How To Be Your Own Boss

In a previous article on my website I talked about the Great Resignation and how many Americans are quitting their jobs to work for themselves. Maybe you would like to join them but you have this question: Could I be my own boss? In today’s article I explain how to be your own boss in three steps. These lessons come from my experience when I started my self-employment journey years ago. By the end you will know if you are ready to make the leap into entrepreneurship or need more time to prepare.

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Step #1 On How To Be Your Own Boss: Ask Yourself Why

The first step on how to be your own boss is ask yourself why you want to choose this path. Yes, I really want you to ask yourself this question. You need to do this because self-employment is tough. And if you need to hire employees or even contractors to help you that’s more stress to deal with besides running a business. If you aren’t prepared to do either of those things then entrepreneurship isn’t for you and that’s fine.

Working for someone else is not a bad way to work. I believe we should all work for someone else before we start our own business. And hopefully you’ll work for a good company and a bad company so you will see how to run a business well and how to run one into the ground. When you have this experience then you can consider striking out on your own.

When I asked myself why I wanted to be my own boss I came up with the following answers:

  • I have ideas for products and/or services I can’t work on while working for an employer.
  • I’m passionate about certain projects that I can’t do at work because of various reasons.
  • I move faster than what an employer allows because I’m not concerned about “red tape” or following certain processes and procedures.

Step #2 On How To Be Your Own Boss: Develop Your Plan

The second step on how to be your own boss is to develop you plan of action. As I said before self-employment is difficult and should not be entered into lightly. If you do so without having a plan you may fail. Or you could run into more difficulty than you probably should.

So how can you develop your plan? There are several options:

  • Contact your local Small Business Administration for assistance. They can help you develop a business plan and provide a listing of SCORE members who can mentor you.
  • Research how to get a business license or occupational tax certificate from your local city, county, or state.
  • Find a good lawyer and a tax professional to help you with legal issues (like LLC or Incorporation) and tax issues.
  • Determine if you can run your business from your home or do you need to rent a commercial property.
  • Run the numbers on how much you need to open your business. Then determine where can you get that funding (savings, taking out a loan, etc.).

These are only a few steps of how to develop your plan. Depending on your business idea or model, you may have an extensive list or a very short one.

For me, I run a few businesses: This blog, writing books, making videos for my YouTube channel, and my online store.

My writing business was very easy to setup because it’s all remote and I sell books through various online platforms. The same goes for my YouTube channel. However, my online t-shirt store is more involved because it requires me to collect sales tax and actually get a business license.

Final Step: Discuss This With Those Who Depend On You

The final step on how to be your own boss is to discuss your plans with those you depend on you. Because not only will your employment change but also you income and your health insurance.

This is an important step you shouldn’t skip because you need to hear the concerns of those who financially depend on you. And you need to have these conversations long before you quit your job because it will take time for those individuals to prepare.

Look at this way: Your income will decrease and that’s hard for anyone to deal with. That means less spending and sticking to a strict budget. Also, your health insurance will change. You may not be able to afford COBRA so you will have to purchase private health insurance. This will have different benefits and maybe include lower coverage than you had before. If you have a family member with a chronic health condition this may negatively affect him or her. Finally, there are various stressors that comes with entrepreneurship which can take a toll on you and your family. You all need to review these and discuss how to prepare for them.

From this conversation you may discover that you may not be able to quit your day job which is fine. Many people work a day job and run a business too. At the time of publishing this article I’m currently doing that. I know in the future after getting some personal items settled I will be able to quit my job and fully focus on my business ventures.

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