Category: Columns

We all know the truism that art doesn’t exist in a vacuum. It exists within the context of the art that has preceded it, and the art with which it is contemporaneous. It exists within the context of the life and beliefs of the artist who created it, and everyone who helped to shape that person’s life and beliefs.

So, too, your career as a freelancer (should you decide to take that path) exists within a broader context of its own. And just as you can shape the context of your art by studying, practicing, and forming the connections to position your art to its best advantage, you can also shape the context of your freelance career by continuing your education, working to refine your practices, and ensuring that you have effective support systems in place.

I’m fortunate to have an incredibly supportive husband, who has acted as both cheerleader and disappointed school teacher as necessary over the years. Both of our families have offered unconditional moral (and sometimes financial) support, and our friends have been at turns enthusiastic and healthily skeptical of my various harebrained ideas.

It’s these support systems that have kept me afloat in more ways than one. They keep me going, and they keep me grounded. If I can get the musical and non-musical parts of my support system excited about a potential project, I know that I’m on to something; and if I’m met with skepticism and confusion, I know that I haven’t thought things through enough.

Sometimes, though, you don’t have the support system that you need. You may have a spouse or parents or friends who stubbornly refuse to understand what you’re trying to do, and who consistently fail to support you when you need it most. It’s frustrating and can be unhealthy if you let it stand in your way. But how do you fix it?

Sometimes, an appropriately timed, calm conversation can help to make some headway. Explaining your goals and your plans to reach them can assuage fears about your future. How many of us have well-meaning families who want the best for us, but think that we’ve chosen the “wrong” path? One conversation won’t fix everything, but it might open the door to more understanding and to a deeper involvement in your art.

Other times, however, you have to create new support systems to make up for the lack of support at home. Maybe that means forming a local group of like-minded people that meets regularly for lunch or coffee, where the members share their successes and their struggles and offer advice, support, and encouragement. Maybe that means finding an online community that you can join to address the same issues. In case you weren’t aware, you’re in one right now. NewMusicBox has built a wonderful community of artists who are trying to make this whole thing work, just like you. Reach out. Ask for advice. Make connections.

You Are Not Alone

Last week, I mentioned bringing my bad habits from my former day job into my freelance life and struggling to get work done. The morning that that article went live, I was on the elliptical machine at my gym, listening to an episode of the Self-Publishing Podcast about time management, and the guest told the story of her early days as a freelancer. While working 60+ hours per week at a corporate job, she managed to get more of her own work done than when her time later became entirely her own. When she said how aghast she had been at that fact, one of the hosts chimed in to say that that very thing is one of the number one issues that freelancers face. It’s an almost universal problem. Most of our lives, we’re on someone else’s schedule (parents, teachers, bosses), and aren’t trained to value our own time in the same way, or taught how to manage ourselves given total freedom. Fortunately, although the problem is common, it’s also easily remedied with the right tools.

Over the past few weeks, a number of colleagues have written to say that this or that problem I wrote about deeply resonated with them. I say that not as, “Well done, Dennis,” but to point out that you’ll encounter many of these same problems yourself and that you’re not alone in doing so. Knowing the pitfalls didn’t prevent me from falling prey to any of them, though it allowed me to recognize what was happening and gave me a base of knowledge for how to attempt to remedy the situation. And it was hugely helpful to know that my struggles were not unique—that others had gone through the same thing and had come out the other side.

I Wish I’d Known…

About ten years ago, in large part because of the time commitment required to pursue my master’s degree, I spent a period of two years unable to get a day job. I hadn’t yet done any research into being a freelancer and didn’t consider myself to be one. Nor had I started to learn about the intricacies of publishing or the necessity of approaching my art with an eye toward business and my future. I was a graduate student with no job, only a few, barely paying commissions, and a small handful of web clients who rarely needed my services. I maxed out my student loans and did odd jobs to be able to eat and pay rent. Nearly a decade later, I can recognize that I was severely depressed—mostly spending my days watching Buffy on Netflix while tinkering with client’s sites. I barely composed if it wasn’t required of me. Eventually, I stopped paying rent entirely and was nearly evicted.

Sometimes I look back on those two years and think, “I wish I’d known then what I know now.” Honestly, though, I wouldn’t know what I know now if it weren’t for what I didn’t know back then. Recovering from that period set me on the path that led me to learn about publishing and marketing and distribution models, and to start sharing what I’d learned with others.

And, more importantly, I simply didn’t know those things then. I can speculate endlessly over what I would have done differently and how, but the infinitely more important questions is: how can I take what I’ve learned, and do better now?

Parting Shots

Before I sign off, I’d like to thank NewMusicBox for inviting me to write these posts and for offering me the opportunity to be so publicly vulnerable, and to thank you for following me to some of the darker places of my career. I hope what I have shared offers you some help and inspiration. I think we can all use a little more vulnerability in our lives. Our art demands it, and we should demand nothing less of ourselves.

The thought that I’d like to leave you with is that, whether you follow the path of the freelancer or not, when you first start out at anything, you will never be perfect. Composing, engraving, email marketing, publishing, networking: you probably won’t even be good at the beginning. You’ll fail a lot, but you’ll learn from each failure. And every time you do it again, you’ll improve. Don’t let the fear of failure get in your way, or you’ll never get anything done. So go out and fail. Then fail better next time.

Within six months of starting my new freelance life, things had gone off the rails a little bit. Even though I’d read The Freelancer’s Survival Guide and had done tons of research, I really wasn’t quite prepared to be my own boss. I carried my resentment toward my former day job into my freelancing, along with all of my bad habits, and that’s not a recipe for success. As a result, I’ve found my freelance life to be an exercise in course correction.

One way my resentment toward the day job manifested itself was in not wanting to get up in the morning, and I carried this over into my self-employment. Sleeping in is a habit that I’ve cultivated my entire life, made worse by insomnia and a penchant for reading late into the night. I hate mornings and, given the opportunity, I do what I can to avoid them: namely, sleeping well into the double-digit a.m. hours. It’s a source of never-ending amusement and frustration for my husband and our families. However, for a freelancer, it can be a terrible habit and a difficult one to break.

Being a night owl isn’t a bad thing in and of itself, but it forces a different kind of schedule on your waking/working life. A good friend of mine has similar sleep patterns to mine and makes it work quite well. He wakes up at the crack of noon, teaches for the afternoon and into the evening, then composes late into the night. His partner, however, works “regular hours.” As a result, they rarely see one another, but they’ve managed to make it work for many, many years. Fortunately, since they’re both musicians and they perform together regularly, they have built-in time to work together, in addition to the specific time that they set aside to be in each other’s company. Otherwise, they would live their lives as ships passing in the night.

Dean Wesley Smith, another night owl, chronicles his daily writing habits on his blog. He sleeps until between 11 and 1, uses daylight hours to manage the small publishing company he co-operates, as well as the antiques and collectibles shop he owns, then deals with his admin tasks and has dinner with his wife Kristine Kathryn Rusch in the evening, takes an hour or so for TV, then writes until 3 or 4 in the morning. He’s incredibly prolific and has found a rhythm that works very well for him.

Dean and my friend are fortunate not to have children, which would make their schedules untenable. They’re also fortunate to have partners who are fine with the degree of their absence and don’t mind the odd hours they keep.

For myself, I’ve found that because I want to: a) spend time with my husband (who works regular hours at a jingle house); b) be considerate to my neighbors (and my husband) by not working at the piano after certain hours; and c) have a somewhat normal social life, my night owl ways are a hindrance. Consequently, I’ve had to adjust my sleep schedule to ensure that I have more daylight hours in which to work. Admittedly, it wasn’t easy, and I’m prone to relapse; but my husband helps to keep me honest, and we spend our early mornings together at the gym.

I also later came to realize that depression had set in some time during my first year working for myself. It took hold and grew almost imperceptibly: gradually eroding away my motivation and eviscerating my work ethic. I’d never before had cause to worry about either of these, but realized one day that I wasn’t doing what I needed to in order to achieve my goals. As a result, I’ve had to deal with some of the underlying causes for my depression, as well as implement systems to keep myself on track.

Systems

Over the years, I’ve tried a number of different ways of structuring my working hours.

In some systems, I’ve tried scheduling different types of work for different days. For example, only doing web design work on Mondays, blocking off Tuesdays, Wednesdays, and Fridays for composing and other musical pursuits, and leaving Thursday for anything else that needs to be handled. Or variations thereof.

Other systems involve blocking off time for specific types of tasks and creating a template for the week. A block might be anywhere from 30 minutes to 4 hours and may be labeled variously “composing,” “web work,” “admin,” “podcasting,” or “listening & walking.” In one variation on this, I have just a morning block and an afternoon block, each labeled “Tobenski Music Press,” “Music Publishing Podcast,” “Perfect Enemy Records,” or “Tobenski Web Design,” and I address the priorities of each business during the corresponding block.

An attempt to organize my life that seems to be working.

A third system I’ve tried doesn’t parcel out time in increments at all, but sets weekly deadlines for different projects. One week, my priority may be to finish a piece I’m writing, and the next week is devoted to podcast production. Whatever else is on my plate, I have to meet that particular deadline by the end of the week.

I’m still tweaking my systems to find the best solution. Each of the styles I outlined above attracts me for different reasons, as does a more “go with the flow” approach.

I’ve found that the more diverse your activities are, the more difficult it can be to schedule them concretely, especially when they involve working for clients. Anyone who has done client-based work knows that clients can be the most demanding at the least opportune times. They may have an issue that absolutely needs addressing immediately (or that they think needs addressing immediately), and it can be difficult to say no: both to the client and to the money. With these types of interruptions, which can eat up an entire week or more, it’s difficult to keep a system consistently in place.

Finding Balance

As with diet and exercise, the best system is the one you can stick with. Johnny B. Truant, one of the writers I follow, structures his days in flexible morning and afternoon blocks, with family time built in. He’s up before dawn, writes for four hours, then spends his afternoons on the admin side of things. He’s adamant that the writing and the business stay separate, and he’s equally serious about both. He refuses to work past 6:00 p.m. and never works on weekends, instead devoting that time to his family. With this schedule, he and his writing partners publish a yearly word count equivalent to the entire Harry Potter series, while running a network of eight podcasts, managing four publishing imprints, mentoring other writers, and putting on the yearly Smarter Artist Summit.

Aaron Copland was reported to rise at 9 or 10 a.m. each day, linger over the newspaper, then handle correspondence and business every morning before lunch. In the afternoons, he would engage in score study, prepare lectures and articles, meet with musicians, or read. Finally, he would only compose after dinner, but would carry on until after midnight. On average, he composed around an hour of finished music per year.

Prolific, bestselling authors C.J. Lyons and Joanna Penn completely eschew daily schedules. Lyons thrives on keeping her days varied, and Penn merely blocks off a period of days or weeks for individual projects but keeps her schedule otherwise flexible.

At the moment, when I’m asked how I balance composing with web design and engraving and running two podcasts and being a vocalist, et cetera, I respond, “I don’t.” Right now, what works for me is taking things as they come, prioritizing on a daily and weekly basis while trying to maintain a long-term view of my career at the same time.

As I write this, I’m within spitting distance of finishing two website redesigns for clients. So until we launch the sites in the next week or two, those clients’ needs (and the checks they’ll be writing me) are my top priority, while writing these weekly columns, because they’re on a short deadline, are a competing priority. Once these columns and the two websites are finished, composing and podcasting will once again move to the front burners. And because I’ll be recording my second album in the coming months, that will take on a larger and larger share of my time until that project is finished. By the end of the year, I have plans to revitalize an old business that has lain fallow for some time and add yet another income stream, while phasing out my reliance on web design and engraving.

Flexibility has become my watchword, and it allows me to juggle all of my pursuits.

One of the best, as well as most frustrating, things about freelancing is that there’s no one way to do it. There is always room for improvement, but the important thing is that you find what works for you. Mimicking others can only get you so far.  It can give you options for how to handle your own scheduling, but—in the end—the only thing that matters is what works.

Wednesday, April 17, 2013, was my last day as a full-time 9-to-5er. That day, I organized the last few bits of work to pass off to my successor, drank too much at the company farewell party, then went home and packed a suitcase. I had two out-of-state premieres in the ten days that followed, and I was excited to embark on this new adventure of full-time freelancing.

I knew that the freelance lifestyle was fraught with difficulties, so part of my research in the preceding months had been to learn about potential problems that might arise. Kristine Kathryn Rusch’s Freelancer’s Survival Guide (get used to hearing about this book) was an invaluable resource in this respect. In it, she talks about burnout, dealing with client issues, worrying about income, handling the problem of unstructured time, and any number of other pitfalls that freelancers face. I was convinced that I was prepared for whatever life threw at me.

Time Management

One of the things about being a freelancer is that your time is entirely your own. Your days aren’t structured by the policies of whatever business employs you. You’re also completely responsible for your own success or failure, so quite often that means that you end up working long after normal “business hours” to meet your clients’ deadlines, or to stay caught up on all of the projects that you have going at once. Sixteen-plus-hour days can come to be commonplace. They’re equally commonplace with certain types of day jobs, but there’s a special white-knuckled frenzy that can come with being your own boss. The concept of “weekend” loses all meaning, except that it’s the time of the week that your friends with day jobs want you to come out. You don’t have paid vacation, you don’t have benefits, and it feels like the only way to keep up is to keep working more and more.

The danger here is burnout. You work such crazy hours for such a long time without any sort of break—and without rewarding yourself—that something finally just snaps. You’re either a frantic, stressed-out wreck who can’t handle anything anymore, or you’re a vegetable and can barely bring yourself to get out of bed. Burnout can be the kiss of death for a freelance career and recovering from it is a long and difficult process.

One of the other things about your time being entirely your own is that you set your own hours. You have no boss, no supervisor, no timesheets, nobody making sure you’re in the door and at your desk on time. So why not start a little later? Why even set an alarm? A midday nap? Yes, thank you. Feel like knocking off a little earlier? Okay! Just not feeling it today? Don’t worry—you’ll catch up tomorrow. Probably.

Without structure, it’s very easy to slide into laziness. And if you’ve spent your entire life abiding by someone else’s schedule, it’s easy to want to rebel against the clock, especially when you first start freelancing. You want to give yourself a little slack for the first week, and so you wake up later than you really should; but within that week, you’ve formed a habit of sleeping in. There are countless ways that you can train yourself to be lazy when you never were before.

Burnout and laziness are two extremes of poor time management. But the good news is that with some self-awareness and self-discipline, you can find a mode of working that uses your time effectively, and that takes into account your scheduling/motivational strengths and weaknesses.

For those predisposed toward slipping into laziness, it can be important to create self-imposed daily work schedules and artificial project deadlines. Keeping written logs of the work you do can help to keep you honest and motivated. Breaking projects down into component parts and scheduling them out can keep you moving forward.

I keep a bullet journal in an attempt to keep myself honest in this regard. Every weekend I survey the projects on my plate, take stock of the appointments I’ve made, and come up with a loose plan of attack for the coming week. Then every night, I plan out the next day’s agenda. I find it satisfying to check off the things I’ve done; it gives me a sense of accomplishment and motivates me to keep moving. Sometimes, though, I get cocky and think that I can keep my plans in my head without writing them down. Inevitably, I slip back into bad habits within a few days and need to pull out the bullet journal again to get back on track.

Here are pages from my bullet journal during a bad week; pages from a good week appear at the top of this post.

For those headed down the path toward burnout, it’s incredibly important to take breaks and vacations. Schedule regular breaks for yourself—and actually take them! Make it a weekly habit to go to the movies or relax over a nice dinner out. Schedule in time to read a book for fun, check out a museum, or go hiking. And take a vacation from time to time; set aside at least a few days when you’re not allowed to do any work. You’ll thank yourself for it.

Work Load

Probably the most terrifying thing about being a freelancer is knowing that you could have a bad couple of months and suffer financially because of it. Consequently, one of the ways that many of us choose to deal with this possibility is to diversify our income streams. We can take on additional work in other areas to help keep us financially stable if one source of income becomes temporarily unreliable.

One problem here, of course, is that you run the risk of working yourself too hard or spreading yourself too thin, and the specter of burnout once again rears its ugly head.

It’s possible to take on too many different types of work so that it’s impossible to prioritize tasks or schedule them effectively. Personal projects can take a back seat to easy money and clients’ urgent deadlines, making your days feel disjointed and frenzied.

A friend of mine was telling me recently about his freelance situation: he focuses in two primary areas which earn him some income, on top of which he has a time-consuming but stable part-time job and a reasonably low-maintenance yet profitable side business. He would like to shift more of his efforts into his primary areas of focus, but making this shift happen requires that he extricate himself from one of his other, more reliable sources of income. Given extra time to dedicate to his real passions, he could make those areas more profitable; in the meantime, however, he would be removing one of the pillars of his family’s stability, which is frightening.

Juggling all four sources of income plus his family life requires an enormous amount of time and energy, and it has taken its toll on his mental state. He’s constantly exhausted, always feels behind, and knows that the situation is unsustainable. Fellow freelancers in a similar position know this exhaustion, and also know the illogical complication added to the equation by the facts that he takes pride in and genuinely enjoys everything he does, and that he isn’t a “quitter” and doesn’t want to feel like one.

And not to be underestimated here, too, is the investment—of time, of money—that goes into each and every endeavor. There’s a feeling of ownership that takes hold, as well as a reluctance to “throw away” that investment when the time comes to move on. My friend has spent years building his side business to what it is, invested countless hours learning that trade, and spent no small amount of money acquiring the proper tools. For myself, I’ve easily spent thousands of hours and untold dollars learning HTML, CSS, PHP, and MySQL, not to mention what I’ve invested in learning and purchasing all of the software and content management systems I use for my web design business.

Moving on from these businesses, when it’s time for us, will be difficult. But not moving on from them when we need to will hold us back in our true pursuit of making music.

Mental and Physical Health

Last on my list of potential pitfalls this week is your health.

Traditional day jobs can be bad enough for your health. Sitting at a desk from 9 to 5 with only a few breaks to get up and move around has turned us into a very sedentary society, but it also requires that you at least get up and move to go to the office. Most freelancers work from home, so the trip to the “office” doesn’t require a commute. Or pants. Consequently, it’s far too easy to live an even more sedentary lifestyle than if you worked for someone else. And without coworkers to judge you for what you eat in the lunchroom, your diet can suffer as well. It’s easier to snack out of boredom, and you don’t have to hold up any pretense of eating like an adult.

Self-discipline and time management skills come back into play here. Scheduling breaks, taking walks, setting aside time for the gym, getting enough sleep: all of these are necessary not just to avoid burnout, but to avoid health problems, as well.

Breaks and walks don’t just keep your heart in shape and your waistline from expanding. They prevent injuries, too. I can’t count the number of freelance writers I know who have had to deal with carpal tunnel syndrome. Repetitive stress injuries are far too common among the self-employed because of our drive to keep working and working and working. This can ultimately be deadly to productivity, as recovery is painfully slow. And without employer-provided insurance, healthcare is already expensive enough without inflicting completely avoidable injuries and health problems on ourselves.

And finally, breaks, walks, workouts, sleep, and socializing are necessary for your mental health. Being shut away from the world, seeing only your significant other and your cat for days on end does some bad things to your state of mind. Take it from me.

Depression has far-reaching effects and can undermine all of your motivation, planning, and self-discipline. It’s all well and good for me to say, “Be disciplined,” but when depression sneaks up on you and gets a foothold, your discipline is slowly eroded away. It’s insidious. My comment, “Or pants,” earlier may have seemed flip, but in my opinion, repeatedly making the “commute” to your desk without pants is the canary in the coal mine. So in addition to everything else you have to know about the business side of things, know the basic signs of depression, too, and be prepared to seek out help. Because although you’re “going it alone,” you’re absolutely not alone, and the people around you are as much the key to your success as your drive and talent.

Your physical and mental health are closely linked. Being proactive about your physical health can buoy your mental health and boost your motivation, productivity, and self-discipline. Both the upward and downward paths can be circular: poor health can contribute to depression, which contributes to decreased productivity, which contributes to greater depression, etc.; and good health can foster a positive mental state, which boosts productivity, which improves your mental state, etc.

So set yourself up for success by taking care of your health, as well as your career.

Last week I wrote that within months of starting this new freelance adventure “everything had gone wrong.” Next week, I’ll tell you why, and which of these pitfalls I fell prey to (despite knowing about them in advance!) and how I’ve tried to course correct over the years.