How Baby Boomers Transitioned to a Digital World

It’s a Friday afternoon, and I am sitting on a train taking me out of Manhattan into Greenwich, Connecticut. I have ridden this train 50 times, and each ride is the same as the one before. It is 1 hour and 8 minutes long with the seats and aisles packed with passengers. These passengers are between 40 and 60, and they are all wearing tailored suits with designer briefcases. Young and old alike are staring down at a tablet or a smart phone. The car is silent.

There have been ample articles detailing humanity’s addiction to screens. This will not be an addition to that collection. What I find interesting in this scenario, or who rather, are the sea of baby boomers around me steadfastly gazing at screens. In fact, my laptop looks like a 1985 desktop compared to their sleek devices. I may be digitally savvy, but I certainly don’t look it compared to the sea of passengers my parents’ age around me.

I got my first cell phone when I was 12 years old, and I’ve been using computers since well before that. Technology has changed as much as I have in the past 20 years, but like me, it has always been there. I can’t help but to be incredibly curious about life before technology for the gray haired passengers around me. I thank God every day that I did not have to learn how to live, breath and work one way for 30 years, only to have technology come in and turn my world upside down.

The digital revolution was sink or swim for the baby boomer generation as technology became inherent to the functioning of the work force. I consider email as simple as making a peanut butter and jelly… and even simpler than riding a bike. 15 years ago this was a groundbreaking revolution, which is something Millennials can hardly wrap their heads around. Many jobs died with the digital age as new ones were created, and even more were completely transformed. Imagine the role of a “graphic designer.” This job used to be filled with artists (the kind who draw, paint, etc.). Now being a graphic designer requires an in depth knowledge of computer programs like Photoshop and InDesign. A job that required a physical portfolio is now a job that would never be fulfilled by pencil to paper artwork.

The idea of getting a job during a time period where well-crafted introductory emails, LinkedIn profiles, and digital job postings didn’t exist is not only daunting, but seems absolutely impossible. Older generations had to relentlessly research, call, and physically show up with resumes and a personality to impress. If you were blessed with an incredibly likeable personality, this was a huge advantage. In-person interaction was the only thing that was going to get you a job. While a great presence is still important in many industries today, there are just as many job opportunities requiring little to no real-life interpersonal skills. Drive and passion are unteachable, but these two qualities stuck out ten times more in an era where you couldn’t go online and well, teach yourself almost anything if you really wanted to learn.

I can hardly explain why staring around a Metro-North train incited this stream of consciousness. However, as I look around I am dying to know how everyone got their career start- specifically what length they had to go to in order to get through the front door and get their hard-copy (in a world where a soft copy didn’t exist) resumes seen. Nowadays, in-person interviews might not happen until the second or third round of an interview process. Your answers to a job application or a well put together resume can trump unrelenting drive and social skills. Showing up physically at an office you were uninvited to was a commonly used tactic in the 50s, whereas today it could be perceived as creepy or over-eager. Occasionally you will hear someone’s triumphant story about how they used “old” tactics to stand out from the crowd, but there are many cases in which this did not work out for the job-seeker.

Around me on this train are a generation of people who not only successfully fought their way into the white collar workforce (there was no applying online and getting lucky), but they also navigated the transition to a digital world. They grew up in a time period where human to human interaction was how the world functioned, but adapted to a world where technology made even the farthest people and companies a few clicks away. Fifteen years ago as they dealt with a transitioning world, I would not call this generation lucky. Now that they have maneuvered the change, they might just be the last generation to have it all.


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