“Did you remember your wallet?”, is the checklist question you don’t want to hear just as you’re pulling up to Midway Airport at 5:15 AM for a 6:40 AM Southwest flight. At that moment, I thought I was Fu#%ed!

Not enough time to turn back and retrieve it. Facing a post 9/11 brick wall if I tried to continue forward without it. The story would end here for most, in frustration.

“I’ll go back and get it!” Tara, our intern, volunteered. She’d graciously offered a last minute ride, after Sharyl came down with the flu. Now she was stepping things up another notch.

Grateful for the offer, my hopes weren’t high given time and distance. The drive had taken longer than expected, after her dyslexia revealed itself in a series of turns that bucked the GPS’s commands. Only when she asked me to translate by physically pointing the directions, did her challenges all start making sense to me.

“Will you be able to get back OK?” I asked. She said she’d memorized the directions, and that the talking GPS was hindering, not helping, her coping mechanisms. So we agreed to give it a shot, said our goodbyes, and parted as the snow fell harder. A flight delay would be a savior.

Stepping into the terminal, I felt the gaze of a hundred eyeballs. The beard was triggering the classic “Bearded Muslim Terrorist” stereotypical response. My job just got a thousand times harder.

After sharing my predicament with the Southwest handler managing check-ins, she suggested I go home. Not an option with ten inches of snow on the way. I had to get my body out of Chicago, everything else could follow.

First challenge, get a boarding pass. Credit card powered kiosks weren’t an option. I was going to have to go human. That meant the long meandering cattle line. More time for Tara to make it back.

“Can I see your ID, please?” the agent asked. Game on. “I’ve done something stupid. I left my wallet at home, and a friend is racing back to retrieve it”. Cue the puppy eyes. No effect.

“There’s no way TSA will let you on board without proper documents, and doors close at 6:30 AM”. The deadline was set. I pulled up my confirmation email, and that was just enough to get my bags conditionally checked. Provisional Boarding Pass secured!

The long security line bode well for our effort. As long as I was on the outside, there was a chance of physically connecting with Tara. By the time my turn came, Tara texted she was just arriving at the Safehouse.

The first TSA agent you see, has the responsibility for catching idiots without an ID. He did a great job. I failed immediately. Needing a second chance, I explained the situation, and volunteered for the extreme security screen — if they would just look up my credentials. He grudgingly agreed.

I was passed through X-rays, sniff tested for explosives, patted down, and metal detected, before being asked for my hand. My fate now lay at the tip of a finger — my fingerprint being read by a scanner.

Jackpot! I’m in the database, as is anyone that’s ever applied for a green card. Hurray for biometrics and the police state, my identity was confirmed — just as Tara texted she was leaving the Safehouse, with wallet in hand.

We were now divided — the insecure and secure. Meeting her on the other side would mean repeating all the above. Not an option. We needed a runner to meet her at passenger drop off, and race the wallet to the plane. These heroics are what supposedly make Southwest Airlines great, but there were no heroes to be found that morning.

Tara stood waiting in the snow, while passengers were herded onto the plane. The best Southwest could offer was a later flight, but Chicago would be shut down before then. It was time to leave. Tara’s mission was aborted.

“Take pictures of all my cards, my license and insurance”, I texted Tara from the plane. Bit by bit, my wallet was being digitized as we taxied to the runway.

When we reached cruising altitude, I tried to buy WiFi access, but stumbled when asked for my card’s security code. All the photos were front shots. Argh. I entered three digits with not much confidence, and was surprised to find they were correct. I was connected at 30,000 feet!

The next challenge was ground transportation. I couldn’t get a flight
into Austin, so decided on Houston. The original plan was to take a Megabus between Houston and Austin. That required taxis from Houston Hobby airport to their downtown pick up point, and from their Austin drop off point to my final destination.

Having thought through the logistics of trying this with 100 lbs of luggage in tow, I had opted a few days ago, to rent a car — but couldn’t get a refund from Megabus. My frustration with Megabus turned into a potential saving grace, as those old Megabus reservations were now still in play.

However, with only a loose $20 bill in my pocket, there wasn’t enough money for the Megabus taxi rides, or the extra bag. Visions of a bearded dude panhandling began to fill my head, as a rental car now seemed like an impossibility.

In flight, I surfed Budget’s site and confirmed my fear. They require presentation of a credit card and valid license, with only ONE exception. Unpaid tickets and summonses, prior to hearing dates, also qualified. I kicked myself for just paying off a parking ticket, and finally getting a Chicago City Sticker!

From an earlier SxSW car rental experience, I knew they weren’t going to budge. That time, my friend Harper saved the day by charging my car on his card. Unfortunately, I didn’t have a Harper with me.

I texted Sharyl in flight to see if she could call the Budget counter at the airport, and work something out. The hope was that a local manager would be more inclined to bend the rules, versus the scripted automatons manning the 1-800 number.

An hour later on final approach, Sharyl texted that a Manager had agreed to accept the photos of my credit card and license, in lieu of their physical incarnations. Success!

The only problem was that she didn’t get the agent’s name, and could only identify the person, based on their accent, as African American.

Walking into a centralized airport rental car facility in Texas, asking for African Americans wasn’t going to fly — that Cinderella’s slipper would be a one size fits many proposition in the hard working service industry.

Fortunately, one of the counter reps overheard me explain the arrangement, recalled the name of the agent that Sharyl had talked to, and summoned the Manager to assist.

After much chiding and laughter, she handed me the keys to a black VW Bug, called ahead to the gate to let them know I had no ID and to let me pass, then sent me on my way. I had a car!

Halfway into the three hour drive, I pulled off the highway, laid down half of my $20 fortune for a chopped BBQ Beef sandwich at Kinze’s, a BBQ joint with a drive-thru (gotta love Texas), and pondered next steps.

My next challenge was going to be money. My wallet was being sent via FedEx and the earliest it would arrive was Monday. It was Saturday. I had $10 left to my name, a long drive, and much to buy in preparation for Conclave. It was time to call American Express.

For all the gripes folks have about credit card companies, Amex changed the game when I joined them after getting my MBA. We created and launched a slew of new benefits, including Global Assist. I called the 1-800 number, and they verified my identity with a series of True/False challenge questions. I was then given the address of a Walmart seven minutes away, where I could pick up the $500 that they were wiring. It’s true. I walked into Walmart and left with cash in hand. Miracle.

I’ve never been one to accept an answer as final. To accept the status quo as unchangeable. Or to believe that rules were anything but bendable. In a performance review, I was once told that there’s a fine line between being tenacious, and being a pain in the ass, and that mine was dotted. I took pride in that because it meant I was always pushing the envelope. I tend not to give up.

How else would I have had the good fortune to be sitting here in the 80° Texas sun, eating BBQ, versus griping about Chicago’s never ending winter?

Serendipity? Yes. That’s a key theme in my life. Friends? Mine are awesome. Resourcefulness? Absolutely.

In the desert in which I was born, there are a nomadic tribal people that live in what we would think of as a barren wasteland. They are called the Bedouin. They have a saying which loosely translates to “Pack less. Rely on your resourcefulness more.”

There’s a lot of wisdom in that saying. That’s how I got to Austin.