I told you I wouldn’t recommend anything to you that I hadn’t applied in my own life. So here is my own story of how I applied the Four Steps to Aligning Your Money and Meaning, in my own life. Through following these steps, I was able to transform myself from being basically a miserable, broke loser, just four years ago, to having my current career, which is both profoundly meaningful to me and financially lucrative.
Pre-Step 1: Broke and Miserable Loser
Seven years ago, at age twenty-seven, I became possessed with the idea that I wanted to write and publish my first book, a manuscript of creative nonfiction I was working on, and become a literary superstar.
Laid off from my first postcollege job in corporate America, after the dot-com bubble, I moved back with my parents into the room I lived in as a teenager, with the idea that I would enjoy subsidized rent while I pursued my passion of writing and tried to make it as an author. My parents tolerated this because I also offered to use my writing skills assisting my father on a professional project for which he needed help; this was my day job, which also paid my basic expenses and some rent to my parents.
I ended up writing a wildly sexual, experimental, caffeine-pot-and-wine-charged attempt at autobiographically based comedic nonfiction, almost wholly devoid of any structure, weaving in manic political rants and fragments from my senior honors thesis in international relations at Brown (“Black Masks, White Guilt: Cultural Appropriation, Multicultural Consumerism and the Search for a Meaningful First World Existence”). My literary idols were Henry Miller, Hunter S. Thompson, Michel Houellebecq. I was certain my name would be joining their names at the table of “bad boys” in literature. The manuscript was entitled, ironically enough, Rock Star Envy.
Here is a selection from one of the twenty-two rejection letters sent to my agent at the time:
“I couldn’t tell whether he was trying to write a satire/be humorous when he discussed things like his ecofeminism, or whether he was trying to write a straight memoir. His story picked up speed and kept me interested when he let his too brief anecdotes breathe and become a linear narrative, but the asides, rants, and portions of his college thesis distracted me and stopped the story in its tracks.”
Another letter, from a famous literary editor at a major New York publishing house, in its entirety:
“I’m going to pass on this project. Mr. Ellsberg’s writing is not strong enough to overcome the simple fact that he is not a very likable person.”
At the time, of course, I viewed these letters as pure confirmation of my worst suspicions: the corrupted aesthetics of middle-class consumerist mediocrity and philistinism, the complete venality of corporate publishing pandering to those tastes, the wickedness of the profit-motivated media-entertainment complex—unable to recognize the genius of Art even if they were hit over the head with a two-pound manuscript of experimental nonfiction-in-fragments.
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 Chapter 2 on how to be a great connector!)
I moved to Buenos Aires, 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 footing, I very quickly began asking myself: Is this how I want to spend the rest of my life? This is the next step Aligning Your Money and Your Meaning.
In his book The Monk and the Riddle, Randy Komisar advises you to ask a simple question about your current mode of income: Would you be willing to do this for the rest of your life?
The point is not that you will do it for the rest of your life. But would you be willing? If this was all there was—no brighter tomorrow, no magic promotion or raise or investment that vaults you into the shrouded next level.
Just this. Now.
Would you be happy with this the rest of your life?
If the answer is no—the thought of doing your current gig for the rest of your life makes you totally depressed—then you owe it to yourself (having only one life to live) to figure out what kind of pursuit you would be willing to live till the end.
And in so doing, it’s important to look at the whole package, both the money and inner rewards. Is the whole package, the money and the meaning, of your current life tolerable to you if this was it for the rest of your life? If either one (or both) of these aspects is off, then you’ve got to start making the appropriate adjustments.
Writing my “subversive” incoherent mess of a memoir might have been metaphysically rewarding to me at that time (Pre-Step 1). But at a certain point, the whole “starving, debt-laden artist” thing was no longer appealing to me.
So at first, I swung totally in the other direction (Step 1) and focused entirely on paying the bills. Which made sense for a while—it was like “financial therapy,” weaning me off my artistically underearning ways of the past.
But as soon as I was on my feet again financially, and I had some flexibility in my workday to ponder such things (Step 2), Randy’s question popped into my mind. And the clear answer to his query was no. I would not feel satisfied spending the rest of my life as a book proposal writer, direct-response copywriter, and marketing consultant. Not to say it was a bad situation. A lot of people would have killed for that setup, with such good money on such a flexible schedule. But I had to add something in order for my life to feel meaningful.
I always knew that my great passion was writing books. Not editing other people’s books, not writing book proposals for other people’s books or marketing them. But writing my own. That’s what I was originally doing in my “starving memoirist” phase.
Well, with Steps 1 and 2 handled, I now had the flexibility to write on the side, exploring this passion, yet without having to do it in a “starving artist” way. I wrote a proposal for what became my first published book, The Power of Eye Contact. My income in 2008 and 2009 included $10,000 each of those years in advance money from that book. That certainly wasn’t enough to quit my day job, but it at least contributed to my income and allowed me to explore even more this passion on the side.
For these two years on my path of the Art of Earning a Living, I was solidly at Step 3. I had a great freelance income on a flexible schedule, and I was reengaging with my passion for book writing.
Step 4: Toward Full-Time Author
However, in 2010, I got the idea that I wanted my passion—book writing—to be my main income. This is Step 4 in Aligning Your Money and Your Meaning—integrating your money and your meaning fully. I continued to grow my freelancing day job, in a still-shaky market, by 50 percent in 2010, to $75,000. I’m proud of this growth in the freelancing business over the past four years—about 75 percent per year annualized, including two years of a recession. I credit this growth to the sales, marketing, and networking skills I describe later in this book. (It’s often easier to get far greater results with much less risk by investing in your own earning power via sales and marketing skills, than is available on the stock market. See Chapter 5 on investing in your own earning power.)
But in line with my new resolution, I continued nurturing my side career, in a more serious and devoted manner than before. It paid off big-time for me. I came up with the idea for this book, wrote the proposal for it, networked my way to a fantastic literary agent, and received a six-figure offer from Penguin. Now in 2011, I am now massively toning down my freelance business, turning my attention almost exclusively to my career as a book author, and starting to conceive of the next book project.
My own Art of Earning a Living, so far, culminates in this book. It is both the most financially lucrative and the most personally meaningful project I’ve ever had the privilege to be involved with. Through a lot of trial and error, and through going through the Four Steps to Aligning Your Money and Your Meaning I describe here, I seem to have found the sweet spot of overlapping money and meaning in my life.
How will you meld together money and meaning in your life?
This is one of the most important skills you’ll ever develop. By definition, it can only be studied in the real world, outside of class, because the method of instruction is trial and error, with real-world feedback. I hope the stories I provide in the book—and the steps I’ve given you here—offer inspiration for getting started.
Next: Without Failure, There Is No Learning (or, Why Entrepreneurialism is Like Dating)
