Every Choice Is a Risk, Except the Right One

Years ago, as a Harvard Law School–trained attorney, I left everything to discover my true dreams. And now I’m privileged to help thousands of others trust the truth within them and unpack their gifts and career transformations.

As a career/success coach, here’s a question I’m often asked: “What do you do when you’re trying to choose between the familiar and safe versus the unknown and unpredictable?” I’d say forget your idea of “safe.” Choose a life of meaning. Because maybe you’ve noticed—life is transitory. Meaning is the only security in town. And sometimes love, or that which means the most to you, requires you to move, voluntarily, deeper into uncertainty.

Where did we get the idea that life was supposed to be safe? What joy of significance has ever been safe? Giving birth to a child? Taking a road trip? Kissing that dark rogue stranger?

There is no risk-free life. Staying inside in your bed is a risk. Taking the bus is a risk. Staying in a marriage or job that crushes your soul, though it isn’t “that bad,” is a risk. There is no opting out. You only get to choose which risk you'll take.

And my best rocket-fuel expert tip here?

Bet on the sure thing. Bet on love. Spend your chits on faith. Take the road that makes you stronger. Going after things you want, whether or not you get them, makes you stronger.

You are going to have to choose between the illusion of safety and the ultimate safety. The ultimate safety is the life that calls you. Sometimes, you don’t even know what it is. Sometimes, it seems as though there are only more exhausting questions. But it may be good enough to start by moving away from whatever steals your spirit.

Let me tell you a story about choosing to face uncertainty rather than choosing a sense of comfort that would have taken my life, literally. Many years ago, I went hiking with a long-haired poetic boyfriend, somewhere in the wilds of Oregon. We scampered along the trail for hours, in the cool green of the forest. Then, we practically fell to our knees upon seeing the Pacific Ocean at the end of the trail. This is what happens when you live in land-locked Colorado. At the first sight of a body of water, you act like puppies. Giddy as we were, we ignored the time. The sun began evaporating from the sky. This wasn’t good. It was a time of year that turned very cold, once the sun set.

Just like that, we realized we were in danger.

We’d both dressed lightly in shorts and tee shirts. We hadn’t intended to hike this far. We had no camping supplies, jackets, pants, or milk chocolate, so, really, I couldn’t see how we were going to survive. The moment we saw that draining sun, we started high-tailing it on the trail back to the car. The light grew dimmer. We walked faster. My lawyer brain kicked in seeing possible liabilities everywhere, which is oh-so-helpful, when your heart is already pounding so fast you know the vultures are taking dibs on your body. Then, halfway out of the forest, we heard an unusual knocking noise. A tribe of birds squawked and fluttered away. They left a hollowness in their wake. Something didn't feel right. Something didn’t feel right at all.

The creepy, unsettling noise continued. "Maybe it's a moose," said Kir eagerly, looking around. He was one of those people that thought seeing wildlife was a good thing. He stopped and dawdled. Type A to the core, I power-walked up ahead and peered into the trees. I saw darkness behind them, almost a blackness. Then in the hideous slow motion of terror, I realized that the darkness was not some nice woodsy, amorphous darkness, but rather a shape peering at me, the shape of a bear. Now, for the record, I am not the type of woman that looks at a bear in fascination, even at a zoo. I grew up in Brooklyn. I am way more comfortable pressed up against a thousand sweaty strangers in a subway car than witnessing actual wildlife in a forest. But I was a long way from Brooklyn. And I was a slice of pizza to that bear.

I instinctively walked backwards on the trail cautiously, like a cartoon character. Then I ran further back until I was at a distance where I could imagine breathing. Kir followed me, wondering what was going on. "It's a bear," I said to him, terror and adrenaline lighting up my senses.

Then our negotiations began. We started realizing the horrible Zen predicament of it all: We had to walk back past the bear to get out of the woods.

We had to walk in the direction of our fears.

Because it just so happened, as it always seems to do, that the direction of our fears was also the direction of our freedom. If we walked the other way, nightfall would set in, bringing its wet ocean breath of cold and death by hypothermia. We were already beginning to shiver.

I imagined being mauled. Hypothermia sounded nice, just going numb forever. I really wanted to avoid that bear. I’m not big on facing things I can’t predict or control and knowing they have the upper hand, with claws no less. But then if we avoided that scenario, we were facing the guarantee of a slow, insidious death.

Believe me, the symbolic choice here was not lost on me.

At the time, I had only recently left my prestigious legal career to dare my crazy dreams of becoming a writer. I had left the "safe position" because I knew it was numbing and annihilating my heart, minute by minute. The comfort of that paycheck and validation was seducing me into a stupor in which I abandoned my will and lapsed into a menacing indifference about my own life. It was the hypothermia of having my heart go cold.

But in that scenario, I had decided to fight to save my own life. I chose the terror of choosing a creative, unpredictable, alive life. I faced the immediate risk of not knowing how things would work out. I felt exposed and naked. Yet I also knew that at least now I possessed the chance of something working out. My job had been "safe," in worldly terms. But I knew I had not one shred of hope of living my true life while there. I was unequivocally dying every single day. It wasn't savage death. But it was certain death.

It hit me then that I would have to walk in the direction of my fear. I would have to walk toward the bear. If I walked by the bear, I might make it to total freedom. It held the only possibility of what I really wanted. I'd at least have a chance at life. But I'd have to walk by that bear. I'd have to risk unbearable (no pun intended) uncertainty.

So, yeah, the fact that I’m writing this is a spoiler alert. I lived. We walked by the bear, slowly, praying silently to ourselves and to the God you pull out of your back pocket when you hope there is a God and you hope he has instant messaging. We surrendered to the vulnerability of our desires and the purity of our instincts. Then we ran—and, if memory serves, I kissed that rental car's thin tin sides.

That night we ate at a local diner and I told the waitress about the bear and how happy I was to be alive. I have no doubt I sounded like someone who had just seen a UFO. She gave us French fries on the house. I have never tasted better French fries. I know they were probably wilted with grease, ordinary, or even too salty. But I was alive—and everything tasted alive to me.

What is your bear in life?

What action or direction calls to you right now, but might leave you bare or unprotected? Where do you have the best chance of at least moving towards something you desire? The need for certainty costs too much.

There are no guarantees in anything. But love will find you as you go in the right direction. And love is safety.

I suggest you walk by the bear.

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