Why You Shouldn’t be an Entrepreneur

Why You Shouldn’t be an Entrepreneur
choice between dream or reality

how far apart is your dream from your reality?

The Enduring Spirit of the Entrepreneur

Most people shouldn’t try to be entrepreneurs. 90% of startups fail. What makes you think you’re so special?

These days, everyone is in love with the idea of becoming an entrepreneur.  And while entrepreneurs come from nearly every walk of life, you can generally separate them into 2 groups: old money and pedigree vs new money and the self-made man.

I recently posted a link to a controversial post on how entrepreneurs come from money – or at least have access to capital and advantageous connections.  All of this leads to stability which gives a safety net allowing the entrepreneur to be a risk-taker.

A number of people took offense to the post, assuring me that they work like crazy and weren’t blessed with such opportunities.

Yet, there’s a hard truth in here that many don’t want to admit.  If you don’t have the money, resources, and connections, you’d better have 10 times the hustle and be prepared to work harder than you ever have before.

Disagree with me? Good! Maybe you have what it takes after all. 😉


Reality Check Checklist Time

Before you jump out into the world, consider the following points/questions:

  1. Do you stop yourself from holding back?
  2. Are you able to work your day job while starting your dream job slowly? (Quitter is a must read for this to be effective).
  3. Do you have a partner/spouse that is also working and can live on their income?  Do they support your decision to be an entrepreneur?
  4. Do you have enough savings to weather 1 month of no salary? 3 months?
  5. If you are laden with debt/ have a high standard of living (Think student loans, mortgage, car payments, credit card debt, costly hobbies, vacations) Are you willing to engage in delayed gratification?
  6. Are you willing to do the work only an entrepreneur can do (and no, just looking like you are posing for the camera as an entrepreneur on good days doesn’t count)?
  7. Are you able to delegate all tasks you aren’t good at? You must either be great at or have help in: accounting, sales, marketing, and product at a minimum.

If you answered yes to all, you should be good to go!

One Last Important Thought

Remember, there’s a big difference between being a subject matter expert in the corporate womb where all your work-life needs are met vs being an entrepreneur.  Remember this well before going out there on your own.  It’s tough out there!



  1. Jim Boston

    How right this is! I have started a few companies in my time and can testify that
    you will absolutely work much harder (if you want to succeed) for yourself than for
    even the hardest boss. Late nights, early mornings sometimes it all runs together.

    However, it is a great feeling being successful, loving every minute of working, reaping the rewards of hard work!

    If you have a great service idea, have the expertise & know how, GO FOR IT!!!!
    Remember as Mr. John Michael Montgomery so aptly puts it… “Life’s a dance, you learn as you go”! don’t wait until you think you need to know everything about business etc.
    That’s what advisers are for!

  2. Still Struggling

    I wonder if I would have heeded this advice if I had read it seven years ago. Probably not. I can say this much: if you’ve only got 1., 5., and 6., don’t even think about it.

  3. Brian Wallace

    It’s hard advice to take believe me! Nobody wants to hear that their dream isn’t good enough. But that’s not really what we are saying – we are saying that they may lack the fortitude to see it all the way through.


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