10 Questions Every Entrepreneur Should Ask

Small business questions to help you move on from "what now?"

Entrepreneurship is often likened to a roller coaster — full of many interesting ups and downs, twists and turns. You’ll find yourself shifting acceleration from one project to the next, learning new things, and tackling challenges. But a lot of the time, you’re not sure exactly where you’re headed — or where you want to go.

Often, the question of “what now?” silently plagues many entrepreneurs. The overwhelming vastness and vagueness of executing non-stop can weigh on the best of us. Entrepreneurship then brings up lots of questions. Yet if you don’t ask the right questions, you could possibly forever remain stuck.

After you’ve embarked on your entrepreneurship journey, learning, searching and relentlessly driving your ideas forward, here are 10 questions I believe every entrepreneur needs to ask to be successful:


1. What is my higher purpose?

You’d like to make a profit? Great! But once you do — what’s next? As Tony Hsieh, chief executive officer of Zappos has often noted, every business must “serve a higher purpose beyond bottom-line metrics.”

“A business absolutely devoted to service will have only one worry about profits. They will be embarrassingly large.” ― Henry Ford


2. What can I do to improve my thinking?

The world’s most successful people have one thing in common: they think differently from everyone else. It is the “thinking” aspect of success that lends itself to conversations, which in turn birth ideas.

As logic would have it — if you want better ideas, you’ll need to change your conversations and think better thoughts. Whether you pick up a new leadership book, download your favorite inspirational podcast or call another entrepreneur for a quick injection of inspiration, entrepreneurship is an inside job.


3. How can I do more with what I have?

Have you ever considered that all of us, every single on of the 27.9 million small businesses and counting, started precisely where they were — with what they had? Never waste time coveting or imitating what another business has, where they’ve been or where they are going.

Instead, ask yourself, “How can I make each moment in my business count?” “What can I do to take my moments, and maximize them — and make them big?” When you do this you’ll find, we’re all alike really — taking small moments and making each one count.


4. What unspoken fears are holding me back?

What is holding you back from acting on your next big business idea? Every stepping stone to success can seem a bit unsteady. Consider why you haven’t: made the next call, booked the meeting, reached out to forge a partnership. Dig deep; beyond the surface excuses and ask yourself, “What is keeping me from taking more action?”


5. Have I created a simple plan of action?

Grab your to-do list a take a quick look (or mental snapshot) … “Go ahead! I’ll wait.”

It’s pretty intimidating, huh? Well it doesn’t have to be. All of those tiny tactical plans can carry huge weight in your daily business routine. Instead, it’s time to roll them up to simple, time-based objectives. Let’s get clear and simplistic about your primary goals.

For example, there are 4 quarters in a fiscal year. What 2-3 things would you like to accomplish in each quarter? Once you understand your broad goals, reassess your to-do list and ensure that all of those things are contributing to your big and simple picture. Then prioritize accordingly.

“Nothing is particularly hard if you divide it into small jobs”  ― Henry Ford


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