It was a huge relief to get away from the comedy duo of Pinhead and Rich Kid, but I was also nervous about providing for my family.

Could I do it? Sure, I had contracts with clients already but there were also more expenses. Thanks to our screwy healthcare system, medical insurance now came completely out of pocket and it was several hundred dollars a month.

The tax man also took a good percentage of my paycheck. And I still don’t know what the tax man does with our money. Do you?

Another concern was that client companies are fickle. Just because you have contracts for a few months and do a spectacular job doesn’t mean that the contracts will be renewed.

So out of fears real and imagined, I did what most of you would probably do in the beginning.  Every project – big, small, regardless of profit margin, I accepted.  In retrospect, this wasn’t the smartest of moves.

Some clients were great. They paid well. They paid on time. They were easy to work with. Other clients, however, were timesuckers.  At first, it looked like good money because they paid $5k, but their projects consumed 1,000 hours. So I was making $5/an hour. Saying, “Do you want fries with that?” would have been more profitable. Worse than making bumpkus per hour was the time it sucked away. Those 1,000 hours could have been spent finding clients that paid real money.

After making this mistake repeatedly for a few months, I finally learned.  Now, when clients offer projects, I try to define the work more clearly and then calculate a projected hourly rate.  When their projects don’t meet my hourly rate goal, they’re diplomatically declined. 

In fact, my very first client – the one that helped me break free – pays so little that I rarely accept projects from them.  Although it’s important to still maintain a amiable business relationship with them – just in case I need some fill-in work.  It hasn’t happened yet though.

The point is try to be selective.  It can be a balancing act. 

Telling pinhead that I was bolting toward freedom was a great feeling.

It was perfect timing as well. Previously having been promised a substantial raise, that promise was broken during a performance review a week earlier.  We’ve all been there, getting our hopes up and receiving nothing - but broken promises.  It was time to take a stand.

After handing him my resignation letter, of course, pinhead offered me the promised raise plus an additional 20%. Turning it down was easy.

Once you taste freedom and plan for it, you can’t go back. The dream was close to becoming a reality.

Pinhead then tried to convince me that when Rich Kid sells his business that I would get a huge bonus. Rich Kid, mind you, has never promised such a thing nor would I expect him too. A man who doesn’t give loyal employees one day of severance after laying them off is going to give me millions just for surviving?

Pinhead evidently believed that we were all in a game of corporate Survivor. Pinhead even said that he was sticking around for his big payoff. I shook my head and asked, “I feel sorry for you, you’re building your future based on a promise from Rich Kid?”

Pinhead then offered me a retainer fee. He wanted to pay me less than my current clients. I countered with a truly exorbitant hourly rate knowing that it would completely irritate him.  Bingo!  He got red-faced with anger.  I gave him a “you can kiss my ass” grin and politely excused myself from his office.

There’s one final Pinhead story for you.  Co-workers arranged a farewell party at a local bar.  Pinhead appeared about an hour late, ordered multiple plates of appetizers, and inhaled every stuffed mushroom and hot wing in sight.  Then,  Pinhead stuffed to the gills in his gluttonous glory, books.  That’s right, he leaves without paying a dime.  Leaving the bill for the staff that pulls down a fraction of his income. 

He dined and dashed on his staff.

Please Mr. Pinhead, will you come party with us again?

So after experiencing the scene of The Pinhead Who Stole Christmas, I worked diligently day and night to escape the idiocy.  The big break came when I answered a want ad in an industry newsletter from a major company.  After applying and performing the work for them, they demanded that I completely revamp it.

Talk about self-doubt.  Could I make it in this business? Angered and crushed, I didn’t even know if it was worth attempting again. After all, life was hectic. Not only was there my real job but I was in the middle of playing counselor to a friend-turned-bridezilla.
 
But I had my eye on the prize - freedom. So, in the midst of a wedding weekend from hell, I redid the project. The client loved it.

After grinding out the projects for the client, and completing nearly every task on schedule, the client rewarded me with a series of projects equal to the annual cabbage from Rich Kid.

That was my freedom day. We’ve all had those milestones in our lives.  The crowning achievement that makes all your hard work pay off.  Your head is in the clouds and you feel like you’re a Super Bowl champion - “I’m goin’ to Didneyland”. 

Ahhh….the Magic Kingdommm. 

So, back at Rich Kid Inc., they serve up a fresh plate of “motivation to leave” nearly everyday.  Pinhead, the management guru (and Mr. Cliché), is an incredible team builder. 

Every year at Christmas our largest supplier drops off a huge tower of treats.  It’s five feet high and includes cookies, candies, fruit, and pounds of delectable treats. The staff makes an entire day out of stuffing themselves. Everyone would congregate in the break room so we could slowly unwrap each beautiful package.

This year the delivery man with the tower cruised right past my office, so I jumped up and followed him.  Pinhead was no where to be found, but the delivery guy put the tower in Pinhead’s office.  Taking a quick peek at the tag on the tower, I confirmed it was addressed to “The Staff at Rich Kid”. 

An hour past and the tower disappeared.  Is it in Pinhead’s office?  How about the breakroom?  Maybe Rich Kid got his Ferrari leather smelling hands on it.  No one had seen it. The staff was in a panic. 

So, it’s 5:00, the time they open the prison door, and I walk to the parking lot with Pinhead a few steps in front of me.  Pinhead opens his car door and in the passenger seat there sits the tower of treats. “What’s that?” I asked.  And, he says, “A gift for my wife. I picked it up today. She’s going to love it.”

Unbelievable, simply unbelievable! 

At the same time he opened the door, Lucinda the 350 lb. accounting clerk was walking by and saw that Pinhead stole the tower.  She had been salivating the entire day for the treats in that tower.  And had this menacing look in her eyes like she wanted to body slam Pinhead right there on the parking lot asphalt.  Can you picture this pencil neck Pinhead getting crushed on the pavement?  I’d pay to see that.

“Yes, Mr. Rich Kid, I saw the whole thing. Lucinda “accidentally” tripped and just happened to fall on you know who.  No…no…it wasn’t intentional.  She must have just tripped over her own size 14’s.”

There’s some top flight pay-for-view entertainment.  The whole staff would have pitched-in to buy Lucinda her own personal treat tower.

Witnessing Rich Kid accumulate untold millions only spurred me on to start my own business. I’ll never forget the episode where Rich Kid came into my office and announced he plunked down $150,000 for a new home entertainment system. Why, because he could turn it on from outer space. So, he’ll play a trick on his kids and have the stereo start playing the theme from Space Odyssey 2000 while he lunches on the Starship Enterprise.

Then Rich Kid dumped people without severance.  For him it was a choice between a new red Ferrari (not a blue one, that was for special occasions only) or keeping employees on the payroll.  He cut people loose without any personal sacrifice. This makes people mad. So I did what most would do, I started planning for the day when I could quote the eloquent Johnny Paycheck and say, “take this job and shove it.”

Working a side gig can be tiring. Mentally exhausted and wanting to quit my day job, I accepted all the new projects that were offered. Business was so good, there wasn’t any time to spend the extra cash.  But, I made time and rewarded myself.

There was self-doubt. Did I really want to leave a company that provided a steady paycheck? That had paid fairly well? That had given me good raises? And what about benefits and insurance? And, wouldn’t it be more work to have your own business?

So as I mentioned yesterday, Rich Kid’s company was his playground.  He made his staff sing to his dog, and his office Halloween parties were accented with sexually offensive toys.  But, it was the layoffs, that lit a fire under me.

We’ve all worked places where good people were cut. Rich Kid, however, didn’t only lay people off but also offered zero severance. There was no warning. While the workers were expected to give two weeks notice, people were laid off without two weeks severance. Without one day severance. With nothing. At the same time, Rich Kid buys a new Ferrari and drives it to work for the rest of the staff to admire.  Are you f’ing kidding me!

Pinhead, my boss, was the hatchet man. He gathered us together after the layoffs and gave us some story about how sad he was. And, then told us that sometimes it’s the best thing that can happen to people. He, you see, was laid off at a previous job and was given a golden parachute which bought a lake cabin for his family. He then proceeds to tells us how much his severance amounted to (in the six figures) while some of our coworkers and friends received zip from Rich Kid.

Over several months before leaving Rich Kid, while all this insanity was occurring at work, I met Work Nakeders. They were inspiring, and still are. They told me stories of how they got started. They offered contacts. They helped put my mind at ease.

Calling all my contacts from my previous jobs, I asked them about outsourcing work. They threw me a few bones.  As time progressed, the bones got bigger, much bigger.  Working 40 hours a week for Rich Kid, I did the outsourcing in the morning, at lunch, and in the evening.  Working that much was wearing me down.  It was time to pull the trigger on Pinhead.  

Most of us have seen an opportunity and sprinted toward the bigger money, accepting the new gig against our better judgment.  Count me in as being blinded by the cash. 

Big Daddy’s smaller competitor, Rich Kid, paid exorbitant salaries and hired marginally incompetent “yes” men.     

The president of Rich Kid was a 50 year old adolescent megalomaniac who just reached puberty.  The all male management team left in the early afternoon during the summer to play golf while all the women were left behind to work. At the office Halloween parties during the workday, men dressed like flashers and had penis-shaped squirt guns filled with milky water. The owner staged birthday parties at work for his dog and the staff was “encouraged” to sing to the dog.  Or else, not be a team player.  Please!

Rich Kid eventually hired his “yes” man neighbor, a pinhead, to play the role of my boss.  Pinhead was a guy who quoted all these trendy management philosophies and had no idea what they meant.  You know the kind – totally full of crap. 

Luckily, these idiots wore me down.  They drove some people to drink.  They drove me to launch a business on the side.  After seeing Rich Kid stumble to business success, it provided inspiration to pursue my business.  Sometimes I’d think “if these jokers can be successful, I can too.”

Tomorrow, you’ll read the story about how I told Pinhead to kiss off.  And, he hated it.

It’s been a winding road to work nakedness. 

For many of us, coming out of school we had idealistic expectations.  We wanted to “make a difference” or somehow “change the world”.  Back then if we would have been asked where we’d be in ten years, it wouldn’t have been working naked.

My first job out of school was as a waitress at TGIF Friday’s.  All decked out in “flair”, like in the movie Office Space.  There’s a difference maker for ya.

After months of job interviews, a Fortune 500 corporation offered a job.  Big Daddy provided money (though meager) and benefits.  Big Daddy demanded that we all blindly walk in lockstep trudging toward the corporate goal of raising our stock price.  I really loved my coworkers, but most fell into the corporate mold as mindless 8 to 5 robots.  Do you know people like this?  Yeah, we all do.

Talk about a dynamic workplace, with Big Daddy I worked for five bosses, in four divisions, and performed three different jobs over a two year span  Ping pong anyone?  Raise your hand if you’ve been bounced around.

After two years of this, I wanted control and independence.  Did I get it right away?  No.  The lure of bigger money at a competitor was a diversion.  Who else has chosen money over independence and eventually had second thoughts?  Many of us have.

Please excuse me.  The telephone is ringing and hopefully a client is calling to offer more projects.  In tomorrow’s column, we’ll talk the escape.  See you then.

I’m from a small town that has only one Italian restaurant, Mama Milano’s. Fortunately for the residents they serve excellent food. While visiting over the holidays, my best friend Marie and I had the best lasagna God ever put on this earth.

Marie, generous as she is, went to the counter to pay and whipped out her gold AmEx. The old Italian owner stroked his short beard and sneered, “can’t you read?” and he then pointed to an index card taped to the side of his register where bright red letters screamed, “no credit cards. cash only.”

Marie replied, “I’m sorry, I’m unfamiliar with the rules on Planet Zagnon.”

On top of that, Mama’s is closed every year for two weeks during the holiday season.  You know, the season where money is spent more freely.  The season that’s the biggest spending event of the year.

This owner is an Italian space alien.  From Planet Zagnon.

Be an earthling.  Be an earthling who makes it easy for your customers to give you money. 

I survived the corporate grind for one more year than necessary because I was so worried about health insurance. In fact, most of you have health insurance as one of your top considerations as you decide to leave corporate America and transition into working for yourself.

You do, however, have options. Due to medical concerns, I wanted a traditional plan. As my husband and I were building the business together, I was able to classify him as an employee. With our tiny two-person “group,” we were able to get a group plan. It’s not cheap. It’s about $6,000 a year. After deducting these expenses from our taxes, however, it’s only about $3,500 for the two of us. And the plan is the same one that much bigger companies use. If you go this route, your spouse or other employee has to be a legitimate employee and not one in name only.

If it’s only you and you are in fairly good health, you can consider a high-deductible plan. These plans generally have a $5-10,000 deductible and qualify for a health savings account. With a health savings account, you can save money before taxes and use it for any medical expense and it rolls over every year.

Be sure to investigate all of your options before deciding that you can’t leave corporate America because of health insurance!

That used to be my attitude. I was taking every job from every client that was offered when I began my business.

Once I had some cash in the account and some experience behind me, my tune changed. I realized that some jobs just aren’t worth the money. For example, let’s say a client offers you $5,000 for a job. Not bad money. After the contract is signed, you begin the project only to put 500 hours into it. That’s only $10 an hour and you could do better at your local retail store folding shirts.

Here are some questions to ask yourself before agreeing to a project:

1. How much money does it pay?

2. How much time will it take?

3. Do I understand the client’s expectations clearly? Many business owners think they know what a client wants only to spend hours on the work and find out that it isn’t. Put it in writing and have the client agree to it.

4. How will the project move my business forward? For example, maybe this project is an area that you would like to get into but you are not in yet. Or maybe this client’s prestige will help you through the association. Or maybe this client has many projects that you could bid on and you want to get your foot in the door.

5. What is the pain factor? If you have worked with this client before, then you know whether they pay on time, change their expectations mid-stream, or are difficult to work with in other ways. If you have not worked with the client before, ask around and see what you can find out.

After you answer these questions, you can decide if the client is worth your time and effort or if you would be better off marketing to other clients.

It’s that time of year again where I promise myself that I’m going to work out for two hours everyday, lose 15 pounds, clean out my closets, and refrain from gossip. I’m usually able to keep these resolutions for about six hours. It’s a fun mind game that I like to play.

But this year is different. I’m a Work Nakeder and I’m going to make New Year’s resolutions to ensure my success for next year. Feel free to take my resolutions as your own. They are:

1. Shake your moneymaker: Look at ways you can increase profits. Is there another service or product you can offer? Are their other outlets for your skills or products? Think upscale. Think luxury.  Provide something that customers are willing to pay much more for, that costs you only slightly more. Another approach is to build alliances with other businesses to offer customers a complete solution.  Think about the process of how your customers use your product or service and couple it with other businesses to provide an end-to-end solution.
2. Take every tax break you can (legally): Keep track of mileage. Take the home office deduction if you qualify. Keep track of meals with clients and all the business’ postage. All the small stuff can add up to thousands of dollars and will force Uncle Sam to take less of your money.
3. See the big picture: You are a business owner and not just the worker bee anymore. You have vision and plans for where you would like to take your business. Once you have a vision then every business decision you make should be about supporting the vision. A business plan can help you with this.
4. Have fun: You became a Work Nakeder so you could have more control over your life. Have fun with your business and work with clients whom you enjoy. Life is too short to not enjoy your work and another year, and another set of resolutions, will be here before you know it!

I’ll keep you updated on my progress with the resolutions and I want to hear from you on your progress. E-mail me to let me know how your business is going.

Look for my column next week and until then don’t forget to shake your moneymaker.

I deduct everything business expense possible, but I want to do so within the bounds of the tax laws. That’s why I have found the book Deduct It! Lower Your Small Business Taxes by Stephen Fishman and published by NOLO to be essential.

The book tells what you can deduct based on what type of business you have (S Corporation, C Corporation, Sole Proprietorship, Partnership, Limited Liability Company). There are discussions on every tax break imaginable including detailed discussions on, start-up deductions, home office deductions, vehicle deductions, retirement plans, and health insurance.   When I started, this book was consulted nearly every day and it has never failed me.

It’s much cheaper than calling my accountant every time I have a question.  And, it’s saved me thousands of dollars in taxes. 

So a friend calls and asks me for advice about starting his own company. Before I can dole out my wisdom, he interrupts and says, “But it would be so stressful, I don’t know if I can do it.” I surprised myself by saying that it is less stressful than working for someone else. And as soon as the words were out of my mouth, I realized how true they are.

It sounds counter-intuitive. Working for someone else and you know how much money you’re going to make every week. Whether you are gossiping about the latest office romance or you designed a killer product, you’re still getting a paycheck. You have a paid vacation. You know what your benefits are. Working for yourself and your pay fluctuates. Your vacation isn’t paid. You have to deal with taxes and fill out IRS forms. You pay for benefits.

And yet, it’s less stressful. You set your own schedule. You do things the way you want to do them. You control your own destiny. You reap the rewards for the hard work you do. And in my first year of business, I’ve doubled my salary and I’ve taken four weeks of vacation. I don’t have to “save up” time so I can go the Grand Canyon or see a doctor. I don’t have to be in the office early and stay late just because it’s promotion time and I want people to think I work really hard. I don’t have to play any kiss-up and nod games with the boss. And I don’t have to work with people I don’t want to work with.

The key for me to be able to go was to freelance on the side and build up my clientele while I was still working a regular job. I did this for a year and it was difficult, challenging, and sometimes took long hours. The reward, however, came when I quit and left knowing that I had secured enough contracts from my clients to replace my annual salary in five months. I’ve never looked back and I’ve never been less stress-free.

Look for my next column next week and until then remember to shake your moneymaker!

Some people just don’t get us. My favorite client hassles me at least once a month trying to recruit me to work for her in her large, behemoth of a company. One of those companies that has great benefits to compensate for the fact that they keep you in a civilized, bureaucratic prison so they can suck your soul out and stomp on your creativity.

While it’s flattering, I always explain that my business and the freedom it provides is the realization of a dream. She doesn’t get it. And the conversation is always the same. “But you don’t have a steady paycheck,” she says. Well, I do have a steady paycheck, but I don’t get into that level of detail with her. I just tell her that so far it’s worked out well. In reality, there’s a few ups and downs in cash flow, but I’m making more income now than ever. And, more than she could ever offer. “But your job isn’t guaranteed,” she says. 

Work Nakeders know that no job is guaranteed, particularly in corporate America Personally, if there’s one person that I’d prefer to have control of my career, it’s me (not some cut-throat manager). “And the health insurance, I mean…no benefits.” Yeah, it’s a bummer that someone else isn’t paying my insurance bill, let me tell ya! But, you can get a health plan and while it is pricey, I more than make up for it with my higher income.

“But….promotion, you’ll never get promoted,” she says. There it is. She’s a ladder climber. I’m not. I don’t need some spot on a manmade hierarchical org chart to validate my self-worth. Besides, I’m CEO of my own company. How much higher can you go? She’ll never be a Work Nakeder. And that’s fine. We can’t all be. But for those of us who are or want to be, there is no better way of life. No commute. No idiot bosses.

No cranky coworkers. And, room for creativity. I can’t think of anything more challenging and invigorating than trying to build a better mousetrap and knowing that there is no bureaucracy or boss standing in your way. Feel the freedom, work naked. Look for my next column and until then remember to shake your moneymaker!