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Over time, my views of this episode in my life mellowed and matured. The word “undisciplined” was used by several different editors rejecting my manuscript, and I have come to see that they were right—in fact, all the rejections were right.

I was a cocky kid, convinced that I was creating a new form of writing (doing away, for example, with the oppressive confines of narrative arc, plot, or character development) and that my vision was poised to take over the world, whether the world cared or not.

You could say I was trying to blaze a trail. And perhaps I was doing so.

But there was a problem with this trailblazing. No one really wanted to go wherever the trail I was blazing led. In fact, I didn’t really know where it led. In reality, it led to some dark, tangled forest bog in my depressed soul, with peat so thick and brush so dense that the trail back out got erased no sooner than it was blazed.

After a second round of submissions of Rock Star Envy bombed, in 2006, I finally got the message: I was not going to make a living as a bad-boy literary enfant terrible of memoir writing. If I wanted to continue to pay rent and buy groceries, I would need to be more flexible about how I interfaced my main set of skills (writing and editing nonfiction) with market realities.

■ STEP 1: Freelance Copywriter (Getting on My Feet Financially)

And so began my journey in the Art of Earning a Living, in 2007, at age twenty-nine. I began seeking out every gig I could get. Editing gigs. Ghostwriting gigs. Copywriting gigs. I helped people self-publish their books. I wrote book proposals for aspiring authors. Anything that had $$$ attached to it, and somehow involved words, I would do it. (How did I get all these gigs? Mostly through networking. Read Success Skill #2 on how to be a great connector!)

I moved to Buenos Aires, for a while, where I knew I could live very cheaply, worked for mostly Australian clients over the Internet (it’s a long story), and pursued my freelance commercial writing and editing writing full-time. I brought in $8,280 of gross income in 2007, which I was able to live on with a combination of living in pesos and drawing down some money I had saved from my last corporate job.

At the end of 2007, I moved into a $350-a-month room in San Francisco. I kept my business humming. The recession hit in 2008, but through mastering the skills of marketing, I expanded my business by 600 percent, to almost $50,000 in gross income per year in both 2008 and 2009, on a totally flexible freelancer’s schedule. I also moved out of that tiny room in San Francisco into better digs.

Obviously, things improved from a monetary perspective. I was no longer going deeper and deeper into debt to cover my living expenses while I “went for my dreams” (as the motivational books put it), hoping some editor at a publishing house would bestow upon me a windfall advance.

I was developing a valuable set of skills. Not editing/writing skills, which were already fine. I’m talking about the success skills in this book, particularly sales, marketing, and networking. Out of necessity (and following the steps I’ll provide in detail in coming chapters), I became good at connecting with potential clients, selling them on the idea of working with me, and leading them to where they wanted to go in their projects. Money started to flow. I had passed through Step 1 of the Aligning Your Money and Your Meaning.

(Step 2 in the Aligning Your Money and Your Meaning is all about creating flexibility in your workday, which allows for more experimentation in integrating your money and your meaning. Because my income in Step 1 was already derived from freelance work, I fortunately had plenty of flexibility—one of the great benefits of being a self-employed freelancer. So I got to skip directly to Step 3.)

■ STEP 3: Freelancer Copywriter with a Side Passion of Writing Books

Once money started to flow in 2008 and 2009, and I was on financially firm