Rewind to about 20 years ago. I was in my early twenties, just learning how to travel on my own. I flew from my home in the Pacific Northwest to San Jose, California for an important business conference I was very excited to attend.

This was before the internet and before smartphones. For travelling I used to withdraw several hundred dollars cash and just carry it around in my wallet. Good intention, bad execution as you’re about to see.

Once I settled myself on the plane I reached into my pocket and felt…nothing. I quickly searched my carry-on bags. The horror finally sunk in. I had left my wallet, with all my cash, cards and ID, back in my car in the airport parking lot. I was screwed.

Back then I cleverly used the airport shuttles for the fancy hotels to transport me to the cheap hotel I would always use. (You can’t do that any more; these days they actually ask your name on the fancy shuttles and compare it to the guest list, and kick you off if they can’t find you listed.)  So I was able to get to my hotel fine. Once I was there I did what most people in their early 20’s do when they do something stupid. I called my parents.

Long story short, my dad was not impressed with my offer of borrowing a few hundred dollars even though I would pay him back the instant I returned home since the cash was waiting for me in my car. I hung up with him and called my sister, who was my only other relative with access to any money. No go there. We could not figure out a way to easily wire the money to me fast enough, considering I didn’t even have any ID.

This was not looking good. I really was screwed. I didn’t have any money at all, so I couldn’t even pay a taxi or bus to take me to the conference which was starting that evening, nor did I know anyone else going well enough to ask. And it was too far to walk.

My options were:

1. Forget about the conference, and spend the next two days chilling out in my hotel room, perhaps finding something fun to do within easy walking distance, then fly back home.

2. Spend one night at the hotel, then check out early the next day, get a refund for the unused second night, and use that cash to get downtown to the conference and hopefully find a very cheap hotel down there.

Option one was the safest and simplest, but I would miss the conference, which was the entire point of the trip.

Option two was very dangerous. What if I could not afford or find a hotel? Would I ended up sleeping in the street? How would I get downtown? Walk? I was miles and miles away in a city I had never visited and knew nothing about. No maps were available at my current hotel.

Finally I made up my mind. It was option two.

The next morning I checked out of my room and got my $60 refunded to me for the second unused night. Problem. The $60 was now $34.17, because I had made several long-distance phone calls with the hotel phone. This was back in the pre-cell phone days when long distance was expensive as hell.

I grumbled, took my $34.17, walked out onto the street with my luggage in tow, and glanced down at my meager cash. This $34.17 was going to have to support me for the next 48 hours. Food, lodging, transportation in an expensive California city…for 48 hours…for $34.17.


Dressed in my business shirt, business slacks, and business loafers, which was the only clothing I had packed for my trip, I started down the street in 100 degree sunny California summer weather. Oh, did I mention I’m pasty white, sunburn within minutes, and had no sunscreen? Yeah.

I had no sense of direction. All I could do is occasionally spot the skyscrapers in the distance and make my way towards them, knowing the conference was going to be held downtown. I walked and walked and walked. Often I was miles off course.

I was hungry and thirsty, but I knew I had to preserve my $34.17. Eventually my starvation and thirst cracked me and I bought a small lemonade and candy bar and wolfed it down. When I started walking again my feet burned. Blisters had formed all over my feet because of the damn business loafers, which were not meant for long walks. My skin was also turning a nice shade of red.

There were points where I suddenly found myself in…um…”bad” neighborhoods. Mexican gangs gave me the evil eye and shouted at the haggard-looking young white businessman as he staggered through their turf. Several times I had to cut across people’s backyards and private parking lots.

Twice I had to scale chain link fences by throwing my luggage over first then climbing them like Bruce Willis in Die Hard. The second time I tore my slacks and when I landed blood was seeping down my leg. I looked like a very successful young businessman.

Sweaty, sunburned, and bleeding, I kept going. At one point I staggered into a convenience store and asked the Arab employees directions to “downtown”. Their answer was mostly given in their language. The only word I understood was “freeway”. I did my best using slow words and hand signals to indicate I was walking and had no car. The problem was this was Southern California. “No car” is not a concept easily understood there. When they again insisted that I take the freeway, I sighed, nodded and left.

Hours later, well into the evening, after going miles off course several times, I made it downtown to the correct hotel where the conference was being held. I staggered into the place, hoping no one would recognize this stupid, disheveled, bleeding, limping, sunburned kid. I make it into the auditorium and made sure to sit waaaaaaayyyy in the back away from everyone.

The conference was fantastic. It included one the best speeches I’ve ever heard in my life, and that’s saying something, since I’ve heard many. I recorded it all on cassette tape and to this day I have it in digitized MP3 form. The conference was so great I temporarily forgot about my current situation.

After the evening session was over reality returned. There was another all-day session the next day followed by my flight leaving back home. I had nowhere to stay that evening. I knew no one. What few people at the conference I did know somewhat I did not want to see in my current condition.

I checked my cash reserves. I had 31 dollars and twenty-two cents to my name.


After a few minutes I formulated a plan. I would go without food tonight and all day the next day and do my best to find a hotel that only charged thirty bucks a night in San Jose.

Yeah. Good luck with that. But it was either that or sleep on the street, and that was never an option.

Walking out of the hotel my feet burned and I could feel fluid from my blisters soaking my socks that was not sweat. I tried not to think about it and pushed on, gritting my teeth as I walked down the street. I came across Alameda Avenue and figured it looked as good as any other street to start my search.

The hotels around me were the big fancy kind. These had rooms that started at $150 a night, so that wasn’t an option. I walked down Alameda, slowly watching the hotels get smaller and crappier as I ventured further away from the city core. Finally I found one that looked pretty cheap. I went in and asked for a room. $70 a night. Damn. I exited and kept walking. It was dark outside and the pedestrian traffic became lighter and lighter, the streets darker and darker. Finally, the pain in my feet from blisters and the pain in my shoulders from the sunburn blasting at maximum, I found another hotel. It looked like a real piece of crap, which gave me hope.

I went in and asked for a room. The guy smiled as he quoted $50 night.

“Are you kidding me?” I cried, “For this place?”

He was not pleased with my attitude and showed me to the door.

I kept on. After about another 45 minutes of painful walking I wasn’t sure if I could keep going. My feet started to give out and started stumbling as I walked. Finally I came across a motel that looked like it was exclusively used by drug addicts and hookers. I crossed my fingers and entered the “office”, which as simply a tiny alcove full of nudie magazines and Hindu statues manned by a guy from India who barely spoke English.

“How much for a room?” I asked. My voice was gone. It came out as a wheeze.

“Thirty-nine dollars,” he said in heavily accented Indian, eyeing me suspiciously. (I’m sure I looked great.)

I only had $31.22 in my pocket. I knew that. It didn’t stop me.

“Okay!” I said, trying to sound confident, “I’ll take it!”

He nodded and watched me like a hawk. I slowly withdrew a ten dollar bill. Then a five dollar bill. Then another five dollar bill. I kept withdrawing money slowly, to make sure he saw every withdrawal, like I was showing him a diamond ring at a jewelry store. I noticed his pupils dilate as I put more and more money on his counter. Always a good sign during business negotiations.

Finally I got down to the change. A dime. A nickel. Another nickel. Two pennies.

I paused. I rummaged through all of my pockets, slowly, methodically. Finally I stopped, looked at him, looked down at the money, and using my best Academy Award winning acting, I said sadly, “I’m sorry. I guess I don’t have enough money.”

Then I slowly put my hand on the tiny money pile and began to pull it towards me.

“Wait!” he said, “I’ll take it!”

I looked at him with mock surprise. “But…” I said

“No no!” he cried, “I want to help you!” He put on a big smile.

Thank god. Or thank whatever Hindu god he worshiped. At this point I didn’t care.  I breathed a hidden sigh of relief as he pulled the last of my funds towards him and handed me a room key.

“Checkout time 7:30am!” he said with a stern look. I guess he didn’t like his typical clientele hanging around his rooms long enough to do too much damage.

I nodded my understanding and proceeded to my room. It was the size of my current closet. Laying on the bed felt like laying on a concrete slab. I crashed into it anyway and tried to sleep.

The next morning at exactly 7:30am, the phone rang with a loud BRRRINGGG BRRRINGGG and I jolted awake. It was the Indian guy, telling me in no uncertain terms that my time was up and that I needed to get the hell out of there. I mumbled something and hung up. I lumbered into the shower and screamed in pain as the water hit the puss-filled blisters on my neck, shoulders, and feet and my sunburn everywhere else.

Ten minutes later I was out on the street again. Dragging my luggage behind me I started the long, slow, painful walk back to the business conference. I was there the rest of the day and did my best to enjoy it despite my pain, which I did. After it was all over, I sneaked back onto the fancy airport shuttle and soon was on the plane headed for home, all the while trying to avoid any mirrors which reminded me my skin was as red as a Coke can.

Hours later when the airport shuttle brought be back to my car in the airport parking lot, I staggered into my car, opened my glove compartment, and glared with hatred at my wallet filled with several hundred dollars cash.

Oh well. At least now I have a fun story to tell.

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