Ready To Be The Boss?

October 5th, 2008 by | Print

Ask most people what The American Dream is and they will usually answer, “owning your own home”. To me, the second American Dream would be being your own boss. To see if you share this dream, you need to ask yourself some tough questions so the dream doesn’t turn into a nightmare.


  1. Am I ready to manage me? Am I good at keeping myself focused and motivated?
  2. Can I swim with the sharks or should I get back in the boat?
  3. Can I be passionate about the process – or am I just in it for the money?
  4. Is that my Ego talking? What track record do I have to indicate that I can succeed at this?
  5. If the game is 1% luck and 99% work, am I still willing to play?
  6. Am I just playing or do I have a plan?


Being the boss is not an easy thing – especially as a solopreneur. There is a comfort working for an employer – including benefits. Why not let the employer come up with the plan on how best to earn profits, deal with customer issues, sales and marketing strategies, rent, insurance, legalities, and reviewing P&Ls? As a solopreneur, you have to manage each of these critical business issues on your own.


Don’t let the little gremlin in your head sell you on “how fun it would be if …..” or “how great would it be if ….” especially if these questions are followed by statements that have you running FROM a job or a boss instead of TO a passion. Hard work and challenges lie ahead.


I believe in being an optimist. These questions are not intended to discourage, but to inject a dose of reality prior to quitting your day job. You need to know your limits. No matter how much you have studied up on how others became their own boss, your situation is unique.


Some common key characteristics of successful entrepreneurs (and thus solopreneurs) are:


  • Passionate
  • A drive to succeed
  • Self-confident
  • A high level of energy
  • Self-motivated
  • A thirst for knowledge and creativity
  • Competitive
  • A focus on the goals and not the obstacles
  • Open to outside advice
  • Effective at problem solving
  • Resourceful
  • Ability to make decisive decisions quickly


You have to KNOW that you have these traits. But, a good test is to see if those that know you best would also agree that you possess these qualities.


A little Introspection goes a long way in saving time and money before you venture off as a solopreneur.


All the Best,

Doug Dolan
The Solopreneur’s Guide


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