note: this is a special web-only chapter and won’t be appearing in the actual book. It’s a chance for me to address some of the most pressing questions readers have asked me to date.

I’ve laid out a roadmap. So what are the obstacles? What prevents someone from putting these tactics in action? In this installment, I’ll go through each of the major obstacles in turn.

1. Either you don’t agree with me, or you’re too rich or happy to care. Some folks don’t believe that their 9 to 5 careers are going to let them down. And they may be lucky enough to be right. If you have a steady paycheck and don’t agree with my conclusions about the instability of the “careers” we put our faith in, then there’s no urgency. And if there’s no urgency, then why make the push? Of course, for some, it doesn’t feel like a push at all. These unbalanced people (myself included) are infected with a passion for the entrepreneurial life. Absence that passion, we generally have to be punked out of our jobs before we rethink. Of course, you could also be too rich or happy to care. Why go back to the lab when you’re rolling? I just hope that those who are currently too happy to need this book have that foundational happiness, not the fickle kind that leaves you single and broke.

2. You don’t see yourself as creative enough to make the leap. You need the structure a 9 to 5 job provides. I run into people who agree with what I’ve written, but don’t see themselves as “creative.” We’ve been fed a line of b.s. which claims that only certain people are creative. I’ll grant that creative thinking comes easier to some than others. And not everyone is cut out to be an artist. But a creative approach to life is not confined to art. Creative living is not something to dismiss as New Age pap, due to its link with happiness itself. It’s hard to be happy if your life doesn’t have your own stamp on it. Imitation might sell records but it doesn’t save souls. The broad definition of “creative” I’m using here simply means the ability to initiate, manage, and market projects. Anyone can learn those skills.

The payoff? If you can learn how to conceive your own undertakings and then get other people to buy into them, there will come a time when you don’t have to work for anyone besides yourself. Creating assets is how you take advantage of the economic rules of an “ownership society.” The alternative? Grow gray hair for other people and let them cash out on your life. But what about those who excuse themselves from this conversation because they need the structure a 9 to 5 provides, no matter how crummy that structure is?

In truth, all ventures have structure. But sometimes you have to wipe the foundation clean and build your own structure from scratch. Maybe you’ll start with the intimidating emptiness of a clean desk, but pretty soon, you’ll fill that space with a structure of your own making. And it will be infinitely more rewarding than the one-size-fits-nobody-very-well structure that is imposed on you from corporate entities. And remember, you don’t have to start your own business to use the principles in this book. You can use a lot of these tactics within corporate settings to advance your interests, or you can launch side projects that will be your ultimate job security when they are fully formed.

3. You want to get started, but you have no time. You are waiting for a window of time to make your move. It’s easy to put off getting started on the basis that there’s no time. Our friends and family will nod in sympathy; no one will prod us to make it happen. I ran into someone the other day who dreamed of being a writer but had no time. He had a management position and a family to support. It sucks to admit it, but the time excuse is almost always a smokescreen for being afraid to get started. I used to fall into the trap of waiting for the right time. The right time never came, and the years piled on until my best dreams were buried far beneath. I finally learned that awful lesson: what you are doing now is who you are and who you will be. That is why it’s so important to establish a “theme” of change in your life.

Even if you only have one hour a week, that one hour makes a huge difference – not only in terms of getting projects off the ground, but in terms of the basic psychology of freedom. Knowing you are facing the challenge and taking action changes how you carry yourself. It seems odd, but once you put a theme in place, you will sense the shift. Even if your progress is molasses, you will feel movement where you were previously stuck in self-defeating excuses. You will start to get into a flow. I wrote this entire book during a year when I was deliriously overworked.

This particular chapter I am writing on two hours sleep. I’ve set aside three hours a week to write this book, and a year later, it’s almost done. Themes are very powerful. Legend has it that Toni Morrison wrote her first books with her children swarming around her. John Grisham was a full time attorney when he wrote his first book. The bottom line is that we almost always have time if we’re willing to give blood, so that excuse falls under the “failed attempt to justify my life” column. When we peel off the rationalizations, we expose someone who is understandably scared to get started. I know: I was one of them.

4. You can’t figure out how to make your passions marketable. You are torn between hobbies with no economic future and dull work that pays the bills. The majority of Americans hate their jobs. They see work as a means to an end. In some cases, they are correct. But according to the value of time, dull jobs are not only dull, but an unacceptable means to an end. Ultimately we stand a much better chance of enjoying our work and improving our financial picture if we launch some effective side ventures. And we should lean towards ventures that capture our imagination.

But the challenge remains: we still have to make our passions marketable. The marketplace is a constant negotiation between what we want to do and what other people are willing to pay us to do. Choose ventures that strike a balance between work you care about and work that has economic value. Sometimes that means recognizing our biggest passions should remain in “hobby status.” I love my guitar, but there’s no chance anyone’s gonna pay me to play it. Classifying guitar as a hobby clears the garage for projects that are a better mix between the market and what I’m good at. This book represents an attempt to find that sweet spot by writing about a subject I care about – one that I hope is compelling enough to find a marketplace.

Before you put your metaphorical guitar on the hobby shelf, first make sure that you can’t put a spin on your talents and make them pay off. There’s no tougher field than music, but I’ve seen musicians stay in the industry by becoming session musicians, studio producers, wedding singers, and even Elvis impersonators. Often they keep their own bands on the side. Sometimes what we just need to apply an entrepreneurial spin to the hobby and suddenly it’s a legit breadwinner.

I have a buddy who made a lot of money gambling online, a profession with a sketchy future to say the least, especially for a family man. I’ve encouraged him to look into setting up a tutorial web site and even writing books documenting his card-playing techniques. There are many ways you can spin your passions in a more marketable direction. And you don’t have to abandon your end game to do so. One example: actors like Nicolas Cage who take big Hollywood parts in order to finance their involvement in low-to-the-ground independent films.

5. You love your work but it pays like crap. Most people who love their work but have no money don’t view it as a problem. To be fair, they may be right. Most of the happiest people I’ve ever met fit this description. When you truly love your work, even when it doesn’t pay fairly, you’ve got your life in pretty good alignment. Still, some in this situation do get bogged in financial stress. It’s great to love your work, but as we get older, we see that our financial problems are going to undermine us when it comes to providing for our families and our own retirements. I know some social workers in this situation.

Social work is a potent example because the common response is to push for management roles where the pay is better. Problem: most social workers got into the field because of how much they liked working with people. The grassroots nature of what they were doing was a key part of the appeal. And from this book’s vantage point, the financial difference between being a social worker and a social work manager is not something to get worked up about. Unless the management track is appealing, it might make more sense to launch a side venture that pertains to the field. There are numerous options that might to the trick – writing a book on how to avoid burnout in the field, taking on a private practice, developing a series of weekend seminars. It’s all in how you spin it. An entrepreneurial approach to your chosen profession changes everything.

Some people make a huge mistake by avoiding low-paying fields even if that’s where their passion lies. I know people who are avoiding environmental work for that reason. But it’s not a particular field that pays badly; how you approach that field has a lot to do with how lucrative it can be. I have some buddies in Hawaii that started a car business for vehicles running on vegetable oil (good old-fashioned grease).

They stand to make a lot of money while innovating in a field they care about. Finding a way to make the profession you love lucrative is a damn sight better than choosing a job in a cynical way because it’s supposed to pay well. That’s a recipe for burnt rubber. Money can solve a lot of things, but it can’t inject passion where there is none. Another solution for someone who loves their work but needs a better upside is to launch a side venture, for example, developing a video game for PDAs or writing a children’s book.

5. You have more pressing issues than money. Books with endless disclaimers are tiresome. It goes without saying that this book is only directly relevant to those in market economies, and within that context, that there are plenty of people too focused on pure survival to take these tactics into account. Beyond that, there are many whose lives are too wrecked to deal. Take the example of the gambling addict: it doesn’t make much sense to spend two hours a week on a new business and three nights a week pouring paychecks into slot machines. There are times when we are legitimately pre-occupied with things more important than anything in this book. I have a friend whose child is going through hell in the public school system. Another just lost her best friend; her 14 and 16 year old daughters have no mother. I extol the virtue of relentlessness, but there’s a time to let forward projects slide and focus on righting the ship. Still, we should be a lot less tolerant of our excuses than we typically are. We need to insert these positive themes in our lives sooner rather than later. Eventually they could become a legitimate source of good news.

6. You hate capitalism; thus you hate entrepreneurialism. Or, entrepreneurialism is irrelevant because you are a dot.org. Let’s tackle the .org objections first. Some dot orgs believe that they don’t need to deal with business because they are provided for by academia or the public sector. Dot orgs may be less impacted by the globalization of labor, but this book still applies. Some of the most successful teachers I know found a way to market their ideas, reaching more people and boosting their revenues. The bigger stumbling block is ideological: what if you have contempt for capitalism? I draw a different line. I have a chip on my shoulder about big business but love the entrepreneurial life.

I wasn’t always this way, but I found that small businesses had more energy and less bureaucracy than the non-profits I did time with. Bottom line: if you hate capitalism, this book is the least of your problems. It’s hard to function in a market economy when you are superior to the system you are a part of. What I usually see is not revolutionary conviction but radical posturing combined with a half-hearted one foot in the boat/one foot out philosophy that gets everyone wet. It’s easy to rationalize a bad job by cloaking it in working class romanticism. My feeling is: either oppose the system with your heart and soul, or find a way to use it for your own ends. There’s so many ways to work the market, from ecological investing to the fair trade movement. Standing on the sidelines drinking coke (Coca Cola Corp) and smoking butts (RJ Reynolds) while pretending you’re not participating as long as you keep a low profile isn’t a bold stance.

Owning a business gives you a chance to leverage an asset as you see fit. Working for that same business doesn’t change much. You’re still playing the game, but your hand is inferior. Some people think if they stay close to labor they have more integrity than everybody else. Labor organizing is a worthy cause, but creating good jobs through entrepreneurial savvy is no less worthy. Struggling to the pay the bills might have more blue collar credibility, but being economically powerful is more effective. The glamour of sweat wears off; funding the causes you care about doesn’t. Academics with too much time on their hands are always the first to criticize my ideas. I can live with that.

7. Money doesn’t concern you – material goods aren’t important to you. This is a valid viewpoint only if you’re rich. In a market economy, those who are indifferent to money sooner or later pay the price. Rich is not the issue. The issue is financial self-sufficiency – the ability to call your own shots without being dependent on handouts. The more you can pick and choose how you participate in corporate America, the happier (and more effective) you will be.

This is not a great economy for martyrs. There was a time in the ’60s where you could dedicate yourself to a cause and know you’d have a couch to sleep on. Couches are hard to come by these days. There are a handful of folks (who are not rich) who can afford to be indifferent to the market. These are the geniuses and cultural warriors who are provided for by their handlers. For the rest of us, that’s not going to get it done.

I used to think that money was a sign of corruption. I had a higher purpose (teaching). My high purpose would allow me to coast over the demands of the material world. Turns out my high purpose was no match for the rent. Because I was expecting the world to take care of me in exchange for some kind of holier-than-thou contribution that no one asked me to make in the first place, I became a bitter man.

But I was able to get around the bitterness by changing my values. Not only was money important, it was largely a neutral value, assigned meaning by how I earned it and what I spent it on. The more I realized my job was to make money to take care of other people and finance my dreams, the more passionate I felt about unlocking the best in myself.

We each have our own financial riddles. We don’t have the same starting line or the same finish line. So forget about fairness, forget about getting back what you deserve. Focus on harnessing your talents and brining them in line with the marketplace – remembering that once you master the marketplace, you can pick and choose your involvement in it.

In an era of hyper-commercialism, the ability to use our money to build a fence around that which is not for sale is vitally important. Otherwise, we’ll sell everything we own to keep going, and we’ll lose track of where that soul-killing line in the sand was in the first place. Ending the month-to-month financial struggle will give us the time to make a bigger contribution on our own terms. If there’s such a thing as leaving your mark on the world, there’s no better way to do it.

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