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Want to Be Your Own Boss? Ask These Three Questions First

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In the last few weeks I’ve talked to over a dozen people who all desperately want to change course. When I ask them why, they all say the same thing. “I want more control and flexibility over my life and time.” “I want to call my own shots.” “I want to do work I really enjoy.”

But that’s where the similarities end.

In my estimation, about 20 percent of the people I spoke with will realize their dream of being their own boss. The other 80 percent won’t. Why? Because some people are in love with the “idea” of being their own boss – but they’re just not cut out to actually be self-employed.

Which group are you in? Here are three questions to help you decide:

Question 1: You see a door in front of you marketed “Possibilities.” You:

A) Refuse to walk through unless you know exactly what’s on the other side

B) Are a little nervous but never the less, you walk through the door, eager and curious to see what lies on the other side

If you answered A

Generally speaking self-employment is probably not for you. Don’t panic. Just adjust your goal to finding a job that lets you work from home or offers flex time. Of course, it may not be doing what you love, but that’s the trade off.

If you’re determined to be a business owner, then consider going the franchise route. (Something Barbara Winter refers to as “buying a job.”) There is nothing wrong with buying a job. At least you have a good idea of what’s on the other side of the door. However, predictability doesn’t come cheap. 

The reason a Blimpie sandwich shop franchise is going to run you between $145,850 and $397,000 is because you’re paying for a relatively sure thing. Even here, there are no guarantees. By law no franchise can cite potential profit figures – although they do encourage you to talk to franchisees. Even then you never know. The Blimpie in my town shut down after a year while a nearby restaurant is thriving.

If you answered B

You are open to possibility. The fact that you trust your instincts more than your fear means you’re well-suited to be your own boss. Once on the other side you’ll find the road to possibilities offers interesting sites and even more interesting people.

Unlike a franchise, this path offers very little predictability. You think your business is going to look one way. Then suddenly you meet a person or stumble upon a path you had no idea even existed.

Suddenly you find yourself heading in a whole different direction. A direction you would have never known about had you not been willing to walk through the door.

Are you also going to hit some dead-ends, detours, and construction slow downs? Yup. But you accept the inevitable ups and downs because in business as in life, you know these are all part of the journey. And for you the destination IS the journey.

Question 2: You have the chance to do something you feel passionate about.

A) You’ll do it – as long as it doesn’t require too much time, effort, or sacrifice.

B) You’ll do whatever it takes to make your dream happen. 

If you answered A, I recommend you look for a job in your current field. Why in your current field? Because whenever you change careers – whether as an entrepreneur or an employee you’re always going to have to put in time, effort, and sacrifice to get there.

If you answered B – once again, you are well-suited to self-employment. Anyone can be an idea person. However, effort is the fuel that’s going to turn your creative mind into income.

People who succeed at anything do so because they work incredibly hard at it – a habit often instilled at a young age. Black Enterprise magazine founder Earl Graves Sr. sold Christmas cards when he was 7. He got his work ethic from watching his father hold three jobs at once. In a USA TODAY interview Graves said, "I was always thinking of where I was going to make more money — and how," he says. "People who don’t have ambition — they get a regular job.”

To be fair, I don’t think it’s always a matter of ambition. I think because no one ever taught us how to market what we have to offer we’re intimidated by it. That’s why I like Suzanne Evan’s approach so much.

Rather than focus on how to sell more stuff, Suzanne more about how to help more people. And, like me, she is not averse to hard work – especially when it’s in the service of your dream.

(If you missed the inspiring Marketing call I did with Suzanne earlier this week, you can still listen to the replay at

Effort also includes a willingness to make short-term financial sacrifices. I read recently about a cancer survivor named Rory who quit her job to travel in Asia for a year. She and her husband paid the trip by selling their possessions, staying for free by volunteering, and living below their means.

For you it might mean taking an evening class… even when you’re tired, downsizing that pricey cable television package and using the money to fund your business, or selling a second car.

Question 3: Would you rather…

A) Feel totally secure doing something that offers little potential to grow financially, but is guaranteed to bring in a set amount of money every year?

B) Control how much money you can make based on your level of creativity and effort?

If you answered A

What you want is called a job. Don’t be discouraged. It just means you have to change your goal from being your own boss you want to changing careers or perhaps finding a job in your present field that you will enjoy more.

If you are intent on being a business owner, again the franchise route might be your best bet. You can make more money, but how you do it is limited. After all if you own a Blimpie sandwich franchise you can’t just decide to add sushi to the menu or come up with some innovative ad campaign.

The only way to make more money is to buy another franchise – which is what 70 percent of Blimpies franchisees do. If creativity is not important to you and you like managing people – this is the way to go.

If you answered B

You are entrepreneur material. Instead of spending years searching for the illusive “sure thing” you get energized by the idea of creating your own thing.

Even if you knew you could make more money selling someone else’s products or services and using someone else’s franchise formula you know you’d be bored out of your mind. For you, the whole point of being self-employed is that you get to make money doing the thing you love to do the way you want to do it!

Let me give you an example.

Last year I conducted a survey of people considering signing up for my Passions into Profits Coach training program. Partly, I was curious about why they wanted to do this kind of work. Partly, I wanted to screen out people who valued security over opportunity. One of the people who responded was a college administrator named Sylvia.

Throughout her 28 year career Sylvia said, “The whole concept of ‘work’ has always fascinated me because it represents such a large part of a person’s life, and too often among my peers, their identity.”

She adds… “I love talking to people about their work experiences, whether they were happy… what they would REALLY be doing if they could do anything they wanted to. [It’s] fun to brainstorm about ‘what ifs’.”

Notice the language: “fascinated, love, fun.”

You can feel the sense of possibilities! Instead of worry about what will happen if it doesn’t work out, people like Sylvia consider how their life will be different if it does!

Calculating Passions into Profits

Yet, even the Sylvia’s of the world often underestimate how much their curious nature and creative mind are actually worth. But self-employment advocate and author of Real Success Without a Real Job Ernie Zelinski doesn’t.

“If you are serious about attaining real success without a real job,” says Zelinski, “start with the premise that from both a financial and a personal point of view, your most valuable asset is not your job, your house, or your bank account. Plain and simple, it’s your creative ability.” Ernie’s calls creativity “the poor person’s wealth”! I LOVE THAT!

Being creative in your job is unlikely to earn you a dime more. But the way Ernie sees it, “Being creative while operating your own unconventional business is a much better way to get ahead financially than being creative while working in a large organization.”

I’m not talking here about leaping blindly into a financial void. In fact, before you start any business you should crunch some numbers. And start small. For example, if you’re starting your business while holding down a full time job, don’t think in terms of making $50,000. Think, “How can I make $10,000?” and start there.

Say you want to board dogs in your home and you figure you can charge $150 a week. To get to $10,000 you would have to book 66 boarding appointments. You could think in terms of around one dog a week or maybe one owner with two dogs for 33 weeks.

Keep in mind too that you can also add on related profit centers… making and selling organic dog treats or dog sweaters, breeding dogs, running a summer dog camp. You could also have other income streams from any number of unrelated things from real estate to selling Avon. The possibilities are endless.

Reinvest in More Possibilities

The 80 percent who won’t make it only want to know one thing:  “How much can I make?” If it’s not a “sure thing” they get scared.

Obviously entrepreneurs are interested in making money too. But they also ask “How can I re-invest some or all the money I just made so I can make more money?”

Education is always a good bet. For example, you could get trained to be a dog trainer or to teach classes on pet CPR. Or you could upgrade your web site or rent a location where you can board more dogs.

Then, the next year you want to make $25,000. Now you’re looking at 166 dogs a year or three a week. Again since you want to re-invest in your business, at this stage you might hire a marketing coach or a part-time assistant. Maybe take out an ad, do a local radio spot…

Just make sure you invest in things that will have a good chance of paying you back. If you purchased a $500 program on how to start a dog boarding business and you generated $1,500 you got 3x your investment back. So it was worth it.

To help you calculate your own earnings, click here to download a free Multiple Income Streams Earnings Calculator.

My Big Investment

In the last issue I told about my own big investment. I laid out what to me was an enormous amount of money to be one of only 10 entrepreneurs at a brainstorming session with British billionaire social entrepreneur Sir Richard Branson.

Branson’s company, Virgin Group (Virgin Atlantic Airlines, Virgin Records, Virgin Mobile, etc.) employs 50,000 and has over $10 billion in annual revenue. But like every business, he began small, starting a magazine for college students while he was still in high school.

Really my money was a donation as it all went to Branson’s non-profit organization, The non-profit’s goal is to harness global resources and entrepreneurial energy so that business becomes a force for good.

Me, Yanik Silver, Robin Robins, Eben Pagan

Me and brainstorm event organizer Joe Polish.
Joe has raised over a million dollars for Virgin Unite.

Jean Oelwang, CEO Virgin Unite and Boston Celtics fan!

Still even I know it was a very expensive door to open… especially with no guarantee what so ever of what would be on the other side. I went in trusting that no matter what happened, I’d realize some kind of return on my investment. I just didn’t know whether it would be intellectual, spiritual, financial, or all of the above. The first two were met completely.

Did I “make my money back”? That’s the wrong question. As an entrepreneur I know the payback from financial investments is often long-term and intangible. The real question is, “Was it worth it?”

You tell me. I got to ask THE Richard Branson several questions about my own business – and a major passion of mine, teaching people how to be Profits into Passions Coaches.

Valerie: When you started your first business in high school your mother Eve was tremendously supportive… which is pretty unusual. Looking back would it have been helpful if there had been a career advisor who knew how to help young people with entrepreneurial aspirations figure out ways they could to monetize their interests?

Richard: That would have been wonderful. No one was talking about these things then. It’s so needed.

Valerie: I’ve trained over 125 people in 9 countries how to be Passions into Profits Coaches. I’d love to coordinate opportunities for them to somehow help disadvantaged people start small businesses – maybe even with the Branson School of Entrepreneurship in South Africa or somehow in the Middle East.

Do you think the concept of turning passions into profits would translate into developing countries?

Richard: Absolutely. What you’re doing is so timely right now. It’s really needed now more than ever.

Valerie: Is there anything else you’d like to add?

Richard: Just that I think what you’re doing is absolutely brilliant!

How do you put a price on that!

Sir Richard Branson and me. No, I did not twist his arm!

To see more photos (including a couple of celebrity shots from the big Rock the Kasbah red carpet gala) from my time with Richard Branson go to the Changing Course Blog.

The Choice is Yours

So, which group are you in?

Is it the 80 percent who talk about changing course or the 20 percent of the doers who make their dream happen? Whether you opt to remain an employee or become an entrepreneur, know that there are no guarantees.

Today Rory sees her journey as a metaphor for life. “When your purpose, thoughts, and emotions are as aligned as possible, take action and trust that the outcome will be exactly in line with what you want.”

George Bernard Shaw said, “The possibilities are numerous once we decide to act and not react.” If you want a life of possibility, one where your hard work can lead to satisfaction, meaning, and yes money, then I hope you will join me and the rest of the doers on the other side of the door.

P.S. If you answered B to the above 3 questions…

You may be eligible for one of a limited number of free 15-minute Business Brainstorming sessions with me. Scroll down to this week’s “Featured Resource” for complete details.

Coming Soon: Stay tuned for details about my very cool 100 Dream Doers in a 100 Days project.

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A New Direction

I decided to take the Work @ What You Love Workshop and also work one-on-one with Valerie. The workshop explored so many unusual and unexpected solutions to my specific questions. I made so many new connections to what clearly works for me in crea...

Julia Raymond
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