People often associate being self-employed with freedom. Financial independence, a flexible work schedule and the luxury of not answering to a superior are common themes in the glamorized entrepreneurial fantasies of many workers. But how many entrepreneurs actually score perfect in the areas of flexible schedules, plenty of money and absolute power? When I look closely at the lives of people I admire, capitalists who I perceive as having “made it” in their respective industries, I observe that most are making a significant concession in at least one of those major categories.

A close friend of mine has a high profile tech start up. He took venture capital money to get it off the ground and has a board of directors over his shoulder monitoring and critiquing his every move. They may tolerate his exorbitant salary but he once described the board to me as the “worst boss he ever had”.
Several of the business people I know started small and built their businesses organically over time. I have two friends who run a staffing firm as principals of the company answering to no one. They also make a very decent living but they work 6 days a week and consistently over 60 hours.
I have another friend who opened a successful boutique. She determines when the store opens and closes, has competent employees capable of running the store so if she wants to leave town for a week for a trip to Spain she can. However, covering the monthly nut on retail space and payroll in New York City is a challenge even when sales are good. She made more money as a medical device sales rep.
And these are my examples of the people that made it.

Unquestionably, there are examples of people who make it look easy, who have it all and who don’t make concessions. More often than not, I have found those people are lucky as opposed to good. My friends and colleagues referenced above and countless others I know failed more times than they succeeded. Their path, even if successful ultimately, was defined by tough times, periods of uncertainty and tremendous personal sacrifice.
I’m an entrepreneur as well, so I should know. Many of my perspective clients are startups, and I help them get off the ground. Almost all of my perspective clients are gainfully employed. Countless times a prospect has described a new business idea to me that, on the surface, seems genius and simple, but as I help them flesh out the cost, timeline, labor and commitment their project will require, they become disappointed. Frequently a comment is made that provides insight into their true motivation for starting this business. They wanted an escape from their current reality. They wanted to never see that jerk boss again. They want to be able to play golf on a Tuesday afternoon if they feel like it. They want to buy the big house on the hill.

It appears many people who dream of having their own business someday are very unrealistic about what that entails. Somehow, they view being self-employed as a destination when it is actually just the beginning of a very long journey. Opening a business is not the easy way to make a fast buck. I can reference personal experience to validate that statement. I gave up having one boss for having dozens; I just call them customers now. My new hours; every hour I am interested in making money I am working.
My life didn’t become less stressful when I went out on my own. At several points I almost went under and came close to losing my nerve. I still haven’t made the money I could have made at this point in my life in a different profession; working for someone else. So why would I make these choices? The answer is because I enjoy what I do, because I am passionate about my business.
My big dream is to grow my business, become significant enough to show up on someone’s radar, get bought out and retire early in Latin America. My dream isn’t all about the ending. If my only interest was in the part where I retire to Latin America, there are easier and more expedient ways to go about that. I could find a firm with an office in Panama City right now, take the Rosetta Stone DVDs from under my bed, put them to use and be there in six months. I find the process to be rewarding and enlightening. I am most interested in the parts where I am navigating my way there.

There is a famous saying that you either live to work or work to live. If you go into business for yourself you had better live to work. Be self-employed because if affords you the opportunity to do something that you love. Do it, because you can’t imagine doing anything else. Start a business if you are interested in creating something of significance or because you want to provide opportunity for others.
If you think being self-employed will make you happy, solve your problems or increase your personal freedoms, you’re doing it for all the wrong reasons.
Perhaps even more apropos is one of my favorite quotes: The Dalai Lama, when asked what surprised him most about humanity, answered “Man. Because he sacrifices his health in order to make money. Then he sacrifices money to recuperate his health. And then he is so anxious about the future that he does not enjoy the present; the result being that he does not live in the present or the future; he lives as if he is never going to die, and then dies having never really lived.”

Want more info on deciding if starting a business is right for you? Here is a list of other great tools and articles on the topic:
- SmallBizTrends: Small Business Failure Rates – Most new businesses fail. What will be the impact on your life if your new business is not successful?
- MarleeWard: The Pro’s and Con’s of Self Employment – and a free quiz to help you determine if self employment is right for you.
- WSJ: How to Decide if Entrepreneurship is Right for You – 5 questions every aspiring entrepreneur should know the answer to before taking the leap.
- About: Starting a Business Quiz – Questions which will help you determine whether starting a business is the right path for you.
- Forbes: 11 Myths of Owning a Small Business – A lot of what you hear about starting a business is just plain wrong.
- Business Owners Toolkit: Do You Have the Right Stuff to Run a Business – An overview of the essential qualities for owners, how to compensate for weaknesses, and the impact of business on your personal life.



I dream of becoming a boss of my own business someday. This can help me in providing the steps on how to have a successful business. Thanks girl!
Never tried to have a business. This is a good idea and inspiration. Thank you.
Yeah right! This us very interesting!
Boss or not you should always equipped yourself by learning new things to become more of what you are.
Yes I tell that to myself. And I feel motivated.
I once tried to have a business it’s fulfilling because I’m the boss and I have staff whom I can ask for the service for the cutomer but when it comes to financial aspect I am the one who is incharge. It went well on the first to third month but suddenly after that my sales dropped off. Maybe I lack of skills that is why on the sixth month I clossed it…☹️
Yah it’s frustrating but you will never learn if you didn’t try. So should try again and think of ways to improve.
Everyone wants to be his/her own boss. And some really think that when you have your own business you don’t have a boss anymore but you’re right that the boss will be your customer at some point.
Oh yeah! You will have multiple bosses!
Sometimes I just really want to laugh at those people who think they can finally work with their feet up while lounging on a beach when they become entrepreneurs. The more my business grew, the more I felt like I could no longer rest. Complacency could destroy everything. Although I’m doing something I love right now, there was never really an opportunity for me to put my feet up. It’s a neverending work day for me. Although I probably should have used some of the time to just enjoy, there’s nothing more fun than seeing your business grow daily.
That’s actually a very good mindset.
I don’t think this is the life for me. Although I do believe that everyone can be successful, they just have to do it in their own way. Entrepreneur or not.
You’ll always have a boss no matter what field you decide to pursue. It’s a mind game when people say you’re your own boss. There’s no such thing.
I’m not against entrepreneurship because it gives a lot of people the opportunity to build a good environment of their own and a lot of people really do thrive in that kind of career. However, if you have mixed priorities, you’re going to have an issue and you’re going to be making yourself miserable. While it’s all about creating opportunities for others and yourself, it can also be an opportunity to create problems for other people and not just solutions. If you’re the type of person who’s into being responsible for all the pros and cons of everybody else’s issues, then this career is for you.
Never be pressured to be an entrep. Let’s just say just 30% of the population has a knack for it.
Financial independence? More like unstable income at first! ? In reality, it’s investing all your hard earned cash and waiting for it to grow on trees.