Podcast: How to Handle Risk Like a Boss

how to handle riskThis is near and dear to me because I know how to handle risk – risk is my copilot. I venture into what-ifs like they’re going out of style. I wasn’t always that way, and occasionally I’m not as bold or brazen as my brochure would have you believe. Most days I’m ready to take on the world and all its wonder, but because I’m still human, I will have “holy crap, what am I doing” days too. There’s no quick fix for all types of risk aversion, but there are a few keys that make it so you know how to handle risk much more effectively.

Today’s podcast is sponsored by Every Man Jack, and is all about taking small risks and putting yourself out there. Life is full of amazing moments and experiences, but we are called to take risks and put ourselves, and what we know about the world, on the line. It can be a huge struggle for a lot of people, but it doesn’t have to be. There are a few keys to help you handle risk, and potentially, made it your copilot. Take a listen:

Show Notes:

Tattooed on my forearms are two phrases in latin:

Audentes fortuna iuvat – Fortune favors the bold.

Sedit qui timuit ne non succederet – He who feared he would not succeed, sat still.

These are my constant reminders to take risks, forge ahead, push when everyone else is pulling, and stay true to my mission. Because there’s so much noise out in the world, it can be difficult to keep clarity and focus. That’s when risk seems to be the loudest voice in your head, right?

how to handle riskWhen you’re trying to focus on making a big change and taking some risk, you find that’s when Murphy’s Law strikes. Life’s small accidents come tumbling toward you as reminders that “change is bad” or “you can’t risk it!” Both of these are total crap, but it happens to all of us.

A bigger issue that too many of you face is settling into a lifestyle you don’t like, afraid to rock the boat for fear that it’s worse than the crap you have to deal with everyday. Ugh. What a shame. I have good friends and colleagues stuck in jobs, relationships, and living situations that make them miserable, but they’re too afraid to take a risk and do something about it. Sometimes it’s the product of systemic guilt e.g. “nobody loves me, I would die if you left me” and sometimes it’s fear e.g. “you’re crazy if you think you can just walk out and start a new career.”

Hope is not lost, my friends. You can make Risk your copilot. Hell, you can make risk your best friend! When you do, you’ll find that you receive a lot more of life’s unexpected surprises (the good ones), and you experience a significant increase in memorable moments. In the movie Yes Man with Jim Carey, he takes a vow to say yes to everything. While it’s absolutely unnecessary to say yes to everything, he experiences SO MUCH in such a short amount of time. The coolest part about that philosophy? It doesn’t just happen in the movies. Let me explain…

Risk for Love

how to handle riskMy story is one of risking it all for love. I feel like that’s been in my DNA since birth. There’s a part of me that always believed that the greatest experiences and stories lived in the “risk it all for love” theme. So back in 2012, I did just that. I had just come out of a relationship that probably lasted a little longer than it should have (something so many of us are familiar with), and my focus was to just keep my head down and work. I didn’t want anything to do with love or relationships because all I really wanted was predictable routines and some easy wins – both easily achievable by focusing on work, right?

I signed up for an online video marketing class to improve my videos, preparing to take my business to the next level. What I hadn’t expected was to meet a woman in that course that would change my life so dramatically. We shred projects and professional conversations at first. Then the conversations got a little more personal, we began flirting, and even though she was in Texas and I was in Chicago, I told her I’d like to go out with her. Strange, I know.

Chats turned into phone calls, and calls turned into Facetime dinners together. Then, risking it all, she bought a ticket to fly up to Chicago to visit me for new years. When I met her in the airport that cold Sunday morning in December, we just said hi and hugged. That was all we really needed in that moment. Over the next few days, we celebrated the new year, I showed her my city, and I watched the rest of my life lay out before me. I knew that very first day in the airport, I was going to marry her.

the greatest love story everFive months later, in May of ’13, I moved to Dallas. We have a house and a cat together. Last May (5/15/15) I proposed (you can check out that story too). I risked it all, packing up my life and everything I knew, and moved to Texas for love. It was the biggest and best decision I ever made. I’ve started and closed businesses, left Corporate America (on my terms), and said yes to projects and commitments that were way over my pay grade, but saying yes to a chance at great love and moving 1000 miles from home will always be the greatest.

Your Life as a Movie

There was a commercial for the Navy a few years ago that asked you, “If your life was a movie, would you be proud to watch it?” That has resonated with me ever since. This is how I look at risk. Imagine that at the end of your life, before you pass on to heaven or hell or reincarnate or whatever you believe, you first find yourself in a type of processing center. Let’s say you find yourself sitting in a comfortable chair in front of a very large projector screen, and a nondescript attendant enters the room and pushes a button on the wall. Suddenly, your entire life –the highlight reel of your entire life– beings to play on the screen.

how to handle risk - your life as a movie

Every great adventure, every love, every heartache, every triumph, victory, failure, struggle, connection, collaboration – all the moments play out before you. This is your life. Everything about you is summed up here in video. Here are a few questions to ask yourself about it:

  • How long is this movie? Is it short because it’s uninteresting? Is it long because your life is packed with so much?
  • Do you feel proud to have that video be YOUR highlight reel?
  • Do you wish you could share this movie with people?

The way you answer those questions greatly determines how you feel about your life, and how you compare it to what’s possible. The hardest truth in these answers is that you always have the opportunity to improve your movie, if you’re willing to bite into some risk. Risk adversity is personal, I know. What one man sees as simple, another may see as a big risk, and consequently difficult. The key here is to understand that you always have the power to change it. Get out of your head and into your heart.

Your Thinking Sucks

When I was in college, we studied the brain and risk/reward systems. We studied chemical reactions to different triggers, and one of the coolest things emerged: left and right brain decisions are different. It’s been said that the right side of the brain is more creative, leans more into the colorful and fun side of the spectrum, and likes undefined parameters. The left is the opposite: calculating, finite, black and white, math, math, and more math.

In coaching school, we learned to ask questions differently to keep clients from entering their headspace too much. An example of this is avoiding the word “how” at all costs. Asking what, who, where, and why are all creative inquiries. You can tell a story from those questions. How is an analytical question. You go into your head (left brain), and calculate your probability of success and most of the time will talk yourself out of it.

“Time is the only commodity you cannot rent, buy, save, return, slow, or stop. It keeps moving forward whether you like it or not. Use every last moment to the fullest.”

how to handle risk - approaching beautiful womenWhen you want to take a risk, you think about it, right? Well, stop doing that! Let’s jump in the way-back machine, and take you to a time when you were single at the bar. You want to make a move and go talk to that beautiful woman across the bar, right? Okay Stud, now’s your chance. You make quick eye contact and BOOM! Your brain starts thinking…

  • What if she rejects you?
  • What if other people see you get shot down?
  • You don’t want to embarrass yourself, do you?
  • You should just stay put and see if she comes to you. (this very rarely happens)

You’ve talked yourself out of it, haven’t you. That’s a damn shame. The risk of looking like a fool was too high because you thought about it. If you didn’t think and you just went for it, you might have a completely different experience! Stop thinking. My friend and inspirational speaker Mel Robbins has her 5 second rule. She tells it like this: “Every time you get an idea, a thought, an urge to do something, you have five seconds to act before your brain talks you out of it. Decide in five seconds, or it’s not gonna happen.”

Answer Three Questions

This is a pretty simple three-step process to getting out of your own way. The first two involve you being honest, and I mean truly honest. The last step is for you to get creative, crazy, excited, and pumped-up. When you are looking at possibilities and opportunities in front of you and trying to weigh risks and whether you should or shouldn’t “go for it” ask these questions:

  • how to handle riskWhat’s the worst that could happen? (be honest with this one)
  • What could happen (honestly) if I fail?
  • What could happen if I succeed? (get creative and crazy with this one)

Too often, people make up that taking any risk or rocking the boat will cause the end of life as they know it. If you finally quit that terrible job you hate, you’ll be forced to find a new job. What’s the worst that could happen? You might have to move to get a different or better job? You might not get a recommendation letter so the job hunt may be more difficult? You might have to rely on the support of your friends and family (possibly turning yourself into a burden) until you can get back on your feet? There are a lot of possible outcomes here, but the key takeaway is that you’ll still be alive, your life won’t be over, and you’ll get through it. So ask yourself that question and answer it honestly.

The second question is more of the same. What happens if you go for it and you fail? Honestly? If you man up and go talk to that beautiful woman, you might get rejected. So what? You’ll be the same guy you were before you took the risk. Except now, you’re a risk taker! Way to go, Ted!

The third question is where I invite you to get creative. What could happen if you succeed? Seriously, go crazy with this answer! You could end up getting a new and better job, which allows you to focus more, which gets you promoted, which helps you pay off your car, which improves your credit, which allows you to refinance the house, which allows you to finally take that three week vacation to Europe! You don’t know the future, but you do know it feels better to imagine the possibilities than it does to imagine the pitfalls. When you feel better, you’ll take more action, and you’ll find that you experience more positive rewards more often. That, I can promise you, for sure.

“What you have to lose is often an indiscernible fraction of what you have to gain. Even if you don’t lose or gain, you still gain. Get out of your head and go for it.”

It’s been said a million times that life is really short. Well, it is. But it’s also really long. Very long. You owe it to yourself to create the life you always imagined (risk and all) because you’re going to be here a while. Make your moments count, my friend.

SPONSORED by Every Man Jack

Every Man Jack knows how to take grooming to the next level with amazing (and natural) skin, hair, and shave care products that are second to none. As a reward for getting to the end of this article, I have a discount code for you to use at checkout: 1SHARPGENT – that will get you 25% OFF your order! Enjoy!

What risks have you taken in your life? What’s your best advice for people struggling with risk?
If there’s something you think I missed, please share it in the comments below.

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The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.