Being comfortable with risk is pretty rare these days. Whether we’re transitioning from school to work, trying to move from one job to the next, pitching a new idea to the boss, or making a romantic move on a long-time friend, risk puts our confidence, money, reputation, and even our community on the line.

Risky business is known as scary business. But it shouldn’t be.

Last weekend I was on Salt Spring Island celebrating my mom’s 60^th birthday. During one of our hikes I decided to climb a tree. And then I came up with the idea to jump from the tree, swing on a branch, and land safely on the ground. The conversation with my dad went like this:

JOHN [in tree, gesturing confidently]: “So, I’m going to jump from the tree, swing on that branch and then land on the ground over there.”

DAD: “Don’t do it. The branch is dead and it won’t hold you. You will impale yourself on the rocks. Don’t do it.”

JOHN [jumps]

Lying on my back – impaled on the rocks, just like my dad said – looking up at the sky and my concerned/incredulous wife and parents, I smiled and reflected on my failure, knowing that the next time I attempted such a maneuver success would be achieved because I learned from my mistake. But don’t just take my word for it. Other thinkers, like Historian Engineer Henry Petroski, have opinions about the relationship between failure and success, too. According to an article in the Huffington Post by Ben Michaelis, Petroski argues that “limited failure early in your working life can be immensely helpful to your career trajectory. The takeaway message is that if you are not failing you are not trying.”

The world needs more risk takers, which is nicely evidenced by this Fast Company article that features the travel company Kayak – their Chief Technology Officer, Paul English, has this to say about their culture of innovation: “Everything we do encourages fast decision-making and risk-taking. We don’t do design by committee, and we disable large meetings here. We reward risk-taking and speed, even when it fails!”

Sure, my falling out of a tree is a silly example of risk when compared to some of the other things I’ve done (moving across the country for university, being friends with men from Halifax, studying History at graduate school, going to East Africa when I’m allergic to the Sun, pitching a service learning program to a business school, telling people I love them without certainty of reciprocity), but it is nonetheless an illustrative example of what I’m talking about.

With this in mind, here are five things that you need to know about being a professional risk-taker.

1. Be authentic. Following a risk I took and a failure I experienced, my past boss and current mentor said this to me: “When you make a mistake and fail you will always be okay because you are genuine and authentic. People know that you are doing things for the right reasons and have the best of intentions, never selfish ones.” When you genuinely have your community’s goals at heart then risk – and the failure that often comes with it – becomes more acceptable.

2. Jump in with both feet. A former student and current friend, David Singh, just left a great job in Deloitte’s Consulting group to join Kira Talent. This guy doesn’t know how to not go all-in, as he’s already wearing the value proposition of this awesome interviewing start-up on his sleeve.

Kym Banguis (shop.herrohachi.com) jumped in with both feet. The only problem was that she jumped off of a moving scooter. #risktaking

3. Take responsibility for your success (and failure). Managing risk can also involve simple experiences, as demonstrated by my former colleague and current friend, Holly Langland, who inspires teams with pop-fresh dance moves: “I was first on the dance floor at the xmas party on Friday. What this says about me is that I don’t hesitate to lead the way when needed…or I just don’t mind looking bad!” Regardless of how she looks, Holly owns it.

4. Have an eraser. Risk-takers need to have a long memory, for those who forget the past are doomed to repeat it. That being said, it’s important to reflect on risks-gone-wrong and then erase them. As her tone-setting speech to ring-in the New Year (“September” is what people outside of Higher Education call this time of the year), my boss read us this awesome letter from everyone’s favourite holiday cop storyteller, John McClane Stuart McLean. The letter ends with this gem: “Don’t mind mistakes. The mistakes are how you learn. You have an eraser. Go ahead make the messes. Then … clean them up. Try again.”

5. Be playful and have fun with it! My Frientor (friend + mentor = Frientor), Rodney Payne, eloquently summarized how approaching life with playfulness is an important part of approaching risk: “Teaching myself to kiteboarding when it was really unsafe has taught me everything I know about calculated risk. You need to be comfortable with risk in order to innovate.”

Failure is a part of life. You know this. Being comfortable with and open to failure, which will happen, is the kind of common sense that is not common practice. So, by starting small (talking on the phone to a prospective romantic partner or professional employer instead of texting them) or going big (jumping out of a tree twice the size of the one I swung from and/or starting your own business), think about how you will bring positive and calculated risk to your community today.