If Writers Taught and Teachers Wrote . . .

My teaching and freelancing careers complement each other almost daily. I’ve gradually come to view that mutual reinforcement as a substantial part of what makes both lines of work satisfying.

Yes, I’ve had full-time jobs in both education and publishing, and I enjoyed the dedication to one mission. Maintaining a single focus has major benefits: the time to perfect a craft, the continuous exposure to talented colleagues who keep you on your game because of their constant proximity, the sense of having a second home. (Not to mention the concrete benefit of employer-subsidized health insurance.) Over time, though, the singularity can breed a narrowness of vision. That’s not to say that opportunities to grow within a single career don’t abound. But being truly invested in two separate professional domains enables you, in each one, to have the benefit of an outside perspective while you continue to work on the inside.

In teaching writing, for example, you can be a kickass full-time instructor. But there’s something about continuing to write professionally — not just as a sideshow, but as a core activity with frequent deadlines and other real-world constraints — that helps you offer students a practical, authentic perspective. Similarly, teaching a craft or skill day in and day out brings it to consciousness in ways that simply using it does not. Plus, by being in the classroom, you routinely witness real audiences responding to content in a dynamic forum that no focus group or survey can match.

These are not original insights, and I could have shared them long before I made the decision to simultaneously teach and be a freelancer. But my dual career has started to make me think even more broadly. Specifically, I wonder whether merging the missions of education and publishing might improve quality and relevance in both areas on a much larger scale.

Everyone knows that these two fields are facing major challenges, some of them downright demoralizing. Teachers, even good ones, are finding it increasingly difficult to navigate compliance with ever-changing standards as they teach students whose reading and writing habits shift dramatically with the advent of new technologies. And many in publishing, particularly journalism, are struggling to remain relevant to audiences, even as some continue to produce excellent content. Those audiences, both current and future, are sitting in classrooms every day. Yet most teachers don’t know what goes on in the publishing world, and most people in publishing are not also in schools. Is it time to break down that wall so that producers of content better understand how to engage audiences who, in turn, learn to improve their ability to engage with content?

That’s the practical side of it. But there’s also the prospect of injecting new professional energy into both areas through the complementary relationship between them. The personal rewards of working simultaneously in two distinct but related fields could generate new career opportunities and boost morale in both domains. That energy would have further practical consequences, creating a virtuous circle. And the possibility of invigorating education and publishing in a united effort has a certain “next big thing” allure, provided that conflicts of interest can be minimized.

Of course, this merging of two professional worlds is not something that could happen by fiat. It has to start small, with individuals who are already in both fields recruiting others and then, if that pans out, devising pilot projects and all the related peripherals that really get things rolling. It seems like a daunting endeavor for any one person to contemplate initiating, especially with the issue of health insurance looming for those brave enough to take the plunge. Support from above, both philosophical and financial, would be essential for kick-starting the movement.

But maybe this is all my foolish little pipe dream as I toil away as both teacher and freelancer, trying to find professional partners whose hands are in both domains. Are any of you out there inhabiting these spheres simultaneously? If not, does that prospect seem appealing, whether just personally or as part of a broader effort? Maybe this movement is already afoot and I’m just ignorant of it. Shed a little light on it for me if you can, or at least entertain the idea with me if you dare.

The “Skill Set” Pigeonhole

The phrase “skill set” has always irked me. It brings to mind the many conversations about hiring in which I’ve participated, whether on the employer side or as a prospective candidate. If you haven’t previously done exactly the kind of work someone needs you for, freelance or otherwise, the conclusion often is “the skill sets don’t match.” As if they’re shopping for a ball bearing for a Toyota — or a donor of a kidney.

This inappropriately narrow selection process is a mutual one. Candidates usually market themselves, in part, by making mind-numbing lists of items in their employability repertoire, in the hope that the hirers will find the desired skill in there somewhere. The search for the right employee — or the right job — thereby becomes less of a dynamic hunt than a wild-goose chase, except that the searchers tend to kid themselves that they’ve found the elusive bird. It’s a fool’s errand.

In a freelance context, the immediate consequences of the “skill set” approach to searching are obvious. Everyone gets to check off the requisite boxes, and whether the match will really work is left to little better than chance. That’s because both sides have essentially just queried, rather than interviewed, each other. Not knowing what you’re getting is bad enough when you’re aware that you’re in the dark — it’s even worse when you mistakenly assume you know exactly what you have.

But that short-term pitfall is only the half of it. Multiply this myopia by the millions and you end up with a freelance labor pool that’s been ghettoized into highly specialized niches. Work in one narrow area begets more work in that same area, and all the birds nest comfortably in their pigeonholes. Sure, specialization breeds expertise — but only to a point. In time, roles become overspecialized, which leads to complacency and stagnation as expectations solidify and everyone involved begins to value predictability above all else.

With the hired birds stuck in their pigeonholes instead of using their wings, it’s quality that starts to go south. Quality of the work, quality of life, and quality of the exchange between the freelancer and the people who pay her.

If, instead, freelancers are permitted to venture beyond their nests and reflect a bit on their work from a perch, they have the potential to offer the hirer a valuable independent perspective (see “Your Freelancer Can Be a Low-Cost Consultant”). And those who hire contractors can actively foster such contributions by providing thoughtful feedback. That kind of dynamism keeps everyone sharp, and it can prevent the misunderstandings that silence often creates.

When skills are allowed to set, they tend to go stale. A feathered nest isn’t so comfortable if the quills are stiff and brittle.

For Big Projects, Try a Cone-Shaped Schedule

Procrastination is one of the most discussed topics in freelance circles. Tips on combating dread, getting started, and powering through abound. Some of the advice out there has value, but the very focus on procrastination is often misplaced. I’ve found that, in terms of productivity, there’s more to be gained from shaping your project’s trajectory than from shaping your anticipation of the work. That holds true whether you’re working for yourself or for someone else.

The single biggest motivator in getting a project done — and done well — is a sense of progress. Sure, there’s an art to getting started (as I’ve discussed previously), but once you’ve begun, awareness of your forward movement is what carries you through. One way to achieve that is to spend less time on each step than you did on the previous one so that your schedule looks like a cone turned on its side — with the broad base on the left and the pointy end on the right. That doesn’t mean scheduling work sessions to artificially force earlier and earlier quit times; that approach just leads to a marathon “final push” right before the deadline. The cone-shaped method, in contrast, means observing these five, more organic principles:

1. Survey the entire geometry. To identify where the base of the cone is, you first need to look at your project in all its initially shapeless complexity. That allows you to see what you have, what you don’t, and how everything might fit together. You can’t possibly create an efficient plan without knowing which end is up — or, in this case, which end should be on the left and which on the right.

2. Respect the inherent properties of the work. Every project has its own deep structure that may not match how the people who ultimately see the work will experience it. In short, the beginning is not always the beginning. Sometimes, working backward from the intended endpoint for your user allows the earlier pieces to fall into place more easily as you develop them. Other times, the most substantive part (the part where you should start) is in the middle. Bottom line: your process and the end user’s experience are often two entirely different objects. Your audience need never see that you’re really just a conehead.

3. Make gross movements before fine-tuning. As soon as you’ve identified the heart of your project, start doing the heavy lifting. The first full-fledged work session should be your longest and most difficult. At that point, the project is likely to feel relatively new and fresh, and fatigue won’t be as much of a limiting factor. Besides, you’ll feel freer to move things around and take risks with the basic structure when you haven’t invested yourself in minutiae and aesthetics, important as those things are in the end.

4. Gradually narrow the window between sessions. As the cone narrows, so should the time between the periods when you sit down (or stand up) to do the work. A key to creating momentum on a project is having session duration decrease as the gap between sessions also decreases. That creates the illusion of speed — like you’re walking downhill rather than uphill. And, actually, it’s not entirely an illusion. You are, after all, moving toward the end at a faster pace. It’s just that you’ve deliberately structured your schedule to achieve that effect.

5. Take pleasure in the polishing. With the toughest parts behind you, enjoy the little pleasures of the tip of the cone — the niceties, the trim, the tassels. Imagine yourself sitting in the audience at your own play and appreciating the small things. Doing that can make a deadline feel like the celebratory debut it should be rather than the exhausting finale it often is. A cone tip is most pleasing when it’s sharp and shiny. Take your finger to it (gently) and see just how good it feels.

Are We Making Things That Last?

I teach, I edit, I write. To some that’s noble work; to others it’s a lotta BS. Words mostly, written in dust on a chalkboard, sitting idly on pieces of paper, or flitting ephemerally across a screen. Nothing you can touch and hold and use, at least not in the way that “useful” things are meant to be. Did you make anything today, Steve, other than some noise? Tomorrow you’ll make more of it, and that too will disappear.

Thoughts like those sometimes give me the urge to pick up a hammer and a nail or a needle and thread, or to go out and find what many people would consider a real job. Not a phony, patchwork freelance existence in which I get paid to put marks on a page and tap on a keyboard — and teach others to do the same. One in which I spend some of my time dreaming up mind candy for this blog, which doesn’t pay a cent.

Obviously, I see value in what I do, especially the teaching. And I’ve written about it many times. But there is something that gnaws at me — at us — as more and more of our time is spent making noise rather than making useful things.

If I were an economist, I’d be tempted now to launch into a boring lecture about outsourcing and the depletion of the U.S. manufacturing base. But there is a nugget of truth to the idea that making fewer useful things slowly guts a nation of its ambition, even its purpose. I think about all those people at the gym, most employed in service and office jobs, doing their “core” exercises and then, on the way out the door, passing vending machines filled with junk food fit for consumption in front of a high-definition TV. There are many ways to fill a void.

As a political junkie (yes, I consume even the TV junk), I wonder why speeches about the importance of developing green technologies don’t focus on an increasingly untapped desire to build and create tangible things rather than on climate change (an abstract concept to most people). “It’s time America gets back to making things that last!” I can hear a politician chanting. “In the 21st century and beyond, it’s green technology built with your hands in green factories that will last, that will make your paycheck last, that will last long enough for your children and your grandchildren to enjoy the fruits of your labor!” Politicians are in the business of making noise, though, so they probably don’t need my help.

My own noise is more muted, much less influential. It’s in the classroom, in my interactions with authors and editors, in this disposable little blog. I don’t know how long any of those efforts will ultimately last, useful as they usually seem to me to be. The best I can hope for is that my students will carry what they learn out into the world and make a living, make a difference, and actually make a few real, useful things along the way.

That’s the noise I’m generating in my own ear, at least today. Tomorrow I’ll make a different sound, and that too will disappear.

Who Do You Really Work For?

I’ve been freelancing for over a year now, and I feel more professionally independent than I ever have. I make my own decisions about what assignments to accept, organize my workday as I see fit, and sometimes carve out time for non-work activities in ways that make my calendar look like a gerrymandered congressional district.

But I’m not a true-blue freelancer. I teach part-time at a couple of local adult-ed centers, where I follow (and enforce) rules that others lay down, albeit with the consent and participation of rank-and-file teachers like me. The schools are, of course, very much social institutions, and I am just one small element among many that make the organizations thrive.

Overall, my work life offers a good balance between the truly collaborative experiences that I get on-site at the schools and the independent, off-site workshop atmosphere that my home has become. But can I call that “working for myself”? At face value, the phrase has a meaning that amounts to little more than the way I file my taxes. When I talk with other freelancers, however, I usually find that the implications are deeper — that the phrase means much more to them than “on my own,” something akin to “for my own purposes.”

To be sure, folks who work for money that they need are, by definition, working for their own purposes. They’re supporting themselves and their families, and trying to build a life that provides both sustenance and pleasure. But I often wonder about the mission of the freelancer (and my mission as one) — in other words, about purpose with a higher aim.

Non-freelance workers typically support an institutional mission, whether corporate, nonprofit, small-business, or government. They don’t all do it happily or mindfully, but just by virtue of being part of the institution, they do it in one way or another. The higher aim of a freelancer’s labor can be harder to pinpoint. Some freelancers commit themselves to the integrity of the work they do, always aiming for top quality. Others, weary of sometimes-narrow corporate goals, selectively take on clients whose work they believe in. Still others have self-fulfillment (for example, actualizing their talents) as the engine that drives the machine every day. And many freelancers are motivated by some combination of these, plus the aforementioned need to earn a living.

I, for one, focus much more on the educational missions of the schools where I teach than on my mission as a freelancer, the need to earn money notwithstanding. Yes, I’m a stickler for quality in whatever I do, and that affects my freelance work, most of which I enjoy. But for the most part, I use freelancing to subsidize the pretty low pay I get from part-time teaching. In a sense, I’ve put one mission in service of another, rather than pursuing each for its own sake.

Who do I really work for then? Is it for myself, for my students, for something larger? That’s a tough question to answer in a byte (I’ve already bitten off more than I can chew in this post). But one thing I do know is that I now score much better on my own 9-month-old quiz, called “Does Your Work Matter to You?”, than I did when I was with a single employer full time. A commenter on this blog reminded me of that quiz last week, and with another gestation period under my belt, the question of mission is reborn all over again.

May I ask you, whether or not you’re a freelancer, to explore your own answer here with me this week? What is your mission? Who do you really work for? Are you “working for yourself” — or for someone (or something) else?

Is This Freelancer a Fake?

I call myself a freelancer, but I might be an impostor. First of all, I spend half my time working as a teacher in adult education. It’s a position I very much enjoy, but it’s not freelancing. Four days a week, I go to a school, where I run a classroom (several in fact), interact with colleagues, share an office, and comfortably inhabit the workplace culture. When I’m not teaching, I do editing and writing that might be more traditionally called “freelance.” But, frankly, it doesn’t feel especially entrepreneurial, since I’m not really building a business — and I’m quite happy with that.

You see, I do my best work when other people are depending on me, expecting me to produce. They might be students in a classroom, editors who need me to help them meet deadlines, or writers who are (by their own admission) swimming in their own verbiage without a guiding hand. But what so many freelancers tell me they love about independent work life is the ability to build your own little enterprise — in effect, to own your own labor.

I’m not much of an owner, though. Don’t get me wrong, I like the partial control I now have over my schedule. But I still get much more of my energy from fulfilling others’ needs than from cultivating my own. Knowing that another, specific person is waiting for my work — even at the other end of a cyber-connection — is what motivates me to deliver and to excel.

My freelance life, satisfying as it is, is pretty much devoid of self-advancement goals, beyond the basic earning of a living. That doesn’t mean that I’m not exceedingly busy, or that I’m not motivated by excellence. Anyone who has ever worked with me would tell you I’m a stickler for quality — and a discerning critic of how quality is defined. But the rewards I get are not quite “mine”; they’re the benefits that direct recipients of my work derive.

Take, for example, the blog I wrote for Harvard Business until last December. The editors wanted something from me every week, and I was chock full of ideas, and often five or six weeks ahead of schedule. The writing came easily to me, as I imagined delivering the best possible product to an editor on the other end. Furthermore, that editor needed my work on time — and often benefited from my early delivery of it. Sure, the whole thing felt sort of self-indulgent, given that it was a blog about my own career transition. But the fact that someone was waiting for me to deliver my drivel made it feel less like drool and more like lip-smacking food I was cooking up in the kitchen for someone else — someone I know — to taste.

Nowadays, my blog posts don’t get “received” by anyone whose face I would recognize on the street, beyond a few friends and colleagues. I put them online at will, and anonymous readers (not very many) wander in and out. Some offer lovely comments that I deeply appreciate.

But I have to tell you it’s not the same. I’m not terribly motivated to write posts without being able to feel a direct need from a person with whom I have a professional tie. And here you are reading my blog. And here I am disrespecting you by saying that that’s not enough, not enough to write about “freelancing” for an audience (of freelancers?) whose hands I cannot touch.

Is that irony or hypocrisy — or just downright boring? Can you even relate, fellow freelancer, fellow reader of drivel about a stranger’s career transition? Set me straight.

Your Freelancer Can Be a Low-Cost Consultant

As any project manager knows, finding good freelancers can be tough. Once you have one who efficiently delivers high-quality work, the seamlessness of the operation is addictive. Everything’s functioning beautifully, so you just keep running the well-oiled machine. That’s a success to celebrate, of course, but it can lull you into overlooking additional value that the freelancer could offer, if only you’d pause a moment to extract it. I’ve seen that value both as an in-house project manager and as a freelancer.

Where is the value hidden? It’s buried among the insights that the freelancer is constantly acquiring about your systems. Not every reliable freelancer will be able to articulate those insights in a form that can be put to practical use; that’s something you have to gauge based on your interactions with her. And even if she is a good candidate for this kind of meta-analysis, her time does mean money. But it’s a fraction of what you’d pay for a high-priced consultant, not least because the freelancer has already done the up-front investigational work. That’s low-hanging fruit you’d be wise to pluck.

Here are some small-scale assessments you can ask a freelancer to do. Different types of outsourced work are likely to merit different types of assessments, many not in this list. And, clearly, they cannot substitute for a consulting task that requires a very broad scope.

1. On an isolated job, have the freelancer keep a running catalogue of things that went better or worse than expected. Ask her to briefly explain why she thinks each outcome was unanticipated, focusing in particular on systems- and process-related obstacles.

2. Over time, have her note which parts of the work you deliver to her have become easier to handle, and which less. If she finds that the level of difficulty fluctuates, have her identify the contingencies, systemic and otherwise, that seem to be responsible.

3. If your relationship with the freelancer is especially trusting, ask her to identify one process or protocol that she uses with one of her other clients that she thinks would serve your needs. Have her explain how it might best be integrated with your existing systems, even if modest ripple effects would be unavoidable. Obviously, make clear that you are not interested in the name of, or any proprietary information from, the other client and that if either revelation cannot be avoided, she should skip this task altogether.

4. Ask her to write a one-page analysis of how your overall systems can be improved. The analysis should include both a brief narrative assessment and specific, bulleted suggestions. Encourage her to be honest yet practical in her recommendations.

Small-scale consultative tasks like these should be assigned to a freelancer only on a periodic, or even a one-time, basis. You obviously don’t want to gum up the gears of the well-oiled machine. Also, be clear about how much time you’d like the freelancer to spend. If in the end you derive value from her assessment, compare it — and the cost — with what you got from your last consultant. There’s no guarantee of comparatively better value, but the experiment certainly will have been worth the low price you paid to conduct it.

How have you managed to derive value from your freelancers, beyond the usual deliverables?

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