I’ve written quite a few business and company profiles in my seven years of experience as a freelance writer and journalist. This means I’ve had to interview many CEOs, executives and owners of small- and medium-sized businesses. Although the question list varies according to the specific style of the magazine and the unique qualities of the business and business owner, there is definitely a core set of questions that I tend to slip in during each interview.

What’s interesting about these core questions is that you can apply them to yourself and your OWN business – after all, we are all business owners as self-employed freelance writers. The answers that you come up with when you interview yourself with these key questions will reveal a lot about your current ideas on being a freelance writer – and whether or not you have what it takes to keep it going in fresh and new ways. Copy the following questions down into a notebook, ask them aloud one by one while you record yourself on a tape recorder or copy and paste the questions and answers on your computer – whatever method you’re most comfortable with. The questions have of course been adjusted for an interview with a freelance writer.

1. How do you see yourself in the big picture of the media world? What do you hope to contribute through your work as a freelance writer?
2. What’s the story of how/why your freelance business came to exist?
3. What is a typical day like for you?
4. What kinds of challenges do you encounter on a daily basis? What is most difficult?
5. What is your favorite part of being a freelance writer?
6. What would be your ideal freelance writing day? Describe in as much detail as possible.
7. What did you always want to do when you “grew up,” and how has that idea changed (or not changed) over time?
8. What do you for fun if/when you have free time?
9. What motivates you, excites you, inspires you? Do you have any role models?
10. What is your specialty, your strength?
11. Can you discuss any specific moments/projects since you began working as a freelance writer that are especially memorable or have impacted you in a significant way?
12. Are you satisfied with the range of your clients at the moment?
13. What kinds of projects do you enjoy most? Why?
14. When you look back on your freelance career, what do you consider to be milestones or turning points?
15. What are your short-term (upcoming year) and long-term (next 5 years) goals?
16. How do you approach the marketing and advertising of your freelance business?
17. What do you think makes you stand out from all the other freelance writers out there? Why should a client come to you instead of another writer?
18. What does it really take to succeed?
19. What are some issues that freelance writers are facing currently? How do you deal with these issues?
20. Anything else you’d like to add? (This is where you get to rant and rave and ramble onóthe last, but often the most revealing, part of the interview. In fact, some business profiles I’ve written end up centering around the significant information that comes up only after the interview is over.)

Now, read over your answers slowly, carefully. See what stands out. If you are repeating a phrase or word or feeling over and over, think about what it might mean.

Maybe you realized that you find your work more challenging than enjoyable in many ways…try to figure out why that is. This can be a good time to take an “inventory” of the projects you’ve done, check for patterns, analyze the efficiency of your work hours and the fees you receive for your efforts. How has the quality and/or quantity of your work changed?

Don’t let the self-analysis stop here. Always take time to look at your work from a business person’s point of view. Regular self-evaluations can teach you a lot about yourself as a writer, freelancer and entrepreneur, show you how to improve yourself in each of these roles, and offer some insight into which direction best suits you and your freelance writing career.

Suchi Rudra, a freelance travel writer and expat, is currently based in Lisbon, Portugal, after having spent 4 years in Prague, Czech Republic. Her work has appeared in a variety of travel publications such as Transitions Abroad, Europe Up Close, International Living, Flyodoscope and PlanetEye.com, and she has recently written a guidebook on Prague. Suchi also frequently writes on the topics of sustainable architecture, business and education. Learn more about Suchi’s work at https://suchirudra.wordpress.com.