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.



Unless you’re 100% ready to give up your time, you can’t be your own boss just yet. That’s the reality.?
Unless you’re 100% ready to give up your time, you can’t be your own boss just yet. That’s the reality.?
What I love the most about being my own boss was that the fact that I had the opportunity to create jobs for others. I was able to support other people now when back then I had very little to no support and I was overworked and underpaid. I had the opportunity to hire people and create my small business. I was happy that as a result, I help others pay their bills. I train them too whenever I could. I was able to feed families that aren’t just my own while I was making a decent living. It wasn’t an easy journey as I had set myself up for failures that are almost countless, I nearly gave up. But it’s worth it in the end.
There’s is no reason you can’t pull as much or more money than you did when you were traditionally employed. I left my job to start my own business, initially, the income was not that much but it grew and is much more than what I used to earn.
Being self-employed is overrated!!
When you are self-employed, you no longer have a “higher-up” governing your every move. You control how your work is done and that’s the best part about it.
While one of the benefits of being your own boss is taking your own time in doing things, it doesn’t mean that you don’t have a deadline. If you take too long, you’re not going to make any progress. Freedom here is just a state of mind…
Wow, this is very true. There’s really no such thing as having your own time.
Every plan in this world has it’s drawbacks. Consider them first before leaping for something you don’t know the pros and cons of.
When you are self-employed you know you are your own boss. It’s the one we all dreamed about when we realized self-employment was an available option. Being our own boss. Escaping the rat race and living life as we pleased. Remember that. Every thing has there own pros and cons. But I still chose to be my own boss.
Can you just imagine a life in which you can live on your own terms? That would have sounded really fun. I’m sure most of us wanted to be ‘our own boss’ at some point in our lives because you wanted that ‘freedom’. Let’s face it too, we probably had that job that sucked the life out of us, which led us to this decision that we wanted to be the boss of our own company. Self-employment can be really tough though, no matter how dreamy it all sounds. All the problems that arise will be our own and we have to fix it on our own too. However, you will take pride in all of it once you’ve achieved something. It’s not for the weak though.
I totally agree that this isn’t for the weak. It’s basically shouldering everything.