and continue next time. I rambled for so long about tattoos and scars and badassery that I didn’t even get to my main point. But hey, two posts for the price of one? Not bad.

The timing was perfect (being able to learn from Question the Rules in order to create Question the Rules), so I figured I’d share with you some of the biggest things that Lee and I somehow taught ourselves about how to create a course while creating a course about how, among other things, to build a business capable of creating a course that could teach us something like how to create a course.

I’m confused too.

Think of that illustration of the snake eating its own tail and you’ll get an idea of what I’m talking about here. And if it doesn’t help, at least the thought of that misguided snake will hopefully amuse you. Stupid snake.

Here are our top four takeaways:

1. You only need to see five feet in front of you

From the beginning, Lee and I worked under the guidance of a metaphor given by Stephen King. King said that he doesn’t believe that stories are created by the writer. He said that they already exist, buried, and that the writer’s job is to excavate them.

When Lee and I first talked, we wanted to create a networking course. Or maybe something about how to find and go after your real goals, because it seems like so many people are chasing things that are really far away and that they don’t actually want if they stop to think about it.

So we started making recordings for what we imagined our course could be. We didn’t create a big-picture, as-a-whole plan at the outset. We couldn’t, because our course was still buried, and we were still excavating.

We could only ever see what was immediately in front of us. We could only ever see the very next piece of the puzzle. We just kept moving forward and trusted that whatever the hell we were “excavating” would turn out to be as cool as we suspected it was.

2. Trust your gut, even if it tells you something weird

I’m going to go out on a limb here and suggest that ours may be the only business course in existence with a punk rock and faith module. And why is ours the only one like that? Because the notion of adding either of those modules to a business course is fucking retarded.

So why did we include them, then? And the answer is: Because it occurred to us. Because we had asked ourselves, “What are the components of our success so far?” For both of us, a punk rock attitude mattered. And for both of us, unflinching faith was nothing short of essential. It didn’t matter that neither of those modules made sense. What mattered was that it felt right, so we included them.

And what do you know? It all made sense in the finished product, despite the fact that it felt like a very strange choice until the very end.

3. Shoot first and ask questions later

Very shortly after Lee and I started recording sessions for the course, I started promoting it. In fact, it’s even possible I started promoting it before we recorded any sessions whatsoever.

If you’re thinking, “Well, you have to start buzz early, so that makes sense,” consider for a second the reality of the situation:

• We didn’t know what the course would be called.

• We didn’t know what the course would be about, other than vagaries.

• We didn’t know any of its features, modules, prime benefits, or really even its target audience.

• We had never worked together, had no reasonable expectation that we’d have good chemistry or that the other could deliver, and had no real timetable for completion.

• We didn’t know in any real way what would make this course different from all the other courses out there, how we’d price it, or what kind of a response we could expect.

Starting to promote a course that’s only the vaguest kind of an idea is a strange, strange thing. And trying to get people excited about a course that we couldn’t explain to them was far stranger.

(You should have heard me attempting to explain it to Naomi at the South by Southwest conference in mid-March. At the time, we were planning to launch on March 23rd, and Naomi’s response was, “Are you high?”)

But we wanted to commit ourselves to a course of action and to completing and delivering the thing, so we started telling people about it.

Yes, we launched a month later than we’d planned, but we did launch. If we hadn’t gone out on the limb and committed ourselves to generate momentum, we might not have ever gone anywhere with the idea. It might have remained “something we should do sometime.”

4. Uncertainty is part of the game

I’ve told this to death, but I’m going to tell it again anyway because it so perfectly makes my point.

There’s a Stephen Wright joke that goes, “You know that feeling where you’ve tipped back in a chair, and you’re just about to fall over backward? I feel like that all the time.” And that’s exactly what independent business is like.

If you enjoy the feeling of firm and unshakable ground under your feet (or more accurately, the illusion of firm and unshakable ground), then get a 9-5 job. Do not become an entrepreneur. Sorry, fledgling entrepreneurs, but there is no such thing as certainty here.

And that fact, by the way, is not a downer. It’s the path to freedom. If you don’t know what’s going to happen next, then you can have a hand in shaping it. (Philosophy majors: Don’t be assholes and lecture me about omnipotence vs. omniscience. I’m speaking generally here.)

We had no idea what was going on for the majority of the time we were creating Question the Rules. Not “sometimes” — the MAJORITY of the time.

We recorded the modules out of order. We didn’t know what material would be included in the end, so in the middle of any given recording, we could only refer to “other stuff we talked about” on a vague assumption that we’d cover it eventually. We couldn’t describe our venture to our big affiliates in advance. We couldn’t write sales copy. We just kept working and trusted that it would work out.

The cool thing is that the four above lessons had a surprising added benefit to us, as salespeople.

When people ask me if they should get it (yes, people have actually asked ME — one of the course creators — if they should pay us for our course) I can say yes without hesitation. Will it help you? Sure. It helped us, after all. We created this great course using the things we learned from this course.

The really neat part is that Question the Rules has been off-the-hook popular and successful (almost 300 people signed up last week), and has kind of opened up a whole new line of work for Lee and me. The course we launched last week isn’t the culmination of the Question the Rules “thing.” It’s the beginning.

So the question in front of me, then, is: What next?

And the response is: How the hell should I know?

Which is, of course, exactly the right answer.

—–

Did you miss Question the Rules during launch? Yeah, we’re hearing a lot of that. If you don’t want to miss out the next time, be sure to join my Advance Discount List.*

* I can’t imagine that Naomi Dunford originated the term “Advance Discount List,” so just so that everyone understands, she’s the specific person I’m stealing the phrase from.

Back in 1995, I bleached my hair so blonde that it became translucent, because I thought that’s what you did when you were into punk rock music.

When you use off-the-shelf products to do this, you can’t get like Clairol Light and Easy or whatever; you need the two-stage salon hardcore stuff. And if you don’t like the effects the first time (like in the above photo), you maybe do it twice the second time, ill-advisedly and counter to directions, until your hair shimmers like a Twilight vampire and your mother good-naturedly looks at you in that way that suggests that she doesn’t have any idea what the fuck you’re doing and has stopped trying to figure it out.

So I was blonde. And I sprayed my hair so that it stuck straight up, and wore badass sunglasses. And sometimes, I’d go to four punk shows in a week. In cities as far as three hours away. Yes. I was that awesome.

Around this time, mainstream internet was starting to gain momentum (people talked about “maybe getting some of that email thing or whatever”) and I was in college, which meant that I spent a lot of time on alt-dot newsgroups looking up low-bandwidth porn and other low-bandwidth low-browery, like the stuff my roommate enjoyed from alt.tasteless. And of course, I spent a fair amount of time reading the righteous discussion on alt.punk.

Surprisingly, the folks on alt.punk were somewhat rigid about the rules that defined punk rock. If you worked in the mainstream, you weren’t punk rock. If you were over 30, it seemed unlikely that you could be very punk. If you watched The Price is Right, you were not punk. If you clubbed seals at the Republican National Convention while smoking cigars lit with hundred-dollar bills while schmoozing senators who had plans to take over the world, somehow that made you less than punk.

One poster on alt.punk said that he used to skate every day and go to see the Descendants, but now he was a 32-year-old dentist who skated on the weekends and listened to the Descendants on his office CD player. He said it was possible to be punk as a dentist. When nobody agreed with him, I figured it was time to stop reading alt.punk.

It suddenly seemed to me that one of the least punk rock things in the world was to establish rules for who was punk and who was not.

And while bleaching my hair was fun, it suddenly felt like the least punk rock thing I could be doing, if my reason for it was “because it felt like the punk thing to do.”

And I realized that it’s not what you do that makes you punk rock. It’s your reasons for doing what you do. If your friends like Rush and you like Samiam and you listen to Samiam, you’re punk. If your friends like Samiam and you like Rush and you listen to Rush, you’re punk. If, on the other hand, you listen to Samiam because it seems like the punk thing to do, you’re just an asshole poseur.

Punk rock isn’t about breaking rules. It’s about questioning rules. You keep the rules that feel like they serve and fit you. You break the ones that don’t work.

Punk rock isn’t about being a rebel. It’s about being conscious enough to look at everything in your life and ask if it makes sense, or if there’s a better way to do it, regardless of how popular that better alternative may be.

Punk rock, when you get right down to it, is about being making choices consciously. It’s about not living by default.

You — yes, YOU — are punk as hell

I’ve mentioned a few times now that I’m co-creating a new course with Lee Stranahan. It was supposed to debut on my birthday, on March 23. But the project kept growing and growing and getting so damn cool that we gave ourselves another month or so to let the project be what it seemed to want to be. So now it’ll launch at the end of April.

And although it’s still officially unnamed, we’re thinking of it as Punk Rock Entrepreneurship, or maybe the slightly less abrasive Nonconformist Entrepreneurship.

Because one of the things you have to understand when you’re building or running your own business is that you’re a screaming hardcore punk bastard whether you know it or not.

You’re the punkest motherfucker I ever did see; hell, you’re even more punk than me.

(A virtual high-five to anyone who gets the reference I just made. In reality, you’re probably not more punk than me. I had translucent hair, remember?)

I’m going to take a wild guess that some of you don’t currently self-identify as being punk, so let me explain why I think you are, you rebel:

• Despite what “most people” do in getting a job, you have either started your own thing or are trying to do so, which is totally giving the finger to the normal way of doing things.

• You have an idea that is kind of out there (sell hot dogs across the Net; consult virtually on dog training) and are determined to do it no matter how wacky it may seem to others.

• People in your life have probably told you that your idea is stupid, or risky, or ridiculous, or else they’ve accepted it with an indulgent, patronizing nod, “knowing” you’ll fail but not wanting to break it to you. But — and here’s the thing — you’re doing it anyway.

• In line with the true punk rock DIY ethic, you’re forging out on your own and are “doing it yourself,” running mainly on instinct and guts.

• Punk rock was the genre that realized, “Hey, we can form a band first and learn to play later.” In the same way, I’ll bet there are things about your business that you still don’t know how to do, but you started anyway and figured you’d learn as you went along.

• Your independence may have cost you some old friends from the old world, but you had to go with your gut even if that meant leaving them behind to make new friends in your new world.

• Each and every day, you’re making and playing by your own rules, even when the lack of a clear path scares you.

Dude, you’re punk rock.

And if this is just dawning on you, I have more news: The rules you used to live by no longer apply in quite the same way. The judgements of the same old people no longer matter as much as they used to. You’re operating by a different set of standards, among a different set of peers. And I’m betting you’ve never even thought about it.

I’ll bet you figured, “I’m that same ‘normal’ person, but now I run my own business.”

Um, no.

Now, you’re in a new world. You’re with the rest of us punks. Welcome aboard.

You don’t need business help. You need a whole new paradigm.

One of the reasons that Lee and I decided to create our new course is because so many entrepreneurs are “accidental punks.” They grew up in the normal world, played by normal rules, and associated with fellow Normals. Then they created a business, and kept thinking of themselves in the context of the normal world, playing by normal rules, and relying on the guidance of those same old “other Normals.”

So many accidental punk rock entrepreneurs thought they just needed business tips, when in fact they needed perspective on a whole new way of being.

What we wanted to do was to take that new punk rocker, and introduce her to herself.

We wanted to give her new guidelines, and teach her how to find her own new rules by exploring her probably-as-yet-unappreciated rebellious spirit.

We wanted to show her that her goals are probably closer than she thinks, once she loses the veneer of outdated “normal” thinking.

We wanted to show her how to break the rules she’s been living by that no longer matter and are holding her back, while showing her which rules make sense to keep abiding by.

We wanted to arm her with a new set tools that will allow her to start from where she is today, with the resources she currently has — and move stepwise toward exactly where she wants to be in life.

We wanted to show this newly realized punk rock entrepreneur how the people she respects got where they are today by knowing who to talk to, how to talk to them, how to make deals that win for everyone, which rules to break, and when and how to break them.

Lee and I are behind on launching this course because the content keeps growing and growing (we’re adding a lot of bonus stuff that we hadn’t planned on having, contributed by successful folks you may know and/or aspire to be like), and because Lee keeps twisting my arm to lower the price. It’s now half of what it was a week ago.

When this project started, we began with Stephen King’s metaphor that says that stories are objects that already exist, but that are buried. It’s the author’s job not to create those stories, but to excavate them.

Projects are like that, too. What we’ve unearthed isn’t what we expected. It’s way cooler. We thought we were unearthing a buried Cadillac, but it turned out to be an alien spacecraft with two-foot tailfins and a really badass sound system, and a disco ball hanging from the roof. And there was a cooler in the back that was full of bottles of Yoo-Hoo.

You absolutely have to check it out, you punk bastard. Fill out the little form below to be notified when we launch in a few weeks, and to have a shot at a pre-launch discount.

And rock the fuck on.

My son Austin is five. The kid is brilliant. I know that all parents think their kids are smart, but this is no joke.

Austin knows how to do the basics of multiplication and division. His vocabulary rivals mine (“celtic punk” and “pneumatic tube” were probably among the first 100 phrases he learned, no joke). And for some reason, out of the aether, he’s got this fantastic artistic ability. The other day he was copying a detailed illustration out of one of his Transformers books (it was a plane air-dropping Optimus Prime into battle) and was doing it freehand, without tracing, and did a better job than when Robin tries to draw stuff at his request.

This year he’ll go off to kindergarten, and he’s going to be bored as a motherfucker. He got bored with preschool over a year ago, and the fact that he’s the oldest kid in his class isn’t helping. They have to move at the speed of the slowest kids, so as not to leave anyone behind. You get a spectrum of kids with different abilities, but it’s one class with one teacher… and so one size must fit all.

I find myself wondering about this, and other things I’ve never thought about when it comes to school, and education, and development.

All the things I’ve always taken for granted as immutable truths — school starts at five and continues for thirteen years, college follows high school, job follows college — are suddenly coming into question.

All at once, I’m no longer sure that what I learned in school is what I’d most like for my kids to learn.

This is the fault of you online weirdoes.

I’ve met a lot of entrepreneurs in this last year. And entrepreneurs are wackos. They’re not normal; they break the rules; they’re shit out of their minds. You spend enough time around people like that and suddenly it becomes really obvious that:

1. They owe their success not to their knowledge of Greek history or geometry, but to something closer to wily “street smarts” — an understanding of human nature and human motivation.

2. They’ve been able to do what they’ve done not because of their ability to memorize facts and take tests, but because of their willingness to try things that most people won’t try.

3. They achieved not because of any ingrained sense of wanting to be secure and safe, but in spite of it.

I don’t think school is bad, but I don’t think it taught me the most important things that drive me today, either. I think I spent thirteen years learning what the state wanted me to learn, and then another five learning what the previous thirteen years had led me believe the world wanted me to learn.

And then I think I set that aside, recalled a lot of good times (and some bad) from those years, and then, bit by bit, re-learned what I needed to know in order to do what I do today.

I ask myself, what has been the most important stuff I’ve learned? Was it history, math, and science? Was it home ec, or literature, or business management 101?

Or did it come from experience at the School of Hard Knocks?

And so I wonder: What would be the curriculum at Johnny’s Entrepreneurship School?

So let’s think about that. I’d offer:

1. Independence and self-confidence.
A successful entrepreneur has to be able to be able to look at his situation and his surroundings and then do what he thinks he should do in spite of the opinions of others. Nobody around you will take you seriously when you say you want to create an internet shoe empire, so you have to have the nards to do it anyway.

2. Fierce (almost stupid) determination and a willingness to make big mistakes.
Nobody gets everything right the first time. An entrepreneur has to be willing to take a leap of faith with the full knowledge that his venture may fail. Successful people have to be willfully irrational about their ideas, and have to be able to learn the tough lessons that can only be taught through failure.

3. Faith.
In spite of failures, an entrepreneur has be willing to keep going on faith alone. And when faced with blood-chilling obstacles (like financial upsets), he needs the ability to determine if they’re actually worth detouring around, or if they’re what they are a lot of the time: phantom obstacles that don’t really exist.

4. Creativity.
Successful people need to be able to come up with a lot, lot, lot of ideas and possible courses of action. Many of these ideas will and should break existing molds.

5. Optimism.
Some of the successful folks I know have caustic exteriors, but all believe deep down that what they’re doing is right and will all work out in the end. By contrast, I’ve met people who don’t truly believe the glass is half full or that things will eventually turn around. Those people will never make it.

5. Flexibility.
A successful entrepreneur has to be able to be totally packed, dressed, and ready to move in one direction, encounter a new bit of information, and go in the opposite direction instead.

6. Problem-solving ability.
Problems are everywhere when you work on your own, and because you’re forging a new path, there’s usually nobody to ask how to solve them. Entrepreneurs need to be able to develop solutions to problems, no matter how varied and wacky those solutions may seem.

7. An enterprising and capitalistic spirit.
All of the successful people I know have something good to offer the world and have the balls to ask people to pay for it.

8. An ability to follow your instincts and live by your wits.
An entrepreneur has to learn to trust his gut, and then keep trusting it on the fly. Many of the things I’ve done — including some of the best things, yielding the best results — have been done on a whim. I do most things for no other reason than that they feel right to do.

I could go on and on. But succinctly, if someone is really good at the above skills, I’d wager that they’d do fairly well as an entrepreneur, or as a trailblazer in any field.

The problem I have is that I don’t know how well schools teach those things.

Enter the ridiculous concept of unschooling

Those wacky online weirdoes I mentioned? A lot of them do what’s called “unschooling.” I thought it was just a clever word and only recently learned from Lee Stranahan what it actually means.

Unschooling is not formally teaching your kids. It’s guiding and supporting them, but letting them find their own path, and largely letting them do what they want to do with their time each day.

I don’t know if I like this idea.

And I don’t know if I don’t like it, either.

It intrigues me, though, and I want to learn more.

It makes me wonder if a kid who had no interest in trigonometry or symbolism in literature could grow up without ever learning those things and be okay.

It makes me wonder if an artistic kid who found ways to get people to pay a pittance for his sketches at a very young age would eventually find a way to turn that ability into a thriving creative business.

And it makes me wonder if you took a kid with a desire to do something outside of the box and put him in school — where he was instructed to sit still, be quiet, and study the lesson of the day so that he could pass a test — if he’d lose that desire to do something outside of the box.

It makes me realize that a traditional education prepares you for a job, and that it seems like so many people want to get out of their jobs and do their own thing.

It makes me wonder if the most important things I ever learned in my life, for my life, were learned in a classroom or outside of one.

If my kids learned the entrepreneurial skill set I outlined above, and then only the book learning they chose to pursue, would that be enough?

I don’t know the answers to these questions, yet they just keep coming to me.

How much conformity is good? I think there’s value in learning how to sit still and be quiet, how to take direction, how to subordinate your id’s desires occasionally to the needs of others. I think there’s value in not always being the leader. But how much is enough? And more importantly, how much is too much?

What it really boils down to is, could I trust the base human instincts of my kids, with guidance from us as parents, to figure things out? Because that’s what it ultimately comes down to: deciding whether or not “what they are inclined to learn” will lead to a good place.

And having faith along the way, I suppose. Lee told me that his kids, who are unschooled, sometimes play video games all day. And that would be hard for me to sit quietly through.

But then he says that they’ll noodle with the Rock Band guitar and decide to pick up the real guitar. They’ll run across something here or there and start reading philosophy. They’ll see how Dad makes a living by working at home and doing what he loves, and become interested in (and inspired by) doing the same.

Ditto the experiences of Pace & Kyeli and their son.

And ditto the mindset of Naomi, who I know is all geeked up over this issue and wondering what to do with her own kid.

Ditto others. And others. And others. Rule-breakers all.

I don’t know where this will lead for our family.

But I do know that I’m not where I am because of what my schooling prepared me for. I’m here because in many ways, I did the opposite.

Your turn. Discuss.

First time here?

You might want to read these three posts
as a kind of “Recent Best of Johnny”

• Revolution and Evolution, Part 1

• Revolution and Evolution, Part 2 (The Dean Koontz Edition)

• How to Write Your Ass Off (on Copyblogger)

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I just got back on Monday from attending the South by Southwest conference in Austin, Texas. It was one hell of a great time, but not for any of the reasons I might have expected.

So, since I seem to have lucked into a way to make conference attendance awesome, I figured I’d spell out a few of the things I’ve learned in the hopes that it will make your future conferences suck less. Or, at least, if you’d like to go back in time and attend this one particular conference, it’ll make SXSW 2010 in particular awesome for you. (I added that last sentence because I imagine some conferences are not salvageable.)

Tip #1: Don’t attend the conference
Pace, who ill-advisedly invited me to sleep on the couch at her and Kyeli’s house while in town despite their lack of knowledge about whether or not I was an axe murderer, argued vehemently that I should come for SXSW but not actually buy a badge to attend the conference.

At first, this seemed strange and risky. I had never been to SXSW before, and I figured that without an event badge, I wouldn’t know what the hell to do with myself. But it turned out that the best stuff happened in restaurants and bars, not at the convention center. Hanging out was cool. Having to leave that to go sit in a classroom and take notes would have pissed me off.

Note: Charlie Gilkey will vehemently disagree with me on this entire tip, but this is my blog, so I’m right.

Tip #2: Be a huge gigantic nerd
Austin in March is a nerd mecca, a sacred homeland to which dorks amble, slumped, ungainly, bent forward by the weight of their overburdened pocket protectors. I hear that bullies wait greedily at the city limits, ready to give endless wedgies to conference attendees as they leave.

So, when in Rome, be a dork. To me, this meant finally buying a smartphone and becoming one of those douchebags who walks around texting and checking Twitter.

As it turned out, my new smartphone (a Droid) was essential. The first place we went was a restaurant called the Iron Cactus, and so when we got there, I tweeted “At the Iron Cactus. Anyone want to join us?” That’s how I finally met Andrew in person. The thing is, you don’t have phone numbers for everyone you interact with online. So you have to broadcast on Twitter, direct message them, or @ them. If you’re not dork enough to know how to do this and be able to do it from a restaurant, the whole system falls apart and you end up eating guacamole alone a lot.

Being a dork was totally the way to go. It’s how I finally met everyone, because while at the Cactus, I saw on Twitter that people were at Jo’s coffee shop. So we went there, and that’s how I hooked up with Charlie, Carl, Karl, Naomi, Megan, Erica, Marty, Baker, Jeff, Taylor, Cath, and a bunch of other people who will probably think I’m a dick for forgetting to include them in that list. (Note: I’m not a dick; I’m just incredibly disorganized. Sometimes I forget to wear pants.)

Tweeting your location, texting while walking, needing to plug in frequently, and being unable to charge your phone because there are cells and laptops plugged into every outlet? All acceptable and essential parts of the experience.

Tip #3: Make stupid business cards
I heard people talking about getting business cards for SXSW months ago and staunchly declared that I would not do the same. After all, I wasn’t going to network; I was going to meet people for fun. But then Jess started goading me and goading me about how I HAD to get business cards; how could I NOT get business cards, and so I finally gave in and had these printed up:

Apparently this was the right choice, because the stack I took on the first day went fast. And apparently I did it right because Sonia asked me how I got so many of Chris’s business cards to do this with and Mark, the lead developer at Wordpress who I hadn’t known before Sunday, gave me a “what the fuck is wrong with you?” look after checking it out and I had to tell him that it was a joke lest he report me for identity theft.

Martin Whitmore’s business card kicked some serious ass, too:

The way I figure it, you’re always going to feel a bit like a douchebag when handing someone a card, because it’s a formal networking move. Having a cool card gives you an excuse to do it, like if you were showing them a porno playing card, like, “Hey, dude, check this shit out!”

The P.S. to this is that on Sunday night, I ran into Chris and he said that people kept telling him that he had to ask me for a business card. Later, after I had given him a few, a girl approached him and this exchange happened:

Girl: “Who are you? You look so familiar, but I can’t figure out where I know you from.”

CB: “I’m Lawrence Fishburne.”

Girl: “No, really… I can’t place you! Who are you?”

CB: [Hands her one of the cards I gave him] “I’m Johnny B. Truant.”

<< UPDATE: I just saw THIS LINK on Twitter. You have to check it out. >>

Tip #4: Don’t network. Hang out.
I just lucked into this one. I’ve gone to plenty of conferences in the past where my prime goal was to find and engage with the people who could most help me move toward my business goals. This time, before going, I declared loudly, “I HAVE NO AGENDA.” I wanted to find the folks I talk to all the time and… wait for it… talk to them. That was it.

So that’s what I did. And you know what? It made it awesome. There’s no pressure to pummel everyone with your elevator speech and to ask what they’re doing even if you don’t care, and there’s no need to go out there and starfuck.

It made me realize how true something that Lee Stranahan told me really is. He said, “Most people don’t have a specific strategy for networking, but when they get in front of someone, they suddenly have an agenda. The opposite is the better way to go about it.”

So what happened? I think I accidentally did some networking. I suspect I have better and stronger connections with a bunch of people now, and it happened because I had no pitch and no business intent. We just hung out. Plus, I took pictures of people when they got drunk so that I can calmly blackmail them later.

Besides, just chillin’ is a lot more fun. I didn’t know Terry before Saturday, but we didn’t figure out how to work together. Instead, we worked out his epitaph based on Prince’s song “1999″: “[year of death], party over, oops, out of time.”

Tip #5: Don’t think of it as a meet-up. Think of it as a reunion.
I figured meeting folks “in real life” that I’d only met before online would be strange and awkward, but it wasn’t at all, because we already knew each other. We just hadn’t formally been face-to-face, but once that was out of the way, it was like starting a relationship on the 10th date.

There were very few people I met cold, who I had never met at all before. But usually we’d introduce each other by name or Twitter username, and we’d both go, “Oh! Yeah, how are you?” That was the way it was when I met Tzaddi and to a slightly lesser degree, when Eric and I ran across each other (albeit briefly). We already had a shared history. It’s as if the definition of “knowing someone” has changed.

Tip #6: Think outside the campus
Since I didn’t have an event pass, literally everything I did was outside of the bounds of the seminars and panels themselves. But especially if you do attend events, make it a point to… oh, I don’t know… commandeer an evil illustrator, a raw foods witch, and a couple of pagan lesbians and play Rock Band until 3am a time or two. Be sure to sing “White Wedding” and demonstrate how well you can do Fred Schneider from The B-52s.

So yeah, my review? It was cool. I didn’t learn anything about the internet or social media, so here are my notes of important things learned at SXSW:

1. Pace is SCARY GOOD at both Dance Dance Revolution and at playing the drums in Rock Band. I wouldn’t have believed it I hadn’t seen it.

2. Apparently if Canadian lass Melle humps the leg of Jeff Moriarty, Jeff leaves with his leg covered in maple syrup. This was a joke that I missed but which Pace found retardedly funny and which would elicit ridiculously loud laughter. Not truly getting the joke will not stop anyone from enjoying it. I was able to get Darren to walk into a room and loudly proclaim “Maple syrup!” and then listen to crazy Pace bellows for like five minutes.

3. Shaking hands over a cactus is a bad idea. I did this with Baker and at first thought that he had a James-Bond-style razor or dart in his hand and almost unleashed some kung fu on his ass.

4. Chris Guillebeau is able to hypnotize people without them knowing it. I saw it happen. Chris Garrett and Andrea might have seen it too, but then again, they were possibly hypnotized into forgetting. In fact, I might even be hypnotized. Either that, or I actually am a goat. Not sure which is the case. Mmm, this tin can looks tasty.

NOTE: Want to hear more of my SXSW antics, and those of Charlie Gilkey? We spoke at length about it in this month’s Jam Session.

Tim and his co-author John Strelecky wrote a book called How to be Rich and Happy and decided on an ambitious goal and an unusual way of reaching it: They decided that they wanted to get a million copies of the book into people’s hands, and would do so by reverse tithing almost all of the money that came from sales of the book back into producing new copies.

In this interview, we talk about values, philanthropy, why Tim and John decided on an admittedly sensationalistic title, and how to get what you really want — but suspiciously little about dolphins and/or ratatouille:

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So how can you help? Well, you can listen to the audio. You can spread the word on your blog, in your newsletter, and on Twitter. And lastly, you can and should buy the book. Remember, nobody is making money on this, if that makes a difference — not me, not Tim, and not John. We just want to make a difference, because it’s a good cause.

But instead, I realize I kind of came off wrong, and that it almost looks like I’m advocating creating actual value in life over materialistic things, or some other hippie bullshit.

Okay, so it’s not bullshit. But I don’t want anyone thinking I don’t like me some good materialism now and again. Just because money has been everywhere from some fat tourist’s sweaty pocket to a stripper’s butt crack, that doesn’t mean that I don’t still want to fill a bathtub with it and roll around in ecstasy.

(And furthermore, since that post ended in the suggestion that I’m going to be launching a new product soon, I don’t want some Robin Hood asshole suggesting later on that I’m a hypocrite when I charge for it. YES, I will want your money when I launch that thing. NOM NOM NOM NOM tasty sexy dirty money.)

Look, I think everyone today has money issues. And I don’t mean issues like you can’t make the car payment and that mutant freak circus from Operation Repo is going to come and take your car away, but more like we kind of all have issues around money, like shrink issues, like lay down on the couch with a wad of bills while some guy with a goatee and a notepad says, “Hmm, and how did that make you feel?” issues.

Like, I think these past few years have been rough on all of us, and what we’ve all kind of learned deep inside is that money equals a common means of exchange (nobody lets you pay your electric bill with a goat anymore) and that the more you have, the better, and moreover that if you have some, you’d better grip it tight and be prepared with some kung fu shit if anyone tries to take it from you.

You know, the scarcity mindset.

I’m trying to break this mindset myself, because I do have issues with money. Money tries to control me; it gets all passive-aggressive with me; when something comes up in my marriage, it’s usually because growing up, my money didn’t love me enough. I lived the past few years in a state of chronic panic because I owned real estate investments in Cleveland, where the market dropped so fast that it actually collapsed in on itself and formed a series of interconnected black holes that now provide superior transportation to what is available via the RTA train.

Live like this for a while, with every cent you earn and a few thousand dollars more flying out the window each month, and see what it does to your hoarding tendencies. In theory, I wanted to give money to the Red Cross, but in reality, let’s see them try and pry a buck out of my hands. The local kids’ clubs would be outside the grocery store collecting for this or that and I’d be like, “Dude, get your own.”

Then I started this business that I’m doing today. And over the course of this past year, things have eased up. That hideous phase of my financial life is finally coming to an end, but now it’s like I want to hang on to my dollars for dear life anyway, and never, ever let them out of my sight.

So, to combat this, I did what most wise people do when faced with financial psychological issues. I decided to become a good tipper in restaurants. You know, to practice.

Flash to my thrilling Saturday night.

We live kind of out in the country, with the “kind of” meaning that although we do have neighbors, those neighbors have sheep out in their yard. So when we go to the areas where there are restaurants, the best places are 35 minutes away.

That’s what we did on Saturday. We drove those 35 minutes, to go to Sam’s Club to stock up, and then to go out to eat.

On the way home, the kids were asleep and so I could woo Robin by showing her how I still knew all the words to “Ice Ice Baby” (“girlies on standby waiting just to say Hi… did you stop? No, I just drove by”) but on the way out, the long drive essentially just gave my daughter Sydney a nice long time to play her favorite new car game.

It sounds like this:

She says, “Daddy.”

And you’re in the middle of a sentence, so you ignore her.

And she repeats, a bit more urgently, “Dad-day!”

And so you stop your discussion and you half-turn and say, “Yes?”

And she goes, “Birdie.”

So you tell her how that’s the most amazing thing ever and resume your adult conversation. As many as ten seconds will pass and then again she’s interrupting you urgently, like, “Dad-day. Dad-DAY!”

So you ignore her a bit, because this is like the tenth time already.

“DAD-DAY.”

So maybe you go like, “Quiet.”

“Dad-DAY!”

“Sydney, knock it off.”

“DAD-DAY! DAD-DAAAAY!”

“What? What is it? What could you possibly want?”

And she returns to her normal voice and says, “Car.”

It goes on like that for like a half hour, and then we get out and buy a bunch of stuff at Sam’s Club, and when we’re done, when we’re leaving and getting really hungry, it sucks because the Girl Scouts aren’t selling cookies yet at the exit, and that’s not cool because I want to buy some of those damn cookies already and I’m HUNGRY, and all of this despite the fact that I pre-ordered 13 boxes through my gym (and don’t even get me started on the notion that this happened at my fucking gym) and Sydney is still like “DAD-DAY!” every two seconds and Austin keeps hopping off of the shopping cart so that I run into his foot and then we try to go to this hibachi place but it’s full out the door and we end up at Ruby Tuesday and I just want some damn food already and to sit down and relax a bit, and we’d promised Austin ice cream earlier (to coerce him into skipping a sledding run we didn’t have time for) and I decide I want an ice cream sundae too at the end, because I’m tired and because the Girl Scouts are entirely too slow on delivery.

But the waiter tells me that the sundae bar is $3 for all-you-can eat, and I’m like, “I just want like one little sundae.” See, I’m getting my winter fat on, and honestly, all I need is all-you-can-eat. Plus, I’m having disproportionate concern over that $3 because, you know, every cent is vital to my family’s continued existence on the planet.

So the kid, this waiter who’s already been really attentive and generally cool and in really positive spirits despite handling a table of like a billion behind me, he says kind of on the sly that he can bring me a single-serving sundae for like $1.19 if he rings it up as the kids’ version.

For some reason, this offer is super-awesome to me. Because I’m tired and because $1.79 is apparently some huge amount of money.

I eat, I enjoy. It’s winter; give me a break.

Five minutes later, the check comes and our total is $40.14 and I mentally calculate, okay, maybe I put down five bucks for the tip.

But then I think, “Dude, this kid did right by you. And you’re not throwing money down the investment black hole anymore.” And frankly, I have this notion that being awesome and not bitching about life should be rewarded, and maybe it’s time to pay attention to that idea myself, for a change.

So I put down $50 and told him I didn’t need change.

Okay, stop here for a second, because this may sound like I think I’m some great philanthropist or martyr or something because I’m giving a few more bucks on a tip. I don’t. But… wow… paying extra for something? You get down to a tip, where it’s up to my discretion, and I give more than I have to? Wow, that’s foreign. That’s a mindbender. You get in this mindset where you pay what you’re asked, and if you aren’t asked, you don’t pay.

Remember the Red Cross and the kids outside the supermarket? They were trying to get me Lucky Charms. That wasn’t cool.

But now I think that a natural part of growth is to start circulating some goodness where you can, even if it’s in small ways like leaving a few extra bucks on a tip or tossing something in the coffee can the kids have outside of your supermarket. Like when that thing comes in the mail for St. Jude Children’s Hospital, maybe you finally write them a check. Maybe you try to remind yourself that you don’t need to hold each dollar in a death grip, so that your brain figures out that you truly believe more will come.

You know, the scarcity mindset. Like, this is how you fight it.

And a few minutes later, after the waiter kid has presumably run our check, he comes back and kind of in a low voice thanks me again, like seriously and earnestly this time. Like you get the impression that not many people tip more than 10-15%.

And I’ll admit it; that felt good. It wasn’t much, but it did feel nice to reward this hard-working kid who was pleasant and friendly and good at his job, and probably kind of needing every dollar that he makes.

I really do love the idea of charity. You read shit like this (last subhead near the bottom) and you think how awesome it would be to do. I know Naomi felt really good after that, like it did her good to do it as much as it helped the kids who’d attend the school she was going to build.

I’ve heard it said that there’s no such thing as a selfless good deed, because people who do good deeds are ultimately doing them to make themselves feel better, to feel noble, or to alleviate their own uncomfortable feelings about seeing the suffering of others. But I don’t see it that way. That’s too nihilistic. I keep talking about win/win thinking, and this is just one more example of win/win. The recipients of charity win. The giver wins. Everyone is happy.

There’s not really a lesson to this story. I was stingy as all hell for a long time, and I wasn’t going out of my way to over-tip even when the waiter or waitress was really awesome. I wasn’t giving to anyone, so I’m not exactly casting a moral imperative as I write this now.

But if you’re hanging on to each buck, consider that maybe there’s a possibility that you don’t really need to be doing so. Maybe you’re not in the dire straits you think you’re in, deep down.

If that’s the case, then tossing a ten or a twenty into the can when the Salvation Army is out collecting might just do you a world of good.

Something to think about.

Like any responsible and loving parent, I always look for as many opportunities as possible to get away from my children. So this past weekend, my wife Robin and I dropped Austin (5) and Sydney (almost 2) off with my mother and checked into a hotel for four days.

When we do this, we get a room with a giant hot tub and spend most of the weekend in it. And we get to do things that we’re not normally able to do, like read books without pictures in them and watch movies that aren’t animated.

When you read in a hot tub, you need a light book so that you can hold it above the water. I was working on Stephen King’s Under the Dome at home, but it’s like 1300 pages and hardback, so instead, I brought along my paperback, 200-page copy of Fight Club, which I hadn’t read in a while.

If you haven’t read Fight Club, do yourself a favor and go buy it now. (And no, having seen the movie doesn’t count.) If you like reading my stuff, you’ll like that book. It’ll put ideas in your head. Bad ideas. Rebellious ideas.

It’s about a group of guys who discover that they’ve been living very sterilized, materialistic lives. You wake up, you go to work, you come home to your IKEA furniture that you just had to have and that felt very important, and you repeat. You behave, you become soft, your emotions and reactions and behaviors dull to the predictable, and soon you realize that the things you own, they actually own you.

What the narrator does — and this is a complicated setup, so I’m simplifying — is that after months of insomnia, and after months of attending support groups for diseases that he doesn’t have just so that he can feel alive enough to sleep, he meets a guy named Tyler Durden. They’re both learning that the things in life they thought were essential, that maybe they’re not essential after all. It starts to feel like the only way to be reborn is to hit rock bottom. But society teaches you to live a safe life. A predictable and behaved life, where you do not only what you’re told, but what is expected of you.

Neither of them have ever been in a fight. So they go into the parking lot, and they take turns hitting each other as hard as they can. Who are you fighting? They ask. My father. My boss. My life.

Well, it goes on from there.

I’d read Fight Club several times before, but I found myself reading it this time and thinking, “I kind of want to join a Fight Club.”

Not literally, I mean. The fights in the book take place barefoot on a concrete floor, two guys to a fight, and the fights go on as long as they have to. Everyone ends up with knocked-out teeth, gashed lips, and broken bones. So yeah, I’m not quite antiestablishment enough to want to actually do that in its full glory, but I’m intrigued by the concept.

Now, try to see beyond what may be an initial reaction to this all as a bunch of macho bullshit, and get what’s behind it: What do we fight (no pun intended) to avoid in our day to day lives?

What is the standard of beauty and order that we’re upholding at all costs? What are we afraid of, and what would happen if we did that thing that terrifies us?

Life used to require exertion and threat. Don’t get me wrong, I’m digging the fact that I don’t have to fight daily to keep my woman and my cave, but would it really be the end of the world if I had to fight? And how would I do in a fight, anyway? What am I made of at a deep, deep, deep and primal level?

I’m not saying that fighting is a good thing. I am, however saying, that most of us are afraid to find out if we could hold our own, because of the threat of pain and discomfort. Again, don’t go thinking I’m saying that we should get in fights to find out. I’m not saying that at all. But I do find it interesting that we’re so very afraid of it.

These guys, these stockbrokers and waiters and customer service representatives in the book, they find out that they can be hit and that they can hit back and that still, life doesn’t end. They’re not as fragile as the world has caused them to believe they are. They find out that they’re different people than who they thought they were. Harder. More resilient. Confidence carries over into every other area of their lives. The petty aggravations that used to upset them can no longer faze them. They sleep well. They have explored that darker side of themselves and found out what’s in there, and it’s like they’re magnified, in person and in personality, as they go about the rest of their daily business.

And all I find myself asking is, Are we really so intent on living and dying a safe existence?

And at this point, I could easily slip into a lot of the themes I’ve been writing about lately, about doing something crazy and breaking the rules and being abnormal. I’ll let you make that connection for yourself, but… you know. There’s the whole “What are you really afraid of?” thing to consider here.

The guys in the book, they decide they don’t want to die without any scars.

I have a pretty fucking badass scar. It’s on my left forearm, and I got it doing a 205 lb. Olympic clean and jerk at my gym a few years ago when at the bottom of the clean, my elbow hit my knee, hard.

That was gross. It was also expensive, and one hell of an inconvenience. I don’t recommend it. But it is an awesome story to be able to tell, I won’t lie. I like that scar. It’s proof that I’m not living my life wrapped in protective bubble wrap.

Some of you ladies reading this are likely disgusted by the testosterone in this post.

Except Jess Commins. I’ll bet she really likes it.

(Oh, and on a side note, when Sonia Simone interviewed me for the Third Tribe, she described a certain masculinely pushy internet marketing technique as “masturbatory,” and I was like “Yeah, it’s awesome, right?” and then I realized she meant it in a negative way. Women.)

I’ve built a career out of saying what’s on my mind whether it’s stupid or out of context or embarrassing or what. And so I’m telling you, whether you think it makes me a macho jerk or not, that part of me wants to get into a fight, for once. To see what I have in me. To take a peek at some aspects of myself that I’m never allowed to let out. To explore my id. To take and overcome a trial.

So maybe I’ll join some sort of a class. Like mixed martial arts (what the Ultimate Fighters do) or Krav Maga, which is supposed to be one of the few self-defense things that actually works in real life. I’d be wearing pads and wouldn’t get the shit beat out of me, but maybe it’s close enough.

I think the essence of pretty much everything I’ve been doing lately is this, to make a point out of this whole Fight Club thing:

I ask myself, “What am I afraid of?”

And then, if I can find a version of it where I won’t die or risk major injury or other huge ruin, I do that thing.

Maybe this is all too macho for you. Maybe a safe life is just fine, in fact. But just for the hell of it, ask yourself what you’re most afraid of, and ask why it scares you.

You try one thing that seemed impossible or terrifying and suddenly, it’s like you’re a new person. You’re bigger and better and stronger and bolder than you thought you were.

All I really want to know is who I truly am.

What I’d like y’all to know is that this isn’t me sitting on some philosopher’s cushion and declaring from on high that I’ve had some esoteric, metaphysical realizations that you might want to try.

This is me living my life and realizing — in a very, very visceral way — that a lot of things have been presented to me that aren’t necessarily true or right, and starting to defy them. To actually do, in my daily life, what I’m writing about here.

However, despite that Cool Guy intro, I’m running into one thing that has me stumped. One convention that is begging to be defied, but which I honestly don’t know if I should maybe just bow down to anyway.

Maybe you can help me decide what I should do.

As some of you may know, I’m an insulin-dependent diabetic. Since 13 days before my 13th birthday (I love that stat), I’ve been monitoring my blood sugar, injecting insulin, watching the things I eat. That is absolutely no big deal to me; it’s simply part of who I am at this point.

But since I moved out of my mother’s house… and here comes the rub… I’ve also been paying for health insurance to cover myself, as a diabetic.

Every year, the rates go up. Almost always significantly.

I got my new renewal rates in the mail a few weeks ago. And I found out that they’ll be going up almost 50%… again. And once that happens, I’ll be paying around $800 per month to insure myself.

And that’s JUST myself. My wife and kids have a separate policy. And by the way –that $800 policy? It’s the worst one I’m able to get. It has a $5000 deductible, meaning that I’m essentially paying for everything out of my pocket anyway.

Now, let’s go back to the rules thing, and to fear.

Society tells you (tells me) that you (I) must have insurance. Plenty of people don’t, but almost all of those people wish they did, and are only uninsured out of ignorance or lack of funds. But the vast majority of those people want insurance. They feel they need it. Because… what if something happens?

But “what if something happens” coverage for $800 per month for the shitty policy, and rising fast? Really?

And so here we come to my rule-breaking question: Can I decide not to have insurance?

I don’t like the idea — not one little bit. It bothers me that I could have an accident, or a sustained illness, and I wouldn’t be able to pay for it. And currently, while it feels like I’m being robbed at gunpoint if I pay $800 per month, I could do it. But what happens next year, when it’s $1100 or $1200? And what happens the year after that, when I turn 35 and move into a new risk bracket, and things really start to change?

What happens when I’m 65? Will the insurance company be asking me for $5000 per month by then?

I’m fucking 33 years old and am in stellar health. I’ve broken a bone one time and was hospitalized only when I was diagnosed with diabetes. I’ve done everything right; I’ve taken care of myself; I’ve done everything the doctor told me to do. But am I being rewarded in any way? Or am I, instead, being lumped in with the people who eat cake all day, don’t check their blood sugar ever, and have a foot amputated every spring?

Am I being treated like — and charged as part of — a demographic that I don’t really match? Am I being punished for the negligence of thousands of people I don’t know?

Do I maybe have a far better chance of costing less than they do as a medical patient — of costing less, even, than what I’m paying in for insurance?

Yes, I could get hit by a bus.

But am I being financially raped each month simply because my fear of a catastrophic event outweighs the likelihood that it will actually ever happen?

I’m really not trying to talk myself into this. I’m trying to raise questions, and see if it makes sense or not. So we’ll see.

But here’s something to think about:

Insurance companies know the odds. They pay actuaries large salaries to determine how much any one type of person is likely to cost for medical care. To them, you are a number. And on average, they know that if enough of your type of people pay in and and then cost what the actuaries tell them you will cost, they will make a lot of money.

In other words, the game is fixed. If you have health insurance, you’re essentially betting against the house. The average person in each demographic will always pay more in to insurance than they will get out of it.

That’s not conspiracy theory. It’s fact.

The question then, is, are you willing to pay in more — to bet against the house — on the chance that enough bad stuff will happen that you will “beat” the odds?

It feels to me like I’ve been lumped in with a shitty group. I don’t think I match the odds of most diabetics — not by a long shot. If their lifetime costs are X on average, I’m going to be a small fraction of X.

So if you’re betting against the house with your insurance, I’m apparently hoping to hit the Powerball.

I’ve gone 20 years without any of the traumatic “diabetic costs” like hospitalization, retinopathy treatment, fancy foot care, amputations, renal failure, etc. etc. etc. Yes, I do have ongoing needs for medications and supplies, but beyond that, I have the medical expenses of a nondiabetic.

Or, I’d wager, I probably cost less even than the average nondiabetic, since most Americans are less active than I am, eat more poorly, and so on.

I insure myself out of fear. We all do. The question will be whether or not the fear is justified. Whether it’s possible to honestly mitigate that risk well enough without insurance (or with some crazy insurance alternative), or whether doing so is a foolish gamble.

So let me pose the question: Should I break this rule? Should I consider dropping my insurance now, while the rates are only moderately fucking ridiculously insulting?

Alternatively, what else can I do?

• I’m self-employed and am not about to go get a 9-to-5 so that I can get on a health plan.
• I already have the worst plan offered. I cannot opt for a plan with a higher deductible because there is none.
• Isn’t there some coverage I can get cheap, even as a diabetic, that says, “If you have expenses over $20k or something, we’ll cover it, but otherwise, you’re on your own”?
• I do have substantial ongoing monthly costs. I pay around $150 per month for insulin, but that’s not even covered by my current plan, so I’m paying that anyway. I also have other stuff (testing supplies, supplies for an insulin pump and real-time blood glucose monitor) that is apparently pretty costly but that I now get for free as part of a diabetes management plan. Basically, by giving me this stuff free, they reason that I’ll use it and not have kidney failure later. If I ditch insurance, I have to start paying for all of it myself.
• I haven’t calculated that cost yet, but have a really hard time believing it’s EVEN REMOTELY CLOSE to $800 per month.
• My other costs are minimal. Doctor’s visits are infrequent and cheap. Lab work is infrequent and not hideously expensive. Knock on wood, I’ve only had one traumatic medical event, when I broke my arm at the gym while weightlifting.
• This one’s the kicker: If you don’t have insurance for a period of time and then want to get it again later, the company does not have to cover you at ANY price. So if I ever don’t have insurance, I can probably forget about ever having it again down the road, thanks to my rather expensive preexisting condition.

All ideas, thoughts, opinions, alternate means of covering my ass are welcome. I honestly don’t know what to do.

Ultimately, the question is: Is $800 per month (and likely to increase by at least 30% per year going forward) a fair price to pay for “just in case” coverage? Or should I maybe just put that same $800 per month into a bank account, and draw from it when needed?

Ugh, I don’t know. Fucking stupid insurance.