Risk Taking: The Personal, Organizational, and Global Factors

Risk: In a nutshell.   
It's an interesting concept. To have a firm grasp on risk, we need to have a solid understanding and appreciation not only of what we have, but also for whether or not we are we willing to gamble what we have for a possible pot of gold at the end of the rainbow, or our potential happiness or success. This is one of the hardest lessons to learn in life. And two major deciding factors are the underlying cultural and financial circumstances of the individual, or organization.

There are cultures that more readily accept risks, and cultures where risks are to a large degree averted. (Humorous side note: when you spend the first half of your life in one setting, and the second half of your life in another, it's hard too know where you stand and decision-making can sometimes feel downright schizophrenic.)

Additionally, there are people (and organizations) who are blessed with seemingly endless financial resources, and one would think that they may be more likely to take financial risks. But often the opposite is true. Or at least on an individual basis. Those with more to lose are often less likely to take risks. 

Proper risk analysis takes time. 
Being in between jobs is a blessing. Sounds absurd, but sometimes a perceived failure provides you with the time you need to reflect, deeply and thoroughly, on what you want. And there is lots and lots of time for inspiration. In my case, this led me to a recent gem of a discovery: Tim Ferris' recent podcast on "Lessons and Warnings From Successful Risk Takers". In it, Tim talks to three people from his new book, Tribe of Mentors, about - you guessed it - risk. What surprised me was that all three of the people he interviewed - author Soman Chainani (@SomanChainani), author Susan Cain (@susancain), and East Rock Capital co-founder and investor Graham Duncan - seem to agree on one common theme: You have to find a source of income that helps you to keep your head above water, so that you can pursue your passion. In other words, when you rely on your passion to provide sustenance, the pressure is often so high that the creativity is greatly hindered, resulting in substandard work. My favorite quote from the episode is from the philosopher Kwame Appiah,  

“It’s not how well you play the game, it’s deciding what game you want to play.”

And finding out which game you want to play is a never-ending process. If you ever find yourself in a similar situation, I recommend "Finding Your North Star" activities which are generally done with a coach. But again, this is not just limited to individuals. How often have we seen, or worked for, companies and corporations which also seemed unclear of which game they wanted to play? The old adage, "If you stand for nothing, you'll fall for anything" certainly rings true here. But of course, finding your "game" and sticking with it in a corporate setting is, well, risky. Still, companies that take that risk, stay the course, and do it well, are often rewarded. Apple is a prime example.  

Less talk, more action.
So I'd like to leave you with this little exercise, if you dare. Jot down on paper what you stand for as an individual. Then jot down on paper what your company stands for. Are those things aligned? It's any exercise I'm in the midst of now. Why? Again, it's all in the pursuit of happiness. Ultimately, we can't know whether we're ready to jump, if we don't know where that leap will take us. And if you're like me, you are also obsessed with self-exploration and self-development. In doing so, we can become more in-tune with this great world we live in, and make more lasting contributions at work, and beyond.