On Risk, Uncertainty, and Rejection

I had dinner a few months ago with a girlfriend from college. She had been asking about my startup and recent jump from steady employment to the always-volatile world of entrepreneurship when she noted that I have a history of taking some pretty big risks and yet I “always land on my feet.”

She was both proud and a touch wistful as she made that observation, going on to note that she was in a comfortable job (at which she was quite successful), with a loving husband, and had just purchased a beautiful home, all by age 27.  In contrast, I was single, had quit my job, moved into a tiny place in upper Manhattan (where I rented a couch in the middle of the living room), and poured my measly savings into a high-risk venture while deferring 6-figure student loan debt.  She was living the life she wanted – 10 years from now.  I was making the risky choices, which may or may not ever pay off, but are certainly anything but comfortable.  Who exactly should be envious of whom here?

I thought about her comment that night and all through the next week.  I certainly do have a history of big leaps – personal, professional, educational, physical… My story is a long and twisty one with sharp turns that some call brave and others call reckless.  The more I pondered it, the more I wondered: what was it that made me willing to take substantial risks where others might shy away?  I went back through journals from the past decade or so, and began to see three themes emerging:

1. I believe that I am smart enough and strong enough to figure out a solution.

The first time I traveled alone I didn’t believe this statement. I was in Germany and a volunteering gig I had lined up had not panned out as expected. Suddenly I was stranded in Bavaria with three weeks before my return flight to the US and very little money.  I’ll admit, I panicked for a second. More like 60 seconds. But then something just clicked and I switched into problem-solving mode. My instincts identified what resources I needed (internet, train tickets, Lonely Planet) and, despite the language barrier in a rural town, I procured them all.  The thing is, once I had one success story it was easier to go out on a limb next time – I already knew I had pulled it off. When my future travels to East Africa or Haiti or Central America found me in a tough spot I could tell myself it was going to be okay; I’d faced similar problems before and they had all turned out fine; I was smart enough and strong enough to figure this out.

2. I am growing more comfortable with uncertainty

Uncertainty is the hardest part of taking big risks. At least for Type A people, the inability to plan or predict what will happen is the scariest thing we can imagine.  But uncertainty is one of the few guaranteed things you’ll face when taking a risk with a truly big payoff – that’s what makes it so risky. So how does one develop the muscle of dealing with uncertainty? By believing statement #1: I am smart enough and strong enough to figure this out.  Once I truly believed that axiom I was able to relax my death grip on the unknown and embrace uncertainty and the adventure it contained.  I took solo backpacking trips without booking a single day in advance. I ended an unhealthy relationship without any other prospects on the horizon, even as my friends were all getting married and having children. I quit my job and decided to start my own company even though I don’t have a massive savings account or family money to fall back on.  The worst that could happen is never going to happen – my instincts will kick in before it does and I’ll figure something out. It’s all going to be okay.

3. I am getting used to rejection

This was one of the more interesting themes I noticed. When I first ventured off to college I was often timid in asking for what I wanted. I figured that if it was supposed to work out, it would, and by not asking I never had to hear “no”. Imagine my surprise, then, when opportunities didn’t just fall into my lap. This clearly was not a winning strategy.

So I started asking. I applied for jobs I wasn’t quite sure I was qualified for. I asked for promotions and raises. I decided to go to business school even though I’d never met anyone with an MBA and didn’t know what a P&L was. Revise that: I decided to go to Harvard Business School. I even asked guys out. Hot guys. Guys who were totally out of my league. And guess what? I heard “no” a lot.  At first it stung. At first I cried. And ate a lot of ice cream. Then I started to expect “no” and didn’t care; I was going to ask anyway. I cried a lot less. And when the answer was “yes” it was amazing! I was over the moon. I definitely cried then. (No judgement. Steve Jobs apparently cried all the time.)  Getting used to rejection requires developing a muscle, and you can only build it up by practicing.

(Sidebar: I think this is why boys tend to be gutsier than girls; they are the pursuers from an early stage and thus get used to hearing “no”. Girls are told they are to sit tight and wait to be pursued, and thus are quite good at saying “no” but less good at hearing it.)

What do you think? Do you agree that these traits can be developed, like muscles, or are they more hard-wired than that? What other traits have you noticed correlate with risk-taking?

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3 thoughts on “On Risk, Uncertainty, and Rejection

  1. Pingback: An open letter to my sister on Mother’s Day | The Phi Factor

  2. Pingback: New Year, New Adventure | The Phi Factor

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