Questions Every Business Owner Should Ask in January

January is when most people consider what their course should be for the coming year. Find out what questions you should ask yourself as a business owner this time of year.

So the Christmas selling season is over, post-Christmas sales have ended, and New Year’s resolutions are just kicking in. January may not be the busiest month for entrepreneurs or would-be entrepreneurs, but it’s the month that the “Should I?” questions get asked more often — and considered more seriously — than at any other time of the year. These questions are crucial for evaluating your business idea and overall readiness:

  • Should I go into business for myself?
  • Should I expand my business?
  • Should I close my business down?
  • Should I begin to plan my exit as a business owner?

Of course, these questions are applicable throughout the year, but January seems to be the month when many would-be entrepreneurs ask themselves if this is the year to take the plunge into ownership and when most business owners, especially the successful ones, begin to plan or finalize plans for the coming year. Regardless of who’s asking, though, these are serious questions that demand serious and well-thought-out answers.

Reflecting on the Past Year and Planning for a Successful Business

As a business owner, it’s essential to take the time to reflect on the past year and plan for a successful business. This reflection can help you identify areas of improvement, celebrate your successes, and make informed decisions for the future. January is the perfect month to do this, as the experiences of the past year are still fresh in your mind, allowing you to be guided by reality.

What were the biggest successes and failures of the past year?

When evaluating the past year, it’s crucial to acknowledge both the successes and failures. This will help you understand what worked and what didn’t, allowing you to make adjustments and improvements for the upcoming year. Consider the following questions:

  • What were the most significant accomplishments of the past year?
  • What challenges did you face, and how did you overcome them?
  • What were the most significant setbacks, and what did you learn from them?

By analyzing your successes and failures, you can gain valuable insights into what drives your business forward and what areas need improvement. This balanced reflection is key to fostering a successful business.

What did I learn from my experiences, and how can I apply those lessons to the new year?

As a successful entrepreneur, it’s essential to learn from your experiences and apply those lessons to future endeavors. Consider the following questions:

  • What skills or knowledge did you acquire in the past year?
  • How did you adapt to changes in the market or industry?
  • What strategies worked well, and which ones didn’t?

By applying the lessons you’ve learned, you can refine your business strategy, improve your decision-making, and increase your chances of success in the new year. Continuous learning and adaptation are hallmarks of successful entrepreneurs.

How did my business change and grow over the past year?

Evaluating how your business changed and grew over the past year can help you understand its trajectory and make informed decisions for the future. Consider the following questions:

  • What new products or services did you introduce?
  • How did your target audience change or expand?
  • What new partnerships or collaborations did you form?

By analyzing how your business evolved, you can identify areas of growth and opportunity, as well as potential challenges and obstacles. Understanding these dynamics is crucial for planning future strategies and ensuring business success.

Should I go into my own business?

This is obviously a complex question, and would-be owners often get lost looking for the answer because there are so many factors to consider. The trick here is to ask yourself the right question, which is, “Is this the right time for me to start a business?” And the way to answer that is to ask yourself a series of related questions, specifically:

  • Do I have the necessary experience to be successful in my market?
  • Have I conducted thorough market research to validate my business idea?
  • Do I have access to the capital I’ll need to succeed?
  • Have I chosen a business model that aligns with my funding strategy and long-term goals?
  • Do I have the mental discipline and toughness required to lead a business?
  • Am I talented enough to create sufficient gross profits to make a great living?
  • Do I understand the role a successful owner plays in creating success?

If you can’t answer these questions, or your answer to any of them is “No,” you should suspend your quest for ownership until you can honestly say “Yes” to all of them. And if you already own a business and can’t answer “Yes,” you need to get some help, and soon, because you and your business are likely to be in danger

Evaluating Business Performance and Identifying Areas for Improvement

Evaluating your business performance is crucial to identifying areas for improvement and making informed decisions for the future. As a business owner, it’s essential to regularly assess your business’s strengths and weaknesses to stay competitive in the market.

What are the strengths and weaknesses of my business, and how can I use or improve them?

When evaluating your business performance, it’s essential to consider both its strengths and weaknesses. This will help you understand what drives your business forward and what areas need improvement. Consider the following questions:

  • What are the core competencies of my business?
  • What sets my business apart from the competition?
  • What are the most significant challenges facing my business, and how can I address them?

By identifying your business’s strengths and weaknesses, you can develop strategies to use your strengths, improve your weaknesses, and stay competitive in the market. As a successful entrepreneur, it’s essential to continuously evaluate and improve your business to achieve long-term success.

By reflecting on the past year, planning for the future, and evaluating your business performance, you can make informed decisions, drive growth, and achieve your goals. This proactive approach will help you navigate the business world with confidence and help ensure your business journey is a successful one.

Should I expand my business? 

If you’re thinking about this, your business must have had some success, meaning your cash flow is continuously positive and you’re making a profit year after year. Expansion, though, means taking your profits from past years and reinvesting them in the business, so you’re taking a chance not only with your future but, in effect, with your past, as well. In deciding whether or not to make this move, there are three basic questions you need to answer before you do anything else:

  • Will expansion generate more market share and capitalize on what I’ve already accomplished?
  • Will my gross profit percentage increase, or will it remain the same?
  • Is this the right time for me to expand my business? That is, since the skills I need to open a business and expand one are very similar, can I answer “Yes” to the questions I’d ask myself if I was just starting the company? As a new business owner, seeking advice from experienced entrepreneurs can provide valuable insights into the expansion process.

If you can provide positive answers to all of these questions, you’ll have a foundation on which to determine whether or not it would be advisable for you to expand your business.

Should I close my business down? 

The fact is that building and maintaining a successful business is hard — about 65% of businesses don’t last 10 years. So this is a question that, unfortunately, many business owners have to ask themselves not just in January but throughout the year. If you’re in this situation, the most important thing to remember is that your first loss is your least lost. In other words, the sooner you recognize that you’re riding a dead horse and get out, the less it will cost you financially and the less heartache you will have. Pretending things are going well when they’re not, or being overly optimistic, doesn’t work. You have to face the facts head-on.

Should I begin to plan for my exit as a small business owner?

Sometimes it’s easy to answer this question — when you’re tired and worn out, and the thought of running the business isn’t as appealing as it used to be. Unfortunately, it’s rarely quite so simple because, as with the decision to start a business, there are so many factors to consider. There are, however, two realities you should never forget when you’re thinking about exiting your business;

  • The best time to sell is always when you don’t have to because that’s when you have the greatest number of alternatives and the most lucrative payout.
  • If you don’t choose when to exit your business, something or someone else will choose it for you, and that’s never a good thing. A strong company culture can also play a crucial role in ensuring a smooth transition and maintaining business continuity.

This is extremely important because, if you don’t keep these realities in mind, you will be leaving everything you’ve worked for up to chance, and that’s the opposite of what you did to become and remain successful. It’s essential that you continue to control whatever you can control.


As I’ve said, these are all questions that can be asked anytime during the year. However, January is the perfect month to begin thinking about them because your successes, failures, and frustrations of the past year (or years) are still fresh in your mind, and you’re more likely to be guided by reality. Again, though, you shouldn’t answer any of them too quickly because, as with everything in business, they all require serious thought and careful planning.

© Bill McBean, author of The Facts of Business Life: What Every Successful Business Owner Knows that You Don’t.

Disclaimer: The content on this page is for information purposes only and does not constitute legal, tax, or accounting advice. If you have specific questions about any of these topics, seek the counsel of a licensed professional.

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