Tackling Entrepreneurial Fears: Fear of Being Your Own Boss

This post is part 3 in the 5 part series about the top fears entrepreneurs face. You can read part 1 here and part 2 here.


The first positive thought about entrepreneurship that comes to mind to those who aren’t entrepreneurs is probably the freedom entrepreneurship allows. It’s a similar feeling students get when they first enter college after graduating high school. “There’s so much free time!” Entrepreneurs can wake up whenever they want, have whatever hours they want and run things however they want. If they want to work in their pajamas, they can. If they want to take the day off and go wait in line at Franklin Barbecue for hours (that’s an Austin restaurant reference), they can.  But in reality, the freedom entrepreneurs have is a top fear for entrepreneurs, as shown by the results of the Entrepreneur Magazine survey.


There’s no one to tell you how to run things – great, I can do things how I want! – but there’s no one to tell you how to run things – ah, what am I supposed to do? Being your own boss can be a pro and a con. The biggest concerns that come with the fear of being your own boss is the uncertainty of stability, security, and guidance and the need for all of these things. As an entrepreneur, the feeling of uncertainty is something you need to get used to, but there are things you can do to keep your sanity. Consider these questions:


As an entrepreneur, you can run the show how you want to, but how do you know you’re doing it the best way?

Open your mind and learn from everything around you – your peers and mentors, business books, seminars, past experience, observations of how other companies do things, etc. There are also many entrepreneurial groups and organizations such as Entrepreneur Organization (EO) and Accelerator. Leaning on people and resources and learning from them will guide you to success. Having a strong support system and sounding board also gives you security in moving forward with your venture. Some situations may require trial and error to find the best way, but remember failure is also an opportunity to learn and grow.


When you are the boss, a majority of things rely on you to accomplish them. How do you build structure to stay on the path to success?

Remember to set specific and attainable goals, map out the route to achieve them, and track your progress. Focusing on your goals and driving your ambition will help you build a steady pace, giving you stability. Also, setting a routine for your day and blocking out specific hours will help you accomplish your tasks. This will also help you accomplish tasks you’re not as excited about.


What are/were your fears about being your own boss and how did you overcome them?

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