Quit Your Terrible Job Now! 7 Tips for Tomorrow’s Entrepreneurs


“Find something you love to do so much that you’d do it for free and find a way to make it into a career.” — Anonymous

I don’t know who came up with that quote, but it changed my life. You see, I’ve always been an ambitious person, but the only thing I knew for sure was what I DIDN’T want to do. I didn’t want to be a corporate wage slave doing a job I didn’t like, for bosses I didn’t respect — so I could retire and start doing things that I wanted to do in 40 years.

Besides, I was utterly unsuited to scale the corporate ladder. I hate wearing suits, I’ve got an anti-authoritarian streak a mile wide, and I have an almost pathological inability to pay attention to useless tasks. That’s probably why I used to regularly fall asleep in meetings, even when I was sitting next to my boss (Yes, really).

Then there was the big three-day-long shindig at work where all the managers got together off-site to have a corporate trainer do utterly pointless exercises that had almost nothing to do with what we did day-in-and-day-out. At the end of the session, the trainer went person to person and asked us to tell everybody what we thought about the training. Every last person talked about it like it was the single most wonderful experience of his life….except me. I told the truth, which was that it wasn’t very useful and we’d have probably been better off back in the office working. I actually got dinged for that months later in a performance review.

But, if I had to give you one story that sums up the corporate experience for me, it would be from a job I had earlier in my career. I was a peon hoping to make assistant manager and I came up with an innovative plan to make an extra $10,000 a year for the company. I jotted it down, handed it to my boss, it was implemented, and the firm made a lot of money. Later, after he passed me over for a promotion, he told me he was completely unimpressed with what I came up with because it was written in pencil.

On top of all that and perhaps most significantly, work just wasn’t “fun” for me. Of course, most people reading this are probably thinking, “Oh, so work wasn’t fun for you? Well, join the club, jackass. Work’s not fun for me either!” This is where I probably part with much of humanity because I viewed this as a problem. My thinking was that if I am going to spend 1/3 of my life for forty years engaged in an activity, I should enjoy it. Sure, this isn’t the way it works for most people, but I never bought the idea that I had to be “most people.”

So, I started thinking about what I like to do. Writing was at the top of the list and the Internet was just starting to take off. Unfortunately, there was very little evidence that anyone could make it as a professional political blogger when I created Right Wing News in 2001. Back then, to the best of my knowledge, Andrew Sullivan was the only political blogger making a living at it and he was already well known before he became a blogger. Meanwhile, ad sales were in a freefall. You see, the Internet was a very new market and when the economy took a downturn, the first thing people cut from their budgets was advertising on the web. Worse yet, the advertising model at that time was based on paying websites a set cost per thousand impressions; so when the market collapsed, it completely decimated the entire industry. There were stories floating around about ad networks stiffing websites on five and even six figure checks as they went out of business.

Still, that’s what I wanted to do and although I couldn’t figure out exactly how I would make it work, I essentially was an advocate of the Underpants Gnome philosophy of business — Step 1: Get visitors to my website. Step 2: ????????? Step 3: Profit!

Although I didn’t have a lot of advantages, I did have one thing going for me, a ferocious level of commitment. I took a customer service job, in part, because the managers didn’t care what we did on the net while we weren’t busy. That meant I could work on my website while I was on the clock. Of course, that wasn’t the only time I was working. A typical day for me was working at my day job, eating dinner, doing a few things around the house, working until the wee hours of the morning on my website, getting 4-5 hours of sleep, then getting up and doing it again the next day. After a full year of putting in that kind of effort, probably 40 hours a week out of my free time, what did I have to show for it? About 1000 readers a day and a monthly income of exactly zero. It was that lack of success that prompted a family member to suggest that I should quit blogging and get a job as a bagboy at the supermarket so I could at least get paid for all the time I was putting in. Most people would have agreed with that assessment at the time. Yet and still, after putting in five long years of work, I was laid off from my job a few months before I was ready to go full time. It was a little scary, but I decided not to get another job, moved to the beach, and I’ve been a professional blogger ever since. During that time, I picked up a number of lessons about being an entrepreneur that you’ll find applicable whether you want to be a professional blogger or go into another field.

1) Be prepared to work: You will work longer and harder for yourself than you will ever work for another person. You want to be an entrepreneur? Then forget about 40 hour work weeks and be prepared to do what it takes to succeed.

2) Automate your business as much as possible: You will not ALWAYS be able to work like a slave to keep your business going. You’re going to get sick, you’re going to take vacations, and at some point, you may even want to move on to new challenges. So, at every opportunity, look for ways to allow your business to function without your micromanaging every aspect of it.

3) Never stop improving your business: The world does not stand still. If you can do something for a profit, other people can do it for a profit, too and they will be trying everything they can think of to put out a better product than you. So, if your business doesn’t continue to evolve and improve, chances are it will eventually shrivel down to nothing and die.

4) Save up a nest egg: When you work for someone else, you have a steady paycheck coming in every two weeks, but when you work for yourself, the revenue may come in spurts. You need to have enough money in the bank to make it through the lean times without going belly-up.

5) Keep your fixed expenses to a minimum: If your flow of revenue drops significantly and fixed expenses stay high, you can get upside down in a hurry. That’s why it’s absolutely crucial to keep your “must pay” expenses at a level you can afford to cover.

6) If it matters, measure it: How do you know how much you’ve slipped or improved in an area unless you measure it? How do you take something “to the next level” if you don’t know what level you’re already at? How do you set concrete goals without a sense of where you are and where you want to go? If the success of your venture depends on it, you need to find a way to measure it.

7) Spend your time doing what you do best: When you run your own business, you often end up having to put on hats you’ve never worn before. Soon you’re doing sales, marketing, managing, accounting, customer service, and a zillion other things. If you’re not careful, you can wake up one day and find that all your time is being consumed by sideline activities. Make sure that you don’t lose sight of your strengths and end up consumed with grunt work.

Being an entrepreneur is not for everyone and it’s not easy. However, if you like the idea of taking more control of your life and betting on your own abilities, running your own business is a great way to go!

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