9 Biggest Pitfalls of Being an Entrepreneur

All by myself.

A lifetime ago, before having my kids, I was in banking and bond trading at the Chicago Board of Trade. I retired when my oldest was about 2 to be “just” a mom. Divorce about 10 years later shook my sense of security and I was again in search of reinventing myself.

By then I knew having a boss, even the best boss might kill my now very free spirit and certainly would kill my lifestyle which included summers in a place my kids and I call heaven in Northern Michigan.

Being the eternal optimist, I set my mind to finding something that would give me all the things I imagined being an entrepreneur would give me; time freedom, flexibility, the big bucks and best yet I had illusions of finding my “passion”. Ok, ok, entrepreneurs out there….feel free to laugh.

That was about 15 years ago and a whole lot of life experiences ago. Hey, I even tried to start a carpet cleaning business. Suffice it to say, that was not my passion! I had no stomach for real estate rehabbing. Lessons from a failed startup included a big one: know your business partners.

Finally I found my thing. I work from home, can work from anywhere, have unlimited income potential, but along the way I learned a few lessons the hard way. Maybe these will help you. #9 is my FAVE!


  1. I am my own boss. Ok, ok that was what I wanted, but it may be the biggest pitfall for entrepreneurs. In fact, my next blog may be all about that one issue. It is critical to remember that you may not have all the answers, be open to learning from others. Surround yourself with people who are willing to challenge you and be open to their ideas. Be honest with yourself about what YOUR strengths are and find others who can fill in the gaps. I find this book, test included, to be hugely helpful in identifying our own strengths, some that may be so much part of who we are that even we don’t recognize them.
    Strength Finders
    I find this book, test included to be hugely helpful in identifying our own strengths, some that may be so much part of who we are that even we don’t recognize them. And on this “being your own boss” topic, last but not least, be willing to pivot and change when the evidence points that way. Frequently we are so tied to our own vision we are blinded by reality.
  2. Work from home. Again, this was what I wanted, but another catch 22. It is so easy to get distracted with the refrigerator, watching the news, throwing in a load of laundry, the local park calling your name, and a ton of other shiny objects. Just because you are working from home does not mean you do not need a rigid schedule and systems in place to maintain it. It means it is more important. No one I know is better at systems than David Byrd. His short and inexpensive book is invaluable!
    The Tripping Point in Leadership: Overcoming Organizational Apathy
  3. Work from home. No, you are seeing this right. This one is worth two mentions. This one is a serial mistake of entrepreneurs. Working for yourself means you are ALWAYS working. 24 hours a day you are ON. Like Pavlov’s dogs your brain is programed to interpret every email and phone call and text as your next big break. You MUST schedule in some free up your mind time. Again, I will refer to the David Byrd book above. His books on leadership and systems are the shortest, easiest to read and best books on the topic of systems. As entrepreneurs we NEED time to free our brain of the endless clutter that comes with having our own business. FREE brain time is when ideas flow, and our unfettered thoughts can turn into things, things that will truly be our next big break.
  4. Parent syndrome. As our business grows, just like in parenting, it is often easy to fall into the trap of “I can do it better, faster and more efficiently myself”. The only way kids learn to pick up toys, clear the table, do the dishes is by DOING it. Same with our business partners. And allowing our kids to do these things, frequently imperfectly at first, empowers them and we all know practice makes perfect. This applies with our co-workers. Let go of control and let them do it. Your business can only grow exponentially through empowering others. Be encourager in chief with them (not constant critic) and they will soon fly. Do it all yourself and your business will be forever stunted.
  5. Show the love. There are two main leadership styles (think Phil Jackson vs. Bobby Knight). The Phil Jackson style is more zen, encouraging, team oriented and builds an atmosphere where new ideas flow. People are free to share ideas that fly or fail, and the more ideas that flow, the more will fly. The Bobby Knight style is fear based (who wants a stadium chair thrown at them?). The biggest pitfall of this last style is the shutdown of creativity and the ability for your teams to share ideas freely.
  6. I can do it myself. The best advice I can give to entrepreneurs is to network, network, network. Build strategic alliances. Build relationships. Make friends, even with those that may not seem to be of immediate benefit. People and relationships may be the biggest free resource out there. Be a giver. Maintain an abundance philosophy. Befriend competitors. You may learn more from them than you think, even if it is what NOT to do.
  7. I am the expert. This mindset may be the most damaging of all. Experts are not learners, they know it all. (har har) Wake up every morning eager to learn something new. Be a reader. If someone spends the time writing a book, maybe, just maybe they have something to say. One small nugget could trigger an idea for your business that makes or breaks it.
  8. Go slow to go fast. This phrase was coined by Jeff Olson, author of The Slight Edge: Turning Simple Disciplines Into Massive Success

Again, this book is transformative in many ways. But, the go slow factor is so important. Our need for instant gratification can trip us up. Entrepreneurs sometimes tend to have the attitude, if I throw enough ideas at the wall, some will stick. A bunch of ideas stuck to a wall does not breed success. Be picky about the ones that have merit and slow down to work them, mold them and implement them. Remember that old adage, if you can’t do something right, don’t do it at all. This is never more true than for entrepreneurs. Half baked great ideas are still half baked. Do it right, the first time.

9. Finding your passion is a cosmic joke. As I mentioned, one of my goals was to find my passion. HA. It has taken me a long time to realize that the “find your passion” craze is a huge mind trap. Think about it. If you are lucky enough to know you love playing basketball or the cello when you are 5 and good enough to get good enough that someone wants to listen to you or watch you, good for you. Most of us are not that lucky. Most people spend their entire lives bemoaning the fact that they never “found” their passion. It finally occurred to me that it is not something you “find”. It is something you bring with you wherever you go, or not. Even those who seemingly are living their passion are not doing what they are passionate about all day every day. Michael Jordan spent about 98% of his time practicing, mentally and physically preparing for the 2% of time he was on the court in front of a crowd. Oprah does the same. 98% of her time is in preparation, and real WORK before she appears on TV with for a dream interview. Michael Jordan and Oprah were able to BRING their passion to the 98% of their work that looks like work, transforming it. Same with entrepreneurs. The best thing we can do is BRING passion to our projects, our life, our relationships, our friendships, our family and the rest will work out.


Betsy Smith has her own business in anti-aging and brain health….learn how you can increase your memory, focus and energy.

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