Revisiting the “Oregon Trail Generation”



One year later, we revisit the Oregon Trail Generation to examine how this group of individuals is firmly entrenched in the work place, and their dispositions and abilities are impacting businesses in a big way.


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The most popular article to ever be published on Social Media Week discussed the “Oregon Trail Generation” – those persons born in the late 70’s and early 80’s who were on the leading edge of technology’s changes to society.

In many ways, they experienced most of the positive aspects of these changes while managing to avoid the damaging side effects (over sharing on social media, the digital rumor mill, etc.) Now, this generation is firmly entrenched in the work place and their dispositions and abilities are impacting businesses in a big way.

Life on the Trail

“Trailers” are nearing or have completed the first third of their professional careers. After leaving college, they landed decent starter jobs before the financial crisis and many retained them after the fallout. This provided them with stable job experience, giving them a solid footing on which to build a career.

Leveraging their inherent talent for technology in conjunction, with this experience, has led them into low and mid-level management roles within their organization. Demographically speaking, they probably are married and have started families (but as statistics have shown, they’ve done so at a much later age than previous generations.)

You are now at the river crossing, would you like to look around?

This generation is now performing an essential function in the workplace that goes unnoticed – intergenerational mediator.

“Trailers” are now found managing true Millennials, a generation that has been on the receiving end of every negative stereotype that older folks can throw at them. But, Millennials managers see their potential and are working to harness it. Trailers understand and share true Millennials enthusiasm and their world view. This gives Trailers the unique ability to inspire Millennials to produce and work hard while fighting for the beliefs and work life balance that Millennials hold so dear.

Meanwhile, slightly up the management chain, Generation-X looks on in bewilderment, failing to understand how anything is actually getting produced, but appreciating the forward momentum. The Trailers are making them look good to the apex managers.

At the top of the chain sit the Boomers in their upper management and C-suite jobs. They don’t care how the sausage is made, just that the job is done. Oh, and when the job is complete, don’t come looking for a pat on the back and a reward.

As one Boomer Boss once told me “you know you’re doing a good job when you get to keep it and come back tomorrow.” Thus, the task of making the Millennials feel good is pushed back down the chain, through Generation X to the Trailer, who knows how important that pat on the back is, providing it the Millennials.

Congratulations, you have made it to Oregon!

As Boomers exit the workforce, Gen-X, Trailers and Millennials will begin their slow advance up the seniority ladder. Trailers are in a position that will continue to be necessary for business success – they can take the ideas and needs of their Gen-X superiors and focus the attention of the Millennial to get the job done.

Trailers are set to become some of the most important managers in history, as they “talk the talk” of the generations that come before, but “walk the walk” of the generation that has come after.

The real danger for the Trailers is “breaking a wagon wheel” – getting stuck in the middle so to speak; because they are so good at managing expectations and producing results, they may not be given the opportunity innovate, with senior management instead looking to the big, optimistic ideas of the true Millennials. Only time will tell.

For now, the Oregon Trail generation is a great place. They have become critical to corporate success by fording the river of the intergenerational politics in the workplace. If they can continue to translate the needs of management into the production power of the front line, they will have bright futures ahead of them.

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