Apps for a paperless trip
Apps for a paperless trip

It began as a dare: Take an entire business trip without touching a piece of paper.

I nearly choked on my half-finished beer, wondering if I’d been poured malt liquor by mistake. “An entire business trip? Haven’t I already done that in my Geek’s Guides to Air Travel and International Travel?”

The GeekWire editors who were meeting with me at the Fremont pub shook their heads, almost as one (though that image, too, may have been due to the alcohol content). “No. In those cases you provided tips on how to be more digital. Go all digital. Are you up to the challenge?”

Challenge accepted: This practical nerd would attempt to make a routine work-related trip entirely paper-free. Besides, it would be a useful litmus test. How fully digital can we really be in this so-called digital age?

My trial by Kindle Fire was to be a five-day, Sunday-through-Thursday business trip to Manhattan complete with client meetings and office work. I could not have foreseen exactly what Mother Nature had in store — and how the weather would impact my quest.

The Saturday before I left, I printed out my sole pulpy backup — a boarding pass for my outbound flight in case I forgot my phone Sunday at dawn. My digital survival kit included a Google Nexus 5 smartphone, Lenovo ThinkPad T430 laptop, Kindle Fire HDX tablet (with Bluetooth keyboard), New Trent dual USB port external battery pack, Monster Outlets to Go multi-plug adapter, and several chargers. I’d need them all.

Day One: Departure

Sun 6:47am Arrived at WallyPark garage at SeaTac and scanned the barcode on my WallyClub parking card. Though this was plastic and not paper (a distinction probably irritating someone in the Seattle Mayor’s office), it immediately made my more digitally focused self wonder why WallyPark didn’t have an app for its frequent parkers.

7:05am Having checked in for my flight on Alaska Airlines’ Android app, I had my digital boarding pass. Pulling out my driver’s license (more plastic) and flashing the Alaska app to the TSA agent, I got a quick nod of approval. No scribbling of illegible initials on the paper equivalent.

7:17am Entered the Alaska Airlines Board Room airport club and scanned my boarding pass again. Despite some difficulty with the scanner and screen brightness, it confirmed I was allowed in thanks to membership information embedded in the digital boarding pass.

NJ Transit's MyTix app
NJ Transit’s MyTix app

After I sat down, I opened up the relatively new NJ Transit MyTix app I had downloaded the night before and bought a one-way train ticket from Newark airport to Manhattan. Very slick, but I would have to remember to “activate” the ticket before I boarded the train. The app replaced a paper ticket with a magnetic stripe I used to wait in line to buy after I arrived at Newark, generally behind people who don’t know how to use the ticketing kiosk.

I plugged everything in and grabbed a cup of coffee, eschewing the paper cup for a glass mug.

8:25am At the gate, I again scanned the Alaska Airlines app boarding pass and took my seat. I zipped through the Ubersocial Pro and Breaking News apps on my phone for news updates. After the door closed, I read the New York Times on my Fire HDX. At 10,000 feet, I took out my laptop and connected to Gogo Internet which, like clockwork, failed shortly into the flight as we passed over the Canadian border where GoGo is still building out its network.

5:14pm (ET) On the Newark airport AirTrain, I tried to check the NJ Transit website on my phone to confirm the trains were on time. It was an awful experience: not only was the site not mobile-friendly, it only showed the next train, not the next several. I activated my train ticket in the MyTix app, scanned it at the station turnstile and raced down the escalator, a bag in each hand, to hop on the 5:15pm to NY Penn Station as others behind me still struggled to insert their paper cards in the turnstiles the correct side up.

Conductor-required paper
Conductor-required paper

On board, the conductor glanced at my smartphone screen, nodded – and promptly tucked a paper seat check in the metal holder in front of me. I didn’t touch it.

6:15pm After taking the New York MTA subway (scanning another plastic card with a magnetic strip with stored value for fare), I checked into my hotel. My client was a not-for-profit, and the hotel required a government-issued tax-exemption form. A paper form. I hopefully asked if they’ll accept a PDF – and they told me yes, as long as I emailed it to them. Victory for next time.

As I was handed my plastic room key card, I was told this hotel would soon be piloting keyless room entry using a smartphone app. I smiled.

I bought dinner to take back to my room at the local market and was offered a paper receipt. I realized that I have no choice, if I wanted to have my expenses reimbursed. I frowned.

But I made it to my room with minimal paper exposure and no cuts. I relaxed by reading a Kay Kenyon novel on my Fire.

Days Two-Three: Office

Mon 8:07am Mornings began at Starbucks for oatmeal and coffee, where the Starbucks app worked fine but I again had to accept a paper receipt for expenses. I read the New York Times on my smartphone as a pile of paper ones sat behind me, unpurchased and unloved.

In the office itself, I used my laptop and Evernote in meetings, read agendas in email and begged that planning handouts be sent to me as PDFs. Hilarity ensued as I literally found myself backing away from someone trying to hand me a printed budget. “What’s wrong with you?,” I was asked. “Paper cooties … I mean, allergy,” I responded. They relented.

Days Four-Six: Disaster

Wed 4:15am I woke up from a light sleep with the dawning realization that I was probably not going to get home the next day as scheduled. A Nor’easter was on track to slam into NYC, ultimately dropping 11.5 inches of flight-canceling hell on Central Park.

But I was still committed to the experiment.

How a trip goes from 5 to 7 days
How a trip goes from 5 to 7 days

When I got into the office, I monitored useful travel websites like FlightAware for airport conditions and airline cancelations and ExpertFlyer (subscription) for available seats and routings, called Alaska Airlines to rebook my ticket (thankfully, I acted early before the flight was officially cancelled and snagged a seat two days after my original return). I used the NJ Transit app to buy a return train ticket, knowing that it would be good for a year or so after my purchase unless I activated it beforehand.

I signed up for NJ Transit and MTA email alerts for updates on which subways and trains were delayed or canceled.

Thu 8:07am Stuck in the hotel because the office is closed, I charged everything. I listened to WNYC through its smartphone app for snowstorm updates. I ventured out to take many digital photos of snow with my phone – which, naturally, I Tweeted and posted on Facebook.

But the extended stay meant bills I had sitting at home weren’t getting paid. So I logged onto my financial institution’s site to schedule payments for three credit cards and my mother’s gas company bill. After I fired up my secure WiTopia VPN, of course.

Printed copies for my records? Google Cloud Print inside the Chrome browser meant statements would be waiting for me on my home office printer when I returned.

Day Seven: Triumph

TSA paper worth handling
TSA paper worth handling

Sat 8:07am It was threatening to snow again, but I was hopeful the couple of inches it eventually dropped wouldn’t impede the evening flight (it didn’t, though it was delayed an agonizing two hours on the tarmac as we waited for de-icing to occur). I checked out of my hotel, childishly jumping up and shouting, “Yes!” when asked, “Would you like us to email your receipt?”

After scanning my boarding pass, the TSA agent told me that – even though I had the treasured “PreCheck” icon – that the PreCheck lane was closed. He handed me a piece of paper to show the screeners that read, “You are exempt from removing: footwear, headware, and light outer garments.” Not an idiot, I took it.

And I had made it longer than I expected – a full week – without voluntarily touching almost any paper on my business trip. Takeaways?

1) Government loves paper. The only times I had absolutely no option but to touch paper was to meet government requirements. Receipts, so expenses could be documented for my client or me, and subsequently to the IRS. Cardboard, so the next TSA employee at the airport would know that I was exempt from full screening. It turned out I also didn’t touch one other form of government-issued paper: money. All my payments were electronic or credit card.

2) Plastic cards could be replaced by bar codes in secure apps. Everyone from WallyPark to New York’s MTA could learn from Alaska Airlines and NJ Transit: purchasing and tracking loyalty programs and transit tickets does not require a plastic card. Secure apps aren’t the future. They work today. And they mean one less thing for a customer to carry.

3) If I lose my smartphone, I am screwed. Or if the battery dies. That is the single point of failure, and it shouldn’t be underestimated.

As I unpacked, I unzipped the outermost compartment of my briefcase. In it was my original outbound paper boarding pass that I had printed as a backup, looking the same as any other wood pulp travel document on this trip: untouched. It likely would remain that way next trip, too.

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  • WS84

    I hope there was an exclusion granted for personal hygiene?

    • FrankCatalano

      Um, yes, one particular aspect. I did have to purchase additional underwear, but it was because I was stuck in NYC an extra two days. No other reason.

  • clibou

    Losing receipts to do expenses gets me. Save expenses. Wash jeans. Pulp…

    • FrankCatalano

      It’s been suggested that perhaps I should just take photos of my receipts and abandon them (without touching them, which could annoy retailers) and upload the images with my expense reports. Not a bad idea, but since I tend to scan my receipts and submit them as a single PDF, it might require a few extra steps and not be as time-saving as digital should be.

  • David

    Next time you should try Concur® for Mobile, write a review and see how it works for you? I have heard good things. There website says:

    Concur® for Mobile complements our Web based solution, allowing you to manage anything expense and or travel related, wherever you are. From booking and managing itineraries to capturing receipts and submitting expense reports, your smartphone can do it all with Concur:

    • FrankCatalano

      The Concur app is not standalone (at least for Android), requiring an existing Concur installation and account. And as a one-person business with multiple clients, I use Quicken Home & Business for invoicing and expense. I’ll have to see if I can find something that integrates similarly with it.

  • Mithun Dhar

    PS: I am surprised you didn’t use TripIt, its by far one of the most popular Travel Apps out there. And, Concur really takes the pain out of filling and filing an expense report. Happy to give you a demo, if you need one. (Disclosure: I work for Concur

    • FrankCatalano

      Not a fan of TripIt. Tried it a while ago, and it didn’t work well for the way I travel (I don’t need help organizing travel docs). Though I see it integrates with Concur, which is, I suspect, one reason Concur likes it. But thanks.

    • FrankCatalano

      My opinion of TripIt has evolved. Last time I tried TripIt, it was (IIRC) before Concur owned it and it was annoying in its spammy LinkedIn integration. So I stopped using it. After writing this column and seeing your comment, I decided to try it again, both on the web and with the Android app. Much improved experience. It even intelligently parsed auto rental details that were embedded into a PDF attachment from Costco Travel. TripIt is back in my app toolkit and it now holds nine upcoming trips.Thanks for getting me to look at it again.

  • FrankCatalano

    Based on my quick check of Concur’s current website, it appears my one-person consultancy needs are too small for Concur. (And I don’t want to use separate apps for invoicing clients for expenses and fees — going digital should simplify, not complicate). But I appreciate the suggestion.

  • Kish

    Thanks, this post was both hilarious and informative…I found myself wishing for a Vine of your paper avoidance dance with your colleagues. Some friends have suggested Expensify and other expense management apps for the receipts, but so far after only eyeballing them, they seem to be more work than they’re worth. I’ll try some of these in Austin next week, can’t wait to try out Google Cloud Print. Thanks for taking one for the road warrior team!

    • FrankCatalano

      My pleasure, and I’m honored I’ve inspired you to try some of these tips. Just avoid the snow part. I don’t recommend that. Especially in Austin.

      • Kish

        I just checked, we’re both attending SXSWedu, can I buy you a coffee there? Or whatever they drink in Austin? :) We’re mutual friends of David Samuelson, who suggested that we meet sometime. I “starred” you on their social tool if you’re ok with a follow up, thanks!

        • FrankCatalano

          Even though I’m still on the SXSWedu Advisory Board, I’m unable to attend this year due to conflicting speaking engagements at another conference that’s going on simultaneously, sadly. But I hope the tips are as useful for you in Austin as I expect they’ll be for me in Scottsdale at the same time.

          • Kish

            No problem, I’m sure we’ll cross paths at some other edtech thing. And yes, looking forward to road testing some of these! Thanks again.

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