I started my first business at 14 yr old. Maybe my age makes it sounds like an impressive accomplishment or just something to say for bragging rights? I can honestly tell you, it doesn’t matter. What does matter is “starting” and defining success.


Thomas Edison once said, “If we did all the things we are capable of, we would literally astound ourselves.” Have you ever taken the time to quiz yourself or dream about this statement? The catch 22 is we have no idea what we are capable of until we enter the territory of the unknown. People seem to have no problem being “brave” and discovering the answer to the question “how much alcohol are you capable of drinking?” There seems to be little fear of the consequence of “failing” while learning the answer. When I was a child I watched many successful stock brokers, archaeologists, treasure hunters, and real estate moguls (including the one with small hands) on T.V.  I remember thinking, “I wonder if I could do that?”.

American Dream

I was fortunate enough to grow up inside one positive aspect of American culture often referred to as the “American Dream.” Americans seem to gobble up as many stories as possible about people who have gone from rags to riches. In my earlier years far more inspiring was watching teenagers who by a stroke of luck, or brilliance became successful in tech or trading stocks during the dot-com boom of the 1990’s. I’m not sure if it was my 9-year-old pride, arrogance, ignorance, insecurity or an open mind. But I remember thinking “if these kids can do this, I should be able to as well.” Any why not? Every success story comes from a baby human being, born ignorant and uneducated, right?


Starting. Often the biggest hurdle to any of my past success was the failure to even start. I phrase it that way on purpose. Failure to start is a failure. Starting something and learning after awhile that you will not be able to continue,
2 scenarios.

1.Failure to start=definate failure
2.Starting something and learning after awhile that you will not be able to continue=potential failure

What one will you choose?


I could write feel good headlines like “Quit my day job, became a travel blogger, now my life is better than yours” or “I used to suffer the 9-5 routine but now that I have mastered social media, I only work 1 hr per day from a penthouse in Singapore”.
These kinds of headlines are good and fine, but is everyone really looking to quit a “normal job” and start making a living from a computer? Probably not.  Often there are far more relevant headlines that I wish saw getting the same amount of attention. Our society is quite focused on money being a measurement of success. Until this changes, I guess we will keep focusing on these types of headlines.

defining success.

So how would your defining headline read? “I finally started going out in public with very little makeup on because I’m ok with the way I look” or “I got the courage to speak about what happened to me in my past” or “80% of my choices used to be dictated by what others thought of me, now it’s nearly 0%”
The point is that if there is something in your life you think you should start doing then do it. If it’s starting a business GREAT! Get some good books, read up about what you would like to do and learn from people who have done it or are already doing it. Work for someone (for free, if you must) who is a master in this just to learn the ropes. See what is done well, see what can be done better.


If it’s about becoming a more courageous person. Maybe consider what steps you should start taking to free yourself from fear.  As Aristotle taught, one of the best ways to become virtuous is by developing virtuous habits. For example, courage. Each time you are faced with a small choice to be courageous or fearful. (even with a silly choice of trying a new food) choose the courageous. By doing this, in time you will have series of courageous choices that amount to you being defined and growing into a courageous person. Click HERE for a pretty great write up on his teachings.


When I started my first business, a small I.T. helpdesk, and service company at 14 years old I can honestly say I didn’t know that it was possible to make a successful business out of it. But I intended to find out. I calmed my childish fears by saying. I have 4 years to figure this out then by the time I graduate I will have to be a serious adult, if things aren’t working out by then I guess I will have to get a “Real” job like everyone else. Although these thoughts seemed to pacify my fears at the time, they didn’t resolve my core fears of taking steps that most others in society didn’t often take or didn’t approve of. These fears would continue to haunt me for years. They would affect the choices I had to make in business, relationships, and life. I had some positive support from my family that I could try to do this if I wanted to. This certainly was a huge help during “difficult” times.

Commented insecurity

Most other people’s comments (extended family and often friends) only increased my insecurities if only temporarily. If I would have a slow week at work, comments like “it’s the middle of the day, why aren’t you working” or “I had a friend who tried to have a service business, but he was so sick of it after 2 years he quit” or even the innocent “I could never do that.” . These comments made it very difficult for me to stay confident in the fact that I COULD do it.

Fear & Doubt hesitation and regret.

A wise old man once told me, “Charlie, there is no room for unwanted house guests in your life. I asked him what he was talking about. “fear and doubt have been lodging with you too long,” He said. “Also their cousins’ hesitation and regret. It’s time you throw them out”. Certainly hearing someone say they saw these “house guests” in my life and defining it this way made me more aware to not allow any space for them anymore in my choices and though patterns.

Learn to define success based on your own desires and goals. Don’t get discouraged by headlines that seem impossible for you in your current situation. Likewise, don’t be discouraged by headlines that don’t reflect outcomes that would enrich your life.

The unsettled settler.



Charles Driscoll is a writer/blogger, musician, entrepreneur and an explorer of humanity. Learning to take the time to enjoy life, love, share and encourage others. You can follow his blog at www.theunsettledsettler.com. You can also find his musical musings at www.rivertidemusic.com


  1. “These kinds of headlines are good and fine, but is everyone really looking to quit a “normal job” and start making a living from a computer? Probably not”
    I cannot agree more with these statements. I think so many of us just want to find short-cuts to being happy and blindly follow people. What we often fail to register is that so much of life is about having your own trials and errors and what works for one, isn’t always the right path for another. Loved your post!

  2. Thank you for your input! You are right, each is looking for a shortcut to some kind of happiness. If we see someone else happy with their life (living it a certain way) we somehow assume this is what we need to do to find happiness! Best wishes on your blog also!

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