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12 Questions to Ask Yourself Before You Quit Your Job to Start Your Own Business

Written by Jeff Steinmann
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If you want to live a passionate life of freedom, quit your job and start your own business. Escaping the limitations of 9–5 is the only way to experience true freedom. But to be sure your transition will be successful, ask yourself these 12 questions before you take the leap.

1. Are you willing to do whatever it takes?

To start your own business you have to be willing to do whatever it takes. Sometimes that’s not fun: it’s inconvenient and you can’t do what you really want to. The willingness to do whatever it takes comes from a deep commitment to your business that all successful entrepreneurs must have.

2. Are you willing to adapt your approach often?

The only way for a business to fail is to stop adapting. If a product doesn’t sell, keep adapting, modifying, changing and improving it until it does. You might change its color, change its price, change who you sell it to or change its stated purpose. You may need to change the product, change the service or change the product into a service. Keep changing until you get it right. Failure only comes when you stop doing this.

3. Are you focused enough to start your own business?

Focus worked for Bill Gates and Warren Buffett, so it will probably work pretty well for you. There are only two resources you put into creating a business: time and money. Even Warren and Bill have a limited amount of both. So do you. To successfully start your own business, you have to pour all you have into it. Your business needs as much of your resources as you can possibly give it, so pour it all in. Don’t spread your resources among several small things; none of them will get enough of what they need to succeed.

4. Are you willing to give up some things in the short term?

The only time you should give up things that are important to you is when giving them up will allow you to have more of them in the future. This is one of those times. There may be no vacations for a year, or two, or three. There will be way less TV. There will be less time with your kids, friends and family. If you want the increased time and the increased quality of time (which comes from money) in the future, you must give up some of it now. Do it for your future.

5. Are you ready for the most intense psychotherapy you’ve ever undergone?

Aspiring entrepreneurs often believe they will learn about business plans, marketing, accounting and business models. You will, but that will be small compared to the self-discovery process you will go through. You’ll learn about your strengths, weaknesses and everything in between. Starting a business is a very personal process and one that will test your limits and make you realize you had capabilities you never even thought possible. You’ll also probably cry a few times.

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6. Are you able to listen without judging or evaluating?

When you start your own business, you must develop your listening skills to a level beyond what you ever thought was possible. You have to listen to your customers and prospects so closely you can even hear what they don’t say. You need a level of understanding of your customers that you can’t get unless you listen to every word they say and understand their needs and aspirations better than they do.

7. Are you ready to fire your ego?

Your first dirty job as CEO of your own business is to give your ego the pink slip. If you don’t fire your ego, it will be the worst employee on your team. Your ego makes you think you’re right all the time and won’t let you objectively consider all the relevant facts. When you start your own business, you have to be humble and able to consider all information (remember number 6) without feeling threatened by the possibility of being wrong. Ego, pack up your cubicle!

8. Are you ready to accept feedback?

As an entrepreneur, you have to be open and willing to accept the information you receive as feedback. Then you have to take the feedback and use it to make your business, product or service better. You can’t do this if your ego is standing guard — defending you as perfect and all-knowing (good thing you fired it in number 7). You have to be able to accept the feedback and realize that, perhaps nobody wants to buy your little blue widget. However, if you’ve been listening (there’s number 6 again), you’ll know they would buy it at a higher price if you just painted it red and added googly eyes.

9. Are you confident enough to ignore feedback?

Yes, this is the opposite of number 8. Sorry about that. But as an entrepreneur, you’ll have to confront conflicting information often. While you do have to be willing to accept feedback, you also have to have enough confidence in your vision for your business that you can ignore feedback as well. One person says emphatically the widget must be blue. Another says with equal emphasis that it must be red. They have equal credibility. It’s your company, your vision and you get to decide: you must decide. Confidently make a decision and let your vision for the business guide you. If you make the wrong decision that’s OK. Speaking of that, we probably need to talk about failure.

10. Are you cool with failure?

The media loves failure. They love to see businesses, celebrities and entrepreneurs fall on their face because it makes great news. They’ve convinced us that “failure” is a big, catastrophic event and (worst of all) the end. It’s not. Failing is just part of the process. It’s just another step toward success. The important thing is to never believe that failure is the end. Just get back up and keep going.

11. Are you willing to take full responsibility for whatever happens?

My high-school English teacher would cringe because each of these headings started with “Are you,” but that’s intentional. When you start your own business, you must believe that everything that happens, good or bad, is because of you. Blaming any other person, entity, organization, situation or the weather will doom your business because it takes you off the hook. It gives you someone else to blame, which your ego will temporarily enjoy, but in the longer term it will spell the end of your business. Because by giving away responsibility, you’ve given away your power. Keep your responsibility and keep your power.

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12. Do you care about starting your business more than anything?

You’ll never be able to start your own business unless you care about it a whole bunch. That doesn’t mean there can’t be other things you care about — there should be. But your business has to be up in your top two or three. If it’s not important enough, the daily grind and to-do lists will push your business to the bottom of the heap and you’ll never give it the focus it needs to thrive.

Business plans, market analysis, financial cushion and all that are great, but none of that matters if you can’t say, “Yes!” with ten exclamation points to each of these things. The happiest and most successful people in the world are entrepreneurs and that’s because they have answered a euphoric yes to these questions and created a business and a life they are passionate about.

If you answer no to any of these questions, it doesn’t mean you can’t start a business, it just means you’re not ready. Keep reading, studying, dreaming and hang out with some successful entrepreneurs. You’ll get ready.

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