The 3 Questions No Entrepreneur Wants to Ask (but You Must)

You’re new to the game and motivated to achieve greatness in the realm of entrepreneurship. Undoubtedly, you’ve asked a lot of questions — to yourself, your mentors, family, friends, and others.

But you ask the easy questions. You ask questions presupposing you’ll be successful.

“What do I do if I can’t fill an order?”

“How do you manage to keep up when your schedule gets busy?”

Important? Maybe. Probably not now. You’re romanticizing more than you are playing in the real world. There are some seriously important questions you should be asking yourself at this stage in the game. They may not be attractive, but they will help you rise above when they play out in real time.

Take these three questions that no one wants to ask about becoming an entrepreneur to heart.

The 3 Hard Questions No Entrepreneur Wants to Ask (but You Must)

The 3 Questions No Entrepreneur Wants to Ask (but You Must)

The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy.

— Martin Luther King, Jr. (more quotes)

1. What happens when you fail?

The key word in this question — and I suppose, this article — is when. When is the key word in all three of the questions presented in this piece. Your experience will be different than mine, but these things are inevitable.

As a culture, we now romanticize failure. We talk about how it’s crucial and how regular failure is the only way to be successful. Some say they like failing. My guess for those people is that they’ve never actually failed at anything. Sure, it’ll help you in the long run. But it sucks when you go through. And there’s a good chance it will crush you entirely if you don’t ground yourself in what could happen and how magnificently you might fail.

You may lose your life savings and have to start over. Your product might not be something anyone wants. Hell, maybe you think you have a product and realize you’ve got nothing at all. Maybe you’ll realize after six months that you don’t want to be an entrepreneur at all. Imagine you’ve already told all your Facebook friends you’re a digital nomad, but now you need a 9-5 job.


How are you going to handle that?

What’s going to happen when resistance presents itself? Are you going to let it swallow you up, or will you be strong enough to bounce back from the hole it puts you in? What are you willing to sacrifice or move on from once you realize you’ve hit rock bottom?

2. What happens when you realize your plan isn’t working, but you find something that might?

This is called “pivoting,” and many of us in the game of entrepreneurship know it well. There’s a good chance you will have to pivot to make your dream come true. It might mean destroying the vision of your product or service that you’re holding in your head. Are you willing to do that?

When you pivot, it usually means that your initial product or strategy for selling didn’t go as planned. Call it failure if you want. The thing with pivoting is that if you open yourself up to new opportunities and possibilities, your micro-failure might ultimately lead you to the thing that will sell, work, or make sense for you as a business owner.

Hard questions for entrepreneurs: What do you do when your plan is not working?

But most people fail as entrepreneurs because they fixate and become rigid on ensuring their original vision plays out. “It has to be this way, or it means my idea wasn’t good enough to hack it and I’m not a real entrepreneur,” they subconsciously tell themselves. It’s silly and shrouded in ego, but people do it all the time.


Will you? Will you be willing to scrap four to six months of hard work to start a new project that doesn’t seem as sexy or interesting as your vision does? You may have to if you want to make it.

Having a plan B is not necessary right now — but being willing to endure the pain of blowing up your own work is almost guaranteed. Check your ego at the door and proceed into the next phase of your business without hesitation. You won’t be the first person to have something not work as planned.

3. What happens when the people around you change their attitudes towards you?

All the talk about having to sacrifice big to make it is about to play itself out. There’s a big difference between knowing you shouldn’t care what haters think about you and having and dealing with haters.

If you cause any measurable ripple at all, you will be noticed in a negative light. People will judge you for your efforts and talk about how what you’re doing is so out of character for you. Are you prepared to handle it? Do you know and trust yourself enough to be authentic when no one else knows what you really are?

There will be more than just haters. At some point, even the most supportive people will stop keeping tabs on what you’re doing. They will stop encouraging you to reach your goals. But that’s a good thing. Eventually, you get to a point where you’ve done and achieved enough that your journey can no longer reasonably be tracked. Celebrate this. The day you exchange “atta boys” for measurable income statements and intrinsic rewards as the fuel keeping you going is a huge milestone.

My advice? When all of this happens, embrace it. Recognize that it’s something others have gone through. Understand that it is a requirement to live your life the way you’re saying you want to live it. Most people have no desire to run their own business, and so they will never understand what is required of someone with that dream. Everyone has other stuff going on and will forget about your thing, no matter how great you think it is. Go about your business and make daily 1% advancements no matter what people say.

Shift your perspective

These questions all pertain to inevitabilities in the game of entrepreneurship. The hope is that you shift your perspective on what’s important by asking yourself these questions and seeing what you come up with.

The good news? If you’re serious about making it, none of these questions matter. Nothing else matters, truthfully. Your grit and determination to succeed will reign supreme if you decide that you have it inside of you to win the game.

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