For the first three years of Bonobos, I lived with $3,000 in the bank, a $3,000 apartment, and $150,000 of debt. During that time -- 2007 to 2010 -- I was only a month away from being out of cash. I was paying myself, initially, $70,000. This is plenty of money in most places, but in NYC it can fly you pretty close to the trees on just rent and alcohol.

Sometimes I wouldn’t watch my cash balance relative to my next payroll direct deposit. As a result, I’d occassionally become illiquid. With financial weapons of mass destruction like credit cards readily available to most anyone with a pulse, normally this is no big deal.

Other times it is.

I’m at dinner on a first date in the East Village. It’s a new place -- for me -- and I discover half through the meal the sneaky Cash Only sign on the wall. I excuse myself from my date somewhat awkwardly to go to an ATM. After much HAL-like deliberation, it expressly does not make the dispensing cash noise. Instead it starts printing a receipt — always bad news — which contains two of the most dreaded words on the planet:

Insufficient funds

The feeling of no money in the bank, of rejection by ATM, is always a bad one. With a cash-only date in progress it became in fact one of the most sickening feelings I have ever experienced.

I knew that I was running thin, but someone else possibly discovering this financial fact moved my balance sheet from a mostly private matter to semi-public shame.

I felt like a fraud.

Here is this poor woman -- pun intended -- around the corner at dinner who mistakenly thought I was financially viable as a human, and I’m in front of an ATM which is reminding me that I am not. Without the protective safety net of deferred payment that is a credit card, I was exposed.

Let her pay? Nope. Way too much pride for that.

It’s also the most unromantic thing you can do on a first date as a man outside of spitting on her, and I wasn’t about to spoil the evening.

At the same time I was running a cash flow negative company which was 90 days from being out of cash. There was no venture capital belief in the company in the early years, so I raised $8 million over four angel rounds from over one hundred angel investors to keep us afloat.

The amount of financial stress was extraordinary. To be 30 days away from being unable to pay rent personally and ninety days away from lights out professionally for three years takes its toll.

My company had insufficient funds, and so did I.

Why would anyone put themselves under that much pressure?

The Decision Elf

That personal debt stemmed from a decision I made in 2003. Though I didn’t view it that way at the time, it was — in retrospect — an investment decision.

Four years later, in 2007, I faced a second decision, and a related one. It was something I had been turning over in my mind for two years, really, before the decision came to me.

Given what’s become of my life, I literally cannot imagine life without having made either of those decisions. But neither was a no-brainer at all at the time.

I’ve found that I don’t make decisions. Instead they come to me like a visitor does to your doorstep.

Here I am! I’m the Decision.

The Decision doesn’t always come when you want it to. Sometimes it shows up annoying early, when you’re still setting the table for dinner, and the turkey’s still in the oven. Other times the Decision comes rudely late and spoils the evening by not being there for the surprise.

For me, the Second Decision came to me right when I needed it. When the Decision Elf showed up, I was in the shower, and he looked familiar.

“Have I seen you before?” I asked the Decision Elf.

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

If you can’t decide what to do, get on the road. You won’t find the answer. It will find you.

Chicago

Someone once told me:

The hardest part of a long-distance relationship is when the long-distance ends. That’s when the real relationship begins.

I laughed at this, humoring the conveyor of the wisdom with a polite chuckle. I secretly knew him to be wrong. Our love was too strong for that.

Snow fell on a spring day in March. I walked across Oz Park, tear-caked eyes.

He was right.

The First Decision

The next day I walked into the offices of Bain, my then employer. Do you want to move to San Salvador? You’ll be living there for the next six months.

“It has the highest murder rate in the western hemisphere,” said my dad.

“You don’t really speak Spanish,” said the voice in my head.

I looked at the Decision Elf. He winked at me.

“The risk not taken is more dangerous than the risk taken,” he said.

(I would later forget that he told me this.)

Do you want to move to San Salvador?

“Yes I do,” I said.

And just like that, the First Decision was made.

Had I made it, or did it make me?

San Salvador

The six months I spent in El Salvador were the most impactful of my life. Living in a country where — in 2003 — the nominal GDP per capita was $2,503 quickly woke me up to how much privilege and standard of living I enjoyed in the developed world.

It reminded me of what my history professor Peter Hayes once said in college:

Live somewhere else, on the terms of the people who live there, for six months. It will change your life.

Though I’m the son of an immigrant, who herself grew up in constant fear of not having money, her hard work and provision insulated me from the reality which shaped her.

What a strange thing multi-generational struggle is. One generation’s work and sacrifice creates over-confidence and perhaps hubris in the next.

I was working for an airline, and the travel on that airline was free if there was an open seat. I spent my weekends in Roatan, San Pedro, Antigua, Guatemala City, Havana, and San Jose. Fried chicken was often put in the overhead compartments of the planes.

I stayed at the Hotel Intercontinental and ordered fajitas as room service. I went to a nightclub called Code three nights a week and learned to close the night to Timbiriche.

I was only doing half of what Peter Hayes had asked me to do.

Havana

Once in Cuba, I met a man precisely my age. Let’s call him Luis. We were both 23. It was a favorite age for me as it coincides my favorite number, the number worn by childhood idols Ryne Sandberg and Michael Jordan. A song was popular at the time: Nobody likes you when you’re 23. I wondered if that singer-songwriter was experiencing a lot of self-loathing.

I don’t remember what Luis and I spoke about exactly.

I do remember him asking me if I’d send him shoes. I do remember feeling that it was mostly being lucky, not good, that led to his asking me for shoes and not the other way around.

I lost his address. I didn’t know how to ship to Cuba. I wondered if I’d get in trouble with the government. The shoes never got sent.

There are a lot of good excuses for not helping someone.

Travel doesn’t shape you so much as the people you meet along the way shape you. While living in San Salvador, I became friends with a number of South Africans who approached life differently than I did.

For me travel was a novelty; for them it was a way of life. From observing them, I came to the self-assessment that I had been living my life wrong. I had the ability to go just about wherever I wanted, and yet I had lived the first quarter century of my life more or less tethered to Chicago.

Two South Africans in particular, Matt Bresler and Dave Eadie, inspired me to change. Four years later they’d both wire money into Bonobos as angel investors without really knowing a thing about the company.

I wanted to be like them. Imitation, it turns out, is a great engine for personal growth. I decided to travel as much as I could. Over the next four years, squeezed between another job and two years in business school, I went to 30 countries. Over the past decade, I think the number is closer to 50.

The number doesn’t count; I quit the tally when my accomplishment orientation to travel thankfully evaporated.

We did this place, we did that place. Really? You did it, and now it’s done?

What does count is a perspective on what wealth really is that set into my bones. Wealth is the substance in you, it’s the people that care for you and that you care for, it is experiences had and perspective acquired.

Johannesburg

When I went to Joburg the summer after living in San Salvador, Dave Eadie shepherded me everywhere: A great sleeping bag set-up on his hometown floor, karaoke with all his friends, nights out at the Nite Fever, a chauffered drop-off on the way to his beloved field hockey match for me to take in a solo, biltong-filled viewing of the Lions-Sharks rugby.

Kalaw to Inle Lake

Two years later, on a trek in Burma, my cousin and I stayed with a family. The father was an doctoral engineer relegated to plowing due to the lack of opportunity in the country. Let’s call him Sing.

The night we stayed with him Sing slaughtered a goat so that we could eat in style.

We slept above cows.

The palpable closeness of Sing’s family was a reminder of what we sometimes lose in the developed world, as we move away from extended family tribal living into suburban-cloistered nuclear family living. Everything else about their lives in now Myanmar was a reminder of what we do have.

The developing world gives you this gift of realizing you have everything you need, and that maybe you are lacking some things you could have but have opted out of.

During two months in Southeast Asia I traveled on twenty-five dollars a day including lodging. My only possessions were books, a small backpack, and a camera. I realized that everything I needed to be happy was already inside me.

I spent every dollar I had on travel and adventure and ended up in the described financial hole.

An open heart finds friends almost anywhere it goes.

Dave Eadie, one of the two men who had inspired me to travel to begin with, took the risk of traveling first and then the risk of quitting a job he didn’t love second.

He was an inspiration when it comes to avoiding the risk not taken.

He is also a past tense person, because he’s gone. Unfathomably we lost Dave in 2011. Too bright a light to go out at 35, and yet on he went. He was too alive to die, and yet that’s not how it works.

Is it too much to say that Dave changed my life, and that in that way he lives on? That the way in which we influence and change others — when we can — is the only way to stay alive? It’s probably too much to say that.

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 failed 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. 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, they scream. They scream in anguish. She wants to know if I do the same.

Atherton

A week later I turn on the shower at my palatial second year house. Called the White House, it looks like the 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 ecommerce photography was shot. The shower has two heads, impossibly good-feeling after dumping water over my head just a week earlier in the outhouse. I’m doing good thinking in the shower that day, and 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, and I’ve got a chance to provide security, half-Indian son style, for myself and my family, once I pay down my debt. Meanwhile my own startup 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. My own start-up idea is going nowhere.

One of my most influential professors tells me that if it were him, he’d take the VC job. Ironically, 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 where a shower was manually dumping water over my head, 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 impored.

He returns right away.

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

“What do you mean?” I wondered.

That’s when it floods in: It was the same Decision elf I had met in 2003, he was just wearing new clothes. I had to smile. He was making a point. I already knew what to do, I had already made the Decision before in 2003.

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,” he had said.

“How did you get here?” the Decision elf continued.

“What do you mean?” I replied.

“What would Luis want you to do? What would Stanley want you to do?” he asked me.

Since I’d left Kenya, Stanley wrote me to see if I could help him come to America.

There was nothing I could do.

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 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.

There is risk in taking the steady job. The risk is generally not financial.

It is spiritual.

It is the risk of the door not opened.

It is the risk of the risk not taken.

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 be come 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 startup 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 had has now been in the US for four decades, had never been to Lake Tahoe. My dad, a US history teacher, had not been 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, ask them what they did when they were your age, and then inform them of your plans.

What risks had they taken, or had taken them?

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. She said yes; luckily so did her daughter.

We circled the lake by car, getting out only occasionally at vista points, content with California’s beauty from behind the wheel. We’d have gotten out to hike, but considered it less risky than doing the most dangerous thing healthy people do — which is we drive. We don’t know what would have happened that day if we’d gone hiking. We’ll never know, for a simple reason:

We never went.

[This post was originally published on Medium.]