Risking It All!


When you believe in yourself, you take risks. When you don’t, you play it safe.


“When you believe in yourself, you take risks. When you don’t, you play it safe.”


The more of a sure thing, guaranteed money, safe bet you need, the more you’ll be controlled by other people.

If you’re dying for freedom, longing to live a lifestyle of your choosing, you’re not going to find it in the confines of safe predictability.

Freedom to live the life you want is a messy, risky, up & down roller coaster ride, especially while you’re trying to figure things out. Before it gets any easier, your life can get a lot more difficult.

There are no maps for sale. Each of us has to chart our own course. Sure, there’s help along the way, if you’re willing to reach for it, and pay whatever price it takes, but there are no guarantees. None. It’s all on you, baby!

Quick Summary

  1. Self-Belief and Risk-Taking: The article starts with a powerful assertion that believing in oneself is directly correlated with the willingness to take risks, while a lack of confidence leads to a preference for safety and predictability.
  2. Control and Freedom: It highlights that seeking guaranteed outcomes often results in relinquishing control over one’s life, whereas true freedom comes from embracing the uncertainties and messiness associated with risk-taking.
  3. Navigating Uncharted Territory: The journey towards personal freedom and success doesn’t come with a roadmap. It’s a personal journey filled with ups and downs, requiring individual resilience and often, a willingness to seek and accept help.
  4. Consequences of Choices: The article underscores the profound impact of personal choices, suggesting that the fear of negative outcomes can paralyze individuals, preventing them from taking the necessary leaps toward their goals.
  5. Real-Life Risk Examples: Through personal anecdotes, the author illustrates real-life scenarios of risk-taking, emphasizing the courage it takes to invest one’s last resources into uncertain ventures, as exemplified by his father’s actions.
  6. Corporate Safety Net: The author shares his experience of retreating into the corporate world, highlighting the comfort of predictability, regular paychecks, and shared responsibilities but acknowledging the trade-off with personal freedom and control.
  7. Team Synergy and Hidden Inefficiencies: Corporate life taught the author about the power of collaborative effort and also exposed the survival of inefficiencies within systems, which would not withstand the ruthless scrutiny of the free market.
  8. Self-Discovery and Return to Risk: The stint in corporate life, while comforting, was also a period of self-reflection, leading the author to rediscover his confidence and make a deliberate decision to leap back into risk-taking by pursuing his entrepreneurial aspirations.
  9. Resurgence and Success: Post his return to the entrepreneurial world, the author faced initial struggles but persevered, leading to eventual success and recognition in his field, thereby validating his decision to take risks.
  10. Concluding Reflection: The article concludes with a contemplative note, prompting readers to introspect on their willingness to take risks. It reinforces the idea that self-belief is the critical determinant of whether individuals will stay within their comfort zones or take bold leaps toward their aspirations.


You live, or you die, on your own choices, and frankly, that’s too much pressure for some people.

The risk is not worth the potential reward because they freeze up when it comes time to take the risks necessary to leap towards freedom.

I suppose this is normal, logical behavior. I mean, who purposely leaps on purpose knowing the odds of a successful landing are less than 100%?

I’m not nearly as impressed by people who dare to do great things with a full bank account as I am the guy who bets his last few dollars on a tank of gas to drive out to his best prospects.


Some of you know, my Dad was a singer.

He would take off with me, my brother, and my Mom, driving out to start a concert tour knowing he only had enough gas money to get us there, but not enough money to get us back home.

On many occasions, I can remember him pulling out the phone book in a hotel room and cold calling people to book concerts along the way back home. He was good on the phone!

As a kid, I didn’t think much of it because my Dad always got us home, but I’ve come to realize my Dad was a stone, cold, closer with ice water in his blood who always preferred to jump, in spite of the risk, than to live life as less than what he dreamed for our family.

He never surrendered control of his lifestyle for the safe, guaranteed, sure thing of living in the suffocating confines of somebody else’s dream.


I wish I was always as strong as my Dad was, but I’ve faltered and fallen along the way.

There was a short time when I traded my freedom for the corporate confines of upper-middle management.

I was so tired of fighting, swinging, going down, and drowning, that I took the safe, easy, guaranteed paycheck, and wonderful benefits, of life inside corporate America for a few quick years.

And it was great going to bed at night without feeling like an elephant of financial pressure was crushing me in my restless dreams each night.

The people I worked with, all those wonderful, amazing, talented people, were very good to me, and respected me for my natural talents and abilities.

It was nice to know that paycheck was getting direct deposited in my bank account like clock work regardless of whether I knocked it out of the park for them that week or not.

It wasn’t all up to me, although I was extremely intense, acting like the success or failure of my department was solely resting on me.

I seldom considered it, but I could have coasted if I needed to and my co-workers would have picked up the pace to cover for me. They were hard workers who earned my deepest respect.


What I learned in my time in corporate was sometimes 1+1 can equal 3, 5, or even 10.

There are exponential rewards when people work together toward a common goal. We can be stronger together and weaker apart.

I also learned that a less-than-qualified person, system, or product can hide and find political refuge in spite of their short-comings. It is extremely hard to uncover and unroot deficiencies hiding in plain sight.

In my mind, I knew these things could not make it on their own, out in the wild, living in freedom. They would be devoured because the market would chew them up and spit them out on their own. Inefficiency is inexcusable when you run a one-man show.

Try and sell a bad product to your customers without an air-tight, long-term contract and a team of high-powered lawyers to get your back when it fails short of expectations. You can’t sell crap when you work on your own and survive for very long.

I learned so much about myself and how the rest of the world thinks and acts because I did duck and take cover for a short time from the cruel risks of reaching for a lifestyle of freedom.

I believe it was valuable, but I gave up on myself in that time. I paid a high price for my education, including 3-4 hours a day locked down in rush hour traffic. That was time totally wasted.


I didn’t believe in myself so I didn’t take the risks. For good reason, too. I had all the scars to prove I was not winning.

It took me grabbing the lifeline of corporate for a short time to get my confidence back and learn to jump again.

I did jump again. I gave my notice and I leaped out again in the Spring of 2010 to chase a hail storm in Oklahoma City with a small team of salespeople I had recruited.

And after a few weeks I was drowning again. I cashed in my corporate 401k and put my head down, picturing my Dad sitting on the side of a motel bed booking last minute concerts to take care of his family.

Later that Fall, I started writing the Roofing Salesman website. A few years later, GAF called because they had been watching my videos, and now I’m consulting with roofers all over the nation.

And the rest, as they say, is history.

I took a leap and made it to the other side.

When you believe in yourself, you take risks. When you don’t, you play it safe.

Which choice will you make?