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20 (More) Reality-Checking Questions for Would-Be Entrepreneurs

Before I go into my list, I want to clearly state that I am 100% for starting a business and chasing your dreams. But I will never imply that is easy or that even a majority of people are good candidates to try it. It can be a nightmare and it can severely alter your life in unpleasant ways.

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Editors’ Note: Seth Kravitz took exception to Dan Isenberg’s 2-minute test to determine if you should be an entrepreneur. Too facile, too upbeat, too disconnected from what its really like in the trenches every day. With his permission, we have reprinted Kravitz’s post identifying the real 20 questions entrepreneurs–in–waiting need to answer honestly before embarking on a life-changing venture. It originally appeared on his blog, SecondCityCEO.

I find too many business bloggers fail to describe the real experience of starting up a company. They ignore the human aspects. It seems like there is some unwritten law of business blogging that says you can only write about the inspirational and positive aspects of creating a start–up business.

Yes, starting a company can be a wonderful experience. It can be empowering, life altering, etc….

But what so many business bloggers forget to mention is everything else: stress, anxiety, doubt, heartbreak, sleepless nights, emotional roller coasters, destruction to relationships, lost friends, embarrassment, failed marriages, financial ruin, lawsuits, failing health, creating family rifts, social isolation, unrealized dreams, favors for family and friends, guilt, and the always painful “if” thoughts (“If I just would have…” “If he just could have…” “If I had just bought…” “If the bank just would have ….” “If the customer just…” — Yes, the wonderful if statements that can haunt you for life.).

I read blog posts like this and I cringe. That idea a simple checklist of idealist generalities can be a qualifier for a potential entrepreneur is leaving a big chunk of questions out.

I answered a definitive yes to 18 questions on the list. But I feel that is missing another 20 questions that are just as important.

Before I go into my list, I want to clearly state that I am 100% for starting a business and chasing your dreams. But I will never imply that is easy or that even a majority of people are good candidates to try it. It can be a nightmare and it can severely alter your life in unpleasant ways.

My list pulls from my personal experiences, but it also pulls heavily from my friends’, family’s, and associates’ business ventures too. Hopefully you didn’t think everything I listed below as a negative happened to me alone. I have experienced some of them, but thankfully not all.

In addition to the 20 questions Dan Isenberg asks, ask yourself if you can answer “yes” to this list of statements before deciding whether or not to become an entrepreneur:

  1. I am willing to lose everything.
  2. I embrace failure.
  3. I am always willing to do tedious work.
  4. I can handle watching my dreams fall apart.
  5. Even if I am puking my guts out with the flu and my mother passed away last week, there is nothing that will keep me from being ready to work.
  6. My relationship/marriage is so strong, nothing work-related could ever damage it.
  7. My family doesn’t need an income.
  8. This is a connected world and I don’t need alone time. I want to be reachable 24/7 by my employees, customers, and business partners.
  9. I like instability and I live for uncertainty.

10.  I don’t need a vacation for years at a time.

11.  I accept that not everyone likes my ideas and that it’s quite likely that many of my ideas are garbage.

12.  If I go into business with friends or family, I am okay with losing that relationship forever if things end badly.

13.  I don’t have existing anxiety issues and I handle stress with ease.

14.  I am willing to fire or lay off anyone no matter what — how good of a friend they are, if they are my own sibling, if they just had a baby, if they have worked with me for 20 years, if their spouse also just lost their job, if I know they might end up homeless, if they have cancer but no outside medical insurance, or any other horrible scenario millions of bosses and HR people have faced countless times.

15.  I am okay with being socially cut–off and walking away from my friends when work beckons.

16.  I love naysayers and I won’t explode or give up when a family member, friend, customer, business associate, partner, or anyone for that matter tells me my idea, product, or service is a terrible idea, a waste of time, will never work, or that I must be a moron.

17.  I accept the fact that I can do everything right, can work 70 hours a week for years, can hire all the right people, can arrange amazing business deals, and still lose everything in a flash because of something out of my control.

18.  I accept that I may hire people that are much better at my job than I am and I will get out of their way.

19.  I realize and accept that I am wrong ten times more than I am right.

20.  I am willing to walk away if it doesn’t work out.

Seth Kravitz is the CEO of InsuranceAgents.com, an insurance marketing company based in Columbus, Ohio. Seth started his first business at age 19 and has been in the internet marketing industry since 2002. He also writes a weekly blog about the struggles of running a small business.

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http://blogs.hbr.org/cs/2010/02/20_more_reality_checking_questions.html?cm_mmc=npv-_-MANAGEMENT_TIP-_-MAY_2010-_-MTOD0527&referral=00203

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