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The Art of Risk-Taking: Creative Strategies to Facing the Uncertain

Los Angeles last month saw the largest annual gathering of Jewish community visionaries, activists, and catalyzers of change in North America, led in partnership by UpStart and ROI Community, the Collaboratory.

This year’s topic of the Collaboratory was ‘The Art of Risk Taking’. The ability to navigate risk is one of the most useful skills to have in our professional and personal lives. No journey is risk free and being able to face risk, evaluate it and overcome it often differentiates between success and failure, happiness and unhappiness. According to difficulty is the reward, we read in Pirkei Avot (The Ethics of the Fathers), and risk adds to the difficulty.

Those who succeed take risks. In truth, “I wish I had taken more risks” is one of most common regrets people cite at the end of their lives. Many feel that the possibility of failure made them play too safe. They also felt that taking more risk and disturbing the status quo would have yielded a more fulfilling life.

Risk-taking is an art. And there is a science to this art. We make about 35,000 decisions per day – from the moment we open our eyes and decide (not) to turn off the alarm clock. As children, we only face around 3,000 decisions per day so adulthood is quite an upgrade to this gamble.

Knowing which risks to take and how to take them can be a powerful tool to stack the odds in our favor. Some of the basic pieces of advice to face the risk include to have as much information as possible, assess risk, and learn from failure. In order to hone your risk-taking skills more, here are a few guidelines from design thinking – an approach that uses creative strategies to problem solving.

  1. Challenge the assumptions: Think outside the box and challenge even the long-held beliefs. Sometime we fail because we cannot let go of the past but it is impossible to assess the future if we are only headed backwards. Learn from the past mistakes but move on.
  2. Ask why: Always ask why, even if you think that you know the answer. More often than not, you may learn that you actually don’t know the answer. The answer can also surprise you and expose the uncertain ahead.
  3. Identify inconsistencies: Sometimes what people say and what people do are two different things. Observe behaviors of those around you and be on the lookout for inconsistencies – they can flash out the potential risks.
  4. Be empathetic: Empathy is one of the key principles of design thinking. It forces us to imagine “walking in someone else’s shoes” thus revealing challenges and concerns around us.
  5. Encourage stories: Stories might not predict future risks well but they expose the breadth of the views and opinions in the world. Stories can unearth perspectives and solutions that have not been considered yet.

Life, in all its beauty and struggle, is unpredictable. Every decision we make has a margin of risk and the life we end up living depends on those decisions. While there always is a chance that our desired tomorrow will never come or the actual tomorrow will never come, there are risks in our professional and private lives that are worth taking because they are almost always necessary ingredients in the recipe that is success and happiness.

And the last piece of advice comes from the great French poet Rene Char:

“Trust firmly in your luck, cling to your happiness and dare to take risks. They will see you and learn to accept you.”

Katia Kobylinski
Katia Kobylinski is an avid brand strategist & social entrepreneur. To merge her passions for causes, stories and arts, she founded ‘creative: for good’ – a virtual ad agency that connects millennial artists and nonprofits for advertising for the good – at JCC Chicago’s start-up incubator Seed613. Katia loves city life, hummus & company.