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Entrepreneurship

The 5 Gut-Check Questions Confronting Entrepreneurs Every Day

The day you forget why you began is the day you're done.
The 5 Gut-Check Questions Confronting Entrepreneurs Every Day
Image credit: Wenjie Dong | Getty Images
VIP Contributor
Author of A Paperboy's Fable: The 11 Principles of Success
7 min read
Opinions expressed by Entrepreneur contributors are their own.

Entrepreneurs make an astounding number of decisions daily. They are faced with choosing which opportunities to move on and must solve problems big and small.

By setting up a framework of questions to ask yourself daily, you’ll give yourself some markers to help guide you through these difficult situations. Knowing where you stand on these questions will empower you to make good choices that ultimately lead you to your desired outcome. It will give you a deeper understanding of your motivations and your feelings about your business, and can help you clarify future plans.

Here are five powerful questions all entrepreneurs should ask themselves daily to ensure they are consistently moving toward their goals and making the best decisions for themselves and their business. Ask yourself these questions with an honest and open mind, and see where they take you.

1. Why are you doing this?

What makes this one little question so powerful is that it forces you to examine your desires and impulses, and helps you chart how those motivations change over time. It forces you to look at things from a different perspective. Asking yourself this question every day reaffirms your ambitions and the mindset behind why you are doing what you’re doing. If you don’t know why, you’re in trouble!

Asking this question opens the door to a plethora of other questions that will give you food for thought. What is the reason for launching your business? Why are you passionate about doing this? Are you the right person to run this business? These answers may change over time. At first it may seem difficult to truly nail down the “why” behind your motivations. Maybe there are competing interests that are driving you. But when you really think about it and drill down into this question, there’s probably a simple answer. Just be sure you’re being truthful with yourself.

Why you do something also gives rise to the question: what do you hope to achieve? You need to know what your end game looks like, and what success means to you. Is it about attaining a certain level of wealth? Is it about being the top in your market? Is it about earning respect? Are you looking to rule the world (or at least a niche market), or are you simply hoping to earn a living doing something you love? 

Start your day by asking yourself this question and see where your answer takes you. By spending a few minutes pondering this, you’ll gain clarity that will help you steer your career in the direction you want it to go.

Related: Why Discovering Your 'Why' Is the No. 1 Business Move

2. What is your company’s purpose?

See if you can answer this question in a single sentence. A good place to start is with your mission statement: what are the formal aims, goals and values of your company or organization? This should be clear and concise -- it should get to the heart of what your business is about. 

Your company’s purpose is the foundation that all else is built on. It should have enough flexibility to grow and allow for change, but be specific enough to be meaningful and relevant. Ultimately, this question should help you understand what the heck you’re really doing here.

This question should be at the forefront of your mind when making important decisions. Ask yourself whether this new venture or idea would reinforce or logically contribute to your company’s overall purpose. Are you staying true to your calling?

That’s not to say that your purpose can’t change over time. However, if it does, the change should be purposeful and executed with care. Thinking about this will help you identify your long-term business goals and may lead to bigger questions, such as: what do you want your company to mean to your customers, what is your company’s place in world and what is its ideal market?

Related: How to Engage Employees Through Your Company Vision Statement

3. Where is your business at right now?

The goal with this question is to take both an analytical and emotional assessment of your business. This is a chance for you to take a hard look at where your company sits. Is it on the right track? What seems amiss? What is going right and how can that be reproduced throughout your business?

It’s also important to acknowledge your emotions and to be mindful of how you are feeling about your business. What is your gut instinct saying? Are you feeling anxious or excited about the business? Whether you are having negative emotions or positive ones, it’s important to recognize what you’re feeling and why you’re feeling that way.

This will give you a chance to better understand your mental state and how that may be influencing your decision making. It’s also about understanding what kind of vibe you are putting out. Are you feeling clear-minded and balanced? Or are you feeling off-kilter and out of sorts?

Being in tune with your emotions and having a clear view of what’s going on with your business will ensure you’re on an even keel. It will help you avoid overreacting or underreacting to situations.

Related: How Listening to Your Gut Can Make You a Better Founder

4. What lessons are you learning?

Every entrepreneur faces an uphill battle to achieve success. Every day you should be learning and growing, and the best way to do this is through a great deal of reflection on the lessons that present themselves each day.

Ask yourself whether you’re learning from your mistakes. Failure is a part of every entrepreneur’s journey. The question is, will your mistakes allow you to learn and grow? If not, you’re liable to fall into the same pitfalls and missteps. Conversely, are you learning when to jump at an opportunity and when to let it go? This is the ultimate lesson every entrepreneur is trying to learn, and it’s never an easy one.

The next time you’re weighing whether or not to take a risk, try asking yourself: “When I’m 80, will I feel sorry if I hadn’t gone for it?” Jeff Bezos does this as a way to crystallize whether he will regret not taking action on something. In the big picture, it’s often what we fail to do that we see as our biggest mistakes in life.

Related: The 7 Business Lessons You Should Learn by 30

5. What’s next?

If you ask yourself one question every day, this should be it. As an entrepreneur, you always need to be anticipating what’s next. You need to anticipate what’s coming down the road and formulate a plan to take it on. This is the question that forces you to look up from that pile of work on your desk and think about the big picture and next steps for your business.

What strategies will you need as you keep pushing your business into the future? What trends or shifting interests are coming up that may affect your business? How will new technology impact the way you manage the company?

Disruption will happen in every market because change is inevitable. Businesses that survive see that wave coming and start making adjustments early on. So, in a way, change is predictable because it will always come. Innovation and ingenuity will always be the key to success -- and those who seize opportunity will ride the crest of the next wave.

So when you ask yourself “What’s next?” make sure you have your blinders off and are looking at things with a curious and open mind. Make sure you’re staying open to new ideas and embracing creative solutions. Keeping looking for the “wow” factor.

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