The allure of self-employment is powerful. Who doesn’t want to be their own boss, work when they want to, from wherever they want to, and have complete control of their income potential?
Unfortunately, it doesn’t really work that way. Becoming self-employed is a life-changing undertaking. I wouldn’t change my decision to become self-employed for anything in the world, but I didn’t decide to become a solopreneur without taking all possible factors into consideration.
Over the next several weeks we are going to dive deep into the world of self-employment, and talk about how to conquer some of the most pressing issues we face a self-employed individuals.
In my opinion, if you’re self-employed you’re an entrepreneur. Lots of people get in a pickle over calling self-employed individuals entrepreneurs, or solopreneurs, or small business owners.
I don’t think it matters.
What matters is that if you are solely responsible for generating your income through the development of a bona fide business, then I think you can call yourself any of the above. As such, I’ll be using the terms interchangeably.
Being self-employed has it fair share of advantages and disadvantages, so let’s talk about those now.
The Advantages of Self-Employment
Personal Fulfillment – If you start your own business for the right reasons, if you serve people that you were meant to serve, and if you truly enjoy what you do, there is no better feeling than making a living from it.
Professional Independence – Being able to call your own shots, establish your own business philosophy, and make your business what you want to be is not just empowering, it’s fun.
Unlimited Income Potential – Elusive as the concept may sound, most of America’s wealthiest individuals were small business owners at one time. That said, extraordinary wealth as a solopreneur is not the norm or average outcome by any measure. Many entrepreneurs make a satisfactory living, and are very happy, despite not being bazillionaires. Going into business for the right reasons to begin with, will greatly impact how you feel about the income you make in the end.
Tax Advantages – Believe it or not, owning a business can make you eligible to make use of tax privileges not available to employees such as deductions for costs, insurance, and an increased cap on tax free retirement savings.
The Disadvantages of Self-Employment
It’s All You – When you first become self-employed EVERYTHING is your responsibility. You can read The E-Myth Revisited by Michael Gerber, but you can count on having a hard time implementing his advice at first. In all likelihood you won’t have the financial resources and training systems in place to build a system for your business from the get-go. It takes time to do that. Juggling everything in your business can get overwhelming and intense. Having the right support in place to get through this start-up phase is essential to your success.
You Live With Uncertainty – Despite what most people think, just because you have a job, doesn’t mean you have financial security. As the last several years have demonstrated, your job can vanish like a vapor. The real difference between being an employee and being self-employed is that your level of psychological security is higher when you’re employed because you expect a paycheck.
This does not exist as a solopreneur. The reality that your income source could cease at any time is palpable when you’re self-employed. Thankfully, if you market your business properly, fill your pipeline with customers, develop multiple income streams, and deliver an amazing product/service so that you build a bona fide business this issue becomes less palpable.
Administrative Matters Are Your Matters – Filing taxes, keeping clean records, invoicing customers, drafting contracts, securing healthcare, obtaining insurance, applying for licenses and complying with regulations are all your problem. Thankfully, it’s not as bad as it sounds, and as you grow your business you can outsource many of these responsibilities. But until that day comes – this is all you too.
You Are The Fall Guy – When you first pursue self-employment, you will make mistakes. It’s part of the learning process. Developing a strong positive attitude and learning to “fail forward” is essential to getting your business of the ground.
You Don’t Really Call The Shots – This is the paradox of self-employment. You are in total control of your time, attention, and effort, but if you’re going to be successful your time attention and effort need to be on building your business. This means you’ll work more than you ever have. You’ll have multiple bosses instead of just one (your clients are your bosses). You’ll be able to work when you want to, but it better be quick and great quality if you want to be paid well for what you do. Managing your time, establishing balance, and exercising self-discipline are all part of the package for the solopreneur.
These pros and cons are just the “biggies.” There are many more of them too, and that is why it’s so important to know what you are getting into when you jump into self-employment.
Knowing The Good, The Bad, And The Ugly Are You Still Right For Self-Employment?
It’s often said that just because someone can be an entrepreneur, doesn’t mean they should. Personally, I think every individual should perfect their entrepreneurial skill set because you never know when you might be forced to use them. But if given the choice, you should only consider becoming self-employed if you have the right skill set and you’ve got the right reasons.
Of course, having the right products, services, and target market are essential to becoming successfully self-employed as well, but having the right set of intrinsic abilities to see your entrepreneurial pursuits through goes a long way.
Here are some key skills you will have to learn or outsource to become successfully self-employed:
- Financial Management – You have got to have a handle on your money matters.
- Marketing & Selling – If you don’t do these things you’ll be out of business before you start. Marketing is the lifeblood of your business.
- Leadership & Time Management – You are in charge of yourself and everything else; no one will tell you what to do.
- Confidence – This is hugely important and HUGELY overlooked.
- Trusted Intuition – You will have to make decisions regularly, and oftentimes without full knowledge.
- Positive Thinker – If you have a negative bent, rejection, setbacks, and unforeseen obstacles will throw you off course and you can’t afford that.
- Persistence & Ambition – There is no such thing as overnight success. There is no magic bean. Accept it and get to work.
- Unrelenting Passion – You’ve got to want to do what you’re doing more than anything else, otherwise go do the other things.
Still Not Sure? Take This Test!
Okay, so keeping in step with my philosophy of making work fun and always giving you actionable advice, I created this little online quiz to help you determine whether or not you are truly cut out for entrepreneurship.
This isn’t a scientific test based on years of research. If you’re looking for something like that try a Myers-Brigg exam. This is simply a guide that will indicate whether or not you have entrepreneurial traits working in your favor. It’s fun. So try it!
Then be sure to come back here and share your results in the comments below. And if you’re already self-employed, tell us some of the things you struggle with the most, or wish you would have known beforehand so we can learn from one another.
P.S. If you liked this article, you’ll love my free email business training program call Kick-A$$ Tips. Click here to sign up for instant access today. And don’t forget to join us on Facebook here.
Click here to take the quiz now.



{ 21 comments… read them below or add one }
I am a freelance contractor works in different SEO jobs independently. I prefer to lead a life of my own with my own work rather listening to the complains of the BOSS. I am happy with the life style what I have now.
Great points. I can’t wait to get more info from you.
This was really a great article which is enlightening about the different aspects of self employment. Though there are some disadvantages of self employment, but still I think self employment is the best option for living.
I run my own event photography business and have to agree with all your points on being self employed. I think the main thing you need is control and focus. Without these you can easily become tired and lose direction.
Also on a lighter note- the most common description of the self employed.’They moan when they are busy and moan even more when they are quiet’
This is an excellent post. So many people quit their jobs thinking that they are going to start their own thing from home, just to end up failing. The reason is that they don’t do the required research upfront and don’t know what is really involved.
PS Wanted to make sure you saw your blog on my new CommentLuv enabled blog list!
Hi Marlee,
Thanks for addressing this question. It’s a big concern and dream so many of us debate.
It’s definitely scary, but once you’ve made it, it must be such an amazing feeling.
Great work. Hope to be back often.
Hey Bryce,
Welcome, and thank you for being here. I appreciate your feedback. Yes, making the decision is definitely an amazing feeling, but it’s sticking to it that presents the real challenge!
Is self employment for me? NO. Why? Because I do not know the virtues of self discipline. But I have to admit that self employment/freelance work sure seems alluring to me, as opposed to being someone else’s slave.
LMBO! You cracked me up, Wez. But you know, you make a great point. If you don’t have self-discipline, you can pretty much guarantee that being self-employed will be challenging. Then again, with the right support systems – it’s possible. Thanks for stopping by.
Sometimes self-employment seems to be the only option, for some.
Some appropriate food for thought during these economic times~
there were more millionaires created during the Great Depression, than at any other time in history.
Hey Chas!
Welcome. I love the you highlight the bright side. I think that tougher economic time bring out the best in entrepreneurs, so I know that we’ll see some incredible growth as we come out of them.
It says “John Garrett’s Result: Self-Employment May Not Be For You”.
As Scooby Doo would say: “RUH ROH!!!”
Too late. I’m already doing this thing lol.
But this is (another) great article, since it (and the quiz) made me think about a couple of other pieces of business I should attend to.
Sistas (and the brothas) are doin’ it for themselves!
LMBO! ROFL! Oh, John. You kill me!
I’m glad it made you think, and most importantly remind you to get the support you need to shore up loose ends. Sometimes we try to do it all or ignore the small stuff and long-term that becomes a trap. I think you are totally made for self-employment, JG. I think my answers tricked ya.
Marlee – I am made for Entrepreneurship!
First of all, I love the new design. I had to take a second look to make sure I was int he right place but Im diggin’it! Very clean and professional!
Anyway, I took your quiz (pretty cool by the way) and it looks like I am ade for entrepreneurship. Of course I already knew this ( I think I’ve been knowing this since the time I was grade school and would collect and sell pogs to my friends, earning a small profit but enough to buy a snack a few times a week during lunch
).
Anyway, I’ll keep this short and sweet. One of the things that I really loved about this post was that you identified some of the skills that you have to master to become an entrepreneur.
Among them was, financial management. I think most small business owners, especially Internet Entrepreneurs, don’t really pay much attention to this but this is so KEY!
Americans have a crisis in their hands – a financial crisis, and if aspiring entrepreneurs mange their business finances anything like they do their personal finances, it’s the surest way to failing and possibly even bankruptcy.
This is one of the main reasons that I now only talk about Internet Entrepreneurship over at IEC, but also about Financial Intelligence.
Anyway, there are so many lessons to take from this post but the one that jumped out to me the most was Financial Management.
I hope my views resonate with you and your community! Keep bringing the awesome posts!
Hector – WORD!
You are so on point about not tending to financial management. Honestly, I think it’s just intimidating to a lot of people. Personally, I hate it. I do it, because I know I should. But believe me – it’s the next thing on my list of things to outsource! I’ll definitely be using your expertise in the areas of financial intelligence as it relates to entrepreneurs in the future!
Marlee,
Great quiz and even better points. In order to be willing to do it yourself we have to understand that there is a lot more to it than making a product and cashing checks. When I was in college I though that being an self employed individual was a cake walk. I thought it was a simple process to start and run a business. Let’s just say i learned a real tough life lesson. I started a business and it tanked quickly. So quickly that I haven’t talked about it with anyone for years. I found I just had a very competitive niche and a low value product. This post will save a lot of people from jumping in too quickly without understanding what is involved. Great post.
Hey Frank,
I’m glad I’ve got your stamp of approval. Thanks for sharing your experience here. It’s important for people to know that it’s not as easy as it looks, but it’s totally worth it!
Marlee: What a great article. I really love this article and analysis on becoming self employed. I think it is amazingly helpful for all of us that are out there in the self employment world or evaluating if it is something we want to pursue. I also appreciated that list of skills … I must admit I was wondering how many of those I am either missing or need to strengthen
Great post and information Marlee. Thanks for sharing it.
Hi Sibyl,
Thank you for your feedback. I truly believe that we should focus on our strengths, but that in the same stride, it’s important to know our weaknesses. Doing so also us to build the support systems we need to increase our likelihood of success. Glad you enjoyed it!
Marlee – what’s up!
Let me begin by sharing my results from the quiz:
Jk Allen’s Result: You Are Made For Entrepreneurship!
At the tender age of 24 (at the time with 1 kid and one on the way) I left the confines of the corporate world and ran my own business. The first few things I learned were:
1- it’s easier, sometimes having a boss, because that means there’s someone else to absorb some of the stress!
What stress? Dealing with demanding clients who think they own you when on retainer. Clients who constantly blow up your phone for the smallest non-issues in the world. And of course the $$ when times are slow.
2- freedom comes with a cost… which happens to be a lack of freedom.
During the 2.5 years I was self-employed I had never worked so hard before then…and to be honest, since my re-entry back into corporate America 4 years ago, I’ve never worked so hard since. It’s a different type of freedom.
This post was a great reminder for me…and I even learned that I’m MADE FOR ENTREPRENEURSHIP! Thanks Marlee!
PEACE
Of course you are made for Entrepreneurship! Were there ever really any doubts? Not in my mind. I love your examples, though. They are SO on point!