5 Questions to Ask Before You Jump Into Entrepreneurship

Written by Corbett Barr

Entrepreneurship is all the rage. It’s everywhere.

In TV and movies (Shark Tank, Silcon Valley, The Social Network), in books (The Four Hour Workweek, The $100 Startup, Lean Startup), in podcasts (StartUp, The Smart Passive Income podcast), and of course in blogs (Techcrunch and countless others). Entrepreneurship has gone mainstream. There are at least 400 startup incubators and accelerator programs in existence.

Being an entrepreneur is glamorized, and for good reason. Startup companies are capable of transforming entire industries and of solving important global problems.

At a personal level, becoming an entrepreneur has the ability to create extreme wealth and personal freedom, along with a deep sense of purpose and meaning.

But all the amazingness that being an entrepreneur can deliver comes at a price. The simple truth is, not everyone is cut out to be an entrepreneur. Most people would be better off in a supporting role, or in joining a startup that already has some traction.

Even people who have the kind of personality and skills that are compatible with entreprenurship may not want to put up with all the baggage that comes with it.

Before you jump into entrepreneurship with both feet, here are 5 important questions to ask yourself:

  1. Are you comfortable with uncertainty?

  2. The only thing certain about building a business is uncertainty.

    There are so many things you won’t have answers to. Should you choose this niche or that one? Is $40 the right price, or is $57.99? Should you hire Brandon or Katie? Should you look for outside financing, or are you better off bootstrapping? How much of your personal savings will you have to spend before you earn a salary?

    Hundreds of questions. Thousands of potential answers. Zero certainty. To thrive as an entrepreneur, you have to master the art of making decisions quickly, based only on imperfect evidence.

  3. Are you willing to sacrifice your income for a considerable period of time without a guarantee that it will pay off later?
  4. Results are not guaranteed as an entrepreneur.

    You could invest years of your life and much of your life’s savings and forego income you would earn as an employee somewhere else, only to end up with a complete failure. All of that time and money and sacrifice might earn you nothing more than a learning experience.

  5. Do you have both the ability to see the big picture and the discipline to stay focused on the most critically important tasks in front of you, combined with the self awareness of when to switch between being CEO and worker bee?
  6. You absolutely have to be able to act effectively in both roles. Strategy and action must be in balance or your business will never have a chance.

  7. Can you tolerate maximum levels of anxiety and stress while being on a daily emotional roller coaster that vascillates between elation and despair?
  8. Being an entrepreneur will be the most emotionally difficult challenge of your life. The action between your ears will be as important and trying as the work you do in building the business.

  9. Will you remain religiously committed to building a successful business, despite endless roadblocks, setbacks, failures, dead ends and forced changes of direction?
  10. Everything and everyone will seem to be telling you that you’re crazy for thinking you can build a successful business. Most of the time they’ll be right. Most businesses do fail, after all.

    To succeed, you’ll have to ignore the setbacks and refuse to take “no” for an answer. You’ll have to finely tune your internal compass and trust it even when it seems stupid to do so.

Being an entrepreneur isn’t impossible, but it’s one of the greatest challenges most of us will ever face. Many will tell you that becoming an entrepreneur was the best decision of their entire lives. I’ll tell you that building a successful business is my life’s greatest accomplishment.

But if you’re not cut out to be an entrepreneur, there’s no shame in looking for a better path. Some other direction will be the right balance of freedom, purpose, challenge, meaning and wealth potential for you.

Before you make a decision either way, please ask yourself the five questions above, and be as honest as you can be about your answers.

What questions would you add to this list? What questions do you think are essential to ask yourself before becoming an entrepreneur? Please share in the comments below.

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