It is a paradox.

The risk is not in doing something that feels risky. The risk is in not doing something that feels risky.

Very little is obvious in the research on human decision-making and happiness. Very few things are proven. One thing that is proven is this: the only regrets octogenarians have are for the risks not taken.

Here’s why:

If the risk taken does pan out, it is good. But if it doesn’t — and here’s the key thing — we find a way to justify the risk taken as learning.

Gretzky knew this:

You miss one-hundred percent of the shots you don’t take.

North of Kisumu

It’s now 2007 and I’m in southwestern Kenya, near the city where Obama’s father was born. I’m with the cofounder of Kiva, Jessica Jackley, and she has organized home visits for us with local entrepreneurs.

I stay with Stanley and his family. He runs a small grocery store, and has two kids not unlike the ones you see in the photo snapped above. My mandate was to do MBA analysis to help him with his grocery store.

There is nothing to do; it is very well run.

The mornings are spent in an outhouse which doubles as a shower. A normally cold bucket of water to wash is a heated one for me, their guest. I dump it over my head, and watch my soap co-mingle with a lot more as it rolls down the drain.

Chickens walk the yard, Stanley’s children are smiling at their guest from far away lands, the feeling of family bonds is strong, and the sense of future prospects dim. After dinner Stanley’s wife tells me how when people die, the grieving scream for the dead. They scream in anguish. She wants to know if I do the same.

I don’t know how to answer. It is four years before Dave will die. It seemed impossible at the time. When he left, I didn’t scream at all. I went numb in the cab on the way to a charity event in Manhattan. I went through the motions. I told myself I was fine. The next day I cried a lot and bought a piece of art with a thousand faces on it.

Atherton

A week after returning from Kenya, I turn on the shower at my palatial second year share house. Called the White House, it looks like Tony Montana could be doing lines off the glass kitchen table.

My bathroom is on the ground floor, and set off from a backyard entrance with hedges where the original Bonobos e-commerce photography was shot. The shower has two heads, impossibly good-feeling after dumping water over my head just a week earlier in the outhouse.

That’s when it hits me.

The Second Decision

Should I take a job or start a company?

It’s my second year of business school, and I’ve been agonizing. The job offer is good, it’s with a venture capital firm. It’s more money than anyone in my family has ever made. Recently my parents tell me they never had more than $12,000 in the bank from when my older sister was born until I graduated college.

I’ve got $150,000 of debt and growing, the job offer is for more than that. Meanwhile my own start-up idea of building a platform for reading and writing is floundering.

This is a no-brainer, right?

And yet something tugs at the soul. I want to build something. I want to create something. That’s why I came to school. From my experiences on the road, I know I don’t need much. My housemate has developed these better-fitting pants and they are selling like hot-cakes. One of my most influential professors tells me that if it were him, he’d take the VC job. Ironically a few months later he’d become our first angel investor. As the warmth of the shower hits me — the sheer engineered heat and luxury of it all washing over me — the answer shows up.

I’m in 94027, the wealthiest zip code in the country, I’ve just come from one of the poorest places in the world, and the Decision elf is back.

“Have I seen you before?” I asked him.

“You don’t remember me?” he smiled back. Before I could reply, he was gone. I was left standing in the shower, dumbfounded.

“Come back!” I implored.

He returns right away.

“Haven’t I taught you anything?” he said, smiling.

“What do you mean?” I wondered.

That’s when I realize: it was the same Decision elf I had met in 2003, he was just wearing new clothes. I had to smile. I already knew what to do. It was a different question and a different life moment, but it was the same Decision. He didn’t need to say it again; his words from four years earlier rang in my ears:

The risk not taken is more dangerous than the risk taken.

I realized that I had defined risk the wrong way twice. The first time was thinking it was risky to travel abroad in the developing world, and yet what a risk it would have been not to have done so. The second time I had been thinking risk was not taking a steady job. No — I realized — risk is not having access to food, healthcare, and education. Risk is what is facing Stanley’s children, it is not what is facing me.

It turns out there is risk in taking the steady job. The risk is generally not financial.

It is spiritual.

Palo Alto

The day after the Decision Elf visited me in the shower I saw a close friend at Stanford. I informed him of my decision — against an intimidating financial backdrop — to start a company instead of taking the job. I’ll never forget what he said because it rang true to the moment:

You’ll never starve, and you’ll always have a place to sleep. Worst comes to worst, you can always stay on our couch.

It was a passing comment, but it stayed with me. There is protection for you in this world if you make it known that you need it.

I stayed on that couch many times.

Lake Tahoe

I met my parents for a graduation trip to Tahoe not long after to tell them I was not taking the steady job. Instead I was cashing in my last remaining asset, a 401K, and becoming a founder. My debt would increase, not decrease.

I was going to prove that the world had changed — that you could now build a brand online. We were going to take Brian’s pants and sell them online. We were going to prove that the internet was going to become the core medium for story-telling, for delivering great service, and for transacting goods: that it was the future of how brands would be built.

I failed to wow my parents with start-up speak, about how we were going to “bundle” great-fitting clothes with a better experience of buying those clothes through an online-driven model, how we were going to “disrupt” the industry.

They supported me with confident smiles and measured encouragement nevertheless. My mom, an Indian immigrant who has now been in the US for four decades, had never been to Lake Tahoe. My dad, a US history teacher, had not been there since he was courting my mom.

I didn’t consider then that while they had not taken the risk I was taking, they had taken other kinds. Don’t ask your parents what to do. Instead inform them of your plans, and ask them what risks they took at your age.

For my mom, coming to the US at 19. That elf showed up when her father got sick. For both of them, a cross-cultural marriage long before it was accepted, let alone in vogue. My dad wrote to my grandmother, asking her permission — translated into Punjabi. My grandmother gave her approval. Luckily, so did my mom.

It is a funny thing about life: we honor the sacrifices of our forebears not by doing precisely what they would choose for us at that moment, but by following the spirit of them wanting us to be happy. We do not do the bidding they would prescribe for us a generation away, but instead by doing what they might choose for themselves if they were our age. If they’ve done well by us and we by them, perhaps we accomplish more each generation as we go.

My parents and I circled the lake by car, content with California’s beauty from behind the wheel.