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How to Make Money by Breaking the Rules

Valerie and her rescue dog,
"Cokie Roberts"

By Valerie Young

This article originally appeared in Issue 191 of the Changing Course Newsletter.

Too many people who want to work at what they love seem to suffer from the misguided notion that there are certain “rules” that must be followed. Let me give you a quick example. At the beginning of every career consultation, I ask clients to describe their ideal life. To prompt their thinking, I pose a series of questions such as what time do you want to get up in the morning, would you like to work at home or outside the home, do you want to work with other people or do you prefer to work alone? The question that gets the biggest reaction is, “Would you like to have summers off?” Invariably someone will say, “Oh, can you do that?”

I’m always tempted to say, “I don’t know, let me consult the official Work-Life Rule Book.” The thing is, I don’t know if you can have summers off or not. But what I do know is this – if the desire to have your summers free is not consciously on your mental radar screen, then the likelihood of it happening is next to nil. If, on the other hand, you were crystal clear that you’d love to take summers off, then you’d be in a better position to make a conscious effort to come up with ways to generate income that would allow for a lengthy work break.

This self-limiting belief that you somehow have to do things a certain way also hampers to a lot of aspiring entrepreneurs. For example, this week alone I’ve spoken with two people who had considered taking the
American Writers and Artists Institute course on how to become a freelance copywriter. The reason they decided against it was they didn’t want to have to write promotional copy for products and services they don’t believe in. Who would? I know I certainly wouldn’t want to pitch Dr. Zildo’s amazing watermelon diet or some shady work from home program.

But where is it written that you HAVE to take on clients you don’t like? I once had a client named Donna whose idea of heaven on earth is to have some kind of a portable income so she can spend months at a time with her daughter in England. Donna enjoys writing and even has a background in advertising. She’d considered the copywriting option in the past but again rejected it because she didn’t want to write about products she didn’t believe in.

Instead of letting this values clash be a show stopper, Donna needed to ask herself, “So, what do I believe in enough to promote?” For Donna it’s the whole mind, body, and soul connection. In fact, her dream job is to organize events for motivational speakers. Because it would be difficult living in a relatively rural area to make a full time living organizing events, we had to come up with a supplemental – and portable – income stream.

This meant challenging the idea that to succeed as a copywriter, or for that matter, in any business, you have to do things a certain way. What if Donna intentionally structured her copywriting business to focus entirely on motivational speakers and authors of mind, body, and soul type books? This kind of niche marketing offers a whole host of advantages.

For one, Donna would genuinely enjoy doing the research on topics she finds interesting. She’d also get a great deal of satisfaction from helping spread the word about concepts and practices she believes in.

Another highly practical advantage is that people in the same field tend to talk to one another. In football terms it’s known as going deep and wide. In my small world, I get to talk to like-minded souls like Barbara Winter and Barbara Sher. I’ve recommended good copywriters to them and they’ve steered me in the direction of great web masters and other vendors. In other words, when you niche market, ultimately you’ll have to do less self-marketing because your business becomes primarily referral-based.

Okay, so what misguided rules are you operating by? Do you think you have to come up with just one way to make a living? Think again. Think you can’t turn your hobby into your career, get paid to work with animals, or that changing course means having to choose between money and happiness? If so, check my ever-increasing list of Cool Jobs at

Oliver Wendell Holmes, Jr. once said, “Man’s mind, once stretched by a new idea, never regains its original dimensions.” How can you stretch your mind today? Once you realize that some misguided rules about work and life can, and should, be broken, a whole new world of opportunity can open up.

There are 5 comments. Add yours.

  1. Judy Newman

    I was on the point of signing up for the copywriting course when I discovered a lot of info suggesting that it was a scam. I would be very disappointed to think that you would recommend anything that wasn’t above board but don’t want to invest $500 of my hard earned money to find out.

  2. Hi Judy,

    First, thanks for posting your concern. If you’re having questions surely others are too so always better to raise your hand!

    I have learned the hard way that sometimes the Internet can be a bit like the wild, wild west. What I mean by that is sometimes disgruntled customers or even just disgruntled people who “heard from someone who heard from someone…” will accuse perfectly reputable companies of being scams. (I once had a guy write a very nasty post on a MAJOR web site flagging Changing Course as a scam. His rant had nothing to do with me at all. Instead it had to do with an article I where I casually mentioned a career changer at a conference. It seems the poster had a bone to pick with that guy and I got slammed in the process. It took months of following to get them to take his damaging and misdirected post down.)

    But I digress…

    Without knowing what exactly you are reading online it is hard to respond to any specific concerns about the AWAI copywriting course. If someone is not satisfied or has a problem, say making a return or something of that nature, then I consider that a “customer service issue” — which is very different than a “scam.” In those rare cases where there is some customer related problem I have been known to personally call the top person at whatever company I might have endorsed to straighten it out.

    As I said in the newsletter, I have reviewed the course and found it comprehensive and exceptionally well done. I have met many people – and by that I mean dozens and dozens — who have taken the course and are now successful copywriters. I have hired many course graduates to write for me in my own business (in fact, I will ONLY use AWAI trained writers). In fact I’m working with a writer from Montana now. In addition I have met the people who run the company, I have met and in some cases, worked with, some of the people who developed this and other courses including Michael Masterson himself. I recommend this company AND this course without hesitation.

    The thing you need to realize Judy is that this is not a get rich quick course. Like anything — you do have to apply yourself. But if you do, you can do well. Since they obviously want to sell their course, AWAI is going to focus a lot on the major success stories that they are (rightly so) most proud. I think when a lot of people see claims that you can earn six figures they become convinced that it’s a scam.

    I personally would prefer that AWAI talk more about the people who are earning $50,000, $60,000, $75,000 a year. For one, anyone starting out has to start at the bottom and build from there. But the other reason is that I find most people can’t relate to the kind of money Bob Bly and Paul Hollingshead earn – especially women. Yet having met people like Krista Jones (more on Krista in a minute) and many others, I also know that there are people who have been able to successfully transition out of their jobs.

    To give you an idea of good copywriting — and to get a sense of the earning potential — go to That copy was written by a wonderful copywriter named Jen Stevens. I paid Jen $3000 to write this. For most people Jen would charge closer to $5000-$7000 but I know Jen so she gave me a break. I know for a fact that while she was working on this for me she was working on several other well paying projects at the same time.

    It may be helpful to know that a lot of people go into copywriting because they like the lifestyle – the ability to work from home or from anywhere in the world, the ability to be their own boss, and the ability to generate potentially very good income. They do NOT necessarily become copywriters because they have a burning passion to write marketing copy.

    My point is that for these people especially, it will take longer to achieve their financial goals because they may be focusing more on writing their novel or other interests and using the copywriting to generate income in the side.

    All of this is to say… I stand by my endorsement 100 percent and without reservation. If you still have concerns I urge you to contact AWAI, tell them what you are reading online, and give them a chance to address whatever it is you are reading. Or feel free call me directly.


    p.s. Before you spend a dime I suggest you listen to my interview with Katie Yeakle and Krista Jones at

    p.s.s. The special offer I wrote about ended today at 5 p.m. eastern. If you still want to take advantage of that contact Lisa at [email protected] and she will try to “pull some strings” 😉

    For my complete review visit

  3. Frances Barrone

    It always amazes me how accepting people can be of the perceived ‘status quo’ afraid to think act or seek to be “above their station”. As a Certified Lifeskills Consultant I use re-framed thoughts amongst other change techniques and delight in “light bulb” moments of clarity when clients see things differently and release themselves form the fears that held them back and kept them stuck. This article highlights this perfectly that we just need to ask the right questions and trust that clients have the most insightful answers.

  4. Scott Poindexter


  5. Great newsletter. Beautiful written, smart and inspirational!


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