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Taking risks: How to become a strategic risk taker?

I remember an exercise I did in one of my coaching sessions that involved picking 3 words to define the best of who I am – or want to be – with the intent to guide my personal life, encouraging my thoughts and actions. One of the words I chose was risk taker. It came to me without effort, as if it were there all the time in my mind waiting to be chosen. Immediately after, I started questioning myself. What did I even mean by being a risk taker? What kind of risks was I ready to undertake? When was the last time I took any risks and why was it important to define myself as such?


Truth is the word risk has a negative connotation in certain cultures. There are indeed cultural differences, combined with one’s own risk aversion. From where I stand, taking a risk does not necessarily mean “go big or go home”, putting everything on the line and then pray for its outcome to play in your favor. Being a risk taker is not putting all eggs in one basket without even knowing how many it can fit, and hope for the basket to return full instead of empty.


It takes courage to be a risk taker, no doubt. We talked recently about how taking bold action, in alignment with your goals and vision, is in itself a courageous act [catch-up your reading here]. In addition, stepping out of your comfort zone and embracing the uncomfortableness that comes with navigating the unknown. Be present, show up and take one uncomfortable step – however small – every day.


Where is the advantage though? How does being a risk taker can be a game changer? Not all of us like risks! In fact, many of us see risks as a lunatic’s act or a personality trait for the upper class. At the end, it is not about the risk you take, as much as where the risk takes you. Everyone can take risks and end up further away from their dreams than when they started. You should be asking yourself instead: How does being a risk taker can lead me to achieve my goals, to live my vision?


Below we focus on 6 strategies to help you become a risk taker in the direction of your goals and vision.


1. Embrace failure: Some people fear failure, others fear success. Sometimes both. Failure is another word (such as risk) which is commonly associated with negative feelings. Who wants to be a failure after all?! However, failure is not a personality trait. There is no such saying as “I fail, therefore I am a failure”. Same way as failure is not exponential to the risks you take. For instance, if I do not take risks then I will never fail. This would only be true if you wouldn’t do anything at all, risk or not risk related. Instead, embrace failure as part of life. A chance to learn, get up and keep going. How many times will you fail until you get where you want to be? No one can give you that answer. But rest assure that failure will not make you weak, only hungrier and wiser throughout your journey.


2. Take worst-case scenarios down a notch: If I quit my job, I will never find a better one. If I start my own business, I will never make enough money. If I say no, he will leave me. If I take this risk, everyone will laugh at me. Catastrophic, doesn’t it sound like it? The thing about worst-case scenarios is that they 1) feed from our vivid imagination, 2) rarely happen, 3) if they happen, are always worse in our minds than in reality, and 4) when they happen, we survive and become often more resilient than before. I am not saying you do not have [good] reasons to be pessimistic and play worst-case scenarios all day long. There is always an angle for everything, a different perspective into the situation. If you want to be prepared in case the worst happens, no one prevents you from having an escape plan. But do not let it ruin your chances to take that risk that gets you closer to your dreams.


3. Stop listening to dream killers: There is that voice inside your head, the chatterbox that becomes louder the minute you start feeling more uncomfortable. And then there are all the other people’s voices, those expressed loud and clear. You shouldn’t do that. It is too risky. You can lose everything. Are you crazy? What will [fill in the blank] think? It is a mined field, one that your inner critic feeds from merrily. When taking risks, it feels good to be understood and supported. But how can you expect encouragement from people who are not risk takers? People who most likely never took any risks in their life, or they did it once, failed and gave up. Stop listening to those who left their goals die, let alone allow themselves to dream. If you are looking for support and inspiration, find people who are successful risk takers.


4. Take one risk at a time: Though you must be fierce, you must not to go all in. It is not about everything or nothing. Having a job you love or having no job at all. Having 4 kids or having none. Buying a million-dollar house or living with your parents. Investing all your savings or not investing at all. Risks have different dimensions and magnitude. They also have different repercussions. Let us say you have quit your job recently to start your own business, maybe it is not the best time to ask for a loan to buy a brand-new house. It does not mean that you cannot have it all, you sure can. Perhaps not all at the same exact time. Being a risk taker is also knowing when to postpone taking a risk in detriment of another.


5. Cultivate a growth mindset: We talked about the advantages of developing a growth mindset before. You have what it takes to go wherever you decide to go, to do whatever you want to do, including taking risks. Believing in your unique attributes, your talents, through your dedication and efforts, you allow yourself to prosper and grow. A risk taker knows that taking risks has its up-the-hill moments as well as its downsides. What makes a huge difference is the mindset you operate under. A growth mindset connects you to your purpose, to your vision. At the same time, it makes you take on challenges despite the uncomfortableness. While you turn mistakes into learnings, you learn how to trust yourself and your skills and stop seeking approval from others.


6. Stay true to yourself: How can I become a risk taker – something I am not – and still be true to myself? It may sound contradictory, though let us clarify what it means. You can define new words to describe who you want to be – your highest self. Afterwards, you must start acting those words. Meaning, matching what you think and do to this renewed version of yourself. In case you have picked risk taker, think about how you can act in consonance. Reflect on what being a risk taker means to you, what kind of risks you can take in the short and long-run. When you start taking risks, you are already being a risk taker. This answers the first part of the equation. Now, staying true to yourself also means not doing something just to please someone else, including taking a risk for another person. If you do not know anything about the stock market, do not invest your money randomly just because your partner or a friend tells you that is guaranteed risk. Whatever risks you take, take them in alignment with your values and your mission.


When I defined risk taker as one of my “wanna be” words, I did it knowing that right now I still wonder if this is really who I can be. I am someone who always liked to-do’s lists, plans and back-up plans, someone who likes to be in control. However, I strongly believe in my mission, in my purpose, in my ability to keep learning and growing. So, if taking risks is what I gets me where I want to be, then risk taker is what I am. And you are too! Be a strategic risk taker, take risks for your dreams.



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