Take this “5 Smart Entrepreneurial Questions” Challenge

When you think about it, the word entrepreneur really says it all.

Entrepreneur is a french word coming from “entreprendre” which means to launch – to start new things.

Webster defines it as: “a person who starts a business and is willing to risk loss in order to make money”.

OK. So think about this then…

1) Do you finish what you start?

You like to start things. That’s what makes you an entrepreneur. You’re also very creative which poses another challenge – the bright shiny object issue. The problem is that you cannot make money (see definition) from things you don’t finish. No way open-ended projects and ideas will pay your bills.

2) Do you have someone (or a system) to keep you accountable?

Without a boss or a clearly defined structure, it’s easy to miss deadlines  – or maybe you don’t miss deadlines because you never even SET any real deadlines for yourself or your business.  I get it and I have the same problem. That’s why I try to ALWAYS work with a mentor, a coach, a mastermind group, or something that keeps me honest – and too embarrassed to show up and report what I didn’t acomplish yet – but meant to.

3) Are you willing to take a risk (risk loss in order to make money)?

We all have fear. Sometimes it’s so deep we don’t even know it’s fear at all. For me it comes in the form of procrastination, of inaction, of staying too far INSIDE me comfort zone.  Sometimes I don’t want to try something new or approach a potential client in fear of looking foolish or making a mistake – but I often hide it in the “I’m just too busy to do that” scenario playing in my head. Any of this sound familiar?

4) Are you willing to look foolish?

This ties in with #3, of course. I heard a terrific story of a woman who is TODAY a very successful marketing coach. When she first started she was trying to be a “life coach”. She had a day job and was doing this on the side. One day she was shopping at Whole Foods and she stopped to ask the manager, “Hey, you guys are whole body / whole nutrition and I’m Whole Life. How about if I set up a booth here next to the bananas and offer folks a free life coaching session?” Now there are plenty of people who would laugh at this lady but let me tell ya, she’s a millionaire now and still has continuing clients from her 6 month stint at Whole Foods 6 years ago

5) Do you surround yourself with people whose talents are different than yours?

Since you’re the entrepreneur, the starter, you need to have people you work with who are “finishers”, real implementers. This is why I generally don’t recommend 2 designers going into business together – they tend to both be ideas people and it’s a nightmare to get the line out on time. Every assistant and top level employew I’ve ever had was extremely detail-oriented. Because I’m not – and I loathe that part of business. My new partner with the Indie Design Association, Boaz David, is the exact opposite of me. It’s incredible! The work he hates is the work I love – we’re like one normal person split in half so our partnership has a good chance of working out well.

Here’s your “homework”…

1) I challenge you to ask yourself these 5 questions and be completely honest about the answers. Write them down here.

  • Do you finish what you start?
  • Do you have someone (or something) to keep you accountable?
  • Are you willing to take a risk (risk loss in order to make money)?
  • Are you willing to look foolish?
  • Do you surround yourself with people whose talents are different than yours?

2) Then pick ONE thing you will work on for the rest of the week. For instance, if you find you’re not willing to look foolish, examine what’s the worst that could happen? Why are you so concerned what others think? Is it holding



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