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Challenges of being your own boss

Being a business owner and being your own boss can be a dream come true for many people. Breaking free from the shackles that can come from traditional jobs, can seem liberating. However, there are challenges that self-employed face, whether they are freelancers, entrepreneurs or small business owners. Running your own business can be very challenging as it will push you to your limits and force you to take control and display leadership.

being your own boss

If you have been working as an employee and have decided to finally make the jump from being an employee to being your boss, then it may be difficult to adjust. At first you will be glowing from the idea of complete control and flexibility. Though, it will soon dawn on you the tremendous amount of responsibility you will have. Being your own boss isn’t for everyone, you will need certain skills in order to thrive as your own manager. Here are some of the main challenges that you may face, when running a business and being your own boss.

Working hours

Although the idea of flexible working is widely desirable, it may be challenging to work with flexible hours, especially if you have been working traditional jobs. The structure that ‘normal’ jobs offer is underappreciated, as most humans need structure in order to function and succeed. To ensure that you are working when you are the most productive, you should set working hours. This will mean you can avoid over-working yourself, which tends to be a huge problem for the self-employed. Your working hours will be suited to you individually, but make sure to have a switch off time.


This is perhaps one of the most challenging parts of being your own boss. Without expectations from a boss who breaths down your neck, you will need to source motivation elsewhere. Losing motivation will happen to you from time to time, and it is normal. However, you will need to ensure to pick yourself up in order for your business to survive. There are multiple ways in which you can do this. For example, frequently revisiting the thoughts that made you want to start the business, or start working for yourself. Additionally, taking time off and away from work can also help you get motivated again.


You have to deal with all the responsibility that comes from running your business, from the small things like emails being answered on time, to finding the funding for your next big project. Being the boss means that you will have to keep on top off everyday operations as well as the long term, bigger picture. The success of your work and business will mean that you have the sole responsibility of making your business a success. You are also responsible for any employees that you have, which also means that you will need to manage your staff which is not always easy.

Business take off

Getting your business off the ground can be a huge challenge. You will likely underestimate the difficulty of selling things until you try to do it yourself. You can create the perfect product but if you don’t market it well, it will likely fail. Therefore, you need to pay attention to marketing as it is essential part of selling a product. Getting your business off the ground is difficult, from securing funding to hiring the right staff, however over time you will learn the skills you need to be a success.


Being at the top can be lonely. There are some benefits of being an employee, which is the mutual place you share with you colleagues. Whereas, when you are the boss of the company, you are in a unique place. To counteract the feeling of being separated from your team, or isolation, create a inclusive culture. You should also network as networking can allow you to build connections with people in similar positions to you.

More on starting up as well as, the benefits of being your own boss.

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