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18 Questions to Ask Yourself Before Becoming Your Own Boss

by | Sep 6, 2017 | General Career Advice

18 Questions to Ask Yourself Before Becoming Your Own Boss

Self-employment isn’t for everyone. As a career coach and a business owner myself, I’ve seen it go very, very wrong at times. It just doesn’t suit everyone’s career needs. While it might sound nice to “be your own boss,” it takes a certain person in a certain situation to make it work.

If you are currently exploring entrepreneurial endeavors or plan to in the future, consider the following questions first. If you cannot honestly answer “yes” to each of these, you may not currently be prepared for what’s involved. That doesn’t mean it can’t still be an option for the future; but you may have some work to do. Just make sure you’re going in with your eyes wide open.

  1. Do I thrive in a role of responsibility and independence?
  2. Am I comfortable making tough decisions?
  3. Do I have a wide network of associates to whom I can market my products or services?
  4. Am I willing and able to work long hours without pay?
  5. Am I comfortable living without a steady paycheck?
  6. Am I passionate about what I do?
  7. Am I willing to invest the time it takes to reach success (possibly three to five years)?
  8. Am I self-motivated?
  9. Do I have a business plan or am I willing and able to create one?
  10. Am I willing to ask people for their business?
  11. Am I comfortable with uncertainty?
  12. Am I comfortable with making the rules up as I go?
  13. Am I capable of managing my time effectively without being supervised by others?
  14. Am I disciplined with money and other resources?
  15. Am I willing to do the tasks I dislike in order to keep the business going?
  16. Do I have the skills it takes to run a business, not just create or provide the products or services I’m selling?
  17. Am I willing to take calculated risks?
  18. Do I have a heartfelt belief that I can and will succeed?

Need help figuring out if self-employment is the right career move for you? I can help. Learn more about career coaching here.

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About the Author

Chrissy Scivicque is a certified Project Management Professional (PMP) and certified Professional Career Manager (PCM). She is an author, in-demand presenter and international speaker known for engaging, entertaining, educating and empowering audiences of all sizes and backgrounds. Learn more here.

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