Risky Business: 6 Tips To Help You Take Leaps of Faith

As a former Marine, a cancer survivor and a successful entrepreneur, I’ve learned a thing or two about risk. If you’re happy languishing in a gelatinous pool of indifference and stagnation then, by all means, keep doing what you’re doing. If you’re ready to take a leap and change things for the better, here’s some wisdom to get you started.


1. You take risks every day.

Getting up, answering the phone and heading out the door are all risks, albeit minor ones. However, every time you do those things, you’re putting yourself out there—you’re even risking rejection daily in your professional and personal life.

You do these things every day and survive. Trust me, it won’t kill you. You are very capable of taking risks. It’s now time to ramp it up. You’ve already got a toe in the water, so jumping in the rest of the way isn’t as big a shock. Taking risks is a state of mind. Knowing you can do it on a small scale makes it a lot easier to start taking risks on a larger one.


2. Find comfort in the uncomfortable.

Life begins at the end of your comfort zone. You don’t have to go skydiving or base-jumping—although you certainly can if you want—but you do have to go beyond doing what you’re used to doing and stretch into new territory.


Learn where you’re most comfortable, most skilled and most proficient—and then step right past that to a place where you feel the most uncomfortable, the most uncertain and the most unsure of yourself. That’s where the real progress begins.

Consider any world-class athlete, artist or entrepreneur. No matter what his or her area of expertise, that athlete, artist or entrepreneur puts in the hours and continually pushes the limits to achieve beyond what anyone thought possible. You don’t break world records, or break out of ruts, without making that push.

3. Act now.

At this very moment, you have everything you need. Sound impossible? It happens to be true; you just may not appreciate it. Do you have food, clothing and shelter? Then you have everything you need. Once you live by this simple philosophy, taking risks becomes far easier.


The most important part of this notion is that most business opportunities don’t wait around, so take action now. Don’t make the mistake of waiting on someone or something to come along to make taking that leap of faith more viable. “Perfect timing” is a fallacy—there are few, if any, such moments in life. Don’t wait so long that you can’t take a risk even when you want to, only to be consumed with remorse for what “could have been.” Now is the time to capitalize on opportunities that are in front of you.

4. Do your own thing.

The concept of going your own way and doing your own thing is not new. The problem is, most people don’t do it because it bucks tradition and goes against the grain and, frankly, it scares the crap out of most people. But on the other hand, it can provide you with a heck of a lot of freedom, and provide you a lifelong exemption from blindly or reluctantly following protocol.


Mavericks live according to their own agenda and goals and, even in the business world, there’s more latitude to blaze new trails than you might think.

The key is to look at each task for the opportunities they present. Sure, there may be a “perfectly fine” or traditional way of doing something to achieve a good result. But when you have a better approach or process in mind that can achieve an even more desirable result, it may just be time to go rogue. In today’s cutthroat culture, originality is perhaps your greatest gift. Use it.

5. Fail.

Don’t just give yourself permission to fail. Actually fail. Go out there and fall on your face. It’s the only way you’re really going to learn anything. The lessons you learn from those failures will be the ones that propel you to success.


Here’s an idea: Try living life like a 2-year-old. In other words, fall down often, screw up repeatedly and occasionally be defiant. Children are extremely resilient and, as adults, we lose this enviable quality. Throughout our careers, we proverbially fall down, get bruised and even skin our knees. We might even literally shed a few tears. But perseverance and tenacity, sharpened with hindsight-based perspective so you don’t repeat the same mistakes, are keys to climbing the ladder of achievement.

6. Repeat.

Taking risks is not a “one and done” proposition. It takes tenacity, the ability to keep forging ahead, trying new things, and pushing past obstacles to achieve results. Tenacity determines how hard we fight for our dreams. A tenacious person never has to look back at all the missed opportunities.

Once you take your first dive off the edge, subsequent dives become a lot easier. In fact, they become a way of life. After experiencing the exhilaration and ROI of risk-taking, you’ll wonder how you ever lived without it.


Posted as a guest blog on The Storage Facilitator Blog (October 1, 2014)


Comment (1)

  1. Claire Dunlap says:

    Wow! I remember when you came to speak at Full Sail University and I was instantly inspired by your resilience and willingness to not give up. Thank you so much for this post. It was just what I needed to hear.

    Claire Dunlap

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