How to Be a Successful Entrepreneur – Making Decisions, Part 1 of 6

Be Kind! New Clutch Driver at the Wheel!

I saw this hand written message on the cab window of a pickup truck the other day. I flashed back instantly to stalling on a hill, in an intersection, on Martha’s Vineyard, with some guy screaming out the window at me, “Why don’t you learn how to drive!” and thinking that is exactly what I was trying to do!

Getting your entrepreneurial feet under you is kind of like learning to drive a standard when you’ve always driven an automatic. Jamie, how do I start a business? What do I do? I’m new to this and it all seems too much! Can you walk me through it step by step?

Yes! Just like learning to drive a standard, there are certain tricks to getting the hang of it as well as some very definite things not to do. But once you know how, you’ll get kind of attached to your new skill and you’ll never look back!

Let’s break down the steps to get started. Employ common sense. Approach the process rationally with your endpoint in mind. It’s almost like a 6th grade English writing assignment – can you answer Who, What, When, Where, Why, and How? Once you can, you’re on your way! See how simple that is?

Here’s an outline of what we’re going to go through. To start a business, take the following steps:

  1. Make Decisions
  2. Take Action
  3. Fail Frequently
  4. Listen Intently

If this is not a list you were expecting, let me tell you how to use these steps to get from where you are now to where you want to be – in a situation where you have a “business”.

Let’s dissect Making Decisions. First, don’t skip the obvious first few steps. I get that you can’t find a job or maybe you’re sick of your boss or maybe you’re ready to find meaning and have what you do make a difference. But what exactly is an entrepreneur?

Are you an entrepreneur?

What are the attributes of an entrepreneur? You are an entrepreneur if you are someone who is

  • comfortable working independently, alone, creating your own parameters, defining your own goals, working without someone watching over your shoulder, driving towards self-imposed deadlines
  • comfortable networking, asking for help, sharing your questions and concerns with others, receptive to feedback, able to set work down and celebrate creativity and people
  • doggedly determined, able to push in the face of setbacks, energetic and optimistic, rigid in devotion to high standards and high expectations
  • willing to let go, walk away, redirect, respond objectively to information that tells you you’re on the wrong path, flexible and comfortable with constant flux
  • a numbers person, constantly watching metrics
  • a people person, in tune with your market, capable of creating a great team

In summary, an entrepreneur is a complicated person with totally conflicting attributes! Is that you? Do you really want to be an entrepreneur? Before you get intimidated, not sure if you’re crazy enough to go down this route, think about things you have done before that you’ve really loved…

  • Have you ever lost yourself in a project or activity, whether it’s gardening, cooking or baking, playing sports, reading about a new subject, volunteering on a project, traveling to a new place? If yes, you know that when you’re in that zone you are not thinking that you might not have what it takes.
  • Have you had a party, helped in a child’s classroom, been on a committee, organized a reunion or family get together or church social or golf outing, or in some other fashion, rounded up people around a common theme? If yes, you’ve got the people part down.
  • If you haven’t pushed for yourself, have you been stubborn on behalf of someone else? Maybe a child having a hard time on a team or in a class, a spouse that was having trouble with family or at work, a buddy going through a rough time, an elderly parent that needed some care or assistance? If you have been involved in any of these situations, you have demonstrated perseverance and determination!

By now, you’ve got the idea. Entrepreneurial skills are ones we use every day in regular life. In fact, I believe the more you can use these skills with conscious awareness, the more you can develop them, the more successful you can be in any endeavor, whether you’re generating revenue from these behaviors or not!

Do’s and Don’ts!

It’s not an all or nothing label. There’s no such thing as you are or aren’t an entrepreneur. You can get quite creative at home or within your department at work and employ entrepreneurial attributes. Do this intentionally and you’ll grow your entrepreneurial muscles to the point you might be curious to try them on larger projects.

  1. Do keep learning, reading, studying, talking to people, asking questions
  2. Do understand that ONE key behavior separates entrepreneurs from want to be’s; entrepreneurs TAKE ACTION, they EXECUTE, they IMPLEMENT. At some point, sooner rather than later, they stop talking, studying, and planning and they DO SOMETHING!
  3. Making money as an entrepreneur is 100{a16d06abe49b7cb280a391e2908a1c67db5c20e235c835a9ae172b47b18e1709} dependent on the urgent needs and desires of THE MARKET! There are plenty of ideas, plenty of gadgets, apps, and software, and it doesn’t matter how much in love you are with your technology or service. If you are not solving a problem the market wants solved, nobody will buy what you are trying to sell. And if nobody buys it, well – I think you can figure out what results in that situation.
  4. Make sure you don’t quit your day job until you have sales. Make sure you don’t spend all your retirement savings without first having solid proof (sales, contracts, orders) the market wants what you’ve got. Hint: don’t get confused – hunches and good feelings are not proof that your business concept is viable!


  1. Review the list of attributes of an entrepreneur and write down things about yourself and your activities that intersect with these attributes.
  2. Start thinking about things you want to do and what entrepreneurial muscles you are going to work on developing.
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