7 Secrets To Succeeding As A Risk Taker


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Let’s talk about risk taking. But before we move on, let’s get one thing out of the way: if you’re reading this (or listening to the podcast)—it’s likely you want to become more of a risk taker in life. I’m sure, of course, you don’t want to start taking risks for no good reason; but because there’s a gap between where you are NOW and where you WANT to be.

Right about now, you might be thinking, “No shit, sherlock, that’s what I’m here for.” But some of us still aren’t quit sure if becoming a risk taker is as fruitful as all the cheesy self-help gurus tell us in their pump-up-speeches… So let’s be upfront about it: Becoming a risk taker isn’t for everyone. If you’re unsure about whether upping your risk-taking game is the right move for you, then you may want to move on to something else. Because persuading you to become a risk-taker is not the purpose of this article/episode. Instead, this piece is for you if you’ve already made up your mind—you currently believe you need to become more of a risk taker—if you want to achieve a higher level of success in life.

The purpose of this piece, then, is to show you—or maybe remind you—what it takes to become a successful risk taker, touching on all aspects of life, but mainly focusing within the context of building a successful career/business doing meaningful work. But regardless of who you are, where you’re at, or what you do, you’ll be able to translate these ideas on risk taking and apply them in your own life. So, let’s dive in, shall we?




Risk taker tip 1: Be ridiculously irrational.

When I quit my cozy corporate gig to start doing what I love for a living—which is to inspire greatness in people everywhere—I took a major, major risk. For example, when I started FlashBooks I barely had enough in the bank to support my lifestyle for more than 3 months!

Back then, I barely had enough space in my apartment to work from home. So what did I do? I invested a chunk of my resources on a quality MacBook Pro. Then I converted my kitchen into an office-space–slash–studio to record audiobook summaries and podcast episodes in.

On top of all that, quitting my job to chase my calling also meant I had to:

  • get a new car (since the one I had—company car—wasn’t really mine in the first place)
  • begin generating enough revenue to support myself before I started seeing too many holes in my (already tiny) 3-month safety net to keep going. And last but certainly not least, I knew I’d have to…
  • bust my ass harder than I ever had before—no matter what—all while making smart decisions about what to focus on (money-making opportunities) and what to ignore.

This is stressful stuff we’re talking about here. No living, breathing human being of average intelligence would do something like this if they were thinking rationally. In fact, studies show that the smarter you are, the more risk-adverse you are. Why? Because rational thinking helps you determine how worthwhile and meaningful a new undertaking (aka: risk) will or will not be. So, if you were thinking rationally about risk taking, you might say:

I’m already making $XYZ per year. Sure, I don’t love my job, but I’ve got some heavy bills to pay…

What if I don’t succeed? What if I fail? What if I screw up and make a fool of myself? What will people think?

Maybe starting that business isn’t a good idea after all.

And on and on and on… Now all the rational, perfectly justified reasons not to become a risk taker start flowing into your periphery and begin clouding your judgement; crushing your dreams for a better future, like Donald Trump’s presidential campaign. Before you know it, you’ve convinced yourself that it’s a bad idea to take that risk. That it’s better to stay safe—to stay rational.

But being ridiculously irrational is a different story.

Being ridiculously irrational is not about “thinking positive” and refusing to acknowledge the realities of a given situation. Being ridiculously irrational is about being irrationally optimistic about the future. It’s about developing a vision and using that vision to help you muster up the—courage/energy/intensity—whatever it takes, to persist until you succeed.

But why go on when you keep falling down? Because…

Risk taker tip 2: A successful risk taker is a short term pessimist and a long-term optimist.

I remember when it was really getting down to the wire for me. When I was trying to figure out a way to sustain my dreams and do meaningful work. I remember how I kept on trying idea after idea, getting super-excited about each of them, only to watch them fail, one right after the other. It seemed like nothing would work.

But for some reason, I knew it would work out. I knew it in my core. Not only did I know I’d be okay, I knew I’d be insanely successful. It would just take a little more time. How much more time? I didn’t know. And you won’t either. But what you do need to know is this:

Most of the stuff you try—most of the risks you take—will not work. And that’s okay. Because what doesn’t work today, will lead you towards what works insanely well tomorrow.Click-to-Tweet

For me, it wasn’t about what didn’t work yesterday, or what’s not working today. It was about what would work tomorrow. It’s always been that way for me, and I can’t point to one specific turning point that made me shift my mindset towards this direction. But I know it works. Become a short term pessimist and a long term optimist. It’ll pay off. Trust me.

Risk taker tip 3: don’t listen to dream killers.

I remember every one around me kept telling me to stop trying and just get a regular job like “everyone else.” I remember telling them to fuck off.

I’d made a promise to myself that I would never allow myself to become enslaved by any person or company in exchange for a paycheck ever again. I’d much rather serve people in a meaningful way, doing something that matters to me.

You can do the same thing. Don’t let dream killers prevent you from achieving your goals. You have greatness within you. And YOU are responsible for sharing that greatness with the world. Don’t let dream killers crush your inspiration. Distance yourself from them. And if your dream killers are people you happen to love and care for, make the intention of coming back to help them out once you’re strong enough to do so. Right now though, you need to be focused on surrounding yourself with inspiring and encouraging people and things. Things like the following little nugget of wisdom written by the famous playwright, Neil Simon:

“Don’t listen to those who say ‘you taking too big a chance.’ Michelangelo would have painted the Sistine floor, and it would surely be rubbed out by today. Most important, don’t listen when the little voice of fear inside you rears its ugly head and says ‘they all smarter than you out there. They’re more talented, they’re taller, blonder, prettier, luckier, and they have connections.” I firmly believe that if you follow a path that interests you, not to the exclusion of love, sensitivity, and cooperation with others, but with the strength of conviction that you can move others by your own efforts—and do not make success or failure the criteria by which you live—the chances are you’ll be a person worthy of your own respects.”

A person worthy of your own respects.

Love that.

Risk taker tip 4: Your success will be in direct proportion to the risk they’re willing to take.

When you walk up to the insanely attractive girl/guy at the mall and say hello—you’re taking a major, major risk. But what if s/he’s “the one?”

When you decide to walk into the gym and start working out—regardless of how fat or flimsy you look compared to everyone else—you’re taking a major, major risk. But what about all the energy, vitality, and physical changes you’ll get to enjoy with your new gym habit?

When you decide to quit your job and take that risky-but-promising leap of faith—you’re taking a major, major risk. But what about the lifestyle that comes with doing work you actually find fulfilling?

The amount of success you experience will expand—or shrink—in direct proportion to the amount of risk you’re willing to take.

I’ve literally 10X’d my I come since I quit my job and started my own business. And that’s just the financial benefit I’ve experienced as a result of making a “risky” career move… When I stop to consider all the other benefits—the emotional, social, and spiritual impact that doing work I love has had on my life—I totally understand that the risk was well worth it. Looking back now, it was almost a no-brainer.

Oh, and by the way: I’m not saying any of this to impress you, but to impress upon you that our success expands to the degree of risk we’re willing to take…

80% of the time, the more you’re willing to put on the line, the more you’re potentially going to receive in return. And that goes both ways—negative and positive. One more time, just for good measure: The amount of success you experience will expand—or shrink—in proportion to amount of risk you’re willing to take.

Risk taker tip 5: Become successful by developing a growth mindset…

Successful risk takers understand the obvious notion that big time risk-taking has its upsides and downsides. And the downsides—like making mistakes or failing at things—can really suck sometimes. But here’s what separates the people that prosper from the people that perish:


Folks that succeed over and over again, have what’s called a Growth Mindset. People that seem to keep getting stuck in life—usually because they’re holding themselves back—have what’s called a Fixed Mindset.

What’s a Fixed Mindset? As Carol Dweck puts it in her (super awesome and mind-expanding) book, Mindset:

“Believing that your qualities are carved in stone—the fixed mindset—creates an urgency to prove yourself over and over.”

“When you enter a mindset, you enter a new world. In one world—the world of fixed traits—success is about proving you’re smart or talented. Validating yourself. In the other—the world of changing qualities—it’s about stretching yourself to learn something new. Developing yourself.”

Let’s talk a little more about the latter…

What’s a Growth Mindset? Here’s how Dweck explains it:

“This growth mindset is based on the belief that your basic qualities are things you can cultivate through your efforts. Although people may differ in every which way—in their initial talents and aptitudes, interests, or temperaments—everyone can change and grow through application and experience.”

Want to boost your chances of success in business? In achieving your goals? In pretty much every area of your life? Develop a growth mindset.

Risk taker tip 6: Learn from making mistakes, rather than letting mistakes make you.

Making mistakes doesn’t feel good. But that doesn’t mean you should let your mistakes make you.

Do not ever label yourself a ‘failure.’ Just because you fail at something, doesn’t mean you’re a failure. Always remember: failure is an event—it’s not a person. Learn from your mistakes, and make informed decisions as a result of having experienced them.

Risk taker tip 7: Learn to deal with your fear of failure.

The idea of trying really, really hard at something, and still failing—of leaving yourself without excuses—is one of the worst fear-driven ways of thinking around.

Nothing will paralyze you faster than the fear of putting forth your best effort—and still knowing that you might not succeed…

So what do most of us do instead? We only try a little bit. This way, in case we experience failure, we can say, “I wasn’t trying that hard anyway.”

This is a bullshit excuse.

Why would you even take the time to do something if you’re not going to do it to the best of your ability?

Effort can be insanely terrifying because it robs you of all your excuses. Without effort, you can always say, “I could’ve been this [fill in the blank]” or “I could’ve been that [again, fill in the blank].” But once you try—really and truly try—you can say that anymore.

We’ve all heard the nostalgic man suffering from a mid-life crisis, talking about his high school football days, and how he coulda been pro if only he hadn’t [insert excuse here] … You remember uncle Rico from Napoleon Dynamite right?—Don’t be that guy.

An honest failure is better than never trying at all. Go all-out. Fail. Learn. Rinse and then repeat. Do this enough times and you’ll succeed. Promise.

A final word: Begin before you’re prepared.

Don’t be a bitch. Be like a bull, and charge ahead instead. Begin before you’re prepared.

Good things happen when we begin before we’re prepared. One of those things is this: we begin erecting our own building of courage… We build up a foundation for that building by taking courageous action. Every act of courage is like a brick. And every brick we lay builds a stronger foundation for our very own building of courage. The more we lay, the more courageous we get. Courage begets courage.

W. H. Murray said:

Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. A whole stream of events issues from the decision, raising in one’s favor all manner of unforeseen incidents and meetings and material assistance which no man could have dreamed would have come his way. I have learned a deep respect for one of Goethe’s couplets: “Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it.” Begin it now.

Be bold like a bull. Charge ahead with courage. If you do it consciously, things will seriously start taking shape in your personal life and your professional life.




Topics Covered:

  • Risk Taking
  • Becoming a Successful Risk Taker
  • Meaningful work
  • Fear of Failure
  • Who to take advice from (and who NOT to take advice from)
  • Success
  • Goals
Books Mentioned:
  • “Mindset” by Carol Dweck

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