Eliminating “Be Your Own Boss” Chaos: 6 Organizational Tips for the Self-Employed

Being your own boss can be a nightmare for all the same reasons that it can be a blessing.  When you take the plunge and become self-employed, you also become responsible for all of the administrative and management tasks your boss was doing for you before. 

It can be both stressful and liberating to know that your success rests on you. Here are six organizational tips for the self-employed to help you cut down on “be your own boss” chaos. 

Eliminate clutter

Going self-employed for the first time, you might be blown away by how much paper you rack up. Finding one specific invoice in a sea of clutter on your desk is a quick way to make your new entrepreneurial venture into a major headache. 

You can work online where possible to reduce paper clutter. Digital organizational tools can help you stay on track and make sure nothing slips through the cracks. For example, you can handle all of your new business mail using a virtual P.O. box. Virtual P.O. boxes intercept and scan your mail for you, meaning you can decide what happens to your mail with the touch of a button on your smartphone or computer. Using this tool, you save money and time while also ensuring no correspondence goes unchecked.

You can also invest in CRM software for keeping track of invoices and reviews. For sensitive documents, you can use free services such as Google Workspace. 

Establish a routine

Gone are your days of working the 9-to-5 beat, but that doesn’t mean you shouldn’t set some work hours. You should figure out how to organize your daily routine for maximum efficiency and productivity.

Start each day with a structured plan that outlines the day’s most important activities. Estimate how long each task should take to complete. Add about 20% to your overall estimate to account for delays or breaks.

Planning out your day and padding in some extra time allows you to take things at your own pace. This way, everything gets done without feeling like you’re constantly rushing from one task to the next. 

Use a calendar

You mustn’t lose track of the long-term while you’re planning out each day’s tasks. Using a calendar can help you visualize your long-term goals and contextualize your work assignments with all of your life events, such as birthdays and holidays. 

Every entrepreneur works more effectively during certain parts of the day. If you work better in the morning, then use your calendar to schedule critical meetings before noon. On the other hand, if you usually crash at around 2 pm, use your calendar layout to plan around the slump.

Avoid procrastination

Procrastination causes many self-employed individuals to fail at running a profitable business. Use the following steps to help you beat procrastination. 

Start by setting goals that motivate you. If your dreams don’t make you excited, then you should go back to the drawing board. The purpose of goal setting is to find a vision that makes you want to jump out of bed each morning. 

Set deadlines to goals. You’ll successfully overcome procrastination tendencies if your goals motivate you and you’re excited about getting them done on time.

Finally, reward yourself for finishing goals and tasks on time. This reward will help you get off the couch if you ever feel like letting your work slide into tomorrow. 

You’ll feel more organized the more you avoid procrastination and see your goals getting done.

Plan one day ahead

Planning out your daily tasks in the morning can leave you feeling like you’ve jumped into the ocean with no clear idea of how to swim or which way to go. Instead, plan the next day’s activities the previous night. 

This method is suitable for bypassing the morning fog by giving you a clear plan of attack to get started. 

It also helps you navigate the ups and downs of each day. Project delays could still leave you out in the cold, even when padding assignments by 20% during the planning phase. Planning a day in advance allows you to get ahead of the curve. If any projects run long, you can mentally file it away as a higher priority for the next business day. 

Use a filing system

Just because you jumped ship from the office doesn’t mean you can forsake the filing. Good organization requires proper filing and indexing. Use a physical filing cabinet with labeled folders to store important documents. You can get the same job done digitally by using digital filing systems such as:

  • Microsoft SharePoint
  • M-Files
  • Rubex

These types of tools and practices will help keep your desk and your desktop clear of clutter.


When you become your own boss, you trade the safety net for the freedom to do things as you like. This switch has the potential for great reward, but you won’t have the benefit of the second pair of eyes, so be vigilant and keep organized.


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