I’m an entrepreneur. What’s more, I consider myself among the ranks of successful entrepreneurs. I don’t say this boastfully. I say it with tremendous gratitude and 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, eight years later, I pinch myself because I 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 takes to be self-employed? Here are 12 questions to ask yourself before deciding to pursue self employment. If you cannot answer in the affirmative to most of these questions, there is a good chance you will struggle making it into the ranks of successful entrepreneurs.

12 Questions Successful Entrepreneurs Ask Themselves BEFORE Pursuing Self Employment

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

Not Negative: Do you have an optimistic outlook? Do you see problems as headaches or as opportunities looking for solutions?

Time: Do you have enough time to launch a business? Is your runway long enough?

Responsibility: Are you willing to take 100 percent responsibility for your life and work? 

Embrace Change: Are you flexible enough to adapt to changing conditions and circumstances? As 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 decision and problems or do you run away from them? 

Economics 101: Do you have a basic understanding of budgeting and finances? Are you a good money manager? 

Networking: Do you get along well with all kinds of people? Are you relationally proactive? Are you a server or a taker? Can you receive advise from others? Do you SEEK OUT advice from people you respect?

Education: Are you a constant learner? Are you a reader? Do you listen to personal-development audio programs? Are you willing to significantly invest in your growth and development?

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

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


Question: Which of these questions do you think is most important for entrepreneurs? Would you add any questions that should be asked before pursuing self employment?