The 5 Hardest Things About Entrepreneurship

Posted on September 1, 2017

The purpose of this blog isn’t to be a “negative Nancy,” but to shed light on the parts of entrepreneurship that I (along with many other people) tend to struggle with. It’s true – things get easier with time. And after five years of being an entrepreneur, I’m slowly mastering everything I’ve struggled with over the years. I hope this is helpful and highlights things to be aware of for those of you considering entrepreneurship!

Here is my list of the 5 hardest things about entrepreneurship:


  1. Working from home. I work from a home office because I haven’t been able to rationalize the cost of an office with two employees who work on the other side of the country. Working from home can be amazing but it can also be challenging, lonely, and hard to self-motivate.
  2. Finding the money. You have to make money appear. You don’t get a paycheck every week unless you find the money. Sometimes I feel like I’m a magician, constantly pulling money out of a hat.
  3. Rejection is constant. It’s like that for everyone in every field. But when it’s your business getting rejected, one could argue that it’s a little harder to deal with. That being said, I feel I’ve come really far with mastering how to handle rejection.
  4. People don’t always understand. My friends and family (for the most part) have 9-5 jobs where they get a paycheck. Sometimes it’s hard for them to relate to the daily challenges you face as an entrepreneur.
  5. The constant need to take risks. When you start your business, you have nothing – it’s easier to take risks. It’s sometimes difficult to take risks once you start making money, as you don’t want to lose what you’ve created.