Where Freelancing Meets Independence

People who work for themselves often cite independence as the most appealing element of their work lives. They praise the flexible schedule, the lack of a boss, and the ability to select the work they do. I certainly value those concrete benefits, but what matters to me more is the freedom to assess quality as I see it, without the burden of internal politics or the sometimes senseless rules, both written and unwritten, of organizational culture. Despite not being bound by those strictures, some freelancers censor themselves, fearing to tread into territory that might displease a client. But that usually diminishes the value of their own work and denies them the sense of satisfaction that only calling things on the merits can provide.

Merits are relative, to be sure, especially in the worlds of editing and writing, where I spend about half my work life. But people with keen, analytical minds who try to honestly assess everything they encounter usually end up agreeing quite a lot with one another about what the merits are — even if it takes a lot of debate and deliberation, not all of it pleasant, to get there. Some organizations have managed to make room for this kind of honesty internally, but they are relatively rare.

Much more often, I have found, work environments function in one of two ways: a moaning and groaning culture, in which people routinely make things more burdensome than they need to be, or an “everything’s great” culture, in which people are pathologically positive and reflexively ignore flaws in the interest of preserving equanimity. Of course, most workplaces have a mix of those characteristics, in part because of the diversity of personalities, work styles, and subcultures in any one institution. But I must say that I have very rarely encountered a workplace climate that simultaneously (1) challenged chronic complainers directly on the substance of their exaggerations and (2) unmasked the type of self-censoring, Stepford Wives–style optimism that, by tacit agreement, keeps everyone creepily content and uncritical. Fear, self-interest, and willful ignorance are usually what entrench these mind-sets, but brute force is not the way to break their strangleholds. Dispassionate leadership-by-example does a much better job, though that can be hard to execute when you’re on the outside.

If you happen to be pretty good at influencing insiders, the outside perspective that freelancing enables still does not entitle you to preside like a robed judge over poor petitioners who seek your counsel, even if you’re explicitly being paid as a consultant. Loftiness is not what this freedom is about. Quite the contrary, it’s about allowing yourself to explore and question with the enthusiasm of a curious scientist, then negotiate the practical value of what you find with the deftness of a skilled diplomat. It’s, in short, the thrill of discovery and the craft of persuasion all wrapped into one. But plainspoken critique is sometimes required, and, yes, that could cause you to lose a client.

In my work life, an independent point of view is what I’ve always valued more than anything else, whether that perspective is mine or that of the people with whom I collaborate. Freelancing has allowed me a bit more breathing room as I try to do the best job of this that I can. And, frankly, it has given me the wherewithal to do some of my own writing, this blog included. Finding time for such independent expression still remains a huge challenge, especially for someone like me who struggles with saying no to people. But independence of mind is, after all, more about space than it is about time. And there’s more of that on the outside than there is within one institution’s four walls.

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How to Wield Your Lance Freely

I have too much reverence for the arts of editing and writing to subordinate them to the sterile science of pleasing clients. As a freelancer, I retain a tall wall between how I speak about money and deadlines with the people who hire me and how I approach and discuss the work they give me. The former I always do with a smile; the latter I do on the merits, letting the smiles (and the frowns) emerge organically. That’s the approach I valued when I was a full-time employee working with outside freelancers, so now I return the favor.

You see, I find good work and salesmanship to be fundamentally at odds. They don’t compete with each other on every single freelance job, of course, but allowing them to preoccupy me simultaneously runs the risk of such competition, and I won’t tolerate that possibility for even a minute. In short, I don’t feel very free (or effective) as a freelancer when I don’t have the room to wield my skills without the impediment of financial calculations. Here are the principles I follow to ensure that doing business doesn’t blunt my efforts at maintaining quality:

1. Treat the work as if it’s your own. That doesn’t mean applying your own tastes and preferences to the material — such an approach would be rude and useless. But within the basic parameters you’ve been given, don’t hold back from showing a client what it would take to make the work as good as it can possibly be, even if that means an overhaul. As a freelancer, I obviously don’t make the final decision about where things will go, but I never refrain from demonstrating where they could go. You may end up challenging an ego or two in the process, but so be it. If those egos are secure enough, they’ll thank you for it in the end; if they’re not, you’re better off looking elsewhere for work anyway.

2. Don’t confuse collegiality with politeness. Mutual respect between capable colleagues involves fully appreciating what each person brings to the table in an honest exchange, not tiptoeing around perceived sensitivities. Many freelancers, however, walk on eggshells, wearing a professional shoe on one foot and a salesman’s loafer on the other. That just makes you seem like the hired help rather than a capable complement to the internal staff. In the end, most clients would rather work with — and rehire — an equal than a lackey.

3. Make “process” part of your purview. Just because you’ve been hired to focus on content, don’t turn a blind eye to process. If you’re wondering why a client is following a seemingly impractical protocol, don’t hesitate to ask about it — and to offer a more efficient alternative. You obviously should make sure you understand the larger context before you suggest process changes, and you should never take a cowboy attitude. But any client worth her salt knows that a deficient process can diminish the quality of the product. Again, the clients worth keeping will respect high-quality feedback, even on process, if it’s offered collegially.

4. Be passionately dispassionate. Whether it comes to the process or the substance, recognize that truly respecting the art of what you do requires you not to have an artist’s temperament. Emotional overinvestment in what a client ultimately does with your work only undercuts your ability to influence the final result. If, instead, the client senses you are like a judge who is simply assessing the merits of the case, your analytical — and even your creative — judgments are more likely to prevail. In effect, you can make the work your own and still make the work larger than you.

The freedom of freelancing doesn’t just mean working for yourself. There’s also freedom to be found within each assignment you accept as you execute it with integrity. How do you manage to remain free as you freelance? My approach is only one of many.

When Focus Becomes Monotony

I’m lucky to have a long attention span — to be able to concentrate for many hours on one task without being distracted. What makes me bored is not working for too long a stretch but rather, over the course of months or years, discovering that all of the things I’m doing serve the same mission. That realization was one of the factors in my decision to leave my full-time job in late 2008.

In some sense, despite my long attention span, I have become a multitasker. Not of the sort who does many things in the same moment, but the kind who craves a diversity of purpose. I feel an acute need to spend my time in a wide variety of domains yet to inhabit each with singular intensity. This kind of multitasking is best understood not in the usual way, as simultaneity, but rather as multidimensionality. It’s spatial rather than temporal.

Case in point. I spend a significant portion of my work life teaching adult immigrants. I believe in what I’m doing, and I feel that in the classroom every day. Yet, as both a math teacher and an English teacher, I must be flexible enough to differ in those two roles, approaching each in the way that the specific merits of the discipline — and the particular needs of the students — demand. In effect, I have two main missions within my role as a teacher, and many smaller missions within those.

But that isn’t enough for me. I do freelance writing and editing in an array of disciplines (business, medicine, the humanities, and others). In each one, I become what the discipline asks of me — on its own terms. And I play different editorial and authorial roles within the various domains. When I contemplate my work identity, I feel like a dodecahedron, and I’m happy to be one. My need for this many-sidedness is fundamental. Without it, I would become flat and voiceless — the thin skin of a drum without its deep barrel.

Some wonder, of course, whether I actually needed to quit my full-time job to achieve multidimensionality. People, some calling themselves researchers, now instead advocate transforming the job you have into the one you want. Sure, that’s better than making no change at all. But if the different niches you manage to carve for yourself within your present job ultimately have you serving the same mission, corporate or otherwise, are you just doctoring your perceptions about your work life or actually changing your reality? A loaf of bread looks different if you reshape the dough — but it’s still a loaf of bread.

That said, each person must grapple with these questions of self-fulfillment in his or her own way. My own conclusions might be wildly off base for someone else. The key is to make sure you’re reflecting on your situation honestly, not navigating a conveniently circuitous path to a foregone conclusion. Only you can make the assessment. If someone else (like me) does, you probably won’t buy it.

If in the end you do decide that serving one mission simply isn’t enough, the practical obstacles to change are enormous, unfortunately. The U.S. economy isn’t set up to make diversity of purpose easy to achieve, at least when it comes to work. Health care, for starters, is not something to which we all have common access — split your time among employers and you usually pay through the nose. It’s dangerously easy, therefore, for freelancers and others who diversify their obligations to slip into the trap of becoming mercenaries, who by definition don’t have a mission other than to earn money. That’s where the line between multidimensionality and fragmentation starts to blur. The former is whole; the latter is a mess.

Still, monotony that masquerades as focus is a frightening prospect to me, despite the risks inherent in trying to avoid it. For now, my long attention span and my acute need for diversity are managing to coexist comfortably. The drumbeat of my heart remains steady. If it starts to flutter, I’ll let you know.

Call Me a Part-Timer, Call Me a Nomad

Many people who make their living working multiple part-time jobs aren’t thrilled with the scenario. They say things like “I don’t know if I’m coming or going” and “I’m spread too thin.” The situation usually arises out of necessity, not choice. For one thing, there’s the difficulty in securing affordable health insurance — it’s the 800-pound gorilla. But if you press these wandering workers about why they dislike the nomadic lifestyle, you find that even without that fat ape, their lives often feel like a zoo.

I, too, am no fan of constant chaos. But I also have a fundamental need for variety in the challenges I confront, the people I collaborate with and serve, and, most important, the ways I use my mind. Given all that, on balance I’ve come to appreciate the hodgepodge of multiple part-time jobs I do, even if it sometimes means feeling spread thin. I would rather keep moving and risk fatigue than sit still while the black flies descend.

For nomad workers like me, variety can have a temporal dimension as well. I work part time in new venues, but I also freelance for former full-time employers. Both connections require direct, ongoing collaboration with on-site colleagues. In this respect, the past phases of my work life persist in the present, so that my experiences feel cumulative and mutually reinforcing, not sequential and discrete. Plus, I retain a sense of belonging to, and remain invested in outcomes at, the organizations where I used to be a full-timer. The proof of that, I recently realized, is in my instinctive use of “we” when I talk shop with former coworkers.

That said, conversations about work identity can be a sore spot for me. When asked to label my career, I often don’t know whether I should call myself a teacher, a freelancer, an editor, a writer, or some wishy-washy-sounding mixture of them all. In general, I try to use verbs (what I do) rather than nouns (what I am), but that can sound to certain folks like dodgy language from someone trying to hide that he’s a jack of all trades but a master of none. The more specialized the profession of the person talking to me, the more suspicion I tend to arouse, especially when one of the subareas I mention as being in my repertoire is the one with which he or she identifies. “Call me a nomad,” I once joked in response to such a person. But that self-deprecating label doesn’t make me seem like someone whose labor you’d want to pay for. The proof comes in the work I eventually produce, and so far reputation has served well enough as evidence of my legitimacy (knock on wood).

I also place a premium on establishing strong relationships with the folks at the new places where I work. I involve myself in decision making when that type of participation is welcomed, and I do other extras when I can. Boundaries can, of course, be tricky to maintain when your zoo of responsibilities is populated with animals that don’t cohabitate comfortably. I try to use fences rather than walls as much as possible — to keep the inter-species dynamics interesting without compromising my own safety (read: sanity). There is that 800-pound gorilla, though.

For the moment, the zoo is my professional home, and the animals are the many jobs I do, each one with its own needs and risks but deserving of my affection nonetheless. An itinerant zookeeper with a feed bucket swinging from my hip may not be the most flattering look to sport. But it’s a small price to pay for the freedom, variety, and sheer fascination I enjoy from almost-daily exposure to the sights and sounds of diverse habitats. I’ll continue to wander through them for now, prepared to reassess my choice if my legs and arms and back tire out before my eyes and ears and brain do.

I Ain’t the Boss of Me

I don’t have a home office. There’s no room or cordoned-off area where I retreat to do my work, prepare my invoices, and rule over my freelance roost. Technically, I’m called a “sole proprietor,” yet I own almost nothing that’s exclusively work-related. Sure, I have a laptop, but it migrates from room to room, even sometimes from town to town, as I piece together my living.

Freelancers vary, of course, in how they define the boundaries of their work spaces, both physically and psychologically. On the opposite end of the spectrum from me is my soon-to-be landlord. I recently went to his home office to sign a lease on a new apartment. His professional domain was a mini-empire, with all the machines, tools, shelves, cabinets, and other trappings that make a freelance entrepreneur feel like the king of his castle. Sure, the dividing line between professional and personal was not absolute (his wife was changing the baby’s diaper mere steps away), but this man made clear that he enjoys lording over his territory. If I hadn’t seen his infant son pee in his wife’s face with my own eyes, I might have assumed the odor of urine was from the father’s scent-marking. In short, he is a businessman, and I am his client.

In my relationships with the people who pay me, “clients” is definitely the wrong word. What I do for them feels like work I took home from the office, not tasks I am “contracted” to perform. I treat these folks like colleagues rather than customers, whether or not I have previously worked with them face-to-face. There’s some risk in that approach in the short run, but in the long run everyone wins.

My non-proprietary attitude, odd as it may strike you, is also essential to my psychological well-being as a freelancer. You see, I’m really a full-timer in my soul, in the sense that I prefer an elbow-rubbing informality as I collaborate with people and create things of value. Overly prescribed professional niceties tend to inhibit my work. And a rigid proprietor/customer mind-set gets in the way of producing high-quality results, at least in editing and writing, where the bulk of my freelance activities lie.

So why in the world did I quit my full-time publishing job a year and a half ago if I’m not really a freelancer at heart? Without rehashing my many blog posts on the subject, I would boil it down to a desire to feel unencumbered in a variety of domains, not just one. I teach English and math part-time, for example, and I need the dynamism of the classroom and the give-and-take I get from fellow educators to sustain me. Yet I also want to have the time and the opportunity to be stimulated by an array of professional activities in publishing, where my impact is much less immediate but where I feel connected, albeit indirectly, to larger audiences.

Where that leaves me as a freelancer, though, is without a single domain that I can claim as mine. I have no urge to hang out my shingle, lay down a welcome mat, and fill a little plastic rack with crisp business cards. I don’t even want to be my own boss. Indeed, I’ve come to accept that my bosses are many — but they don’t own me either. Ownership, in the business sense, is not what I’m after, no matter who holds the purse strings. My professional philosophy is strongly independent, yet my day-to-day actions quietly serve others, and that in turn serves me.

Territories are hard to mark on this sort of landscape, and that may seem frustrating to those who prefer to know precisely where they stand in the professional world. I guess I’m more interested in the topography.

Does Quitting Your Job Seem Sexy?

Quitting a job without a new position in hand is an act that sticks with you for a while, even if you’re sensible enough to do it coolly. It doesn’t quietly recede into memory, precisely because it’s both risky and calculated — and because the danger period lasts, certainly longer than a bungee jump or even a week-long wilderness adventure. Thrill-seeking might be part of the allure, but it is not the reality. Most people who see quitting as a ticket to liberation are tilting at windmills, making something mythic out of the mundane. Quitting might very well be the right choice for you, as it was for me. But its aftermath is usually quotidian — Ps and Qs, not Xs and Zs.

It’s been almost 18 months now since I quit my full-time job. At the time I had a sense of where I wanted to go — back to teaching at least part-time, freelancing to pay the bills, doing my own writing where I could make time for that, studying foreign language again if possible. For those of you who have asked for an update, here’s the short version:

On the teaching front, things could not have been more positive. I quickly found two part-time posts that I have thoroughly enjoyed, and I’ve become involved with a group that works on standardized testing in adult education. If anything, I have to watch myself to ensure I don’t say yes to every request that comes down the pike, especially given the low pay. But it’s mission-driven work that sustains the soul, and that is priceless.

Freelancing has sustained other parts of my mind. I continue to have the chance to work with great thinkers, researchers, and practitioners in a variety of fields. That said, the nature of being an outsider as you contract with clients isn’t without its frustrations, as I’ve discussed in several posts on this blog. On balance, however, this segment of my life has provided intellectual stimulation of a sort that I continue to need, not to mention the bulk of my income. And, for now, I’m enjoying the freshness of an outsider’s perspective.

Writing has been a mixed bag. Yes, I’ve been issuing posts for this blog every week, and I like the regularity of that self-imposed deadline. But I’ve been so busy with teaching and freelancing that time for non-blog writing has been pretty limited. I am currently enrolled in a poetry workshop, but beyond that and the blog, the yield has been thin.

On the foreign language front, I’ve taken just one Spanish refresher class (last summer). And I practice that language briefly with a couple of my night students on our way out of the school building twice a week. Pretty paltry, I know.

All in all, my new professional life feels pretty workaday. For the most part, I do things on my own terms, and that’s a change. And my own results on my quiz titled “Does Your Work Matter to You?” have greatly improved. That’s progress, of course, but it’s not the awe-inspiring transformation that so many quitters want it to be. I didn’t really harbor those kinds of illusions from the get-go, so I haven’t been disappointed.

“Quit” is a funny English word. It’s pithy, and in the right mouth it sounds potent. But I just think of it as a quirky curiosity that, when you boil it down to its essentials, is unremarkable, even humdrum. As an English teacher, I can’t help but reflect on its identical principal parts: quit, quit, and quit (the base form, simple past, and past participle, respectively). It’s a rare verb in English that exhibits such sameness (“burst” is another). I guess your point of view depends on whether you want to be seduced by the sexy rarity or reflect soberly on the sameness. I obviously tend toward the latter. What about you?

Where Freelancers Fear to Tread

Avoidable inefficiency gnaws at me. I hate to see time and money wasted, even if it’s not mine — and even if I’m the one getting the check. To some who work for themselves, that seems like fool’s logic. Call me a fool. A fool who freelances.

I’ve met some freelancers who happily thrive on inefficiency, milking every last drop of pay from the udders of their hirers’ cows and adopting an “it’s their problem, not mine” attitude. Most, however, prefer to take the high road and do the best they can in the time they’re paid to work. Instead of exploiting inefficiency to earn a few extra bucks, they simply tolerate it and smile, streamlining things at the margins where they can but usually saying little about it. It’s all perfectly sensible, above-board, and low-risk.

Maybe I’m reckless, but I prefer to tell the people who hire me — point blank, though in as constructive and polite a way as I can — where their systems are not serving them well. Clearly, only some of those systems are in my purview, and I try to be careful to limit my comments to areas where I can actually see the big picture, making all the necessary caveats. But saying nothing is, to me, a travesty.

To be sure, before you make any critiques as a freelancer, you need to be honest with yourself and distinguish between what inconveniences you personally and what actually compromises overall efficiency for the hirer. If only the former is at issue, just drop it. However, when it comes to the latter, insiders often listen to well-reasoned suggestions with open minds, particularly if your feedback reflects that you’ve accounted for many of the contingencies that they have to confront. And if change would happen to also make your life easier, admit that openly, specifying how the situation is a win-win for both them and you. A powerfully persuasive argument is that their money would be better spent if a greater percentage of your time were dedicated to the core job than to clearing unnecessary hurdles. And, while you’re at it, mention in very specific terms what is genuinely working well.

Even if you have an “on the merits” approach to feedback that includes positive comments, insiders can bristle at point-blank suggestions that challenge their ways. You may be perceived as whiny, or a know-it-all, or just plain irritating. Insiders often assume that the picture of the whole that you’re seeing isn’t quite big enough to account for all the variables. And that certainly can be true. But having been an insider who worked with freelancers for much longer than I’ve been an outsider working as a freelancer, I can tell you that the insider’s tunnel vision is usually much more profound than the outsider’s ignorance. That tunnel is an old friend of mine — warm and cozy, but narrow and dim.

Of course, you can’t compromise your living in the name of shining light into the darkness. Being straightforward as an outsider has potential costs, even as high as losing future work or never getting a job in the first place. You obviously shouldn’t tromp and stomp like a jack-booted thug, but treading too lightly does nothing to stimulate the soil. I’ve decided to let my shoes, even my feet, get a little dirty rather than walk on pristine eggshells. And I must say, a heel to the earth strengthens the spine.

(For specifics about how freelancers can give and receive feedback, see my posts “Your Freelancer Can Be a Low-Cost Consultant” and How to Give Feedback to Contractors.”)