Should you write for free? One author says yes. Here’s why.

Tapping a Pencil

Years back, when I had a full-time job within the not-so-hilarity-filled walls of Harvard Law School, there was one thing I could always count on to brighten my day: 3L Jeremy Blachman’s humor column in the law school’s student paper. (Here’s one of my favorites.)

As it turned out, I was far from the only reader eagerly awaiting Jeremy’s next offering. Unbeknownst to us all, even as he schlepped from class to class in Cambridge, he was (fictionally) thousands of miles away, spewing withering, operatic rants as a West Coast law firm partner—and drawing in thousands of readers with his “Anonymous Lawyer” blog. (One law professor, who used the blog in his class, called it a “cultural phenomenon.”)

“I was just writing satire,” Jeremy said, when he finally revealed himself to the New York Times in late 2004 (and shortly thereafter garnered a major book deal). “In a way I’ve been disappointed that I’ve been able to pull it off. I’ve painted a picture based on a few months of observation and the worst things I saw, heard about, or could imagine about law firms, and experienced lawyers are chiming in, saying: ‘This is exactly what it feels like.’”

Some seven years later, Jeremy continues to write, now from his home in Manhattan. He’s at work on a second novel, as well as a film adaptation of the first, and has written for McSweeney’s and the Wall Street Journal, among other venues.  (And lest there be any doubt, he hasn’t lost his talent for skewering the world of law firms, witness this fictional partner’s memo dating from the economic downturn.) Here, he shares some thoughts about writing, both on and off the clock.

By Jeremy Blachman

Amy e-mailed me last week to ask if I’d write a guest post for Plan B Nation. In her e-mail, she said she felt bad asking me to write for free. She linked to this musician’s post in an online forum:

And, indeed, a quick Google search leads to an endless number of online posts telling people not to give away the milk if you want someone to buy the cow. (Of course, many of these posts seem to either be about actual cows or the raw milk debate, but still, the point is clear.)

I would like to offer hope. In the Plan B Nation economy, a lot of things that might sound silly are not in fact all that silly. In the Plan B Nation economy, I believe writing for free is an actual, legitimate thing to do, even if you have actual, legitimate bills to pay. And I don’t think it’s just about writing. I think the more things you can do for free—the more proof of work you can throw out into the universe—the better off you’ll be. After years of writing things—for free and not for free—I still can’t predict what’s going to bring attention, followers, and potential opportunities, and what isn’t. You don’t know what is going to turn into something real. (And by “real,” I mean useful in paying for actual food.)

Almost a decade ago, I was about to start law school. I was mostly going to law school to buy myself three years—albeit at an astonishingly high cost—to figure out how to be a writer. I had written sketches and songs for the Princeton Triangle Club while an undergrad—and then, having no clue how to turn that into a job as an actual writer, I spent a year and a half working in marketing for a software company. I continued to write on the side—some television scripts, a musical, and some very long e-mails about working in marketing for a software company—and  continued to have no idea what to actually do with my life. To a great extent, I was too risk-averse to move to Los Angeles, be someone’s assistant, and hope that developed into an opportunity to be a writer. Partly because I would be terrible at answering someone’s phones, and partly because I had no idea how the entertainment industry worked.

Having deluded myself into believing that going to law school would open all sorts of doors, I decided, hey, at least I’ll have a degree at the end of three years, and if I can’t figure out how to be a writer, I can be a lawyer. Anyone with any knowledge about anything would have tried to convince me this was a terrible idea, but fortunately I didn’t know any lawyers, had no idea what a law firm was, and didn’t want to spend $25 for the Vault Guide to Corporate Law Careers.

Before starting law school, I happened to read an article about blogging. I decided that starting a blog would be a neat experiment to force me to write every day, and the blog would give me a place to try and turn the law school experience into some sort of comedy. I had never read any blogs, and I knew nothing of the blog world. On August 8, 2002, having received my 1L course schedule in the mail, I began writing.

Cut to a year and a half later. The first e-mail I’d sent with my Harvard Law account was to the Crimson to see if I could write for them. Grad students, they quickly informed me, were not allowed to write for the storied college paper. Instead, I pitched a humor column to the law school paper, and started writing there weekly. My blog had about 700 readers a day, which seemed like a nice number. But it hadn’t gotten me any closer to being a writer for real. My roommate had no idea why I was wasting my time writing for free on the Internet. I could pretend I had a plan, but I didn’t.

I had spent my 1L summer working for eight weeks for a small publishing company and six weeks for a political media firm—both jobs I had found entirely outside the law school career services system—but I figured that over my 2L summer I would try out a law firm, so that at least I would be making an informed decision about what to do post-law school. I interviewed, I got an offer, I accepted the offer. I hadn’t blogged much about the interview experience, for the (sensible) fear that it would hurt my chances. On a whim, 2L spring, thinking maybe there could be some funny blog posts to write in the voices of some of the partners who had interviewed me, I started a second blog, an anonymous blog about an over-the-top, evil lawyer, playing on all the stereotypes I’d heard, and exaggerating the details I’d seen in the interview process.

Now my roommate had no idea why I wasting my time writing two blogs for free on the Internet.

I was not entirely sure either.

The first blog ended up being a year and a half of practice for the anonymous one, which, thanks to some beneficial links early on, quickly grew a larger audience than the blog with my name on it. For a brief moment, I found this irritating. “Why are more people reading my anonymous blog than my real one?” Eight months later, after having used my summer associate experience to obtain more details I could grossly and unfairly exaggerate, the New York Times wrote a story about “Anonymous Lawyer,” revealing that I was the writer behind it. I got over 500 e-mails that weekend, including a bunch from agents and publishers, and I ended up with a book deal to turn the blog into the Anonymous Lawyer novel.

I was, of course, very lucky—I am certain that I benefited a great deal from the accidental timing of my blog. It hit just as blogs were becoming mainstream enough for publishers to start getting interested, but not so far along the curve that bookstores were filled with books built off blogs. I sold a television pitch based on the book to Sony and NBC and worked with them for two years on a sitcom adaptation. I’m currently working on a film version and have other scripts I’ve been writing, along with a second novel. All of this emerged from writing I was doing for free, without any idea about where it would lead.

That’s what’s great about this Plan B Nation economy. Sure, perhaps no one is going to pay you up front. But the Internet makes the world where people do get paid accessible to anyone, and you never know if—or when, or how—you’re going to be found, and what your free work might lead to.

I still write for free because I don’t know what might next hit. (I also write for pay, if anyone out there is open to pitches; feel free to e-mail me.) As it happens, the most e-mails I’ve gotten recently have been after pieces I’ve written for the humor site McSweeney’s, for free. There is no shame in writing for free. Amy had nothing to feel bad about.

Jeremy Blachman is a freelance writer and the author of Anonymous Lawyer, a comic novel about corporate law. He welcomes e-mail.

3 things you should know about transitions

Come Together

Two years and eight months ago, I found myself abruptly launched into a prolonged transition that continues to this day. The job I’d held for the past five years suddenly disappeared when my boss was tapped to join the fledgling Obama administration as solicitor general. (You may have heard of her: She’s now U.S. Supreme Court Justice Elena Kagan.)

As is so often the case with major change, there was much ambivalence. While I was anxious about the plunge into unemployment, I was also ready to move on.  On the one hand, the news came as a welcome push. On the other, I was freaking out.

But whatever my reaction on a given day, there was one thing I never imagined from the vantage point of April 2009: That this transition would go on and on in precisely the way it has.

In retrospect, I shouldn’t have been so surprised. After all, my layoff came at the peak of the Great Recession. Still, I had great references, great skills, and a great education. I somehow assumed they’d ease my way. In large part, I was wrong.

Which is different from saying I have regrets. The more I learn about transitions, the more I realize that what I’ve experienced is completely normal. Just because something is painful and hard doesn’t mean it can’t yield fruit.

Years ago, I took a course with psychologist Robert Kegan at Harvard’s Graduate School of Education, and one thing he said stuck with me. (Well, actually, many things he said stuck with me, but this one is relevant here.)  He said, and I paraphrase from memory: “Growth comes from stretch-not-break challenges.”

In other words, hard times—if they are too hard—can crush us. When they’re just right, they may be uncomfortable, but they also move us forward.

One of the things most helpful to me in navigating this transition has been getting a better handle on what to expect. Over the past two-plus years, I’ve spent a lot of hours delving into the subject, and for the record, here are three of my most useful takeaways.

1. Transitions take a long time.

Three years, five years, seven years—these are the time frames that popped up again and again in my reading.  In New Passages, bestselling author Gail Sheehy ballparks two years as the minimum time needed to stabilize following a layoff or other “life accident.”

2. Transitions have a predictable structure.

Transitions guru William Bridges—author of the groundbreaking Transitions: Making Sense of Life’s Changes—has identified a three-part structure reflected in every major life transition:  An ending, followed by a period of confusion and distress, followed, in turn, by a new beginning.

In Finding Your Own North Star—a book that I count among my personal favorites—life coach Martha Beck describes a four-part “change cycle”: A shocking “catalytic event” is followed by “death and rebirth,” “dreaming and scheming,” “the hero’s saga” (a trial-and-error implementation stage), and finally “the promised land,” or equilibrium regained.

3. Transitions aren’t linear.  

It’s tempting to think that transitions can be neat and orderly, that we can figure out a game plan and simply execute it. In fact, transitions are almost always messy, punctuated with false starts and regroupings.

In Working Identity, an extensive study of successful mid-career career changers, business professor Herminia Ibarra concluded that the “plan and execute model” is not realistic. Rather, successful transitions tend to adopt a “test and learn” approach, following a “first-act-and-then-think” sequence.

Well into the third year of my transition, I’m finally starting to feel that I’m turning a corner. I can’t say for sure that the feeling will last but I’m enjoying it in the meantime.

Looking back, it’s fascinating to see how little I could have predicted where my various steps were leading.  For better or worse, our transitions seem to shape us at least as much as we shape them.

Why you should stop telling me what to do

five

Let me be clear: By “you,” I do not mean you, lovely reader of this blog, but the “yous” who’ve felt obliged to tell me elsewhere that I’m screwing up my life.  And by “me” I do not mean me alone but all of us sharing our tender, uncertain, sometimes-painful stories in the larger blogosphere.

In particular, I’m thinking back to comments sparked by the guest post I wrote for the Wall Street Journal’s “Laid Off and Looking” blog in my early days of unemployment.

In this post—which ran just a few hundred words—I talked about the possible upside of losing my job. Mind you, I acknowledged the anxiety and risk but I also admitted to a certain excitement about embarking on what I described as The Next Big Challenge.

Here are two typical responses:

“Get real folks and stop dreaming. I stopped dreaming a long time ago, and it’s better now because I don’t get let down each and every day.”

“If you’re laid back and irresponsible, then the bills don’t mean a thing to you. Well we’re not blessed with being the laid-back type who don’t give a damn about doing what’s right.”

In fairness, there were many positive comments. Still, I found myself intrigued by the vitriol heaped on this little post by those for whom it hit a nerve.

As I pondered the dynamic, I found myself thinking about risk tolerance—a topic all-too-often left out of the job search conversation.

We frequently seem to assume a one-size-fits-all answer to questions such as: “Should I do everything in my power to keep the job I have, or should I read the writing on the wall and accept the offered package?”

In fact, risk tolerance varies with the individual. Without knowing where a questioner falls on the spectrum, it’s impossible to offer sound advice.

If you have a mortgage, kids, and are a few paychecks away from financial crisis, your risk tolerance—and thus your “right” answers—will differ from those of someone without those obligations who has a financial cushion.

If you’re comfortable with uncertainty, your answers will be different from those of someone who freaks out if they can’t predict what they’ll be doing a year from Monday.

This isn’t because one person is right and the other is wrong: It’s because people have different obligations, different temperaments, different levels of risk tolerance.  Our risk tolerance is ours alone.  It’s not a moral virtue, a settled fact—it’s simply our situation.

And for the record, I’m happy to say that I’m doing fine now. The decisions I made two-plus years ago were—for me—the right ones.  My search for work is now paying off, in part thanks to this blog.  I’ve also had a chance to grow in ways that I wouldn’t have otherwise. I’d be lying if I said that this was the path I would have chosen. But while these aren’t the experiences I would have picked, I can’t say that I regret them.

Do the wrong thing

BSOD 0x07B

I spent last Friday working (for pay), and this week I have phone calls with two more prospective clients.

As you likely know if you read this blog, this is an excellent development, as I’ve been in search of employment for, well, a while now.  Being an analytical sort, I’ve been giving some thought to how this came about (the theory being that, whatever it is, I should do more of it).  My conclusion: I should stop doing things right and keep doing things wrong.

If I were to offer a work-search road map based on my recent success, it would look something like this:

1.  Make a big deal about the fact that you are among the long-term unemployed. Tell everyone you know. Better yet: Find a national platform where you can broadcast this news to the world. No one will hire me! This sucks! You get the idea.

2.  Once you have succeeded in spreading word of your unemployability, do something to up the stakes. For example, you might consider telling everyone you know about your struggle with alcohol and how going public with unemployment reminds you of the first time you attended an AA meeting. Again, this is best done in the most public way possible—ideally on a national platform.

3.  Start slacking off a bit on your job search. Spend a lot of time in coffee shops. Go to the movies. Again, do your best to tell everyone you know that no one will hire you and that this has been the case for a long time.  Actually, don’t limit yourself to people you know—go up to strangers, introduce yourself, and try to work this into conversation.

4.  When the publicity around your unemployment starts to die down—if you’ve done things right, hundreds if not thousands of people will have been informed of your futile search for work—find a way to keep it in the spotlight. You might consider starting a blog about how no one will hire you. Update it regularly and post links to Facebook and Twitter so that strangers as well as friends become aware of your dilemma.

5.  Repeat the above as often as possible.

Okay, this is partly tongue in cheek, but really, only partly. The fact is, both my recent freelance project and one of my new work leads came from people who read this blog and the two much-discussed essays I previously published in Salon. The second lead came from a former neighbor I bumped into at the movies.  (This same friend has also become a terrific source of support and guidance for this blog.)

Before going public with my unemployment—you might even say I’ve made it my “brand”—I spent a good number of months following traditional job search guidelines:  Recognize that if you’re unemployed you’re at a disadvantage, so do your best to obscure this fact. Write enticing cover letters. Hone your interview skills.

Now, this is fine advice, great so far as it goes. At the same time, it clearly has its limits.  As for me, I’ve concluded that the time has come to diversify my strategies. There’s a place for doing everything right. And there’s a place for doing things wrong.

Searching for meaning in Plan B Nation

Searching the Ox  -  I

Earlier this week, I wrote about how much happier I’ve been since moving back to my beloved Northampton roughly a year ago. While I feared this would be just a temporary boost, I’m pleased to report that it’s proven far more satisfying and delightfully sustaining.

At the same time, the past year has (not surprisingly) brought new challenges. Apartment hunting, negotiating a lease, finding movers, packing—these practical tasks amounted to a full-time job that left me little time for worrying about larger and more amorphous questions such as What am I doing with my life? Once I’d landed on the other side, however, they soon reclaimed center stage.

Regardless of where you go for guidance—psychologists, religious leaders, sociologists, friends—pretty much everyone will tell you that purpose is a key ingredient for a satisfying life.

In his celebrated 1946 Holocaust memoir Man’s Search for Meaning, Austrian psychiatrist Viktor Frankl went so far as to say that this search is our primary motivation in life. But while the principle may be a simple one, putting it into practice can be far more complicated—and in circumstances far less dire than Frankl’s Nazi death camp. Frankl himself recognized this in a preface to the book’s 1984 edition, where he glumly concluded: “I do not at all see in the bestseller status of my book so much an achievement and accomplishment on my part as an expression of the misery of our time: if hundreds of thousands of people reach out for a book whose very title promises to deal with the question of a meaning to life, it must be a question that burns under their fingernails.”

If anything our hunger for meaning has only grown more desperate since Frankl penned those words. There may be periods of our lives—sometimes long periods—when we don’t give it much thought. The big questions are (temporarily) settled. The big decisions are made. What remains is execution, the living out of their implications through the days and years.

At other times, however, the big questions are right in our face—and, more and more that’s the case for those of us living in Plan B Nation.  More and more, we’re drop-kicked into unfamiliar situations, left to make major decisions without meaningful guidance.  Our parents’ rules for decision-making no longer seem to apply. Friends give conflicting advice. Depending on our spiritual outlook, we may pray or look inward for guidance, but often we still find ourselves completely at a loss—at a loss and anxious.

Perhaps my favorite description of this muddled state comes from a short story by the peerless Lorrie Moore. Describing a baffled protagonist, she writes, “She hadn’t been given the proper tools to make a real life with, she decided, that was it. She’d been given a can of gravy and a hairbrush and told, ‘There you go.’”

A can of gravy and a hairbrush.

I can so relate.

In the first decade of the new millennium, an evangelical pastor named Rick Warren tapped into this motherlode of anguished confusion with The Purpose Driven Life, now billed as “the bestselling nonfiction hardback book in history.” (The Bible, presumably, is entirely factual so not in the running here.)

While I was raised as a Congregationalist I’ve spent little time in churches in my adulthood—except for a brief foray into Episcopalianism. (“We’re Unitarians who like liturgy,” our priest once said, describing those drawn to this small and decidedly creative church.) Still, I couldn’t help but be curious, so I ordered myself a copy.

The (trademark registered) Purpose Driven Life is described as a “40-day spiritual journey” that “will transform your life.”  Warren urges us to read no more than one of the 40 chapters each day, but I decided that a single afternoon would have to suffice.  After all, I didn’t plan to do the program, I just wanted to get a sense of what it’s about—and indeed, it took just a few chapters to grasp its appeal.

Warren claims The Purpose Driven Life is not a self-help book, but while his understanding of the genre may differ from mine, it strikes me as exactly that. In fairness, I found much with which to agree. In his anti-materialism, his belief in the paramount importance of relationships over things, Warren’s is a counter-cultural voice, exhorting us to care for the planet as well as for each other. To that extent, I’m with him.

This only takes me a short way, though, and I’m soon baffled by Warren’s blithe presumption that all we need to do is listen.

Warren’s God speaks with unmistakable clarity. The problem isn’t that we can’t hear God but that we refuse to obey him.

“If God asked you to build a giant boat, don’t you think you might have a few questions, objections, or reservations?” Warren asks his readers, contrasting our imagined obstinacy with Noah’s eagerness to get right on that ark.

And that’s where he loses me.

Because the thing is, if God were speaking to me—and I knew for sure that this was God—I’m pretty sure I’d be fine with building whatever boat he (or she) wanted. And I’m pretty sure the same would be true for most anyone reading the book. (Or at least almost anyone: My friend Jennifer—a law professor—insists she would indeed take issue with this heavenly directive, explaining she’s not trained in ark-building, though she’d gladly write a paper.)

But this doesn’t seem to be how God usually speaks, even to those of us desperate for guidance.

Not that we don’t wish he did.

I’m reminded of a scene in The Moviegoer, Walker Percy’s National Book Award-winning 1960 novel. “Don’t you see?” the despairing Kate Cutrer asks her cousin Binx. “What I want is to believe in someone completely and then do what he wants me to do. If God were to tell me: Kate, here is what I want you to do; you get off this train right now and go over there to that corner by the Southern Life and Accident Insurance Company and stand there for the rest of your life and speak kindly to people—you think I would not do it? You think I would not be the happiest girl in Jackson, Mississippi? I would.”

For most of us, like Kate, clear direction often proves elusive, however much we long for it. That was certainly the case for renowned writer Dan Wakefield, a novelist, journalist and screenwriter who, after decades of atheism and hard living, rediscovered the religious faith of his youth. Some years later, he reconnected with a childhood friend, a woman from his hometown of Indianapolis (which also happens to be my hometown, but I digress).  After years of tumultuous relationships, Wakefield believed he was finally on the right path, on the road to which God had led him. The couple married.

And then, almost immediately, things fell apart.

In his soul-baring spiritual memoir How Do We Known When It’s God?, Wakefield reflects back on this painful time, writing: “The hubris of imagining we’ve ‘got it together,’ followed by a jolt of reality that plunges us back to earth, is probably one of the most familiar and often-traveled arcs of human experience. And yet we think each time, ‘This is different, this time I’ve really got it right.’”

Wakefield’s experience got me to thinking about how we go about pursuing our goals—how we decide what to do next. It’s all well and good to say, as the evangelical Warren does, that we should just do what God tells us—or some secular equivalent of this—but what does this really mean?  At the most basic, practical level, how do we go about this? And, most immediately, how should I go about it?

The notion that there exists some absolute truth to which we should look for guidance pervades American culture.  For Evangelical Christians like Warren, it’s God. For those of a more ecumenical bent, it may be Your True Self, Your Inner Voice, or some general force for good.

But not everyone buys such theories. Alongside the widespread view that there exists some pre-existing and essential truth is a less well-traveled but parallel track known as constructivism. As constructivists see it, the self is something that we create, not something that we find. Until we’ve constructed our self, there isn’t a self to consult. Until then, to paraphrase Harvard professor Robert Kegan, we’re no more than the collection of beliefs taken on from “important others”—parents, teachers, peers, celebrities, employers, to name just a view. And because these perspectives so often diverge, we often find ourselves in trouble—caught between conflicting demands with no way to choose between them.

Make a lot of money, but don’t overvalue material things.

Put yourself first, but also put your family first.

It’s important to look your best, but don’t think too much about how you look.

Be assertive but modest.

As the old saying goes, you can’t please everyone—and yet, without quite noticing, many of us in Plan B Nation can’t seem to stop ourselves from trying.

But while the constructivists’ theories make a lot of sense to me, they still leave the biggest question unanswered.  If we’re charged with “constructing” our selves, how do we best proceed?

I’ve spent much of the past year thinking—and reading—about this question, and more and more, I’m convinced that life in Plan B Nation isn’t something that can be planned or neatly charted out.

Rather, we need to “live into” our new lives—to discover our purpose through trying things out, regrouping, then trying again. The process isn’t linear. It’s often messy. But it’s also necessary.

And in fact, the process may not be all that different from how we’ve always lived.  After extensive research into successful mid-life career transitions, organizational behavior expert Herminia Ibarra concluded that the traditional “plan and implement” model is at odds with reality. Facing a major crossroads, would-be career changers often spend countless hours and dollars on counseling and batteries of standardized tests, all in the interests of determining what it is they really want.  In other words, first figure out what you want. Then go after it.

This all sounds pretty logical, except that, according to Ibarra, our lives don’t work that way. “We learn who we are—in practice, not in theory—by testing reality, not by looking inside,” she writes in Working Identity: Unconventional Strategies for Reinventing Your Career.  “We discover the true possibilities by doing—trying out new activities, reaching out to new groups, finding new role models, and reworking our story as we tell it to those around us.”  

Over the past months, I’ve taken this advice to heart (in part because it appeals to me and in part because I don’t really see a whole lot of other options). I still feel pulled in multiple directions—at the time of this writing, I’m taking an introductory social work class, planning to teach a writing workshop, actively seeking full-time and freelance jobs, and contemplating taking the Massachusetts bar exam.  (In the dry words of one friend, “Amy, maybe you should consider monetizing your Harvard Law degree.”)

If this post seems longer than previous offerings, that’s because it is: Much of it was pulled from a book proposal that I may (or may not) be reworking.  As with so many other things: Time. Will. Tell. For now, one of the ways I’m finding meaning is through writing this blog.  And while I can’t say where it’s taking me, I’m sure enjoying the ride.

Why you should stop pursuing your goals

SIGNAGE

“Most of my career is based on the fact that I went out for ice cream one night,” my writer friend Megan tells me.

This makes total sense to me.

Over the past week, my two most significant work leads both popped up serendipitously while I was taking much-needed breaks from the slog of job hunting.

In the first case, I was seeing a movie with a friend (the excellent “Margin Call,” in case you care).  We’d just settled into our seats when I espied two familiar faces, my former neighbors Lou and J.R., whom I’d last seen a decade back.

In the course of a brief friendly chat, I learned that Lou now chairs the board of our local employment board, the regional policy-making authority in developing workforce skills.  We quickly exchanged contact info—yes, I’m on Facebook, too—before the lights went down.

The next day I had a Facebook message from Lou with one concrete job lead and offers of further help.

And that’s not all.

As it happens I was in the midst of struggling to launch this blog, and as it further happens, Lou is a total computer genius.  In the course of Facebook and Twitter exchanges, followed by a couple of hours at a local café, he pretty much answered all of my urgent technical questions. (If you’re thinking this blog looks way better than it did a week ago, you have Lou to thank.)

In the second case, I was hanging out with new friends at a weekly coffee klatsch. (I’ve taken to calling our group The Coven, but that’s another story.)  I’d briefly considered skipping this week since I had loads to do, but I do love coffee and I love these friends, so in the end I went.

Good thing, too.

“So what sort of job are you looking for,” Ellen inquired. “Because I have a friend who works at a non-profit that might be looking for a writer.” Within a day, she’d put me in touch, and I’d sent off my resume.

My friend Megan’s story is more of the same: Out with her family at Herrell’s, our most excellent local purveyor of ice cream, she bumped into a woman who’d hired her four years earlier.  “Would you like to do a small project?” her former employer asked, after they’d caught up. That single chance meeting led to six years of steady freelance work.

So what are the lessons here?

Sometimes the best way to pursue your goals is to stop pursuing them. This isn’t to say that standard job search strategies don’t have their place. It is to say that they aren’t necessarily going to be the ones that work. That’s especially true today, when personal connections matter more than ever in a world where, at last count, there were seven unemployed workers for every job opening.

It’s easy to feel guilty for taking a break when you’re looking for work—especially as the days roll by and the pressures mount. You need to remember that job leads can pop up in the most surprising of places.

Plus everyone needs a break: You can’t just live your job search. You also must live your life. And sometimes the best way to do both may be to go out for ice cream.

Note:  The featured players in this post also have blogs of their own. On the job search front, Lou Franco’s Software Business Blog recently offered excellent advice to software developers looking for work. And for amusing musings on life in our beloved Northampton, check out Megan Rubiner Zinn’s Life in the Little City. (I especially loved her recent post There are a Million Viruses in the Little City.)

Good news? Bad news? Who knows?

Question mark

A few years back, while still working at Harvard Law School, I heard this story:

After weighing her options, a soon-to-graduate student turned down lucrative offers at prestigious law firms to accept a low-paying fellowship with a non-profit organization. This did not sit well with her family, who expected her to “do something” with her Harvard Law School degree.

Flash forward a few months: The Great Recession has hit. Both of her parents have lost their well-paying jobs. Classmates who’d thought their post-graduation lives were set are now seeing their law firm offers postponed or withdrawn. She alone, among her friends and family, is untouched by the crisis.

I’ve thought about this story a lot–and what it says to those of us navigating Plan B Nation. As I see it, the take-away is this: We never really know for sure where our choices will take us. This doesn’t mean that we don’t do our best to plan. It does mean that we are well-advised to keep an open mind about what events “mean.”

The past two years of my own life are a case in point.

After my Harvard Law School job ended in the wake of the Great Recession, I embarked on an exhaustive (and exhausting) search for paying work. At the time of this writing, I’ve long lost count of the dozens (hundreds?) of jobs for which I’ve applied. You see, my resume is impressive, but it’s also quirky. I’ve published suspense novels, written speeches for a Harvard Law School dean (now a U.S Supreme Court Justice), and designed a program to bring public school teachers to rural Mississippi. At the same time, I’m not a whiz with Excel or PowerPoint. Basically, I’m a writer, and as smart and talented as I may be, I don’t easily fit into an identifiable niche.

But here’s the thing. If I’d gotten any of the jobs I’d applied for (and believe me, I did my best) I probably wouldn’t be writing this blog, or the pieces for Huffington Post and Salon that paved the way for it. And these essays that I’m writing now—they feel important. Hard as the road to this point has been (and you’ll be hearing much more about that), right at this moment the life I’m living feels deeply meaningful.

One of my meditation teachers told this classic story:

There once was a poor rice farmer, who had a very small field just large enough to feed his family.

Then one day a herd of wild horses came running through the village. They ran into the farmer’s rice field and got stuck in the mud, and since they couldn’t get away, they were his.

His neighbor came running over and said, “This is good news! Such good fortune! You are rich, this is amazing!” And the rice farmer said, “Good news, bad news, who knows?”

A few weeks later the farmer’s 12-year-old son jumped up on one of the wild horses for a ride, only to be thrown off and have his leg broken. The neighbor comes running over and says, “Oh no, this is such bad news!” And the farmer said, “Good news, bad news, who knows?”

A week later a Chinese general is marching through the farmer’s village on the way to war. On this march, the army is conscripting every healthy boy over 10 years of age. So they took every boy in the village except the farmer’s son because of his broken leg.

The neighbor comes running over and says, “Yes! This is wonderful news, how lucky are we!” And the father replies, “Good news, bad news, who knows?”

And the fact is we never do.

Failing at something you don’t really want—even if you think you do—may be a step on the path to a wonderful life you can’t even imagine today.

Good news, bad news, who knows?

Since we can’t know what the future holds, why not keep an open mind?