Dreaming about the freelance lifestyle?

Sure, it has its perks. But, like anything else, where there’s reward there often can be risk.

Consider these thirty freelancing questions before taking the plunge.

PS – I’m not saying these should stop you from becoming a freelancer today. The beautiful thing about freelancing is that you can start small and gradually grow your client base. Just keep these things in mind as you evaluate your career path in the context of freelancing.

30 Freelancing Questions to Consider

Here they are. I think #1 is probably the most important question to start with (hence the #1 status). The rest are not necessarily in order of importance.

  1. How would a client gain value by paying me money?
  2. What is my greatest skill?
  3. What is my biggest weakness?
  4. Is my Internet connection reliable enough?
  5. What is my marketing strategy?
  6. What is the market value for what I do?
  7. Am I willing to swallow my pride and underprice myself to win initial clients?
  8. What software and technology do I need to be successful as a freelancer?
  9. Who are some of the most successful freelancers in my niche?
  10. How will I differentiate myself from freelancers willing to do my job for less?
  11. Do I aspire to freelance as my job – or is this just for some extra cash?
  12. What tasks are outside of my comfort zone?
  13. Do I have a quiet enough work environment to concentrate?
  14. Do I need liability insurance?
  15. If I want to freelance full-time, how will I get health insurance and plan for retirement?
  16. What is my strategy for building my online freelancer reputation?
  17. Are there freelancing books or blogs that I should be reading?
  18. How much money do I want to make from freelancing?
  19. How will I budget my billable hours to reach my financial goals?
  20. What are my tax obligations for freelancing income?
  21. What quality control processes do I need to implement for the work I do?
  22. Is my current email address professional enough?
  23. Will I need my own website?
  24. How much family time am I willing to sacrifice to grow my freelancing business?
  25. Do I really have the bandwidth to give freelancing a try?
  26. Is my computer good enough or do I need a newer one?
  27. Is my desk ergonomically correct to avoid injury?
  28. What skills do I need to develop to earn more money?
  29. What is my long-term plan for boosting my hourly rate?
  30. Should I quit my job, sell everything I own, and do this full-time from a tropical island? (I don’t recommend this idea.)

What Questions Did I Miss?

Already freelancing? What questions would you recommend to new freelancers? If you’re thinking about becoming a freelancer, what questions are on your mind? Comment below to share your thoughts.

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Written by Matt Keener

Matt Keener is the original "Executive in Sweatpants," having built a successful online consulting business (from home). His best-selling book offers tips for capitalizing on outsourcing and freelancing. Matt holds an MBA and has been featured by many recognizable brands, including Upwork (formerly oDesk), Elance, Insightly, the Dave Ramsey Show, and Entrepreneur.com.

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