8 Tough Questions You Must Answer Before Making the Leap to Entrepreneur

Being an entrepreneur is hard work that usually comes with little payoff at first. Are you ready to take the plunge?

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By Chris W. Dunn


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An entrepreneur's life is not for the faint-hearted. The possibility of freedom and wealth are contrasted by high failure rates and an incredibly tough workload.

You will go through many high and low moments, and at times, you will question your sanity for choosing to become an entrepreneur.

Thanks to shows like Shark Tank and the recent tech boom, entrepreneurship has become a highly sought after pathway to wealth. But is entrepreneurship right for you?

Before you quit your day job, here are eight questions that you should ask yourself before you take the leap into the world of entrepreneurship.

1. Why do I want to be an entrepreneur?

"I honestly think it is better to be a failure at something you love than to be a success at something you hate." – George Burns

Even though it's a simple question, many people overlook it. Hating your day job or wanting to be your own boss are valid reasons for becoming an entrepreneur, but it may not be enough to carry you through the inevitable challenges that come with an entrepreneur's life.

Be very clear why you want to do this. It should be something that you want to do, not just because all your friends are making the leap. During the dark moments, your "why" will be something that you cling on to.

As Gary Vaynerchuk says, "There are true entrepreneurs and people with entrepreneurial tendencies. The thought of having a job makes true entrepreneurs sick to their stomachs."

2. Do I believe that I am capable of being an entrepreneur?

"Believe in yourself! Have faith in your abilities! Without a humble but reasonable confidence in your own powers you cannot be successful or happy." – Norman Vincent Peale

Self-belief is especially important when it comes to entrepreneurship. Unlike a nine to five job, there are no clear guidelines, and no boss to tell you what to do.

If you don't believe that you have what it takes, you will be easily defeated when the first wave of problems hit.

3. What do I already have? What do I lack?

You will undoubtedly have some resources - be it skills, monetary savings, time or even connections that you can use as an entrepreneur. Analyze what tangible and intangible assets you have, then identify what else you currently lack.

Savvy entrepreneurs build on what they have, and find creative ways to get what they lack. As an example, you may need to take a coding class; join a business mastermind; or partner with someone else who can provide what you need.

4. What problem am I solving? Who will I serve?

Successful entrepreneurship is about solving a big problem or meeting a need. It is about finding better, faster and cheaper solutions than what is already available.

It's also about identifying who you want to serve. It is easy to say that you want to serve everyone, but when you are first starting out you should have a clear picture of your ideal customer.

This is because different categories of customers have different needs, and you cannot effectively meet all their needs all at the same time.

5. Am I willing to do what scares me, and risk failure?

"If you're not failing every now and again, it's a sign you're not doing anything very innovative." – Woody Allen

Being an entrepreneur will challenge you in many ways. You will be entering a competitive world in uncharted waters.

Are you willing to step out of your comfort zone, and do what others are afraid to do? Are you willing to invest your money, effort and time in something that may fail? Are you ready to be criticized and even be misunderstood?

If you said yes to all of these, you are well prepared to step into the world of entrepreneurship.

Related: 5 Essentials to Becoming a Millionaire Before You're 30

6. What needs to change?

This question is especially important if you are taking a huge step, such as leaving your secure income from your day job, to take on the uncertainty of entrepreneurship.

If you are used to spending every single cent of your annual salary, you may need to change your lifestyle and spending habits. There is no guarantee that you will be able to draw any income (even if you have revenue) in your first couple of years.

Unless you have investors willing to invest large sums in your entrepreneurial venture, the first few years will be lean.

Elon Musk is famous for forcing himself to live on $1 a day before he decided that he was ready for entrepreneurship.

Related: The 4 Easiest Ways to Make More, Yes More, Money in 2016

7. What am I willing to sacrifice?

Long-term success almost always requires sacrificing something in the short-term. For example, your time priorities will have to change. If you are used to spending all your weekends watching TV, spending time with your family and hanging out with friends, you may have to let some of these go.

It doesn't mean that you have to give up everything, you just need to decide what is a top priority and what isn't going to help you reach your long-term goals.

If you are used to taking one-month vacations every year, you may cut it down to a week while you are building up your business.

Related: Inspiring Quotes From 10 Visionary Business Leaders Who Changed Everything

8. How will I know when it's time to persevere or pivot?

Most entrepreneurs struggle to determine when they should keep pushing forward and when they should cut their losses, and pivot to something new.

For some, spending their last single dollar without making any revenue is a sign that it's time to leave. For some, it's a time guideline.

Only you can decide when it's time to move on, pivot or change to something else. Without an exit strategy, you can work hard but make no progress.

The questions above are merely a guide to help you think through your decision on whether to become an entrepreneur. Ultimately, it is your life, and you should go where your heart leads you. There is nothing worse than living with regret and wondering what might have been.

I'll leave you with this quote:

"Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did, so throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." - Mark Twain

Chris W. Dunn

Founder and CEO of Skill Incubator

Chris Dunn is an entrepreneur, digital currency trader and advocate, author, real estate developer and angel investor. He is the founder and CEO of Skill Incubator, which helps entrepreneurs and investors develop valuable skills. He is also the host of the Pathways To Wealth podcast.

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