6 “Gut Check” Questions All Entrepreneurs Should Ask Themselves

questions entrepreneurs should ask

Not everyone is cut out for a career as a self-directed entrepreneur.

Some people are best suited to work for someone else. I know this is a harsh statement to some, but that’s the way it is.

Even if you are starting out a business on the side (a.k.a. side hustle), you still might not be cut out for entrepreneurship. Just like what Gary Vaynerchuk says bluntly, “If you have a full-time job, you are not an entrepreneur.”

But don’t take my (or Gary’s) word for it.  If you think you have what it takes, see if you can answer yes to all of the following “gut check” questions entrepreneurs should ask themselves.

1. Why?

Why do you want to work for yourself? Tony Robbins has quoted his mentor Jim Rohn many times as saying, “If you have a big enough why, you can do anything you want in life.” This is critical when you take the plunge and step out of your cozy employed shell and go out on your own.

If your why fills you with passion, then you should go for it. If you just hate having to get up in the morning or don’t like your current pay-grade, that isn’t enough. You have to love what you’re moving toward or you’ll fail before the check for the business loan is cashed.

2. Are You Self-Motivated or Externally Stimulated?

Entrepreneurship is hard. It’s harder than you’ve ever dreamed of, likely. If you’re the type who has a strong fire burning in their belly to succeed the minute you wake up, you just might have what it takes to succeed.

Marketing a new business is tough, unless you have clients you can bring with you (read: steal) from your current job. Even then, there will be plenty of hurdles to jump and dark, gloomy days to suffer through before the sun starts to shine on your business.

Being self-motivated will give you the strength and perseverance needed to grind it out.

3. Do You Thrive on Endless Variety?

Let’s face it, the majority of people out there do not like change. The brains of most human beings are programmed for consistency. This is a survival mechanism that’s meant to keep us safe.

An entrepreneur has to be willing to embrace change from the first day the doors are opened. If you like everything to stay the same in your life you shouldn’t start a business, because entrepreneurs who’re complacent will always get beat out by the competition.

4. Are You a Good Negotiator and Salesperson?

You may be a highly educated accountant, accredited as one of the best in your industry by your peers. If you decide to open up your own firm, you’re likely going to have to go to the bank to get a startup loan or pitch an angel or VC for money. This requires negotiation and selling skills.

Later, you’ll have to pitch clients. That involves selling them on the value of your product in comparison to the competition. Then, you must understand how to negotiate a deal with them that puts maximum cash in your company account, yet also keeps them coming back time and again.

Negotiating and selling skills are paramount to your success. You’ll never go anywhere without them (or the willingness to learn, no matter the cost to yourself).

5. Can You Survive Personally a Year Without Getting Paid?

Obviously, this is a bit of a self-defeating question because no startup owner should ever proceed with an idea if they don’t plan on getting a ton of sales in the shortest time possible. Still, most startup advisors will suggest that you have another source of cash to rely on for personal bills for at minimum of six months, preferably a year.

This might entail a part-time job, savings, an employed spouse, wealthy parents, etc. With this being said, some people do thrive on having their back to the wall financially and nowhere to go but down the road to success – if they know what they should do with it.

6. Are You Willing to Make Lifestyle and Family Sacrifices?

If you made it through the first 5 questions, this one can be considered the final gut-check before you go out and start really planning and proceeding. Passionate entrepreneurs are willing to sacrifice almost whatever it takes to make their startup a success.

Consider the family time that will be lost, time spent with your significant other (or how your dating life will be affected), vacations you won’t be able to take until the business is self-sustaining, toys you won’t be able to buy, how you’ll have to give up your current employer-paid health insurance, etc. Some sacrifices you can anticipate in advance. Others will present themselves at the worst possible times and you have to be readied in your resolve when the time comes.

How Many Did You Answer “YES”?

Excluding No. 6 (if you can thrive with the threat of homelessness and repo men at the door), you should have answered affirmatively to each of the “gut check” questions listed on this page.

If entrepreneurship seems like your destiny, then say good riddance to your “worker” lifestyle –  go out there and get that business plan finished, pronto!

Looking in Mirror Photo via Shutterstock


Ivan Widjaya Ivan Widjaya is the Founder/CEO of online marketing agency Previso Media, small business online magazine Noobpreneur.com and several other business blogs/online magazines. He is a Web publisher, Web property investor, blogger and Web property builder.

3 Reactions
  1. ‘Why’ may look simple but it is a really hard question to answer. After all, it is not a question that a business owner can answer right off the bat. Some of them are even already in the business and they still cannot answer the question.

  2. Ivan: Great questions to ask yourself as an entrepreneur, including the start-up question, Why. I will debate with you on the word and concept if sacrifice. I don’t use this word in my book. Rational selfisness is my ideal, not sacrificing a higher value for a lower / lesser item in your life.

  3. I think #2 and #6 are really important. I have not found a single entrepreneur who is not self motivated. Also, don’t fool yourself into thinking that your lifestyle will not change as a result of this. Not only you, but your friends and family members need to be willing to make necessary sacrifices.