Course Corrections

Within six months of starting my new freelance life, things had gone off the rails a little bit. As a result, I’ve found my freelance life to be an exercise in course correction.

Written By

Dennis Tobenski

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.

For a freelancer, sleeping well into the double-digit a.m. hours 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.


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.

A bulletin board with an elaborate vertical and horiztal arrangement of large post-it notes on which various task reminders are handwritten

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.

The more diverse your activities are, the more difficult it can be to schedule them concretely.

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.

What works for me is taking things as they come.

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.