The Freelancer’s Survival Guide: Staying Positive

Freelancer's Survival Guide On Writing

The Freelancer’s Survival Guide: Staying Positive

Kristine Kathryn Rusch

It’s been three weeks since I stopped answering questions and in that time, the questions and the comments slowed down. I think I scared everyone with what I called the bread and butter posts—giving a freelancer’s job description, figuring out when to quit your day job, and what you should have in place before you do.

I need to move onto more bread and butter topics—insurance, money, time schedules—and would love to hear which folks want covered first.

But this week, I’d dealing with some issues of my own, mostly to do with my office cat. She has lived alone in my office for more than a decade because she doesn’t play well with others (tries, in fact, to kill anything with fur, including raccoons), and she’s been quite ill. This week, we’ve finally decided it’s time to end her misery.

My office will never be the same.

I’m taking this opportunity to move my office to a new space, where I’ll have three office kitties, and even more privacy than I had before. But it’s an emotional week for me, so I really didn’t want to discuss money.

Instead, I thought I’d answer two questions, both on emotions and freelancing.

The first, from writer Michael Samerdyke, inspired the title of this section. He writes, “Will you include something on how to stay positive?”

Remaining positive sounds like such a minor thing. Yet it is the key to everything. Oddly enough, successful freelancers are the most cynical, hard-bitten optimists in the entire world.

We have to be. Who would believe in us if we didn’t believe in ourselves?

No one discusses remaining positive at a day job, unless it is a requirement of that day job. When I worked as a waitress, I had to smile at the customers and be nice. It was in the job description. The same rules applied, perhaps more stringently, at my very first retail job. We had to be so incredibly nice at that store that we were required (again, as part of the job description) to wish each and every customer a very nice day.

This is not what I mean about positive.

You can grump around your home office for weeks if you want to. You can snarl at the cable news channels, like I often do (particularly during an election cycle). You declare a book useless and toss it across the room if you like without worrying about hitting one of your co-workers, since you no longer have any.

You can be the surliest, nastiest person on earth because you work alone. If being surly and anti-social makes you happy, then by all means, have at it.

When you work alone, you don’t need rules for office behavior. If you don’t receive clients in your office, like most freelancers, then you can behave anyway you want to.

Most freelancers don’t take this acting out very far. Mostly they do a few cosmetic things they would never have done at the day job, like spend the entire day in sweats or in their pajamas. Some don’t shower until they finish work.

Fine. Good. Whatever.

I do dress in Northwest casual to go to my office. I wear the clothes that I would wear to a restaurant or to the post office. My mother believed that appearances mattered, and that part of my upbringing rubbed off.

In fact, something she said (repeatedly) actually stuck. Dressing properly makes you feel better. And you know something? It does. I don’t wear fancy clothes to the office because that feels ridiculous. But I always feel underdressed and vaguely unhappy when I wear my grubbiest clothes.

Clothing sounds like a side issue, but it’s not. It’s all a part of a greater whole.

As I’ve said before, a day job gives you structure. It structures your time—when you’ll arrive, when you’ll leave, and what you’ll do while you’re there. It structures your environment—someone else designs your workspace, and whether you get an office with a window or a cubicle with high carpeted walls. It structures your appearance—you may have to wear a business suit or a uniform with the company logo. Some places have strict rules about grooming. Disneyland, for example, won’t allow men to have facial hair. Many restaurants I worked in didn’t allow the waitstaff to wear perfume, cologne or use scented soaps because those odors would interfere with the food.

And then each day job, whether it’s acknowledged or not, structures the employee’s attitudes. Some, like the retail shops I mentioned above, required positive attitudes at all times. But most emotional structures are subtler than that. Except for discussions of last night’s episode of Lost or some (tame) discussions of this year’s baseball season, personal conversation gets discouraged.

If someone asks, “How are you today?” they really don’t want to know the answer. They don’t want you to launch into a litany of your ills from your aching feet to the hangover that has lingered (been encouraged?) all weekend. In fact, too much personal discussion can lead to reprimand and ultimately dismissal for inappropriate behavior.

You don’t have to be positive at these jobs, but you do have to maintain some sort of professional attitude. You know once you get out of the car in the parking lot that you have to be on your best behavior until it’s time to drive home.

Now you work at home. Home, where you express every feeling, where you stay when you’re sick, where you go for refuge. Home has suddenly become work as well, and the lines have blurred.

We allowed those lines to blur long before we went fulltime freelance. Before we quit our day jobs, we did our freelance work when we “felt like it” or when we “found the time” or when the muse showed up.

In the early days—for all of us—the freelance work was a side business or a hobby, something we did because we loved it or because it filled the time.

The day job, on the other hand, was something we did for the money.

Now we freelance for the money. We forget that we used to do this sort of thing for fun. Sometimes fulltime freelancing takes all the joy out of the operation.

The key isn’t so much recapturing that joy—remaining joyful day after day isn’t something most humans are capable of—but remembering the joy. Remembering that you are doing the work that you love and you’re lucky to be doing so.

One of the best pieces of advice I ever gave one of my writing students was accidental. He was so serious about his writing that every sentence had become torture. I told him to go play. The advice stuck. He made a sign that said Go Play and put it across from his desk where he could see it every single day.

It didn’t put him in a good mood every day, but it did help him feel better about his freelancing.

Staying positive is tough for a variety of reasons. I mentioned one in the essay on priorities. People who spend the majority of their time alone are prone to depression. Study after study has shown this.

The solutions are simple, but do take time away from the freelancing. Some are basic: Get enough rest, eat good food (not junk food), and exercise. In fact, a recent study showed that a half-hour run has the same effect on a person’s mood that a single dose of Valium has. Plus the run is cheaper and has many other benefits.

You must also schedule time to be with other people, doing fun things. This sounds silly, but many freelancers spend their free time with other freelancers, discussing business. Take the time to see a movie (the new Star Trek is good) or to go to the beach or take in a basketball game.

People whose freelancing requires little more than a computer and a wi-fi connection can go to restaurants, libraries, and other places to get some work done. One Christian writer I know spends every afternoon in a local restaurant, researching, writing, and going over his manuscripts. He eats lunch, pays a little extra for his coffee, and socializes just enough to keep his mood elevated.

It works for him. Sometimes that solution works for me too.

But the toughest part about staying positive has nothing to do with the lack of companionship or the right attitude. It takes focus to remain optimistic.

First, you need confidence in your work. Most of us don’t have it. If pushed, we confess to all kinds of insecurities, problems, reasons why our work isn’t as good as it could possibly be.

Yet we need to believe in ourselves to do a good job.

What do I recommend? Act like you have the confidence. Eventually, you’ll improve in this area. I learned this through theater training. Traditional acting schools teach that if you mimic an emotion, you can actually bring that emotion out in yourself.

Think about that for a moment: Before you started freelancing fulltime, you probably described your emotional life as pretty balanced. It had to be. You had to maintain a professional decorum at your day job.

Then you quit that day job, spent all your time at home, and your emotions started running amuck. You didn’t have to pretend any more. You could be yourself—and yourself, like the rest of ourselves, is an emotional rollercoaster.

That rollercoaster is fine—and often good for those of us in the arts—but you have to be aware you’re riding it. You need to assume that mask of professional decorum when dealing with the outside world. You need to filter all the information from the outside world through the same professional mask.

If a new client doesn’t return a phone call on time, it’s not because the client hates you. It’s because the client didn’t have time to get to the phone that day or forgot or something equally silly. But we lose track of that when we work at home, for ourselves, with no one to balance us.

Work to retain your optimism. You quit your day job because you believed you could succeed as a freelancer. You need to remember that each and every day. If that means putting a sign up in your office that says Believe in yourself!, then do it. Who’ll see the little aphorisms you post around your desk? You’re not in someone else’s building any more. Your office is private, so design it in a way that keeps you motivated and happy.

That includes things like music. Or an excellent view. Or a great screen saver. (I have one that makes me smile, no matter what.) I keep a cartoon-a-day calendar, and read it every day, which also helps, believe it or not.

But the most important part of staying positive is to remain realistic. If forty-five people say something nice to us and one person says something mean, we’ll remember the something mean and discount the nice things.

As freelancers, we have to keep track of the good and the bad. And we have to give them the proper weight. Teaching reminds me how to weight the things around me. As I explain things to my writing students, I realize the things I’ve overlooked in my own life.

However, I do work hard to remain realistic. My first and best tool for this is my calendar. I have a New Yorker desk calendar, encased in leather and embossed with my name, at my right hand, just past my computer’s mouse.

I write every single good thing that happens to me in a day on that calendar. I keep track of fan mail, covers, publications, awards, and the amount of money I receive.

I think getting paid for my work is a good and positive thing. Rather than relegate it all to the accounting program, I also keep track in my calendar.

I also keep track of good comments, even from people who have rejected my work.

People who work for themselves have trouble keeping track of time. First-time freelancers soon learn that they can’t tell Thursday from Tuesday without help. Even if you take the weekends off, the weekdays seem remarkably the same.

The good things that happen to you will seem far in the distance, even if they happened a week ago. The bad things, conversely, will seem like they happen every day, even if the last one happened a month before. Remember that we focus on the bad and often forget the good.

So on bad days, I go back through my calendar, and look at all the good things that have happened. It helps me maintain perspective.

I do realize that some professions don’t have the regular positive feedback that my job does. Some people work for years on the same project, or they do healing work (like massage or psychotherapy) that often has no real end to it, or they work in professions with no real feedback at all.

How do you stay positive in jobs like that?

The same way you remain positive when you’re just starting your business and have no real sticks to measure success with.

You have to learn how to measure success from within, not from the outside. In other words, set daily goals and reward yourself for achieving them.

The daily goals must be realistic. They can’t be too easy or you’ll finish in an hour and feel like you haven’t worked. On the other hand, they can’t be too hard or you’ll never achieve them and will always feel discouraged. You must set a goal that makes you put in some effort and gives you a good result at the same time.

Writers generally set a word limit—writing so many words of new material each and every day. Musicians often set a time limit—practicing for so many hours each and every day. EBay sellers will often set a goal of making a certain number of listings each and every day.

The type of goal will vary from business to business, but it must be something that you can achieve daily. I also set weekly goals and monthly goals. Even though I’m very structured, I usually miss my monthly goals—something gets in the way or goes long or (as in this week) life intrudes a bit and puts me behind.

Sometimes I miss my weekly goals as well due to illness or some other interruption. But I rarely miss my daily goals. But I still reward myself for achieving them. The rewards are small—an extra hour of television that night or a brand-new paperback book or just a simple pat on the back. I mark that success in my calendar, so that I can look back on bad days and say, “Well, at least I achieved my goals in the past week.”

Sometimes that’s all I need.

The other aspect to being realistic is to know your limitations. During the same week that Michael Samerdyke asked his question, Laura Ware asked something similar. Laura, a Florida columnist and freelance fiction writer, has had life intrude on her work in a very big way.

She has become the fulltime caretaker for her very ill elderly in-laws. With the help of her family and an occasional visit from home health care services, she tends to her in-laws seven days per week. But Laura is determined to continue with her freelance work in the middle of all of this.

She asks, “When you’re in the kind of place [that I’m in], how do you know what’s slacking, what’s too much, and what’s appropriate?”

That’s a very healthy question. Because if you set your goals too high, you’ll feel bad. People whose lives have intruded on their work (not just freelancers, but everyone) suffer a lot of stress. Whether taking care of elderly parents or taking care of a newborn baby, things happen in all of our lives that cause stress and an additional burden (even if, in the case of the baby, it’s a burden that we want).

What we have to do is, again, be realistic. If you’re the sole breadwinner for your family, you can’t drastically cutback your hours. You may have to hire outside help or work with other family members so that they can share some of the burden.

But if you’re not yet a major breadwinner, if part of the condition that the family imposed on you quitting your day job was to be the stay-at-home parent or to take care of the elderly parents or, in the case of a friend of mine, to be the sole caretaker of a dying spouse, then you must shave your work goals accordingly.

You need to figure out when you can steal the hours to get work done and if you’ll be in any shape to do the work when those hours happen. If you’re under a great deal of stress, like Laura is, cutting back on sleep is a terrible idea. If you’re just overwhelmed with car pooling and running errands, you might have to change your work habits by figuring out what parts of your job you can do on the run.

In Laura’s e-mail, she adds this, “I’m tapping this out on my phone while sitting in a waiting room with my mother-in-law (she has a doctor’s appointment). After I send this, I’ll fire up my laptop and try to get something done while I sit around.”

Laura is one of the hardest workers I know. (Check out her blog here and her columns here.) She gets a lot done while caring for her family. She’s organized and driven, and unwilling to give up her dreams, even though she’s in a tough spot right now. She routinely writes five hundred words per day, which is a great deal given her situation.

Yet, as her question says, she feels like she’s not doing enough.

So let’s take the question bit by bit: How do you know what’s slacking?

I think we all know deep down when we’re not working hard enough. If we’re spending most of our time watching television or playing video games, we’re not working hard enough. Some people compare themselves to other freelancers, and think, I should be working as hard as they are. That’s not the answer either, because everyone is in a different circumstance.

Know your circumstance, know what you’re capable of, and then make a realistic assessment of your life. Try to achieve your new daily goal for a week. If you never reach the goal, figure out if the problem is that you weren’t putting in enough time, that you didn’t have enough time to give (as in Laura’s case), or if the goal is just too hard to achieve in a single day for you.

Then set a new goal and try that for a week. Work until you find one you have to stretch just a little to achieve, but make sure it is one you can achieve. When you’re ill or taking care of something in your life that takes precedence (like sickly elderly parents), then you might have to cut back on your daily goals. When you’re in excellent physical shape with no distractions in your life, raise your goals. Don’t set anything in concrete. Be flexible, but realistic.

If you can achieve your daily goal in fifteen minutes and spend the rest of the day goofing off, you’re slacking. In this case, you need to measure how much leisure time you have. If you’re spending too much time recreating, and not enough creating, you’re slacking.

The next part of her question: What’s too much?

If you have no leisure time, if you’re getting repetitive stress injuries, if the people around you whom you trust start telling you forcefully that you need time off, then you are working too much. In the last two years of our publishing company, our friends started handing Dean articles on stress management. He was putting in 20 hours per day, seven days per week, and it showed. Eventually he collapsed, and no one was surprised, except him.

He’s learned how to moderate, although he doesn’t like it much. I’ve learned that he still works harder than anyone else I know. But now he’s working a more sensible schedule (10-12 hours per day, with one weekday evening and one full day per week off), and getting 8 hours of sleep per night. He occasionally thinks he’s slacking, but no one gives him articles on stress management any more.

And the final part of Laura’s question: What’s appropriate?

Appropriate is an interesting word, because it implies that there are Standards To Be Met.

The cool thing about being a freelancer is that you set your own standards. What’s appropriate for me, a person with few responsibilities and a long-term career with several obligations, isn’t appropriate for Laura or for anyone else reading this.

So let’s rephrase the question in a way that Goldilocks and the Three Bears would understand: What’s just right?

Just right changes. Just right may be 500 words per day because you’re taking five minutes here and five minutes there. Just right might be 5,000 words per day because you have no other obligations or 8,000 words per day because you waited too long to start that book under deadline.

For a therapist friend of mine, four days of client meetings per week was just right. It kept her fresh for her patients. She was able to maintain her emotional balance at four days, with three day weekends to recharge. She figured out how many patients she could reasonably handle, how many she could help, and how many would drain her. And she picked the answer that allowed her to remain healthy and to do the work that helped the clients that she had.

Once you’ve figured out what’s just right for you, then make a note of it. Set it up as a goal to be reassessed when the current situation changes. Then strive to meet that goal every single day.

And reward yourself for doing so.

Early on in your freelance career, the only good things will be subtle ones—meeting your daily goal and enjoying the work that you quit your day job to do.

The best way to remain positive is to remind yourself that you’re now doing the work you love, day in and day out. Most people aren’t that lucky. Most people never get the chance to do what they love.

You have taken that opportunity.

Enjoy it, and value it for what it is—something special. Something worthwhile.

An achievement, in and of itself.

“Freelancer Writer’s Survival Guide:Staying Positive,” copyright 2009 by Kristine Kathryn Rusch

You can now order either an e-book copy of the Guide or a trade paper copy of the Guide. It’s in slightly different format and has been organized, so that related topics are in an easily accessible place.

You can get the print version here.

For those of you who’d like to buy an ebook, here’s the Amazon link as well as the Barnes & Noble link. The e-book will also be available on all the other e-book sites. If you want it in your favorite format, and the book hasn’t yet been uploaded to your favorite site, try Smashwords. You’ll be able to download in a variety of e-book formats.

22 thoughts on “The Freelancer’s Survival Guide: Staying Positive

  1. So sorry for the loss of your cat. I know this is old news, but I am just reading it now. Sorry if I brought up some bad memories. Just wanted to express my sincerity in condolences.

  2. Kris, I keep coming back and reading your blog postings.

    Years ago my sister suggested I write a “Done List” instead of the more common “To Do List”. I found this subtly and powerfully helpful in keeping myself positive. If I ever have a desk/space/room/whatever that I can work at regularly I’m going to do the calendar idea with my done list.

    Thanks Again

    1. I love that idea. A “done” list. I achieve it by checking items off my to-do list. I feel quite good about those little check marks. My current calendar program automatically deletes done items and I had to go into the preferences to change that. It made me feel worse not to see them!

  3. Dear Kris,

    I’m at a time in my young life where staying positive seems like the hardest thing to do. I just happened to search “staying positive” on google and your blog was among the first to appear. I was pretty hooked reading through this whole article, especially because there are several points you made that I definitely could, should, and need to use. I really liked reading about the calendar, because the week does go by pretty fast for me too, and being so busy, I forget about a lot of the goals I set and the good things that happen along the way.

    You write very well, and I enjoyed reading through the whole article. Thanks for the inspiration!

    1. I’m glad this is working for everyone. Staying positive sounds like such a minor thing and it’s so important, as is setting the proper goals. Cindie, I’ll e-mail you privately. I think you might have a writing issue (since I have a hunch I know what project you’re on) instead of a freelancing issue. Mark, I’m like your friend. I think I’ll never work again, and I always do. Yet I keep trying even when I think I’m going to fail. That’s the essence of freelancing, I think. I thought of mentioning the supportive spouse, Wim, since I have one, but not everyone does. Better to work on the things that we can do individually.

  4. Thank you SO MUCH for this. My problem has been that I set my goals based on what I think I need (in terms of income, or hours worked) instead of what I can actually DO. Those goals tend to be overly optimistic, to say the least, and I work myself into the ground trying to reach them, then beat myself up for not having done more.

    I had never thought of taking a more organic, sensible, bottom-up approach like you’ve described. It seemed so obvious, once you said it…!

  5. An excellent post. I particularly like:successful freelancers are the most cynical, hard-bitten optimists in the entire world.

    How true.

    I’m quick to tell my own blog readers that I’m hardly a life-is-good optimist … except … that I am. I’m probably a realist in that I see all the pitfalls ahead, too. But as a freelancer, you HAVE to be an optimist. You have to believe there’s another gig, another customer, another client right around the corner. Otherwise the job will kill you.

    Jeff Cohen, a freelance writer and novelist, commented once about how as soon as he turns in an assignment he’s convinced he’ll never get another writing assignment … ever.

    Yet he’s been a freelance writer for probably 15 or 20 years. Somehow, he knows… there’s another gig right around the corner.

  6. Excellent advice! I’ve been reading this series for a while and am delighted you took the time to answer this quesiton. Staying positive is indeed one of the hardest things.
    I’ve co-written three books on martial arts and sometimes it’s hell to keep the faith. The only thing I would emphasize a bit more is the support of your partner. Without it, it’s twice as hard to stay positive. Or the worst scenario, a partner who keeps bringiong your writing down and wants you to stop. Been there, done that. The partner’s gone… 😉

    Looking forward to he next part,


  7. Thanks for this. You’ve given me much to think about. One of these things is that though I’m a full-time nonfiction freelance writer, I am desperately trying to become a full-time fiction freelance writer. It occurred to me today that my nonfiction has become a day job in many ways. I get much positive feedback on the nonfiction (which I don’t need), but little to none on the fiction (which I do need). I’ve been working hard on the faking it part but am feeling the undertow of why bother. I recently just quit on a project and am working to figure out why (I have excuses, but none of them are the real reason). But while I’m figuring, I’m not writing. And maybe worse, I’m not getting the day-job work done either. Did you ever just feel like you simply didn’t have it in you? When there is no feedback to be had (say, because a project isn’t done and there’s a long way to go), how do you keep going?

  8. Kris, thanks for all these great posts!

    I’m not freelancing yet (not even close) – but I find I’m able to apply so many of these tidbits to my “parallel track” – my “writing life” that currently coexists alongside my “day job life.”

    With these philosophies and perspectives in mind, I’ll be miles ahead of the average freelancer when my time finally comes to shed the shackles of traditional employment.

  9. Thanks, Kris! Now I know what to do with those blank journals people keep giving me. I have enough calendars, but keeping track of the good things that happen sounds like a great use for the blank books.

  10. Kris, thanks for answering my question! And staying positive fits in so well with that!

    Two other things that help me are friends like you and others who assure me I’m on the right track and a husband like Don who does all he can to ensure I don’t have to give up on this dream.

    Thank you again – I hope more people take advantage of this resource you so generously offer!

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