Freelancer’s Survival Guide: Risks Part Two

Freelancer's Survival Guide On Writing

The Freelancer’s Survival Guide: Risks Part Two

Kristine Kathryn Rusch

Part Two, you ask?  Part Two?  Didn’t we discuss giving up on ourselves last week?  What’s this “Risks Part Two”?

Well, “Risks Part One” was so long ago you’ve probably forgotten it.  Back in March, I got inspired by events and wrote a bit about risks, knowing I would delve into the topic more later.

Later is now.  So go back and review “Risks Part One,” and then c’mon back and  join us.

Done?  Okay.  Here goes.

My husband Dean Wesley Smith and I have been discussing risks a lot this week, partly because we’re planning a class in money management for freelancers which we’re holding this weekend.  (Dean will actually do the teaching part.  If you’re interested in this or any other topic, we’re setting up our teaching schedule next year.  E-mail me and let me know what you’d like to hear about in person.)

We’ve also been discussing the risks some friends are taking in different careers in the arts, as well as some risks we’re considering in our own careers.  Risk seems to be in the air.  I think some of that is due to the Great Recession.  People have already lost their jobs and their security, so they believe that now is the time to take a risk.

I think so too. But each person assesses risk differently.

I did some discussion of risk in the Part One, but I didn’t give a definition.  So I’m going to haul out the handy-dandy dictionary again, and give it a go.

(Why do I define words we already know? To make sure there are no assumptions here.)

Risk, according to my lovely Encarta World English Dictionary, is complicated.  I did not expect five different definitions—and that’s just for the noun.  The verb form has a few of its own. Here are all seven definitions—noun first, then verb:

  1. the danger that injury, damage, or loss will occur
  2. somebody or something likely to cause injury, damage, or loss
  3. the probability, amount, or type of possible loss incurred and covered by an insurer
  4. the possibility of loss in an investment or speculation
  5. the statistical chance of danger from something, especially from the failure of an engineered system


  1. to place something valued in a position or situation where it could be damaged or lost, or exposed to damage or loss
  2. to incur the chance of harm or loss by taking an action

Wow.  Look at those loaded words defining risk:  injury; damage; loss; harm; danger.  Danger.  Jeez.  The only time you see a word that’s positive is in the verb form, and even that’s not good—“to place something valued in a position or situation where it could be damaged or lost.”

Yikes. With definitions like that, it’s amazing anyone ever takes a risk.  Even the synonyms are scary:  danger; jeopardy; peril; hazard; menace; threat.  The antonym is a word that makes us all feel better: safety.

Safety is the opposite of risk.

Yet if you’re freelancing, playing it safe is a risk.


To freelance in this culture is to go against cultural norms.  We’re all raised to get a good job with job security, work our way up in that job, and eventually make manager or executive vice president or even president of the company/corporation.  Let the company pay for our vacations, our retirement, our 401Ks, and our insurance.  If possible, get a job with longevity, so you can stay at the same corporation all of your life.

Those myths were myths back when my father spouted them.  My father—a professor with tenure who had jobs at five different colleges and universities (more if you count the summer school classes and semesters away that he taught).  Five different employers in three different states.  Even while he was telling me and my siblings to get a good job with a long-term employer, he wasn’t living that life.

Neither were our neighbors, although the neighborhood looked very Father Knows Best, with the husbands leaving for their corporate jobs and the wives staying home to tend the kids.  Peel back the surface, and you’d see that the family next door had only lived in the house for five years because the husband kept getting promoted and moved to a new area.  Or the family two doors down who kept moving from state to state like we did, following the professor husband from one tenure track position to another.  Or the family across the street with the outspoken wife who didn’t believe women should stay home, and had never ever gone without a job, not even when she was raising three boys.  (Her husband was gainfully and happily employed—the only one who had been in the same job in the same place for more than twenty years.)

I could go house by house, memory by memory, in a time when the myth of the lifetime job got engrained into the culture—the middle of the twentieth century—and show you anecdotally that I knew no one who lived that exact lifestyle.

Yet we all believed it to be a goal.  And that goal continued to be the pinnacle of achievement until the Great Recession began in September of 2008.  Just last week, one of the national news casts revisited the Class of 2009—the first college class of the Great Recession—to see how those kids were getting along in “the real world.”  None of them had gotten the job they wanted.  All of them had learned that life was harder than their parents, teachers, and older siblings had made it out to be.  The world had changed, and that prescribed path—the one that said if you walked this way, you’ll have a job for life—had vanished.

As I’ve said in other parts of the Guide, these changes provide opportunities.  I saw a statistic a few weeks ago which, of course, I can’t find in my internet search this evening.  The statistic stated that the number of new small businesses had grown exponentially in the past two years.  So many people decided that if they couldn’t get a job, they’d create one for themselves.

They took a risk, which may not have been much of a risk at all.  In fact, continuing to search for a job in a tight market might have been more of a risk.

But for everyone who tried, dozens of others did not.  They were risk averse—and really, who in their right mind wouldn’t be risk averse with words like danger, jeopardy, and peril hanging over them?  Why would anyone take a risk at all?

Some people had no choice.  But that’s not a good way to start a business—to do it because there’s nothing else to do.

Why do sane people start businesses? Why do sane people take risks?

Or better yet, how do you correlate all those risk-takers who start businesses with successful entrepreneurs who, as we learned in Risk Part One, are essentially conservative people?  How can you be conservative in your business practices and take a lot of risk?

Ah—here’s where the definition of risk fails.  Risk is not absolute.  It’s relative.  Something that’s risky for me isn’t risky for you at all.

If I decided tomorrow that I was going to become a math professor like my father, I’d be taking a huge risk.  I’m dyslexic, and my dyslexia manifests itself worse in numbers.  I’m not sure I can operate with the precision needed to do higher math.  I learned in school that I can understand the concepts, but I can’t translate them accurately into numerical form.  At some point, I dropped out of higher math, so I have no idea if my understanding would have continued through Advanced Calculus.

However, the invention of the spell-check has allowed me to write, despite the dyslexia.  No one dies if I misspell a word—and writing isn’t about spelling anyway.  It’s about storytelling, which you can do with or without dyslexia.

Yet there are people out there—my husband is one—for whom math is a gift.  He can do everything from arithmetic to calculus with ease.  He was a professional golfer and an architect, so thinking in three dimensions—which baffles me—comes easily to him.

Going to school to major in math wasn’t a risk for him.  It would have been laughable for me.

Innate ability, however, is just one example of different way risk spreads out among the population. In fact, ability is probably the most worthless measure of whether or not someone will succeed.  I’m sure I could have found ways around my mathematical challenges if I were motivated enough.  After all, I overcame the dyslexia to write (yep, before spell-check).  I survived my math classes with straight As, but I had to work harder than I wanted to because I didn’t enjoy the subject.

If I wanted to, I could have learned how to turn that numerical dyslexia into an annoyance rather than an excuse.

So how do you accurately assess risk—for you?

1.  Know who you are. Know what you like and dislike.  Figure out how much work you’re willing to put into something.  Remember “good enough” from last week’s post?  If you constantly skate by in a particular area, doing just enough to be “good enough,” then that’s not an area for you. But if you’re willing to buckle down and work harder than anyone else in an area—even if you have no obvious ability—then that area is a place where you could succeed.  Enjoyment, for the freelancer, is the heart of the business.  It’s what keeps you at your desk for long hours.  It’s what makes all the hard work worthwhile.  Enjoyment is different for each of us.  Tasks that would drive me crazy please a lot of other people.  And thank heaven for that.  Otherwise, there’d be a lot of jobs that no one would want to do, and we’d all be poorer for it.

2.  Understand the economic principles at play.  If you’re going to freelance, make sure you understand the business you’re entering before you go into it.  Or at least, understand it as best you can.  Learn the ups and downs.  Find out who is successful and who isn’t, and look deep to understand why.  Figure out the business part of your business before you jump into it.

3. Use your imagination.  That’s why we’re given one, so that we can imagine scenarios before they occur.  Look at the upside and the downside of any potential business.  Imagine yourself working hard in that business—doing the dirty work, the nitty gritty details, pulling the long hard hours.  If you can see yourself happily working away, then maybe that job is for you.  But if you hear yourself saying “I’ll hire someone to do that task,” then rethink your decision to work in that particular area.  Because early on, as a freelancer, you’ll be doing every job in your business.

You also need to know how to do every job, so that you know how to assess any potential employee you hire.  If you can’t imagine yourself doing the hard work of the business—whatever it is—for a long period of time (more than five years), then this business is not for you.

4. Enjoy the learning.  If you don’t like studying for this business, then you’re not going to like the business.  And if you think that doesn’t matter, then you’re in deep trouble.

Because any business you go into will grow and change over time.  People who keep up with the changes become successful and remain successful. Everyone else falls by the wayside.

5. Learn how to assess risk versus reward.  I discussed this a bit in the previous risk post—would you take something with a high reward that also has a high risk? (Most successful business owners would not.) You want the greatest reward for the lowest risk.  And that risk must be a risk to you.  We all have different levels of risk tolerance. Too much risk tolerance and you become a gambler.  Too little and you will never achieve your dreams.  Figure out the balance, and then find ways to maintain it.

6.  Don’t just assess the financial cost; look at the personal cost.  Starting a business—any business—takes time.  It also takes dedication.  Do you have the time?  Can you work ten- and twelve-hour days? Can you focus on that business at the expense of most other things in your life?

Maybe you already have a job that takes a lot of your time, and you would simply be trading working for someone else with working for yourself.  You still need to look at the personal cost.  Examine the failure post. You might not be taking risks just for yourself, but for others as well.  Can your relationships survive a failure of this business?   Or worse, can they survive its success?  (Look at the success posts to understand that.)

7. Learn to walk away.  We’ve all heard the expression “throwing good money after bad.”  But most of us don’t apply that to time as well.  Sometimes you invest time into something, realize that it’s not working, and try harder.  When you try harder with little chance of success, you’re wasting time better spent on a different endeavor.

Many people cling to a job or a business or a failing relationship because they have already invested so much time and effort into it.  You need to assess whether or not that struggling business or failing relationship can realistically improve.  If the answer is no, extricate yourself from the situation.

Sometimes it’s better to spend a few months or a year winding something down than it is to spend five years trying to save it.  If you’ll end up in the same circumstance in either situation, do the one that will take the least time out of your life.

8. Learn from your mistakes.  Because, as I’ve said before, you will make a lot of them.  Just don’t make the same mistake twice.  Learn from your mistake and do something different next time.

9. Realize that nothing is inherently risky or inherently secure. This used to be a hard one for people to understand—back when corporations seemed monolithic and strong.  The past two years have taught people that anyone with a “secure” job can lose it overnight.  Just like people who have “taken risks” can succeed “against all odds.”

You need to question who is making the odds, and whether or not they know as much about the risky situation as the people involved do.  Just because something looks secure from the outside doesn’t mean that it is.  And the same thing applies to something that’s seemingly risky.

10. Bet on yourself. Which goes back to #1.  If you know yourself, then you can make the best choices for you.  If your choice is between relying on someone else to take care of you or doing it yourself, do it yourself.

Invest in yourself.  Believe in yourself.  Work harder than anyone else.  Work smarter than anyone else.  Learn from your mistakes. Do what you love.

If you apply those six principles to your work, then you’ll mitigate risk no matter what endeavor you try.

But be honest with yourself.  Any time you leap without enough preparation, without enough study, and without understanding what awaits you, you’re taking a risk.  A real risk, with all of those scary words behind it.

If you’re not ready, and you leap anyway, you’re going to hurt someone.  And that someone will probably be you.

Being seriously risk averse is as harmful as having too much risk tolerance.  If you’re seriously risk averse, you’ll never try anything.  You see risk everywhere.

If your risk tolerance is too high, you’ll take stupid chances.

You need to learn how to mitigate risk in everything you do.  Accept that some risk will always exist—that’s life, y’all.  We take risks when we do anything—from crossing the street to cooking lunch.

Accept the risks, try to minimize them, and then follow your heart.

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, trySmashwords. You’ll be able to download in a variety of e-book formats.

“Freelancer Writer’s Survival Guide: Risks Part Two” copyright 2010 by Kristine Kathryn Rusch.

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