You want to be your own boss. This sounds like a dream come true, right?

No more running around after someone else. You get to pick the projects you work on and maybe even choose your own hours. Plus, if you’re the boss, you can create the kind of business that you really love.

Being self-employed or starting your own business is a wonderful experience for many people. However, it also comes with various challenges to consider.

Let’s face it, not everyone is cut out to be their own boss. Some people struggle with not having a consistent source of income. Others hate having to run around marketing themselves to potential clients.

If you’re planning on being self-employed, it’s time to do some self-discovery.

Are you really prepared to be your own boss?

Ask yourself these questions to find out.

Be Your Own Boss

Once you embark on your new career as a business owner, you’ll be responsible for everything, especially at first.

There’s no one else to handle the tough stuff. You’re going to have to find clients. It’s up to you to maintain a consistent income, and you need to be the person who handles the taxes too.

So, are you the kind of person who can handle that kind of responsibility? Are you ready for it all?

To determine if you have a personality that supports your desire to be a business owner, ask yourself these questions:

-Do I need help managing my schedule?

-Do I struggle with things like taxes and finances?

-Do I give up easily if things get difficult?

-Am I hesitant to work on things I don’t enjoy?

If the answer is “yes” or “maybe” to any of those questions, you may want to rethink whether being your own boss is right for you. You may need to consider a partner who fills those weaknesses or find an accountability buddy to make sure you do the hard stuff. Because being your own boss is no joke.

If the answer is “no,” then great, I think you’re ready for the challenge to be your own boss.

Have You Done Enough Research?

How sure are you that you have a good business idea? Are you diving into something that just seems good on the surface?

These days, it’s extremely easy to build a business in the digital world. Around 4.41 million new business applications were submitted in 2020 alone. However, just because you can start a business easily, doesn’t mean you should rush in.

Do your research and ensure that you have a solid plan for making money:

-Do you know if there’s a demand for whatever you’re selling?

-Have you proven/tested your product or service?

-How are you going to find customers?

-What are you going to do if you have a bad month or a rough patch?

-How will you differentiate yourself?

Imagine that you were selling this business idea to someone else. How could you convince them that it was a good idea? If you can’t, then you shouldn’t jump in yourself.

Take some time here. Think it through. Talk with your family and friends. Use your network to test your idea. You might find some great constructive feedback you can use to your benefit to help you be your own boss.

Do You Have a Safety Net?

Part of starting your own business is coming to terms with the fact that you’re not always going to make a consistent income. There are going to be rough patches, particularly when you’re first starting out.

This is well-known among entrepreneurs. It’s a total roller coaster. Some months or weeks are flush with income flowing in and other times are a total dry spell. It can feel like a feast or famine and it’s not always easy to plan for or keep going when there’s a famine.

With that in mind, how comfortable do you feel in your ability to survive if something goes wrong? Can you fall back on your savings? Can you get a loan?

Speaking of initial finances, how are you going to find the cash to get into business in the first place? Even if you’re running your company online, you’re going to need some money for things like software, perhaps a new computer, a website or a camera, or who knows what else.

With a little luck, you’ll have this money saved up from your previous job. If not, go into this new position with caution.

It’s okay to plan to be your own boss. Take a year or several months to build up a little cash so you have something to fall back on and you have enough for that initial marketing push.

Avoid spending all your income every month. Put some money aside whenever you make something, just in case. I always stress this.

Not only should you have a little business savings but you also need to save for taxes! This is all part of planning and knowing your responsibilities.

Are You Ready for the Workload?

Finally, being prepared to be your own boss also means preparing for a boss-level workload.

Eventually, you’re going to be able to hire people who can help you out with all the work you need to do. Or maybe your plan is to keep it small and just do the work you can handle yourself. Either way is fine.

Just remember that this takes time. At first, you’re going to be doing a lot of stuff on your own. That could mean some seriously long hours and stepping out of your comfort zone to do the not-so-fun things like taxes and finances.

Plus, even when you get to the point where you’re confident in taking on employees, that doesn’t mean that you can just sit back and relax. Hopefully, your business will continue to grow. It’s up to you to stay on the move, helping your company to evolve in any way you can.

Ask yourself if you’re willing to push yourself to new levels and keep working until you accomplish your goals. If you are, then you’re definitely going to be a killer boss. If you’re not, then maybe being your own boss isn’t really what you want deep down.

Taking time to ask yourself these questions before you dive into running your own business is important. This process can save you a lot of time, trouble, and money, whether you decide to go ahead with your business idea or not.

Stop Searching Google Nomad Business Academy
RV Tax Queen

I’m a numbers person—but don’t let that scare you. I’ve been an enrolled agent (EA) since 2014 and a nomadic business owner since 2016. Because I’m a nomad myself, I know exactly how stressful life on the road can be.

Nomad Business Academy

Nomad Business Academy offers mini-courses on everything you need to know to run a nomadic business, from which business entity is right for you (and what a “business entity” even is) to how to navigate self-employment taxes to learning if S Corp is a good fit for you and so much more.



This website is for general information only and is not intended to substitute for obtaining legal, accounting or financial advice. It is not rendering legal, accounting or other professional advice. Presentation of the information on this website is not intended to create a client relationship. For specific tax assistance please consult a tax professional on an individual basis.

While I make every effort to furnish accurate and updated information, I do not guarantee that any information contained in this website is accurate, complete, reliable, current or error-free. I assume no liability or responsibility for any errors or omissions in its content.


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