Is It Risky Playing It Safe With Your Life?

During my incredible video interview with Digital Lifestyle Expert and TODAY Show correspondent, Mario Armstrong, we were talking about what inspired us to be an entrepreneur and I said, “I want to be a shining example to my 20 month old twins of what’s possible when you believe in yourself and follow your passion,” and not just play it safe.

Then I said, “It’s risky playing it safe,” which intrigued Mario.


A Life Of Regret

What inspired my risky-safe riff was an article I read a few months back by a palliative care nurse whose job was to take care of patients who were sent home and expected to only live another few months. The nurse said the most common regret from all her terminally ill patients was:

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

Then the nurse said:

When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.

Wow. Powerful stuff.


Passion Doesn’t Pay

Obviously, as an entrepreneur, these insights resonate with me. But I wanted to see what other people thought about the merits of following one’s passion in life. I came across this article in Forbes titled, 3 Reasons Following Your Passion Will Send You To The Poor House. In the Forbes article, the author suggests the 3 reasons are:

  1. Your passion is probably not profitable;
  2. People expect you to do what you love for free; and
  3. Sometimes, life is about solving problems.

As an explanation of the third reason the Forbes author says:

None of us are owed a life in which we get paid to do exactly what makes us happiest and the sooner you get over your resentment at the rarefied few who do make a living from their love, the better off you’ll be.

Really? Wow. Interesting.


According to the creator of this beautiful graphic, Martijn Vreugde, The Greeks didn’t write obituaries, they only asked one question after a man died, ‘Did he have passion?’


Now, I’m no life expert and I don’t have all the answers-mostly all I have is questions. But, while her reasons seem somewhat practical, the Forbes author’s take strikes me as incredibly cynical and devoid of hope, and gives no credence to a person’s ability to choose a life of her/his own.

Since I’m busting my ass on my startup, WeMontage, which has not exactly taken off according to plan, I’m naturally more inclined to live a life guided by the insights shared by the nurse. That is, I don’t want to be at the end of my life and regret that I didn’t honor my truth, or as it is described in the book, The Alchemist, my personal legend, which is to be a successful entrepreneur and inspire others to honor their personal legend.


The Power To Choose

I just started listening to The Alchemist audio book and so far, one of the more noteworthy passages is what the book describes as the world’s biggest lie, which is:

At a certain point in our lives, we lose control over what’s happening to us, and our lives become controlled by fate.

I do not believe the lie. I believe we have the power to choose what we want to be. Maybe this is what drives me so hard.

And, yes, I believe it IS risky playing it safe with life.

What do you believe? Do you relate more to the insights of the palliative care nurse, or the Forbes author? I’d love to hear your thoughts in the comments.

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 Photo Credit (feature image): Steven Depolo, Play at your own risk


  1. Play at your own Risk! Wow, that is a sensitive subject. I have been an entrepreneur for a long time. I will tell you it is hard. So what. If it was easy everyone would do it. I believe another way to look at it is to follow your dreams and work your ass off. I have quit every year for twenty years, only to be more committed each time. I think we equate money with success. When we use that as a measurement we will be discouraged in the short term. When I did that by all standards I failed. When I changed the measurement I realized I had a tremendous impact. When I pursued the impact I made money. Huh.
    How do you measure your success? Then ask yourself do you Want To Play?

  2. I agree with the statement passion doesn’t (necessarily) pay.

    Having a cool product, and passion to promote it…even money to promote it along with the time to promote it, doesn’t mean there is a market, or a market fit. I think most good ideas are wasted on applying them to the wrong crowd, purpose or vertical.

    My first start up is a good example. The tech is ingenious.. the solution to the problem is perfect. The market I chose seems to have no customers willing to roll with it. I’m convinced the solution will be used somewhere, I just haven’t stumbled across the right market fit that will kick it off. All the passion and enthusiasm for the product made no real difference for the long run. But I learned a lot in that endeavor. The old adage that if you work hard enough you can do anything is not exactly true. If you don’t work hard, nothing will come of it for sure, but hard work is not the only factor in a successful business.

    WeMontage may find its fit yet… but be assured that your next idea may be better or worse, but with the knowledge you gained I’m sure the next project will have less bumps and bruises for sure.

    But sitting in the spectator seats or even on the bench is no place to live life.

  3. People are accustomed to playing it safe and following behind the lead of someone who seems to have the answers because that has been ingrained in most of us since childhood development. Me on the other hand could really care less to fit into the system of dependency and being a risk averse person who lives a mundane life. I need the thrill of the unknown, the purpose of overcoming challenges and the pursuit of executing a vision I have within my head. There is too much opportunity in this world to be a puppet who is pulled by the strings of mainstream society. I just can’t do it.

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