Want To Be Your Own Boss?

Do you know what your dream is really based on?


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.

Want To Be Your Own Boss?

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.

Want To Be Your Own Boss?

The reality of being an entrepreneur

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.

Want To Be Your Own Boss?

The fantasy…

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.

Want To Be Your Own Boss?

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 To Be Your Own Boss?

There’s a lot to consider

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:

Avatar of Parker Kaback

Parker is a serial entrepreneur and founder of Techovia, a business consulting agency. He grew up in the Hamptons and now lives in San Diego.

Reader Discussion: 116 Comments

  1. Avatar of Shannon Gutierrez

    Shannon Gutierrez

    This is a very challenging topic! Like it!??

  2. Avatar of Renee Griffith

    Renee Griffith

    Know your weakness and strength. Always learn from your mistakes and never stop learning something new.

  3. Avatar of Angie Becker

    Angie Becker

    I learned that even if you have the all the authority because you’re the boss should also need to listen to your people’s opinions. It may help you create a harmonious relationship with them.

    • Avatar of Edith Glover

      Edith Glover

      Don’t do all of their request just listen to their opinion assess if its good for the business, for them, and for you.

  4. Avatar of Muriel Vargas

    Muriel Vargas

    You should know how to mingle and know how to manage well the people that work for you.

  5. Avatar of Dianne Copeland

    Dianne Copeland

    To be a Good Boss you should need to be a Good worker too!

    • Avatar of Amy Watson

      Amy Watson

      That’s it! Learn the basics! Know the flow of the work.

  6. Avatar of Shawna Henry

    Shawna Henry

    Even if you’re managing a business or managing people in a company both still requires proper training.

  7. Avatar of Melba Harrington

    Melba Harrington

    Scrutinizing your own performance at work can make you grow as a person and can help you to become what you want to be…

  8. Avatar of Sheri Chapman

    Sheri Chapman

    I’m just starting to have my own business right now and I really need this kind of tips. So blessed to found this!?

  9. Avatar of Lillian Arnold

    Lillian Arnold

    Glad that I found this tips I need this to inspire me more! Thank you!?

  10. Avatar of Margaret Palmer

    Margaret Palmer

    My father told me that there is no easy Job in this world. And you can’t be a good boss if you can’t surpass all of the hardships. And it’s really true…

    • Avatar of Brandy Warner

      Brandy Warner

      Sooo True! I also live by my fathers footsteps. And now I’m a successful business woman…?

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