Questions Every Entrepreneur Needs to Ask at Year End

The new business year is right around the corner. And, don’t all entrepreneurs look forward to it with renewed enthusiasm? It’s an opportunity to reboot your goals and look forward to a productive year. To make sure your optimism and enthusiasm is well-placed, starting your year with a solid plan keeps you focused, on track, and moving in the right direction.

Optimism for entrepreneurs is a handy quality to possess. It’s what keeps us going despite any obstacles, challenges, or detours that threaten to temper our passion or slow us down. Although some entrepreneurs would prefer not to bring reality into the equation, the most solid, successful plans are those anchored in truth.

Someone once said, “People don’t plan to fail—they fail to plan.” Before launching into artfully crafted objectives, goals, and plans for the upcoming year, conduct a thorough, end-of-the-ear assessment to bring the current year to a successful conclusion.

To support your planning efforts, we’ve created an end-of-year-assessment to guide you through the process. Here are just a few key decision points included in the assessment:

  • What was your revenue this past year?
  • How did it differ from the previous year? (gain/loss)
  • What accomplishments are you most proud of this year?
  • What was your greatest learning?
  • What impact will your learning have on your new year?

In total, there are 57 questions for your consideration, including some that you’ve likely not been asked before that can have a profound effect on your success and satisfaction in the new year.

What are you waiting for? You can download your End-of-Year Assessment here and start planning today for a prosperous new year. 


  1. Awesome. Thanks Jackie! And for anyone else who is having problems, it seemed that switching to another browser helped as well. I was originally on Firefox and, but it came up without an issue when I used Safari instead.

  2. Thanks for a great post!  At the Women’s Business Development Center, we often see an uptick in the number of new clients in January, who have set new goals and want to put them into action. To all start-ups as well as existing business owners: we hope you’ll consider the WBDC as a key resource to help you meet all your goals and objectives in the New Year.

  3. Thank you for these guidelines, Jackie. Each question is important, regardless of the size of a business. Love having this structure to think through for next year – what I need to change, what I don’t, and how to improve business in a variety of ways.