Outrunning The Little Man: Dealing With Impostor Syndrome

There’s only one person I’ve ever been afraid of my entire life.

He’s average height, and skinny, very skinny. He’s got a bad combover, wears outdated glasses that are too large for his face, and a tie clipped onto a pistachio green short sleeve shirt. He’s an older Kip from Napoleon Dynamite. He’s very officious, and kind of an asshole. The kind of guy who loves wielding his teeny-tiny bit of power over other people’s lives.

I call him “The Little Man.” He’s not little in size, but in spirit and vision.

I live in fear of the day The Little Man knocks on my door. He’ll look at a form on his clipboard and say, “I’m sorry” — except he’s really not — “but there’s been a mistake. You’re not supposed to be a writer. You’re supposed to be a claims adjuster. Sign here, please.” I’m afraid The Little Man is going to show up one day and take everything away because of a clerical error.

Impostor syndrome makes people worry there's some bureaucrat out there trying to get us and fix some error about our lives.I’ve been looking over my shoulder for The Little Man for the better part of 30 years. Ever since I published my first column in my college newspaper, I’ve been trying to outrun him.

It’s like the movies. The hero runs as fast as he or she can, knocking shit over into the bad guy’s path. But the bad guy just steps over everything like it’s not even there.

So I’m amassing evidence to slow him down and prove him wrong. Evidence to show that his form is wrong, and that I’m where I’m supposed to be.

I’ve thrown four books in his path. Twenty-one years of newspaper columns. Thousands of blog articles. Writing awards. Writing residencies. Speaking opportunities. But he won’t stop. I’m throwing it all in his path, and he won’t even look at it. He’s a mindless bureaucrat, a drone who refuses to see evidence in front of him or use common sense. He only believes what the paperwork says, despite what real life is showing him.

I’ve been running for 30 years, and he won’t stop coming.

I thought I escaped him once last year, when I was a writer-in-residence at the Jack Kerouac House in Orlando. It’s a prestigious residency where only four writers are chosen out of over 300 applicants from all over the world. To me, this confirmed that there had been no error, there was no form on a clipboard.

“This will stop him,” I thought. “There’s no way he can find me here. I’m supposed to be here. They said so.”

But when I stepped inside and closed the door on my first day, he was right there on the sidewalk in front of the house, staring up at it. In fact, it was the closest he’d ever gotten.

He chases my other artist friends too. They’ve seen him, following them wherever they go, whatever they do. To a man and woman, they’ve all seen him, no matter how successful they get, no matter how much stuff they throw in his way.

In fact, the more successful they are, the closer he gets. So we all run faster and work harder, and throw more stuff in his way. But he steps over it and continues on.

It’s a rare artist who isn’t afraid of him. Every capable creative professional I know keeps one eye on their work, and the other looking over their shoulder.

The ones who aren’t afraid often don’t know enough to be afraid. They’re not committed to their craft and they don’t take it seriously. The Little Man leaves alone those artists who wait for inspiration or think they’re masters of their craft. (Because even the real masters don’t think they’re masters; they’re looking for The Little Man too.)

So we work, because that’s the only thing that lets us outrun him. It doesn’t stop him. He never stops. Because he’s waiting for the day that I stop, when I give up and quit running. That’s when he’ll get me. That’s when I’ll have to take his pen and sign his form, and finally give up on my dreams.

But that’s not today. Today, I still have things to do and dreams to win. I still have the energy and the drive to work, and to outrun him one more day.

Photo credit: Max Pixels (FreeGreatPicture.com, Creative Commons 0)

How to Learn and Understand Anything

Jon Barney is an up-and-coming writer in the Orlando, Florida area (originally from Lafayette, LA, and has a lot of big ideas about a lot of things. Jon says he has an amazing wife and two kids, and he “loves the hotel restaurant industry and corny jokes,” which makes him a man after my own heart. Jon has an interesting process about he does a deep dive into any idea, process, or event that interests him.

We live in the information age. You can access the entire world from anywhere. Add in 24-hour news feeds, posts, tweets, snapchats, marketing and you are flooded with information.

The problem we face is overload. There is no way possible to download all the information thrown at us. Our brains are like sponges, absorbing information, but it reaches a saturation point. How much water can a full sponge soak up? None. Our brains operate in the same way — if we can’t fit new information into our brains, it gets swept away, and we move on to the next piece. Or we stop taking information in altogether.

Want to learn how an internal combustion engine works? Break down the process and redefine complex terms.

Want to learn how an internal combustion engine works? Break down the process and redefine complex terms.

To understand anything, turn on your childlike curiosity. When I was a kid, I was super annoying (some would say I still am) because I always asked “Why?” Every answer I received led to more and more questions.

After my mom said “Because I said so, that’s why” a thousand times, I realized my parents didn’t have the patience or knowledge to satisfy my curiosity. Instead, they sent me to school to let someone else deal with me for a while. I kept going off on tangents because the “broad overview” we were getting wasn’t enough. I wanted to dive into each subject, but knowing everything about American history doesn’t help you pass math. To satisfy my curiosity and keep my grades up, I had to learn to understand ideas at lightning speed.

I learned from that experience how important questions are. You have to ask the right questions to find the right answers. We all know that, but do we actually do it?

Think about these two questions “What is the meaning of life?” and “What is the meaning of my life?” Which one is easier to answer? The right question leads you to the key concept in the shortest amount of words. To find the right question start with the 5 basic ones: who, what, where, when and why. Answering those will help you create a more specific question and help you find your meaning.

Break Things Down to Their Smallest Digestible Parts

Let’s say I want to know how an engine works. I go through the 5 basic questions to form the right question. Who designs engines? What is an engine? Where do they make them? When was the first engine built? Why did someone invent the engine? The answers are difficult to understand because they are written by engineers for engineers.

I take all the research I’m doing and find any words or processes I don’t know and redefine them. (Good thing I have that Google Dictionary in my pocket.) Next, I remove technical jargon and insider slang from anything I’m reading and replace them with synonyms I already know. Using words you already know frees up your brainpower to search for meaning in the idea instead of being a dictionary.

You have all of this easy to understand information but not enough memory hold every detail in. Use the KISS formula — no, not painting your face — Keep It Simple Stupid.

How do you do that? Think of a deck of cards as your information, and break it down into groups. You know there are 52 cards, 26 of each color, 13 of each suit and 4 of each value. You have to do the same thing with information and go for the lowest common denominator.

It’s actually a complex process to understand and find meaning in things. You draw on all your life’s experiences, memories, emotions, opinions, life situations, and influences just to come up with something you can understand. That’s a lot of mental computing just to see if the story about increasing oil prices will affect you.

Making It Simple Makes It Stick

I mentioned breaking everything down in common language terms earlier for a reason: There is no point in having all the knowledge in the world if you can’t share it.

I had a sales job for a while, but not very long because I was terrible at it. I couldn’t sell water in the desert. One day my sales manager explained why I wasn’t selling anything.

“Jon, no one understands what the hell you are talking about. If you can’t explain it to a 5th grader don’t say it to your prospects!”

I quit eventually because I was tired of not eating, but I also learned two important lessons. Test your pitch on someone first. And big, fancy words are nice for term papers or to impress your snobby friends at the coffee shop, but they don’t help people understand complex ideas. Teaching someone else locks the information in your brain by building mental short cuts.

Understanding anything is simple if you can remember: to be annoying, ask smart questions, play cards and that no one cares if you know what sesquipedalian means.

Photo credit: Mj-bird (Wikimedia Commons, Creative Commons 3.0)

Plagiarism is the Writer’s Cardinal Sin

This whole Melania Trump plagiarism flap shouldn’t be a big deal. I think if it weren’t for the fact that it’s the Republican National Convention, we wouldn’t have even heard about it.

It’s never a big deal any other time a public figure has been caught plagiarizing. Sure, it makes the news, but most people could not care any less. But to creative professionals, especially writers, this is yyy-uge.

News analysts reported that Trump’s speech was 7% similar to Michelle Obama’s 2008 DNC speech. That may not seem like much, but by college academic standards, that 7% can get you an F in your class, and even get you thrown out of school.

A PhD friend of mine commented on my Facebook status yesterday that she normally checks her students’ papers with Grammarly’s plagiarism checker. She ran a quick check on the two speeches, and found that roughly 7 – 8% of Melania’s speech triggered the plagiarism alert, which would have resulted in an F for the paper. Other friends in academia said they have failed students, including those in Masters programs, for 7%.

Some people are dismissing Melania’s plagiarism as “just common words.” That anyone could have used these words, and that we’re making a big deal out of nothing about these “common supportive phrases.” They think it’s a complete coincidence that the same common words and phrases discussing the same ideas were assembled in that same order.

Let’s take politics out of it for a moment. Forget that this is the wife of the Republican presidential candidate.

As a professional writer and adjunct professor, I can tell you that, common words or not, this is still plagiarism. When you take a series of words and string them together in a particular order, no one else may string them together in that order, unless they cite you as a source.

Even failure to cite your sources is enough to fail your paper.

Ernest Hemingway: Common Words Used Uncommonly

Ernest HemingwayOne of my favorite Hemingway short stories, Big Two-Hearted River, is filled with common words. It’s 8,015 words long, and written at a 4th grade reading level. There are no unusual words, and there’s only one character, Nick, who’s going camping and fishing. Two pretty common activities with common jargon. Here’s my favorite excerpt from the story:

Nick was hungry.

He did not believe he had ever been hungrier He opened and emptied a can at pork and beans and a can of spaghetti into the frying pan

“I’ve got a right to eat this kind of stuff, if I’m willing to carry it, Nick said.

His voice sounded strange in the darkening woods. He did not speak again.

He started a fire with some chunks of pine he got with the ax from a stump. Over the fire he stuck a wire grill, pushing the four legs down into the ground with his boot. Nick put the frying pan and a can of spaghetti on the grill over the flames. He was hungrier. The beans and spaghetti warmed. Nick stirred them and mixed them together. They began to bubble, making little bubbles that rose with difficulty to the surface- There was a good smell. Nick got out a bottle of tomato catchup and cut four slices of bread. The little bubbles were coming faster now. Nick sat down beside the fire and lifted the frying pan off. He poured about half the contents out into the tin plate. It spread slowly on the plate. Nick knew it was too hot. He poured on some tomato catchup. He knew the beans and spaghetti were still too hot. He looked at the fire, then at the tent, he was not going to spoil it all by burning his tongue.

No big words, very few 3-syllable words. In fact, he used just 124 different words. But Hemingway could take those 124 words and make cooking a camp dinner one of the most interesting stories you’ll read all day.

Hemingway’s use of common words is not the issue; we’re all able to use them. I could even write a story that only uses these 124 words. The problem is, I can’t put them in that order.

I can’t use the phrase “‘I’ve got a right to eat this kind of stuff, if I’m willing to carry it,’ Nick said.” without either giving him full credit or suffering the wrath of academics and literary types. I can’t even change a couple of words and present it as mine.

That’s plagiarism.

To most of us who actually care about this — the academics, the literati, the word nerds — it doesn’t matter who plagiarized. The fact is, it was done, and it’s being dismissed as unimportant by people who don’t realize the importance of intellectual property.

Probably because they’ve never had their creations stolen for someone else’s benefit.

This is What Theft Looks Like

No Burglars signThis is an important issue to me, because I’ve been plagiarized on three separate occasions, all by newspaper professionals. Two editors, one publisher. Two Canadians, one American. Three people who financially benefited from something I do for very little money.

Three people who worked in a profession where there are only a few important rules:

  1. Don’t steal shit.
  2. Don’t make shit up.

That’s it. Those are two of the most important rules in journalism, and violating them is a career ender.

Of the three thieves — and they are thieves — the American editor and the Canadian publisher lost their jobs. The publisher lost his membership in the Alberta Press Council, and may have even stepped down as the president of the Strathmore and District Chamber of Commerce. The American newspaper editor will never have a job in newspapers again.

You can Google both their names, and their sins still follow them, five years later.

In the world of creativity, especially its written form, plagiarism is the cardinal sin. Of all the Thou Shalt Nots in the world, it is the Thou-Shalt-Nottiest.

Bottom line, it doesn’t matter who did it. I think it was an error of process, not malicious theft. If I had to guess, it was a speechwriter who watched a lot of different convention speeches by candidates’ wives, took notes, and used the phrasing without remembering where it came from.

(UPDATE: It turns out, Melania read some phrases from people she liked, including Michelle Obama. The speechwriter, Meredith McIver took notes, and used them in the speech. Then, she said she never checked Michelle Obama’s speeches to see if the phrasing had been used before. So, not malicious, just careless.)

Because despite what she said, Melania didn’t write this herself. Everyone who gets on that stage gets vetted, ghosted, and edited. There are so many people with so many fingers in every pie, nothing is written by a single individual with no oversight.

But worse, much worse, is the attitude that this isn’t a big deal. That the media is making too big of a fuss. Or that the Obamas did it eight years ago, so that makes this one less bad, or even acceptable.

Politics aside, this is never acceptable. Whether you’re an apologist or a grubby-fingered troll digging up dirt on the other side, plagiarism and theft of ideas is never acceptable.

If you have never created something and had it stolen, you can’t understand why this is a hot button issue for so many of us. As a writer whose books are regularly pirated, as a journalist whose columns are pilfered, I believe this is the one line that writers of integrity should not cross.

Do not justify the sin, regardless of who committed it. There are no excuses, you can’t buy indulgences, and it should never, ever be waved off as a staggering coincidence of “common words.”

Erik Deckers Interviewed on The Business of Story Podcast

I think I could just build a media career by appearing on every Jay Baer podcast he and his company produces.

Earlier this week, my interview on The Business Of Story was released — my third interview on Jay Baer’s third podcast. (You can hear my interview, “Top Tips from a Humor Columnist on How to Tell Better Brand Stories” here.)

Erik Deckers Teaser for The Business of Story podcastPark Howell, a content marketing and storytelling professional, interviews different writers and storytellers, talking about to use proper storytelling in the business world. He’s interviewed screenwriters, film makers, editors, directors, makeup artists, and voice over actors (including Dick Orkin, the creator of Chicken Man, which I used to love!)

We had a chance to talk about humor writing, and how it can be used in the business world. Some of the topics we discussed include:

  • Why infusing your writing with humor will improve it dramatically
  • How to break down comedic theory to make it accessible and useable
  • Why you can absolutely can learn to be funny
  • How stories are more approachable and more memorable with comedy
  • Why some are hesitant to use humor in the workplace, but it is a misplaced fear
  • How to absorb lessons from great fiction writers

Anyway, give the show a listen and let me know what you think. And be sure to check out Jay’s other podcasts for more great marketing information.

Beware Mark Schaefer’s Blueberry Shock

Mark Schaefer alarmed content marketers two years ago when he warned of the impending content shock. The idea that the amount of information on the Internet was going to grow 600 percent between 2014 and 2020.

In other words, if we designate the amount of information online in 2014 as “one Internet,” we will have six more Internets of information by 2020. We doubled in “Internets” from 2014 to 2015, and again in 2017.

Except, we as humans only watch, read, or hear 10 hours worth of content each day. That’s reading articles for work, listening to the radio during our commute, and watching TV or reading at home.

But the amount of information available will continue to grow, most of it bad to mediocre, and all the good stuff will be buried.

Hence the shock.

What does this have to do with blueberries?

Mark Schaefer's blueberry harvest. This is when the blueberry shock began!

Photo by Mark Schaefer

Everything!

Mark Schaefer posted the following on Facebook today:

This is the entire 2016 harvest from my three blueberry bushes. This might seem sad until you learn this is a 100% productivity gain over last year.‪ #‎Winning‬

Winning, indeed.

While Mark laments that he only has two blueberries, he also realizes that he has, in fact, doubled his harvest from last year. If he can continue this trend, he’ll double it again next year, and have four blueberries. And eight the following year.

He’ll be able to celebrate 2020 — the year the Internet will have grown by 600% — with 32 blueberries. That’s nearly 2/3 of a pound of blueberries.

That’s when things will start to go terribly wrong.

There’s an old saying that if you double a dollar 20 times, you’ll have $1 million.

If Mark’s blueberry trend continues, in 20 years, he’ll have 1 million blueberries — 1,048,576, to be exact.

Satirical chart of blueberry growth representing blueberry shock; I adapted it from Mark's original content shock chart.

If we assume an average of 50 blueberries in a cup, and 4 cups of blueberries equals 1.5 pounds, Mark will have 31,457 pounds of blueberries by the year 2035. That’s 15.72 tons of blueberries.

And while that number is only .0055% of the total US production of blueberries in 2015 (563.2 million pounds), it’s still a staggering number.

Will this have a significant impact on overall blueberry prices? What sorts of steps must we as a blueberry-consuming public take? Will his friends and neighbors be flooded with buckets and shopping bags filled with blueberries mysteriously left on their porches in the night?

We need to be prepared for the coming blueberry shock. While this won’t reach Mark’s staggering growth of information, this is an issue we must face nevertheless.

As a leading consumer of blueberry muffins and pancakes, I urge food professionals everywhere to begin to examine how you can deal with the pending blueberry shock, and take steps to incorporate their use in everyday cooking — from bread to soup to desserts.

Additional markets should be explored as well: blueberry-based skincare products. Alternative fuels. Even blueberry milk. (If almond milk is a thing, then blueberry milk can be!)

Thankfully, we have time. We won’t have any major problems for another 15 years, in 2031, when Mark’s blueberry bushes produce 65,536 blueberries, or .983 tons. Hopefully by then, our blueberry infrastructure will be in place, ready to receive the increased blueberry shock.

(Note: This is all satire. I’m also a humor writer. Please don’t think I actually took this seriously. Although I probably put more time into it than I should have.)

Three Security Tips for Freelancers

This is a guest post written by Cassie Phillips, a blogger with Secure Thoughts, an Internet security company.

Maintaining a successful freelance career can be difficult. Oftentimes, the biggest difficulty is finding clients who are in need of your services and willing to pay a reasonable price. There’s another difficulty that is sometimes overlooked: staying secure on the Internet.

With money being moved between multiple accounts and contact with numerous clients, continual daily access to the Internet can be dangerous if certain security procedures are not put in place. To protect yourself against hackers, identity thieves, and other online threats, here are a few security tips for freelancers that can help protect you and your money.

1. Protecting Private Data (and Money) with a VPN

Woman working on LaptopUnlike traditional jobs, freelancers cannot expect to earn a steady income. There is no single employer who is going to regularly deposit money into your bank account. On the contrary, freelancers are likely to earn money from a myriad number of sources, processed through a variety of accounts. From private bank accounts to PayPal to Google Wallet, a freelancer’s money is always flowing from one account into another. Protecting the flow of your money and any associated data is of utmost importance.

Remember that securing your finances on the Internet is not as easy as making a few clicks. If this is all you do, then you remain in an unsafe position where a hacker could see your financial information, hack into your computer or accounts, and steal your identity or just simply empty whatever accounts he can get his hands on. A Virtual Private Network (VPN) is the key to preventing this from happening.

A VPN creates a tunnel between your computer and a third-party server elsewhere. When you access the Internet using a VPN, your data is encrypted and your IP address is hidden. When it comes out of the third-party server, it will appear as if your computer is accessing the Internet from that origin point.

In other words, your server and your connection point remain invisible so you can remain anonymous. However, not all VPNs are created equally. Some have different price tags; others offer different speeds, and others still host various numbers of third-party servers. Do your research to ensure you’re selected the best of the best.

2. Using Trusted and Secure Freelance Contracting Services

In addition to securing your Internet connection, you need to ensure that you are working with trustworthy individuals and companies and secure websites. There are many freelance contracting services available on the Internet serving different types of freelancers. No matter which one you choose, however, you should always make sure that is a reputable service that has not been hacked. There are several ways to do this:

Use Trustworthy Services: If you’ve been freelancing for even a short while, you may be familiar with some of the larger and more trustworthy freelancing services on the Internet, such as Upwork, Elance, Guru and Freelancer. If you stick with the large and trusted services, you will be safer than looking for fringe sites that are unknown and possibly dangerous.

Check for HTTPS: Because freelancing services are responsible for collecting personal data for freelancer’s profiles, facilitating private communications, and shipping money, you need to make sure that the site is secure. One simple way to do this is to look at the URL and make sure that it begins with “HTTPS” rather than “HTTP.” The “S” stands for secure and means that there are layers of encryption being used to protect users on the site compared to the unsecure alternative. Take a look at the address bar in the screenshot for UpWork’s home page and notice the “https” in green:

UpWork's Home Page https

Note the https in the address bar. That means this site is secure. (credit: UpWork’s front page screenshot)

Use Google: If a freelance site is using “HTTP” rather than “HTTPS,” double check its trustworthiness and reputability. You can do this with a simple Google search. Simply type in the name of the service followed by words like “review,” “spam,” “scam” or “hack” to see if anything alarming pops up. For example, if there are numerous reviewers claiming that the site has been hacked or is vulnerable to a hack, avoid that service.

3. Maintaining a Secure Virtual Workspace

There are a few more things you can do to maintain security as a freelancer such as adding a few more layers of protection to your virtual workspace. A firewall will alert you when intruders are trying to access your computer or when your computer is trying to do things without being asked. Anti-spyware or anti-virus software will scan your computer regularly to watch for malware. And a password vault, like 1Password can let you create complex passwords, but store them so you don’t have to remember them all.

These are only a few of things that you need to do to ensure you remain safe and secure as a freelancer. There are certainly other ways to protect yourself. What do you do to keep yourself safe as a freelancer?

As a freelancer, Cassie learned quickly that internet security is a must. She enjoys sharing her knowledge with others because, let’s face it, freelancers don’t make much money and they need to protect their equipment as much as possible!

Photo credit: Moleshko (Pixabay, Creative Commons)

Tax Deductions You May Miss as a Freelancer or Entrepreneur

If you’re a freelancer or small business owner, and you’re only using the 1040 form to do your taxes, you’re doing it all wrong.

You’re missing out on some very valuable deductions and expenses you could take, and if you’re not using a professional, you’re leaving money on the table. If you find you owe taxes each year, you’re definitely not doing it right.

My advice: find a tax professional you can trust and talk to them about using a Schedule C with your 1040.

Income Tax Monopoly SquareThe general rule of thumb is, if an activity costs you money to do the thing you make money at, you can deduct it. For example, I make a few bucks as a travel writer for the state of Indiana. This means I can deduct any expenses related to my travel-writing trips, such as mileage and hotels. A writer friend makes money from, and is taxed for, his book sales. This means he can take deductions for any readings and book signings he drives to, especially if they’re overnighters.

You’re going to be taxed on your income already, so you might as well reduce the amount the government takes by declaring each and every expense related to it.

Here are four important deductions you may be missing as a freelancer, independent professional, entrepreneur, or small business owner.

1. Mileage Related to Work

If you drive to client meetings, conferences, or other work-related events, you can deduct the mileage. However, this doesn’t include mileage driving to and from your regular work; you can only count special trips. Keep track of all your meetings in a calendar, and then list all the meetings and mileage in a spreadsheet. Turn all that in to your accountant and they can take care of the rest.

Erik, how exactly do you think I do this? —Cary, your accountant

Cary, I don’t know. Voodoo or physics or something? I’m a writer, I don’t pay attention to this stuff. This is why I depend on you. —Erik

I use Google Calendar and Google Drive, and I use Zapier to export all my appointments to a Google Drive spreadsheet. From there, I can clean it up, delete all personal/non-paying appointments, and then pop in the mileage for each appointment. This saves me roughly three hours from trying to do it all by hand.

Note: You can also take the mileage out of the company as non-taxable expenses. But once you do that, you can’t take it as a deduction on your personal return because it will be deducted on the business return. If you drive 400 miles to and from a conference, that’s roughly $200 in expenses. You can take the $200 in cash, or you can deduct it on your taxes. Ask your accountant which would work better in your favor. And if you pay for your gas with the company card, you can’t deduct your mileage either.

2. Cable and Mobile Phone

If you work from home, and you rely on the Internet to do your work (and who doesn’t?), you can deduct your cable/Internet costs. The same is true for your mobile phone. If you have a mobile number for clients to call, that’s another business-related expense, which means you can declare it. And if you keep a work-only landline, that’s also tax deductible.

(However, you can also keep your phone costs down if you use Skype as your primary means of communication. This also lets you keep a personal-only phone, and not have to worry about that second phone, or trying to total up the number of work minutes versus personal minutes.)

Remember, you’re not allowed to deduct costs if you’re reimbursed for them in any way. For example, if you work as a remote employee, and your employer pays your cable bill, you can’t turn around and declare it yourself.

3. Office Space

I found a low-cost office to rent, and it’s something I recommend, if it’s available where you live. In Indianapolis, we also have the Speakeasy, which is a shared co-working space. Other cities like Fort Wayne and Evansville also have co-working spaces. If you pay a membership fee or rent to be able to use that facility, that’s considered a deductible business expense. (Working every day from a coffee shop is not considered a business expense, however.)

If you work from home, it is possible to declare your home workspace on your taxes, but it can be rather tricky. There are formulas, and if you use part of a room to work, you need to measure the workspace, and there’s a formula to apply and more of that voodoo physics stuff Cary knows about.

It’s a bit easier if you dedicate one room, like a basement office, to your workspace. But if it’s the desk in a corner of the family room, that’s a bit more problematic. Talk to your accountant, but be prepared to justify it to the IRS, because this often raises flags with them.

4. Food and Entertainment

This is a tricky one. It’s not like the old days when you worked for a company, and you could expense big fancy meals with important clients. Deducting food costs on your taxes can be a problem if you’re not careful.

For one thing, says Cary, you shouldn’t buy food for “working lunches” on the company account. (My wife says the same thing, so this may not be a tax rule so much as a Toni-and-Cary-are-conspiring-against-me ploy.)

One reason is that you can’t deduct the whole meal, only your half. You can’t just take people out to lunch and deduct the entire meal on your taxes. It can also raise red flags at the IRS if they see a lot of entertainment expense deductions on your taxes. So keep this kind of spending to a minimum, lest you feel the cold, probing fingers of an audit.

The problem with doing your taxes yourself is that you may not know the latest rules about deductions and expenses. Basically, if you find that you owe money when you file your taxes, you need to speak with a professional. While you’ll have to pay the accountant, if you’re making a full-time living as a freelancer or entrepreneur, you could find your tax return is much bigger than what you could get doing it on your own.

Special thanks to my own accountant, Cary Hudson of Ashworth Accounting Services for helping with this blog post (and my business!). Cary is a CPA who lives and works in Carmel, IN. He specializes in working with small businesses for their tax and bookkeeping needs, and he’s saved me from hours of headaches for the last six years.

Photo credit: Alan Cleaver (Flickr, Creative Commons)