Wednesday, December 31, 2008

Hello New Year

2008 sure was a crazy year for me. As the holidays wind down, and I have some time to blog again, I reflect on this year and all the changes that occurred. This will surely go down as one of the most significant years of my life. Here are some highlights:

1. I created my own freelance business.

2. I broke up with my boyfriend of 4.5 years.

3. I moved into my own apartment for the first time.

4. I was cast in my first show.

5. My sketch group had their first performance.

6. I learned how to create and edit videos.

Who knows what 2009 will bring. But I'm excited to find out.

Friday, December 19, 2008

Christmas Time is Here

It's been a while since my last post. I've been very busy preparing for the holiday season by trying to get as much of my work done as possible. I'm still going to have to do some writing while I'm in Dallas next week, but I've gotten a good head start on most of my work.

Although the holidays will be a welcome break from work, I can't help but to dread the new year. The economy is still tanking, reports of layoffs abound and I know many companies that are going under or filing for bankruptcy.

But it is these times that test the grit of a freelancer. If you can survive this, you can survive anything. It just takes an added push and effort. Which is why I am planning on launching a large marketing campaign for myself (as mentioned previously). I've been working on a prospective client list, generic proposal letters and sales sheets. I've got my Web site up: So check it out.

If anyone has any advice they'd like to share about finding work during these tough times, then please post a comment.

Have a happy holiday everyone. Hopefully I'll get to post at least once more before the new year.

Oh, and here's my most recent video, which premiered at an Equality Illinois benefit show:

Monday, December 8, 2008

Surfing the Webs

I've been working on a my Web site as a component of my marketing push. You can check it out here: Feel free to give me feedback. It's still a work in progress, so not all the links are up and running yet.

While creating my site, a dilemma arose. I want to link to the various presences I have on the Internet, from this blog to my YouTube videos to work I've done professionally. The only thing is the kind of writing I do for work is corporate. I wasn't sure how well my comedic personality would be accepted by my current and potential clients. But the more I thought about it, the more I realized that these two worlds will have to mesh eventually. I mean, do a Google search of me, and you'll find many articles regarding points of law that I've written as well as me wearing a fake mustache and singing about Vietnam. In fact, you should watch that video because I just posted it. It was an entry into the Second City Training Center's Film Festival.

So although my business site isn't littered with my comedic work, it makes mention of it, and links to examples. Besides, you never know if one of my legal clients might occasionally want someone to write something that injects a little humor into the typically dry area of law.

Thursday, December 4, 2008

Christmas Time Is Marketing Time

As a small business owner, Christmas time isn't just about Santa Claus and presents. It's about giving. And by giving I mean giving holiday cards to your client base.

The power of a handwritten note should not be overlooked. Sending holiday cards to your clients, especially those that have retained your services over time, is a great way to remind them that you truly appreciate their business.

You don't have to write much. No gushing statements like, "Thank you for allowing me to eat and sleep in a bed." But a "Happy Holidays. I appreciate your business," suffices just nicely.

Also, you might want to think about getting generic secular cards (unless your client base is purely Christian organizations). You never know what someone's take on the whole "War on Christmas" thing will be. So find something with a snowman or a snowglobe or snow that says winter without saying Jesus.

Wednesday, November 26, 2008

Holidays Celebrate!

I've been a little lazy with these posts. A lot of this has to do with the fact that the holidays are upon us, and I'm rushing to get as much work done as possible. Work tends to slow down around this time of year, so as a freelancer this is necessary hunting and gathering time so that we can have a stockpile of moolah for the winter.

The holidays can really throw a wrench in a freelancers business. First, if you conduct interviews for your pieces, a lot of sources are out of town. This can make that pressing deadline even more intimidating because, if there's one thing you don't have control over, it's your sources getting back to you.

Second, people just don't have the time to dole out work to you as much. They're busy closing up shop for the year and getting their workload done so they can chug down eggnog at the office Christmas party without having to think of that report on their desk. So it's a good idea to plan in advance for this time of the year, whether that menas doing extra work in October and November or bugging your clients incessantly a month before Christmas.

Finally, you as a freelancer don't want to work during the holidays. You've worked hard all year. Take a break already. But there's no break for a freelancer. No work means no money which means no fun. So although you might feel like kicking back and enjoying a big turkey dinner or a few carols by the fire, you really should be pestering clients, cruising job sites and conducting as much work as possible so that you don't fall out of practice when the real work starts coming in during the new year.

Now if you'll excuse me, I got some stuffing with my name on it.

Wednesday, November 19, 2008

Now There's That Fear Again

Besides being a writer, I am also a performer. I never meant to be a performer. I always wanted to be just a writer. This comes out of a place of fear. I have terrible, terrible social anxiety. The thought of going to a party alone terrifies me as does acting on stage.

Funny thing is, I've been on stage probably about 50 times. I know it's not much, but for someone who harbors the kind of fear I do, that says something. In fact, I have a performance tonight. And I'm more nervous about this one than most because a lot of my friends will be there. You'd think I'd have more security in my performance since I have people that care about me sitting in the audience. But it's the fear of their judgment and letting them down that really bothers me. And this fear is utterly irrational.

Being afraid of networking or giving a public speech or performing on stage is always irrational. But that doens't mean just identifying the irrationality of the situation makes everything okay. You have to first recognize your fear and then accept it. Stage fright isn't going to go away over night, and in fact it may never go away completely. But if you accept that it exists and understand that it is irrational and concentrate on the task at hand, the nervous energy that was once fear will be channeled into your performance to make it even better.

I'm hoping to break a leg out there tonight. I know I got talent, and I have nothing to prove to anyone. I'm giong to go out there, accept my fear, and give a great performance.

Wish me luck.

Tuesday, November 18, 2008

Third Time Is Not A Charm

Ah editing. Is there nothing less thrilling than having to go back to a piece that you already wrote and retool for the sake of a client? No really. But it comes with the territory of being a freelance writer.

Industry standard is to allow two rewrites included in the cost of the project. If you're charging an hourly rate, then you charge the rewrites using the standard hourly rate. If the amount of rewrites goes beyond two, then you should have a stipulation in your contract or Letter Of Agreement which states that there will be additional charges.

I've never really had this situation arise quite yet (knock on wood). But I'm sure it would result in client pushback. And nothing is worse than client pushback. It's a tenuous situation. On one side, you don't want to upset the client because after all you want to retain their work in the future. On the other side, you got to eat and pay rent. My advice is any client that will jerk you around and try to get you to work for free or make additional demands without promise of pay is not a client worth working for. It's tough to cut ties with a client, but in the end it is best for your sanity and yoru busienss. You might be able to come up with a compromise, such as doing the additional work at the standard rate, but you should be compensated no matter what.

We as freelancers need to uphold a certain level of self-respect. If we let our clients walk all over us, we are doing a disservice to the freelance community as a whole.

Friday, November 14, 2008

Where's My Weekend?

I was sick again. Something happened when I was getting better last time, and I regressed. But I'm on meds so I'm getting better.

I'm swamped with work this week. I have three major deadlines looming over me, and it looks like this weekend won't be much of a weekend at all.

A trade off with being a freelancer is that although you set your own hours, sometimes those hours kind of suck. Yeah, I typically pull a 4 to 6-hour workday during the week, but oftentimes that requires me to put some time in on the weekends. I'm fine with doing this. I'd rather have my freetime spread out throughout the week rather than bunched up in two days. But others don't function that way. To each his own.

It also helps that I do my best work on deadline. So I don't mind working on a Saturday or Sunday if my deadline is on a Monday because I know what I produce is going to be solid. Also, it's incentive enough to know that getting an assignment turned in at the end of the weekend will ensure a lighter load throughout the week.

So to all those people that poo poo working on the weekends, remember that while you're sitting in your office watching the clock tick until five, I'm busy going to the gym, buying groceries and folding my laundry. Suckers!

Monday, November 10, 2008

Many Hats: IT Technician

I'm on hold right now with Epson, the printer company. My printer broke a couple weeks ago, right in the middle of crafting several outlines, a process that entail printing out my interviews and reviewing the information I've gathered. I tried my darndest to fix the printer. I replaced the ink. I ran a number of diagnostics and tests to try to get the thing to work. Nothing. In the end I had to purchase a new printer.

But this incident, like so many I've encountered as a freelancer including the destruction of my laptop at the hands of my cat, highlights an important element of freelancing - the wearing of many hats. As a self employed person, you play every role within your company, both front office and back office. One of these back office roles that we must play is IT technician. And despite specializing in writing about technology, I know very little about fixing the stuff.

I think it would probably benefit any freelancer to take a few courses on IT troubleshooting. Whether its understanding how to troubleshoot certain, frequently used appliacations, such as the Microsoft Office Suite or Adobe Suite of products, or hardware, such as printers, computers and digital cameras, learning how to solve your own problems without turning to a costly technician can save you a lot of money.

That said, any expenses accrued from fixing your office equipment are tax deductible. So save those receipts! You might be kicking yourself for having to buy a costly new printer, but at tax time, you'll be happy to see the tax relief you get from your technical incompetence.

Friday, November 7, 2008

What the Hecktomy

Sorry it has been a few days since I last posted. I relapsed and became sick again. It happened at the Obama rally (whooo! Go Obama!). I was standing in Grant Park in Chicago for 5 hours. When I got home, my legs felt like they were on fire. I figured it was due to muscle fatigue. The next morning my entire body felt like my joints had rusted, and my forehead felt like an oven. I went to the doctor who told me that basically anything that could be infected inside my head was infected (sans my eyes thank God). He gave me some antibiotics and sent me on my way. Did I mention this was on my birthday? Yeah. Yay me!

The doctor did mention one other thing. He recommended that I have my tonsils removed. Now getting those little buggers at the back of your throat removed when you're a kid? No problem. You heal in about four days, and you get to load up on all the Ben & Jerry's you want. Getting your tonsils removed as an adult? You bet your sweet ass you're going to be in for a world of pain. People have nearly died from getting their tonsils removed thanks to bleeding that can errupt suddenly and cause you to lose pints of blood in your sleep. And I live alone!

How does this little anecdote fit into the theme of this blog? Well, I think there's a good parallel between my potential tonsilectomy and self editing. Listen.

A tonsilectomy is painful because you are getting something chopped out of you that is literally part of you. Self editing is figuratively doing the same thing. Recovering from a tonsilectomy can be a slow and grueling process. Self editing is most often a slow and grueling process that makes you want to cry and bang your head against your desk at the same time. No amount of anesthesia can truly take the pain away that results from a tonsilectomy. There is no cure for the pain caused by self editing.

Self editing is an art. And you can bet this isn't going to be the only post I write about the topic. It's a big topic for me. As a technical writer, I self edit fairly casually before turning a project in. That's because my client typically gives the piece a first-pass edit themselves. Comedy writing, on the other hand, is much more frustrating. I don't have the luxury of having a comedy editor at my disposal so I bare the entire process of writing and editing on my shoulders. True, I can have fellow comedians look over my jokes and give me tips (which is a great thing to do mind you). But more often than not, I have to rely on myself to trust that what I write is good quality. Luckily I'm insanely hard on myself and am truly a perfectionist, so I'm only content with something when it's probably about 10 times better than it actually needs to be.

Anywho, I'm going to continue reading horror stories about tonsilectomies. If you have any experiene with tonsil removal or know someone who has, leave a comment. I'm really curious about other people's personal experiences.

Monday, November 3, 2008


Oftentimes as a freelance writer you find yourself juggling multiple pieces at once. This can really cause a lot of confusion, especially if your topics blend into one another. Currently I'm working on three major pieces, all dealing with the legal industry and each having to do in some way with litigation. The deadlines are days apart.

Some freelancers probably work on one piece until completion until working on the next. Others flip back and forth from one assignment to another seamlessly. I take a mixed approach. When writing, I make sure to finish a first draft of one piece before beginning another. However, while writing on piece, I can still review notes and create an outline for my next piece. Whichever piece is due first is almost always the first piece I tackle, though if deadlines are no more than a day or two apart, I might weigh it by which assignment is more work intensive.

What it comes down to is knowing your work ethic. If you are a great multi-tasker, than by all means take on as many assignments at once as you can. But if you are a more linear worker, than you might have to really work hard to complete multiple assignments on time. Devise a method that works for you and stick with it. Take some time periodically to scrutinize your method and see if there are improvements can be made. Freelancing is all about efficiency, and the most efficient process will yield the best results.

Friday, October 31, 2008

Happy Halloween

It's Halloween! And I'm not deathly ill anymore! But I feel kind of fat because I've been eating a lot of candy. But it's Halloween! So everyone probably feels fat too. That makes me feel better.

Anywho, because this blog is one part freelance writing advice and one part comedy, I wanted to let you all know that I have completed the short film I've been working on and will post it to the site soon. The movie is near and dear to my heart as I, along with my creative partner, spent about a month on it (writing, acting, filming, directing, editing, etc.). If you like folk music, whiskey and murder, you'll love the flick.

I'm going to the Lincoln Lodge tonight to check out some spooky stand-up and then hopefully party a bit with some people afterward. But all play and no work makes me a poor poor boy. So before the festitivites get into full swing, I should probably get some things done. Actually, I probably should get out of bed first. It's 11 am? Really?

A Day of Pay

The other day I had a client request that I attend a seminar, which I am to cover for a custom publishing piece. She asked me how much I wanted to be paid for the day. That took some thought.

In the relatively brief time I've been freelancing, I have grown accustomed to working from the comfort of my home, oftentimes in my underwear. But sometimes a client requests that you actually leave your dwelling and attend something...with daylight. When this happens, you damn well better request they pay you for your time. Because the last thing any freelancer wants to do is wake up earlier than 9 am, wear a suit and ride a train downtown like a person with a real job.

But how do you come up with a day rate? Should it be a different rate than what you charge for writing? Does it depend on the event and how much work you will have to do there? For my assessment, I first broke the day down into hours. A full workday is 8 hours, so I decided to come up with an hourly rate and multiply it by 8. But what hourly rate should I charge? I typically bill a pretty penny for writing work since I provide quick turnaround and top quality. But this part of the project didn't involve writing. It just involved me sitting there and taking notes.

After wrestling with trying to nail down an hourly rate that A) was adequate for me and B) wouldn't scare away my client, I decided to take a different tactic. I estimated 20 workdays in the month. Then I calculated an adequate monthly pay and divided that by 20. And that was how I came up with my day rate. And my client was pleased with the number. Frankly I'm sure I lowballed myself a tiny bit, but mind you the second half the assignment (the written part) pays at my usual rate, so I was willing to give a discount for the promise of more pay on top.

Monday, October 27, 2008


I'm back in Chicago, and I'm sick. Nothing disrupts business or comedy like being sick. It's worse than travel. At least with travel, you aren't spacey all the time and can write a coherent sentence. That, right now, is a challenge for me.

And because of that, I'm keeping this post short.

Thursday, October 23, 2008

Days Off

I’m in the midst of traveling to Missouri right now to visit my old college town and some old college friends who never left. I’m on a bus, and my Internet connection is very spotty, at best. This is the first time for me to leave Chicago since May. I need to get out more.

Travel is hard for me. And I suspect it is hard for many freelance writers. True, you can take your work on the road. But that can be a pain. Where’s a convenient printer? A fax machine? A decent workspace? And even if you find a decent workspace, it’s still not your workspace because there’s no monkey-head-shaped pen holder or a picture of yourself with a mustache drawn on it to inspire you.

Then there’s the lack of consistent Internet connection. The Internet is my lover. And I am in a very unhealthy relationship. If I can’t check my e-mail every five minutes, I get twitchy. In fact I think I might be freaking out the passenger sitting next to me with all this twitching. Come on e-mail! Work! Anywho, I do always make sure to set up an automatic away message prior to embarking on my travels. It gives me some piece of mind. That way if a client or prospective client or comedy agent or Hollywood producer decides to e-mail me while I’m on the road, they’ll at least know why I’m not pouncing all over their message like a cougar on a fat baby.

Also, I like to not have to do too much work when I’m traveling for pleasure. So I try to do everything I can to clear my schedule before making my trip. This can be difficult in that it either requires me to work extra hard in advance to create some downtime, or it requires me to not aggressively search for new assignments and just take advantage of the lull. This time I did a combination of the two. Last week I worked my fingers to the bone interviewing literally 20 sources for a major feature I’m working on. I also could have pursued some more work to fill up the last part of this month and parts of mid to late November. But I didn’t so that I could really enjoy myself. Hey! I deserve it.

Also, as a freelancer, traveling or taking a vacation requires a cost/reward analysis. Is the cost of losing some work worth the reward of the trip? For me, I needed a break from the city, and I’ve been working basically non-stop since I began my freelancing career in June. So for me, the analysis was simple. In addition, while on the road, I don’t really have the ability to work on comedy. I’m in the middle of editing my second video short (which I co-wrote, directed, filmed and acted in as well). I can’t do any editing while I’m gone since all my footage is on my external hard drive, which I didn’t bring for fear of damaging or losing. I’m also missing an improv rehearsal on Saturday. But still, there will be time for making funnies when I get back. And the rest might help refresh my comedic abilities, since being funny all the time can make one a little too serious.

Monday, October 20, 2008

Different Strokes

Some creative writers like having pay jobs that are as monotonous and mindless as possible. These are jobs like secretary, receptionist and anything with the word "assistant" in it. For these creatives, devoting half the day to being bored creates a build-up of creative juices. When the writer finally gets home at the end of the day and curls up next to his or her laptops with a cup of green tea and a bag of Funions, the dam built up by the work day is torn down and a flood of quirky ideas comes pouring forth. The downside is sometimes the job is so boring that its wears you out. Yes, you can actually become fatigued from being bored. So that by the time you get home, all you wan to do is brew some green tea, crack open the Funions and stare at the wall because you've done enough data entry for the day to fill a Bible.

Other creatives opt to have interesting jobs that they feel facilitate the creative process. Jobs like antique furniture mover, meter maid and baker fit into this category (all jobs I've held by the way). These jobs offer fresh, new experiences for the creative to use as material. The downside: They can be fairly labor intensive. Antique furniture is heavy, and sometimes all you want to do after lugging a 500 lbs. marble birdbath up a flight of stairs is crack open a few beers and call it a night.

Finally, some creative writers actually choose to write to balance their lives. Currently that's what I'm doing. I write technical copy during the day and funny, wacky sketches, jokes and scripts at night. For me, this is the best fit. The two really seem to feed off each other. The techincal writing is very structured, which increases my ability to structure my comedic writing. The comedic writing is about finding your audience, which really feeds into my ability to hone in my technical writing audience. The downside to this is I can get pretty burnt out from writing so much all the time.

Which is why I still don't know why I started this blog.

Let me know what you do to balance out your creative side and keep your checking account above the zero mark.

Friday, October 17, 2008

Let's Be Logical

It's a writer cliche: "There are numbers? I can't do numbers. I'm terrible at math."

The creatives love to boast about their mathematical and logical ignorance. I guess the worse you are at math, the more likely you are to be the next Kerouac. And if that's true, then I'm surprised Kerouac could count to 10.

But it's not true. Creative people can be logical. And it doesn't have to detract from how creative you are. It's a lot easier to think outside of the box if you can measure the dimensions of the box first. Otherwise, how else would you know you were thinking outside?

Personally, I've always tested higher with my math skills. On the SATs I got a near perfect score on the math section. I did well on the verbal section, too. But on paper, I obviously was destined to be a scientist, a savant or a guy that guesses your weight at carnivals. And I almost went to college to become an electrical engineer because, after all, tests don't lie. But what I realized was that my love of logic and mathematical apptitude doesn't counteract or negate my creative abilities. In fact, it can enhance them.

Good writers, good creative writers like Dave Eggers, Sarah Vowell and those of that ilk, do a tremendous amount of research when working on their books. Comedians like Patton Oswalt and Maria Bamford spend a lot of time poring over their jokes, refining them to maximize their laughter quotient. A script writer must calculate the unveiling of a plot in order to ensure that the pacing will be exactly right. All of this takes a very skilled, highly functioning left brain.

So let's do away with the old cliches and embrace our nerdy, logical sides. Pens and rulers unite!

The First Post

We all love blogs, don't we? They're so easy to make. A few clicks on a Web page and you have an open forum to discuss any topic you want. You are publisher, editor and author. Ultimate control!

That's something we often don't get as a writer. If you're in house at a publication or an agency, odds are you're answering to your editor. If you're the top editor, then you're probably answering to your publisher. If you're independent, you're answering to clients. And everybody is answering to an audience.

But a blog is selfish. It's your opportunity to spout off about your views on politics, that Mexican restaurant down the street or your roommate's lack of hygienic knowledge. You don't even have to play to the tastes of an audience because in the world of the Internet, the audience will find you.

However, sometimes, as a writer, it's not a bad idea to actually take this blog thing a little seriously. And although I've birthed countless blog bastards throughout my life, most of them have withered away and died due to a lack of love and affection. And I think the reason being was none of my blogs had a clear-cut goal. They've all been meaningless ramblings about what's going on in my life. They were tickets to ultimate freedom, a world of unbridled writing that didn't have to play to the whims of anybody.

I'm tired of contributing to the overcrowded Internet landfill, which is full of abandoned Web sites and blogs. I want to create something meaningful, something with purpose.

This blog is that. By day I am a technical freelance writer. By night I am a comedian. One is left. The other is right. One is Bruce Banner. The other, the Incredible Hulk. Balancing these two sides of myself is a challenge. But it is possible, and doing it successfully can be very rewarding.

This blog is dedicated to the battle between the left and right sides of the writer's brain, and how it doesn't have to be such a tug-of-war. There can be peace. Even prosperity. You just have to expand your mind.