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How to Take Career Risks Without Losing it All

How to take risks in your career Photo

Say an opportunity arises that piques your interest and passion? But what if this opportunity only has a 50 percent chance of success? Would you still take the risk?

If you wouldn鈥檛 take it, you would be like most of us. Many of us have responsibilities that keep us following the status quo and not taking risks with our careers in order to maintain what we鈥檝e worked hard for, what has been entrusted to us.

We know that the world needs people who take initiatives to turn their visions into reality. Without them, nothing would ever improve. Without people who think innovatively and push us forward into new directions by challenging the status quo, our world wouldn鈥檛 get better.

But how can you make the differences you desire to make, without risking it all? Can you balance both thinking with an innovative, entrepreneurial mindset and successfully changing your career outlook, while simultaneously making sure you don鈥檛 throw everything away?

Thankfully, there is a way. Calculated risk-taking involves planning and strategizing in the right timing, without risking it all and possibly losing it all. However, even the most calculated of risks is still a risk, and involves stepping out and facing the fear of failure to achieve success.

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Who are you called to be?

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Whether you鈥檙e thinking about becoming an entrepreneur, spearheading a new initiative in your current position, or looking for ways to alter your current role into something more meaningful and rewarding, you can learn how to take risks well to pursue deeper meaning in your career and life.

Calculating Risk

Most think that in order to be successful, you have to go all in and take the plunge. But it鈥檚 proven that living out the career you desire actually happens by playing it safe. The trick is knowing when and how to take calculated risks.

Dr. Bruce Schooling, professor of management at 国产剧麻豆剧 (国产剧麻豆剧), believes the real difference lies in the word 鈥渃alculated.鈥

鈥淎lmost everything we do involves some risk and therefore, we are always making decisions based upon our level of risk aversion,鈥 said Schooling. 鈥淲hat moves a decision away from recklessness is the amount of thinking we bring to bear upon the decision; a decision without thought would be reckless. A decision where the variables and possible outcomes are given reasonable and responsible consideration would not be reckless.鈥

Take a look at Warby Parker, the online-based eyewear company that uniquely features a free home try-on program. The founders started the business not by quitting their jobs and fully committing to a risky venture, but by playing it safe. Keeping their day jobs allowed them the freedom to do something completely original; if they had risked everything, they may have felt pressure to release a product immediately instead of taking the time to come up with their ideas. Their success was due to this calculated risk-taking, and as a result, Warby Parker topped Fast Company鈥檚 Most Innovative Companies list for 2015.

Adam Grant, author of New York Times bestseller Originals: How Non-conformists Move the World, was approached with an offer to invest in the eyewear startup but declined because of his then perception that 鈥測ou have to be all in鈥 in order for your business to succeed. Now, he is open about his regret and newfound understanding.  鈥淭o become original, you have to try something new, which means accepting some measure of risk,鈥 wrote Grant.

"But the most successful originals are not the daredevils who leap before they look. They are the ones who reluctantly tiptoe to the edge of the cliff, calculate the rate of descent, triple-check their parachutes, and set up a safety net at the bottom just in case." 

Those who are successful don鈥檛 just leap, but instead have manageable risk portfolios, described Grant. Though they may take many risks in one area of their lives, they鈥檒l compensate by following the status quo in other areas. For example, if a person is going to spend a few hours playing poker, he or she may drive slower than usual on the way to where the game is held. In other words, individuals who are successful in their risk-taking tend to balance out their overall amount of risk.

Great entrepreneurs are still afraid of failing, just like the rest of us. The only thing that differentiates them is the fact that they are even more afraid of failing to try. This doesn鈥檛 mean that every time they鈥檝e tried, they鈥檝e been successful. Becoming an original takes a willingness to risk, and also, a willingness to fail on the way to success.

鈥淯nderstanding that failure is a part of risk and often unavoidable is an essential component to being comfortable with risk,鈥 said Dr. Randal Schober, associate professor of management at 国产剧麻豆剧. 鈥淣early every entrepreneur will tell you they failed more than they were successful, but it鈥檚 how you fail that makes the difference. Successful entrepreneurs fail fast and fail forward. They learn from their mistakes and pivot accordingly.鈥

Failure Is a Key to Success

In the Fortune article, author Ryan Smith, founder and CEO of Qualtrics Survey Software, discussed the role failure plays in his company.

鈥淥ne key lesson I鈥檝e learned in my 14-year journey at Qualtrics has been that as a leader in any role, you have to make it safe to fail,鈥 said Smith. 鈥淲hen taking on ambitious projects, you have to treat failure as part of the learning process, because if you are going to get anywhere worth going, you have to stick your neck out. You have to experiment and iterate. Often that means failing on your way to success.鈥

He went on to share about a weekly meeting segment his company calls 鈥渨hoops,鈥 during which employees volunteer to share recent failures or embarrassments at work. They then vote on a winner, who gets to keep the company鈥檚 stuffed animal monkey named Whoops for a week. This provides a safe place to fail, and therefore, empowers employees to take risks.

As a leader in any role, you have to make it safe to fail

鈥淪ome of my biggest regrets are when I had a big idea and didn鈥檛 hop on it fast enough or go all the way because I was afraid of failing,鈥 he shared. 鈥淚f every bet, every hire, every product release, and every acquisition is safe, it鈥檚 pretty clear that we are not going to change the world. We don鈥檛 always need the smartest, most talented, and most experienced employees. What we do need is to have the fastest learners. We need people who are willing to take smart risks and help us stay on the cutting edge.鈥

According to Schober, facing the idea of failure head-on is necessary for success.

鈥淎 business鈥檚 inability to take risks is like a skateboarder who wants to be an X-game gold medalist but is fearful of falling off his or her board 鈥 it will never happen,鈥 Schober said. 鈥淥nly when you push the limits of what is possible will you be able to create new value and capabilities that will be awarded by market success. With startups, I have failed numerous times with marketing strategies and targeted demographics, but the key is to immediately measure impact and modify or pivot as soon as possible.鈥

Many well-known entrepreneurs have shared publically about their downfalls, in order to share insights about what they鈥檝e learned. In a Fast Company article, titled some big-name business owners opened up about what it鈥檚 really like to fail.

1. Arianna Huffington, Co-Founder of the Huffington Post

When HuffPost was first created, Arianna Huffington received many negative reviews, including one from a writer who called the site 鈥渢he equivalent of Gigli, Ishtar, and Heaven鈥檚 Gate rolled into one.鈥 She also experienced rejection from 36 publishers when trying to publish her second book.

鈥淏ut my mother used to tell me, 鈥榝ailure is not the opposite of success, it鈥檚 a stepping stone to success,鈥欌 Huffington shared. 鈥淪o at some point, I learned not to dread failure. I strongly believe that we are not put on this Earth just to accumulate victories and trophies and avoid failures, but rather, to be whittled and sandpapered down until what鈥檚 left is who we truly are.鈥

"Failure is not the opposite of success, it's a stepping stone to success."


2. Benny Luo, Serial Entrepreneur and Founder of NextShark, NewMediaRockStars, DiscoverMe, and The Other Asians

Benny Luo has attempted to grow many businesses, some of which are thriving today, and some of which ended up failing. But Luo learned from those failed attempts and gained valuable lessons along the way.

鈥淏efore I found success in my first company, I dabbled in many 鈥榞et rich鈥 ventures, including network marketing, online poker, and affiliate marketing,鈥 shared Luo. 鈥淲hile I did find some minimal success, all of these ventures eventually turned into failures. But, one day I realized that after each failure, I always gained some valuable knowledge of things I could apply to or avoid in my next project. That was the attitude I adopted after every failure from then on. I focused on what I had gained instead of what I had lost, because that鈥檚 what really matters in the end.鈥

3. Christina Wallace, Vice President of Branding and Marketing at Startup Institute and Former Co-Founder of Quincy Apparel

After Quincy Apparel shut down, the startup鈥檚 co-founder Christina Wallace stayed in bed for three weeks. After this difficult period, she chose to talk about the realities of her experience in hopes of helping and encouraging others.

鈥... I learned to be as open about my failure with my friends and family as I was willing to be about my successes,鈥 said Wallace. 鈥淪tartups are not just what you read in the press. The real story is much more volatile and human, and we do our community a disservice pretending otherwise. I don鈥檛 celebrate failure for failure鈥檚 sake, but I think there is something amazing about trying to do something at the edge of possibility and potentially failing at it. Senator McCaskill ... said at a Politico conference that 鈥榳inners are those who are willing to lose.鈥 I really like that mentality.鈥

So Be Afraid - and Then Do It Anyway

While it might be helpful to read examples of real-life failures, even still, the fear of failure is a big one. Though many of us know it鈥檚 better to try than to fail, the fear we experience can be so daunting that we still don鈥檛 take risks and move forward, but instead, stay paralyzed.

鈥淎n individual鈥檚 relationship with risk is founded on two main factors: one鈥檚 inherent comfort level with taking risks and the degree of consequences if one doesn鈥檛 take risks,鈥 said Schober. 鈥淭hese are often referred to as 鈥榮inking the boat鈥 or 鈥榤issing the boat.鈥 And sometimes, the latter can be even more devastating.鈥

For many successful people, whether they are starting their own company or implementing meaningful change in an existing one, the fear of missing the boat or experiencing regret can be even more impactful than the fear of failing. As author John Acuff puts it in his article, 鈥淚f fear is a tidal wave, large and loud and temporarily very powerful, regret is a small stream that cuts a canyon into your heart slowly over time.鈥

Business Insider recently shared insights from a commentary thread on Reddit, an online networking service. This included an impactful story of two girls at a public pool when they were young. One of the girls had been loudly voicing her fears to her older sister about diving into the pool. Overhearing the fearful girl, a 75-year-old woman who was swimming laps stopped to interject and share wisdom. With her fist in the air, she shouted, 鈥淪o be afraid! And then do it anyway!鈥

鈥淭hat was 35 years ago and I have never forgotten it,鈥 the writer said. 鈥淚t was a revelation 鈥 it鈥檚 not about being unafraid. It鈥檚 about being afraid, and doing it anyway.鈥

Making an impact, whether that鈥檚 by launching a startup company or speaking out within your current profession to change the status quo, requires facing an inevitable fear of failure. By taking calculated risks, you can face that fear while simultaneously making sure you don鈥檛 lose everything you鈥檝e worked hard for. This will allow you to advance your own ideas, live out the career and life you want, and better our world 鈥 with no regrets.

6 Steps You Can Take Now

1. Broaden Your View

Based on his observations, 国产剧麻豆剧 professor Dr. Bruce Schooling believes it鈥檚 important to be well-rounded when approaching any kind of business venture.

鈥淚t鈥檚 necessary to think, read, observe, and consider across a wide range of cultures and experiences,鈥 he said. 鈥淭he broader the background information you have to draw upon the more likely you will see the pitfalls and the changing environment.鈥

When this comprehensive evaluation or 鈥渄ue diligence鈥 is combined with a vision for the future, (looking at what has happened, what is happening, and what may happen that might impact your venture), it creates a clear direction to take your idea or business.

2. Vet Opportunities Wisely

In the Entrepreneur article author Elise Mitchell wrote about the need to turn down good opportunities in order to pursue great ones. And this process can be difficult.

鈥淎 trusted consultant told me, 鈥榊ou have so many ideas, but you can鈥檛 realistically pursue them all. You have to learn to say no to most of them so you can say yes to the very best,鈥欌 she said. 鈥淥ver time, I鈥檝e seen that saying yes to everything would mean going wide but not deep. It鈥檚 better (and more profitable) to be an expert in a few areas than to offer shallow knowledge in everything.鈥

3. Lead With Weakness

鈥淎t some point, we鈥檝e all considered voicing a minority opinion, protesting a policy that doesn鈥檛 make sense, championing a novel way of doing things, or standing up for a disadvantaged group of people,鈥 wrote Adam Grant in Originals.

The key to successfully going against the status quo is found in knowing how to speak up effectively without jeopardizing your career or relationships. When presenting ideas to people with more power than you, lead with weaknesses, in order to disarm your audience.

鈥淩ampant confidence is a red flag 鈥 a signal that we need to defend ourselves against weapons of influence,鈥 shared Grant. Being upfront about the downsides of your idea makes you trustworthy; presenting negatives can ironically make it more difficult for audiences to think of them. And make sure to repeat ideas. It鈥檚 proven that if an idea is familiar, people tend to like it more.

4. Test The Water

In the Inc. article author Drew Hendricks suggests finding out how far is too far for your business and starting off by taking small risks.

鈥淒etermine what you can afford to lose,鈥 he wrote. 鈥淐ompanies that know they can鈥檛 afford a large flop should start with baby steps. Take small risks to test the water and gain confidence. This should help you build a higher tolerance for risk, which means your business will trust itself enough to take larger risks in the future.鈥

5. Gain Market Feedback

According to 国产剧麻豆剧鈥檚 Dr. Randal Schober, when you move forward with a business or idea, constant communication with your market or customer to modify your strategy or product is essential.

鈥淐ustomer and market feedback is the most critical variable that will determine the potential success of a business and correspondingly eliminate as much risk as possible,鈥 he said. 鈥淭he difference between a good idea and a good opportunity is market demand. The best way to know what the market wants is to ask them.鈥

6. Speak Now to Avoid Regrets Later

Adam Grant reiterated the importance we all place on speaking up. He wrote, 鈥... in the long run, research shows that the mistakes we regret are not errors of commission, but errors of omission. If we could do things over, most of us would censor ourselves less and express our ideas more.鈥

If you feel a call to change the status quo and make a difference through your business, you may want to consider earning your MBA or earning a Master's degree in Organizational Leadership. Many successful business professionals and entrepreneurs have pursued graduate business education to help them gain the skills necessary to take their original ideas to the next level.

国产剧麻豆剧 the Author 

Wendy Cloherty is a former editor for 国产剧麻豆剧's Viewpoint magazine and a contributing freelance writer.