The rewards you reap from taking risks
WHEN I was 10 years old, I didn’t like softball and wasn’t any good at playing the sport — but my dad happened to be the coach, so I didn’t have much of a choice. I joined the summer league. For those of you who aren’t familiar with softball, it’s like baseball — but with a ball the size of a grapefruit. On one rare occasion my bat actually connected with that grapefruit-like ball during a pitch, and I somehow managed to reach first base. As in baseball, beside the first base in softball is a chalk-marked outline — known as the coach’s box — where my dad was standing.
As I stood on first base trembling with wonder, he leaned over and called out to me: “You can’t steal second base while your foot is still on first.”
Unlike me, when Rachel Kastner was a child, she was involved in an activity she enjoyed and excelled at. She acted. Growing up in New York, she regularly performed onstage in theatres on and off the neon-lit streets of Broadway. In fact, before she even graduated from high school she had produced a full-length documentary.
“I never expected to make a feature film at 18,” she told me during a recent Zoom call. “But I fundraised the money. I brought together the team. Together, we told the story of the woman who saved my grandfather in Poland during the
Holocaust. It was an incredible experience.”
An accomplished actor, producer and director, by the time Rachel was preparing to leave college, she had plenty of offers from Hollywood. Her career path seemed clear. But then she veered.
“One Friday night on Shabbat — the Jewish day of rest — my family and I were reviewing my options and I thought: ‘Hollywood will always be there. Now is the time to take a chance on myself and try something completely new.’”
Rachel rejected her offers — and with her family’s blessing bought a one-way ticket to Tel Aviv. This was January 2020, when none of us could foresee the events of the past year. But since when can anyone ever prepare for every single circumstance when evaluating risk?
That’s the concept I’m eager to explore with you today. Most companies create elaborate risk management systems, and I’m sure you’ve heard economists refer to the relationship between risk and reward. Like investment advisors say, “The higher the risk, the higher potential of return.”
But as an individual seeking to advance your career, have you assessed your own thoughts about taking risk? Do you understand your professional “risk tolerance”? Before you consider that, consider a few reasons why people take risks in the first place.
TAKING RISK IS A CHANCE TO LEARN
Before deciding to move to Israel, Rachel told me she had never developed an approach to networking.
“The six weeks before I moved, I made this crazy Excel document with every name I could think of — from start-ups to storytellers — and I started reaching out to them, one by one,” said Rachel. “I crafted personal emails, got on Skype, Google Hangouts, whatever. Within three weeks of arriving, I was employed.”
Taking risks can propel us to think more strategically, to plan, to calculate. There are plenty of lessons to codify if you succeed, and if you don’t, there are still plenty of lessons to learn from and potentially avoid for next time.
RISK-TAKING CAN LEAD TO INNOVATION
Now the chief of staff of a tech start-up, Rachel revealed that if she had clung to her previous vision of what success looked like, she would not be having the many new adventures and experiences she is reveling in now.
“I’ve helped this company build its story and pitch deck, and fallen in love with the team,” she said. “Success can be much larger than our initial vision for ourselves.”
Whether it’s new experiences, processes or products, nothing new can occur without some element of risk to begin with.
RISK SEPARATES LEADERS FROM FOLLOWERS
Ouch. This is a tough one, I know. But in the ever-changing, competitive business environment we live in, leaders are those who take calculated risks to grow, while those who always play it safe are likely to stay in place, or get left behind.
This generation’s biggest risk-taker is arguably Elon Musk who for a while last month edged out Jeff Bezos as the richest person on earth, according to Fortune magazine.
YOU WON’T KNOW UNLESS YOU TRY
“I am now open to other versions of myself,” Rachel told me. “I journal every morning and am proud of my new accomplishments.”
As for me, back on that softball field, when I finally lifted my foot off first base and began sprinting toward second, I could see from the corner of my eye that my dad’s face had lit up.
“Run! Run!” he cheered. I ran. As I neared the base, I stretched out my leg and tried to slide into second. I was tagged out.
But the pride with which my dad beamed on our drive home, knowing that I had taken the risk and tried, was worth it for me. He died the following winter and I never played softball again. My reward wasn’t making it to second base, it was in making the memory with my dad during the fleeting thing called our life together.
If you’re reading this, your life is still unfolding. Maybe you won’t make a career-changing country relocation like Rachel. Maybe you will.
But whatever it is, I urge you to consider taking that risk. Make the memory that you tried. That in of itself may be the greatest reward.