My Digital Vacation

I’ve been in the advertising and marketing business since the late 1980’s. In that time, I’ve seen a sea change in the marketing landscape, going from when the newspaper and radio dominated the local advertising scene, to the digital world of today. This hasn’t only impacted my professional life, where I’ve had to be sure to keep the agency on track with the changing times, making sure our digital creative and media buying skills are constantly evolving. But, it has also had a tremendous impact on my personal life.

Case in point is a recent short vacation I took to Chicago. Now, anyone who has ever driven in Chicago knows that it’s a nightmare of traffic jams and road construction. People may disagree with me, but I say Chicago has the worst traffic in the country. At least in LA the weather is usually nice when you’re parked on the freeway! I was determined to not have to deal with the hassle of both driving and parking in Chicago for my trip.

So, first I booked a roundtrip train ticket from Milwaukee to Chicago on the Amtrak Hiawatha using the AMTRAK mobile app on my iPhone. With the electronic ticket on my phone, I didn’t have to worry about printing anything out.

Next, I found an inexpensive weekend rate parking space right in the downtown Milwaukee Amtrak Station parking lot using the SPOT HERO app.

90 traffic-free minutes later as the Hiawatha rolled into Chicago Union Station, I got on the UBER app and ordered an Uber Black ride to pick me and my over-packed suitcase up to take us to the 5-bedroom apartment a block from Wrigley Field that I booked using the AIRBNB app months earlier.

Once I arrived, I was excited to learn more about the food and drink establishments in the neighborhood, so I got on the YELP app, identified a few that looked promising, and immediately ordered a meal to go since I hadn’t had lunch yet.

Everything went off without a hitch and I was feeling really proud of myself. Here I was, someone who had recently aged out of the prime demo that advertisers drool after, acting like a 27-year old in his targeted demographic prime! Ah, but nothing is perfect, even in this brave, new digital world. Upon my return to Milwaukee on Sunday, I found a good, old-fashioned paper parking ticket stuck behind my front left windshield wiper. It seems that SPOT HERO doesn’t really have access to the Amtrak Station parking lot despite its representations! Now, I have to figure out how to get them to credit me back the $27 ticket cost. Maybe I’ll write them a letter….



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