Should You Work For Yourself? Things You Should Consider

by Hank Coleman

Work On Your Money ever dayBeing an entrepreneur is a goal that many people hope for, especially with success stories like Mark Zuckerberg in the news. It seems so simple to make all your dreams come true just by coming up with the right idea and becoming your own boss. However, what the news rarely shows you are the tough decisions and the struggles that success stories go through before they’re financially set. So, the question remains. Should you work for yourself? There are many things that you must consider before you make that leap.

The economy has improved, but it is still in relatively bad shape. If you currently have a job or stable career, you’re still considered lucky by millions of people. But if you still have that nagging feeling every Monday morning on your commute to work, that you can do it your way and enjoy it a lot more, then you may have something to consider. Before you walk into your boss’ office announcing your resignation, here are some things to consider before making it official that you will be your own boss:

Should You Work For Yourself? Consider…

What Will Your Income Flow Be Like

Are you comfortable not having a steady flow of income for a while? One of the things we take for granted at our 9-5 is that we know when payday is, and we usually know how much to expect on our check. Being an entrepreneur, depending on the industry, you may not receive that consistent and predictable pay period. You may go from getting paid every two weeks to once a month, or be compensated per project when you’re used to being paid per hour. It’s an adjustment you have to be willing to make.

Can You Work By Yourself?

Can you work alone or do you need interaction with others? Entrepreneurship can get sort of lonely for someone who’s used to working in a large company setting. We sometimes take our colleagues for granted until we’re in our home office by ourselves with no one to have water cooler conversation with. That’s not to say there’s no solution for this. There are plenty of people who work for themselves who find co-working spaces to work from to get rid of that lonely feeling. But if you’re someone who works better individually, this may be a good move for you.

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Is Your Heart Really In It?

Are you doing this for the right reason? What is your true motive for wanting to be an entrepreneur? Do you want to work different hours? Are you fed up with your long commute? These are things that you can find while still working for another company. However, if you have a great idea and want to bring it to others on your terms, working for yourself is a great idea. Don’t become an entrepreneur strictly for the status of it. Do it because this is your dream, or a means to an end that is your dream.

There’s many other questions to ask before making the plunge, because it’s a big life decision, and it should not be made lightly. If you have a family, this is something you should discuss with them, as it will most likely affect them as well.

There’s no age limit to becoming an entrepreneur. You can be 20 or 60 and still see success. Be sure you have the right people around you, giving you professional advice and being your support system during this time of your life. Don’t make the plunge unless you’re absolutely sure you’re ready.

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About Hank Coleman

Hank Coleman is the founder of Money Q&A, an Iraq combat veteran, a Dr. Pepper addict, and a self-proclaimed investing junkie. He has written extensively for many nationally known financial websites and publications. Hank holds a Master’s Degree in Finance and a graduate certificate in personal financial planning. Email him directly at Hank[at]

Hank Coleman has written 581 articles on Money Q&A. Learn more about Money Q&A on Twitter @MoneyQandA and @HankColeman.

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{ 3 comments… read them below or add one }


We need more entrepreneurs in this country. When you are younger and have little to no financial responsibilities it is the best time to get going as your own boss. Know in advance that you will make mistakes, but this can be your best path to financial independence. Just ask a 40 year old making $150k if they can walk way from their job!


Edward Antrobus

I don’t have so much of a problem working by myself, as I do working for myself. Even though I am a part of a team, we are often separated from one end of the project to another and out of communication with each other. But I work much better when I am accountable to somebody else.


Stephanie Christensen

I love working myself but it is definitely not for the faint of heart….or in my experience, a person who does not have at least significant savings and/or a spouse who does have reliable income. At least in the writing and yoga instructor world, which is what I do, there is quite a big of “lag time” from when you work to when you are compensated–and you’ll pay taxes quarterly, so you’ve got to have a pretty big financial cushion to account for that.


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