Each week, Clint and I set out to make you guys laugh. That’s a great job in itself. But humor can do way more than just entertain. It can help people learn, it can create a positive environment for debate, it can sell a product…humor is a versatile tool for tons of situations, and if used correctly, it can enhance any kind of freelance writing work.

But if you’re going to use humor in your writing, you gotta learn how to write it. GOOD humor, that is. I’m not talking about those terrible anecdotes about work that you see on websites that were built with Geocities, clipart, and possibly Elmer’s Glue. We’re talking honest-to-God jokes here, the kind that anyone can understand and laugh at. Basically, the kind of jokes a stand up comedian would write.

“But I don’t want to be a comedian!” you say. Don’t worry – you don’t have to be. But learning a few tricks of the comedian trade is vital for understanding how to make your writing funny. And, believe it or not, most of it drills down to understanding one basic rule. Master this rule and you’re well on your way to injecting your writing with delicious humor goodness.

Ready? Here’s the basic rule of humor: it’s all about twisting expectations.

A good joke leads you down one train of thought and then quickly switches gears to another train of thought. (In fact, when I wrote about this in a post on CopyBlogger called The Sideways L, I compared it to a train that jumps tracks right to the moon.) These trains are still connected in a way, but the switch is so unexpected that you think it’s funny and laugh.

I prefer examples, so let me show you what I mean. Here’s a favorite joke of mine from Steve Martin, delivered in his acceptance speech for the 2005 Mark Twain Prize for American Humor. This is how the joke starts:

“I want to thank my family up there in the box, who’ve made my life so rich…”

What comes to mind when you read this? Steve Martin is thanking his family. People think, “Well, people who win awards usually thank their families”. Simple enough.

Now let’s look at the second half of the joke:

“…and my secret family in the other box, who knows nothing about the other family.”

You see what happened there? When people first hear this joke, they expect that Steve Martin has only one family. They may not verbalize it in their mind, but it’s an assumption they automatically make. Then the second part of the joke comes along, implying that Martin actually has TWO families. That’s twisting the expectation. That causes laughter.

Humor might come in a variety of formats, but most of these styles are driven by the basic rule of twisting expectations. In the coming weeks, I’ll show you how to use this rule for your own writing, but for now, just be aware of it.

YOUR CHALLENGE: Whenever you hear a joke or funny story, try picking it apart. (Yes, this does kill the humor of the joke, but in the name of SCIENCE, it’s neccessary.) Try to identify the expectation and how it’s twisted to create something funny. The more you see the rule in action, the better equipped you’ll be to use it.

I don’t know about you guys, but freelancing is an awful lot like online dating for me. For you married people out there or–worse yet–those of you who are happy being single, dating is this thing that you do when you meet a person and then you agree to talk to them over drinks. Then you decide whether you want to see them again or not (which is usually with a frequency of next to never) and then you go home and eat a pint of Ben & Jerry’s and contemplate life plans that involve paying extra for rent.

So how exactly is freelancing like online dating? Well, for starters, there’s a lot of people out there who claim to be looking for someone who’s exactly like you (tall, handsome, charges a reasonable rate) but in fact are interested in something completely different (like your best friend). I can’t tell you the countless jobs I’ve pursued with clients recently who seem totally into me only to find out later that they were just making polite conversation while getting someone else’s number. Maybe humor’s a hard niche to crack, but I’ve had the same experience trying to land even a normal gig of writing terrible product descriptions.

Still, I’ve successfully bid on a number of gigs, put out a quick article, and had a pretty overwrought response. It’s scary to have a client get attached to you so quickly. I’m used to having to work for it a little.

“WE LOVE YOU!” they’ll say, a bit too soon. I’ve only written them one article! How could they love me already? I get anxious. I’m still a man, after all. Even a whiff of the possibility of commitment causes me to run as quickly as possible in the other direction. Maybe female freelance writers have a different take on it. Maybe the promise of a commitment seems encouraging to you. Maybe it means that you go out and start looking at duvets together at Crate & Barrel. Me, I hightail it to the nearest sports bar and drink cosmos.

Sorry, but I’m not that good with beer.

Then after awhile, I start to pull away. I miss a couple deadlines to test if they really like me. I get anxious when they don’t return my emails or my invoices. I know I’ve screwed up a good thing because I’m afraid to settle down, and then I have to go outside my client’s webpage, blasting an MP3 of “In Your Eyes” by Peter Gabriel to show that I’m really the one that they want. Of course, life isn’t a romantic teen drama, so they have already moved on to a humor writer who’s maybe not as funny, but at least more reliable than I was. I find out later that they have a blog together, which sucks because I’ve always wanted to have blogs.

And then I go home to eat more Ben & Jerry’s. My recommendation is Creme Brulée because it really tastes similar to the actual dessert. It also helps you wallow in depression better, which I do after I have my heart broken. But soon, of course, I’m back out there again, bidding for new gigs with a fresh perspective and then I find it: the perfect job. We have so much in common and when we don’t, our interests are complementary. She’s looking to spend, I’m looking to take her money. And then I start to work for her, put out one great article and then…

“We love you!”

We don’t post regular one-off freelance writing jobs here at All Freelance Writing anymore because of the slim pickings for good gigs and because we want to encourage our readers to go out there and find the best gigs they can. But some freelance writing markets still do advertise and still do pay decent rates. These are generally ongoing markets (like magazines or websites with constant need for new material and new freelance writers). Today I wanted to highlight a few examples from our directory of writers’ markets that pay $1000 per article or more.

1. Entrepreneur Magazine — Pays up to $1.00 per word.
2. FamilyFun Magazine — Pays up to $1.25 per word (1000 – 3000 word travel features).
3. The Progressive — Pay is up to $1300 for investigative reporting for this left-wing political monthly.
4. Sierra Magazine — Pays $.75 per word for features (up to 5000 words).
5. The Sun Magazine — Pays up to $2000 for essays and interviews, and up to $1500 for fiction.

If you haven’t checked out our writers’ market directory yet, please do. We list all levels of paying freelance writing markets there, with rates detailed in the summary in many cases. We only feature publications that list their writers’ guidelines publicly online so you can always access their most up-to-date information (no “so-and-so says” stuff is included here). And keep checking back. We’ll continue to add new paying writers’ markets periodically. In fact, I’ll make it a point to add a few more $1000+ markets in there later today. If you have a favorite market that you’d like us to list, you can leave a comment or email me a link to the publication’s writers’ guidelines.

EDIT: As promised, I added another five writers’ markets to our directory today — all with the potential for you to earn $1000+ per article.

At 22 years old, I was making $55K per year and I was the envy of all my friends. But I was still broke and I couldn’t figure out why. For months, I was unhappy about my job partly because I wasn’t enjoying the money I was making. Then, it dawned on me – the money’s going somewhere, I just had to figure out where it was going.

So I started tracking my spending. I was shocked at what I found out. My rent was close to one-third of my net income. My next big spenders were groceries and gas (I lived 3.5 miles from work). Equipped with that knowledge, I put a plan into action that left me with an extra $550 each month. That extra money felt like a raise, but really, I was just making better use of my income.

Mismanaging your money can cause you to dislike what you do for a living. You might feel like freelance writing isn’t paying enough money, when the truth is that you’re throwing your money away. At that point, you need to take a closer look at your spending to figure out whether the problem is the income or the spending.

How to Track Your Spending

1. Get a journal or log where you can write down all your transactions. This log can be a number of things – a notebook, PDA, spreadsheet, financial software, etc. Just make sure the log you create is something you can maintain.

2. Record your purchases at least weekly, but daily is better until you’ve created a routine. You can record expenses in a few ways:

• Write them down as you go.
• Save all your receipts.
• Download transactions from your online bank account.
• Use a combination of all the above.

The key is to make sure you capture everything you spend. Don’t leave anything out.

3. Assign categories to each of your transactions, e.g. Food, Housing, Gas, Car Maintenance, Debt, Clothing, Medical Expenses, etc. Grouping your spending together helps you figure out where big chunks of your money are going. Keeping your categories generic will make it easier to eyeball areas where you’ve spent a lot.

If you want to get fancy, you can create sub-categories. For example, the Food category can be further broken down into Groceries and Eating Out. That way you can compare the two.

4. Total the spending for each category. Using a spreadsheet or financial software makes this step go faster, but if you’re not good with spreadsheets, a calculator will do just fine.

Make the Process Your Own

What I just listed is sort of the “textbook” way of tracking your spending. If it seems too tedious, I give you permission to take shortcuts where it makes sense as long as you track everything you spend.

I rarely have cash or pull cash from the ATM so that means nearly all my transactions go through my checking account. When I track my spending, I copy the data from my online checking account and paste it into an Excel spreadsheet. I assign everything a category and use the pivot table function to make a nice little chart. (The pivot table will automatically adds up your categories and formats the data into a mini-report.)

What the Results Tell You

One of the best reasons for tracking your spending is to figure out where you’re wasting money. After you’ve done this exercise, you might find that your spending is under control. Or, you may see some areas where you could cut back.

The first time I did this I discovered that there were some categories that I could reduce spending. I also noticed that every month there was a different, unexpected “one-time” expense. I started budgeting for these mystery expenses and they became less of a problem.

You don’t have to track your spending every month, but if you’re currently having money trouble, I recommend doing it at least three or four months so you can discover trends with your spending. Or, you can use your electronic banking history to analyze the past few months of spending.

Do you track spending? What interesting things have you noticed about how you spend money?

When you began your career as a freelance writer, you probably did so knowing that you were giving up some level of job security (assuming you left a full-time job to pursue freelancing). But if we’ve learned anything in recent years it’s that very few “real jobs” are actually secure. That’s often a myth.

You’ve probably also heard that working as a freelance writer will involve a feast and famine cycle. I used to believe that too. And when I believed it, it happened. And then I woke up. I remembered that no one controlled my career as a self-employed professional but me. There could only be famine periods if I allowed them to come — if I didn’t market myself effectively year-round or if I didn’t have backup plans in place. And do you know what? Once I realized that, the feast / famine cycle stopped. I haven’t had a famine period in years. You can do the same. You can make your freelance writing career an even more secure job opportunity than a full-time position. Let’s talk about how you can do that.

Diversification

You’ve seen me write about diversification in the past. I consider it an absolute essential these days if you want to succeed as a freelance writer. That said, diversification will mean different things for different freelance writers. For me it involves combining client work with projects of my own. I make money blogging and by selling e-books for example.

Diversification in freelance writing also means taking on more than one client. On the surface it might sound more secure to land one big, regular freelance writing client who pays you for nearly full-time hours — it sounds secure because it sounds similar to a regular job. But it’s not. If that client suddenly had to cut their budget, or they weren’t happy with your work, you’d be flat on your ass with no income coming in. That’s not security. Job security in freelancing means that if a door closes you have enough coming through others that the loss would barely be a blip in your earnings records.

Regular Contracts

That said, I’m all for regular clients. You’ll spend less time seeking work and more time on billable hours when you work with regulars. The key is simply to have more than one. There’s a certain amount of stability that comes from knowing you have a six month contract bringing in $1200 per month from client A, a yearly contract bringing in $800 per month from client B, and a $2000 per month contract from client C that will last at least another 4 months until that deal expires. Then your one-off projects that can fluctuate a bit more really won’t greatly impact your overall earnings so much. If clients like your work enough to commit to those kinds of time frames, chances are that they’ll re-sign when they expire too.

If you’re not comfortable setting up things like six-month contracts, there are other similar options. For example, base your rates on how much a client orders in each month. Let’s say your minimum required rate to meet your earnings goal is $100 per blog post. You could require a ten article monthly minimum for orders. This way you know if your clients are going to come back month after month you’ll have a minimum set dollar amount coming it — it won’t fluctuate radically (or at least not below your minimum).

I mentioned this is a comment on another post here today, but if you take that approach of requiring minimum orders to get your base rates, you can always charge a higher rate to clients who want to purchase less than that. It takes added time up front to get to know a new client, their business, and their target market or audience. So it doesn’t make sense to build a business around little one-off projects that might not lead to something more. If it takes extra time, there’s absolutely nothing wrong with charging more for it. They can always take advantage of your lower regular rates if they choose to order more in the future based on your minimum order requirements.

Waiting Lists

I find that other freelance writers are often shocked to hear that I have a waiting list of prospects built up. These aren’t people I went out and pitched. They’re people who found me on their own and who really want me to work on one project or another. If something needs to be completed immediately and I’m not available, I just refer the client to someone who can help. But sometimes they really want you. In that case offer to put them on a waiting list if the project isn’t urgent (and you’d be surprised how often a project suddenly isn’t so urgent when it comes down to getting exactly what the buyer wants).

Build a waiting list of your own. When you do, you don’t have to worry about one of your current clients leaving you behind. If they do, you just contact some prospects from your waiting list and see who’s ready to move forward — no gaps in work generally. And added bonus? When that first client comes back because their cheaper provider didn’t meet the standards they were used to, you can turn them down or put them on your waiting list for your next opening. That’s a gratifying feeling indeed. And if that client’s lucky enough to get you back, it’s much less likely they’ll leave you again in the future.

Continuous Marketing

I know you’ve heard this before, but it’s the truth. You have to market your freelance writing services all the time — whether you currently need work or you have a full schedule. Not effectively marketing during the busy times is one of the big reasons writers do end up with those famine periods.

It’s understandable. I’ve heard arguments like “well, if my schedule is already full, how can I pitch my services to others?” Simple answer — you don’t have to.

Marketing doesn’t mean actively pitching or soliciting work. That’s direct marketing, and only one small segment of marketing as a whole. No matter how full your schedule is now, you want to keep your name out there attracting interest from new prospects. You can do that through passive marketing tactics — like the ones we promote through the query-free freelancing way.

More passive style marketing might include:

• running your own blog;
• releasing free or paid e-books;
• releasing a white paper;
• updating and improving the copy on your website;
• commenting on others’ blogs (especially where members of your target market are).

It’s all about building your writer platform to build and maintain visibility and interest. Some of these passive marketing tactics can even bring in income of their own, adding to your diversification. If people contact you as a result, this is where you get the prospects for your new waiting list too. If you need more ideas, read 30 Ways to Build Your Writer Platform.

In the end, it’s possible to make freelance writing far more secure than your typical full-time job opportunities. It’s all in what you believe and what you choose to do about it. Are you tired of the feast / famine cycle? Have you already escaped it? Leave your stories, thoughts, tips, or ideas in the comments.