12 Questions Successful Entrepreneurs Ask Themselves BEFORE Pursuing Self Employment

I’m an entrepreneur. What's more, I consider myself among the ranks of successful entrepreneurs. I hesitate writing this because it sounds boastful, but I don't mean it to come off that way. I say this with tremendous gratitude and even wonder. I've worked hard to be in the ranks of successful entrepreneurs and it hasn't always been easy. Yet, once I started down the entrepreneurial path, I couldn't go back. Now, thirteen years later, I pinch myself because I still have a hard time believing it's for real.

Do you want to break into the ranks of successful entrepreneurs? Have you ever wondered what it would take to be your own boss or how to start your own business? Here are 12 questions to ask yourself before deciding to pursue self employment. If you cannot answer most of these questions in the affirmative, there is a good chance you will find the self-employment journey difficult.

12 Questions Successful Entrepreneurs Ask Themselves BEFORE Pursuing Self Employment

Envision It Forward: Do you set goals and plan ahead?

Not Negative: You don't have to be bubbly or giddy to be a successful entrepreneur, but the tendency to see the glass as half empty is definitely a hindrance. So, do you view every problem as a headache or do you have the ability to see obstacles as opportunities looking for solutions?

Time: Do you have enough time to start your own business? Is your runway long enough to launch your dream?

Responsibility: Are you willing to take 100 percent responsibility for your business, your attitude, and your actions? If not, you might not want to be your own boss.

Embrace Change: Are you flexible enough to adapt to changing conditions and circumstances? As my friend Keith Parsons says, “To join the ranks of successful entrepreneurs, you must be bamboo, not oak.”

Passion for What You Do: Do you have a high level of confidence in what you are doing? Do you really believe in it? Will you enjoy this work in five years? Ten years? Twenty years?

Run at Decisions and Problems: Do you run at decisions and problems or do you run away from them?

Economics 101: Do you have a basic understanding of budgeting and finances? It's hard to be a successful entrepreneur if you're not good at money management.

Networking: Do you get along well with all kinds of people? Are you relationally proactive? Are you a server or a taker? Do you seek out advice from people you respect?

Education: Are you a constant learner? Are you a reader? Do you listen to podcasts? Are you willing to invest in your growth and development? Without constant personal development and ongoing growth, it's nearly impossible to succeed in starting your own business.

Unafraid of Sales: Can you sell yourself, your ideas, and your products and services? You don't have to be phenomenal at sales to join the ranks of successful entrepreneurs, but you cannot be afraid of sales.

Risk: Are you willing to risk your own capital in starting your own business? I'm not talking about betting the farm, but will you put your money where your mouth is?


If you're considering starting your own business, I hope you take the time to ask yourself these ENTREPRENEUR questions. Being honest with yourself in these 12 areas will help you prepare for the entrepreneurial journey ahead.

Photography Copyright: 123 RF Photos / Peshkova

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Why My Lifestyle Business Almost Failed and What I Did About It

What picture comes to mind when you hear the phrase lifestyle entrepreneur?

Is your picture of someone sitting under a coconut tree on a white sandy beach with an open laptop? Or perhaps you imagine something a bit more rugged? A bandana-wearing adventurer climbing volcanos or swimming with sharks?

When I started my lifestyle business, I quickly discovered focusing too much on either picture, at least early on, isn’t a great strategy. The reason? Neither picture produces revenue. And let’s be honest, revenue matters a lot more than laptop location when starting a business.

If you’re interested in getting your lifestyle business off the ground, this FREE RESOURCE will help you ask the question, “What kind of lifestyle business fits my vision?”