Man writing on a glass paneEntrepreneurship is one of the most popular subjects on the internet. And why not? It’s all about money, freedom, and the independence of calling your own shots. It’s a powerful siren song, especially when the media is always featuring the latest success story about a new startup that made its owner rich when purchased by a Fortune 500.

Every year, the dream of being an entrepreneur lures thousands away from conventional employment. They plunge headfirst with heart, soul, and savings to try their hand at building a business, hoping to reap the rewards of creating their own financial and professional destiny.

Unfortunately, not all of them find what they’re looking for.

If you’re one of the many who are feeling the pains of boredom and frustration over the sameness of your work, or the inherent income restrictions imposed by budgetary and functional compensation programs, and are ready to leave your employer to work for yourself, you first need to think long and hard about your motives before turning in your resignation.

Sadly, one of the first lessons many new entrepreneurs learn is that they’ve traded corporate boredom for financial stress and logistical overwhelm. And if they lack the personal resiliency to handle it all, they often find themselves wishing for the good old days back at XYZ corporation, where they could call the legal department to take care of contractual issues and liability concerns, where the art and graphics department could turn out a new web page or print ad the same day, or where an administrative assistant handled their correspondence, made routine customer phone calls, and freed up their time for more productive tasks. And don’t forget, all of that “backup” infrastructure was provided without the concern of how the ongoing expense of maintaining it would impact their monthly salary.

Still contemplating leaving your company for self-employment? Make sure your personality, personal values, and work ethic are in alignment with an entrepreneurial mindset. The need to strike out on your own is typically driven by a wide variety of motivations, and pursued by those with an even wider variation of temperament and disposition. Even so, there are some definite commonalities among those who have made a successful transition to entrepreneurship. As you read through the list, ask yourself how you measure up.

1. They have perseverance. When you own your own business, you may take the failures—big and small—personally, but you process them with perspective. Giving up is not a concept you will accept. If every little hiccup sends you into a tailspin, you probably don’t have the tenacity to be your own boss.smiling young bakery owner opening her shop Entrepreneurs are willing to work until they get it done. Regardless of whether it’s a website, a presentation, or preparing a complex estimate for a potential client, they understand the necessity of meeting a deadline, and often work nights and weekends to make sure nothing falls through the cracks. You don’t necessarily have to be a driven workaholic to become a successful entrepreneur, but it doesn’t hurt. Keep in mind that in spite of having intentions to maintain a balanced life, sacrificing health, family time, and personal relationships can be the unfortunate results of working for yourself, especially in the beginning stages, when you’re a one-man show.

2. They have a grasp of the big picture. They understand the industry inside-out. They know the motivations of their customers as well as their buying criteria. They know how much it costs to manufacture their product or provide the service right down to the penny, and they also know how that compares to the product’s perceived value as judged by the consumer.

3. They are goal oriented and use time-management skills religiously. They know how to separate the important from the trivial and make sure they accomplish the highest priority tasks first. They also know that nothing is cast in stone.

4. They enjoy what they do. They like the people as well as the products or services associated with the industry. Doing it only for the money is a fast route to burn out. Building a successful company takes time and dedication, not to mention the investment and re-investment of your own capitol. Unless you believe in what you’re doing, the problems, set-backs, and outright failures will send you running for the nearest job-placement service.

5. They’re not afraid to break the rules. Circumventing traditional procedures and processes is often the key to finding success, especially when it comes to beating the competition. Many times this means being resourceful and thinking way outside the box. For example, when my wife and I started a home-based business back in the late eighties, we ordered an expensive laser-etched redwood sign displaying our company name and logo and mounted it next to the front door. It told our customers they were in the right place and while we still lacked the first-impression credibility of our store-front competition, we conveyed the idea that were every bit as professional. Within two weeks, we received a complaint from city zoning—we were in violation of the signage regulations. Specifically, we were advertising—holding ourselves out to do business—within a residential community, which was strictly against city ordinances. Not wanting to give up the positive impression that professional signage transmitted to clients, we needed an alternative. The following week, we purchased a white Chevy Astro cargo van and hired a graphics artist to paint the name of our business, slogan and phone number on both sides. The result was a high quality visual—in effect, a mobile billboard— that made a far larger impression than our original small ever could have. And the best part? It was legal. We left it parked in our driveway so it was the first thing our clients saw as they approached from the street.

6. They have great rapport and presentation skills. They can make a professional presentation to a group of one or one hundred. They know how to listen, ask the right questions, and solve customer problems. In other words, they know how to sell.

7. They make new connections easily. They are natural net-workers, promoters, and marketers, and are comfortable with social media. They immediately follow up with new contacts and periodically touch base to keep the relationship active. For example, my real estate partner has a Christmas card list with over five thousand names, and each year, everyone on the list gets a hand-signed card. Does it make a difference? Absolutely, especially when it’s a part of the regular effort he makes to contact each person by email or phone at least six times throughout the year.

8. They take calculated risks. For example, they objectively weight the risk/reward ratio of any new product, service, or expenditure and won’t hesitate to put their savings on the line when it makes sense.

9. They don’t see the transition from employee to entrepreneur as an earth-shattering move. In fact, they may view it as the natural evolution of their career. Even as employees, they harbored an entrepreneurial spirit. Most were already thinking in “maverick-mode” long before they left their employer, perhaps operating a small side business or providing non-competitive consulting services.

10. Their business radar is always “on.” Constantly looking for ways to improve existing systems and make them more profitable, they’re always on the lookout for new business opportunities, and if they can’t take advantage of them, point them out to others who can.

The above list is far from complete, but it’s an indication of the wide range of skills most entrepreneurs need to make a successful transition from employee to business owner. Yes, we read about those few brilliant eccentrics that “seeded” a new enterprise solely with their research or original designs for a new piece of software or product, then used others to perform the peripheral tasks. But for every introverted, anti-social digital game designer there are a thousand well-rounded, socially communicative, business-savvy owners who have built their operation from the ground up, doing whatever was necessary at the time to move toward eventual—and more probable—success.

“Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.” –Steve Jobs, Co-Founder, Chairman, and CEO of Apple

Here’s the bottom line on entrepreneurship. If you find several of these more common entrepreneurial characteristics out of sync with your personality, work ethic, personal values, or stress tolerance, you’re probably better off—and will be happier in the long run— if you remain a company man. But if the idea of staying where you are professionally, living the life of a perpetual employee, is affecting your happiness, career satisfaction, and ultimate life goals, try starting a small business venture on the side. Make sure it’s something you can do on weekends and at night without endangering your “day job.” If you enjoy the added responsibility and time commitment and find a profitable marketplace for your product or service, begin to scale the business slowly while constantly measuring the results.

The key to successfully leaving your current job for the life of an entrepreneur is “managed risk transition.” That means not giving up your source of steady income until you’ve proven your new venture will support your lifestyle while providing the needed financial resources for expansion and future growth.

Questions? Shoot me an email at roger@rogerreid.com. I’ll do my best to offer a few suggestions and point you in the right direction.