Dennis Tobenski's Bullet Journal
Pitfalls of Living the Freelance Life

Pitfalls of Living the Freelance Life

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.

“Weekend” loses all meaning, except that it’s the time that your friends with day jobs want you to come out.

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.

Without structure, it’s very easy to slide into laziness.

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.

A bad week in Dennis Tobenski's bullet journal.

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.

Seeing only your significant other and your cat for days on end does some bad things to your state of mind.

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.

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3 thoughts on “Pitfalls of Living the Freelance Life

  1. Michael

    I’ve been freelance for so many years I’ve lost count. I find that a morning routine is essential to both good mental and physical health.
    Goals- deadlines and friends are as you said “essential” .
    Retreats- -and continuing education- seminars and what ever other challenges you might construct are all good things!

    I’m not sure if the occasional bout with depression can be avoided – I just find that
    action- and movement is a way to accentuate the positive-

    Good luck and keep your pants on during business hours :)

    Michael Patterson

    Reply
    1. Dennis Tobenski

      Hi Michael!

      Thanks for your comment! I’m finding more and more that mornings are the key to my daily success. YES YES YES to continuing education – we’re totally not done when we leave school, and are headed for a rude awakening if we think we are.

      And yes, depression is difficult to avoid sometimes. The relatively minor setbacks that send us reaching for the pint of ice cream to assuage our self-pity are inevitable. Few of us are immune. Action and movement are definitely key. I’ve taken to using rejection and disappointment as a “springboard” into new projects. Sometimes it’s a matter of “I’ll do better this time” and sometimes it’s a big middle finger to whoever rejected my latest application. Bigger, Capital D Depression is rather more insidious, but can often be headed off at the pass with self-knowledge and self-care.

      Keep up the morning routine!
      d

      Reply

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