Reflections of an Elder Millennial: 20 Years In

I graduated college in 2009. If you’re having trouble remembering nearly 20 years ago, let me paint the picture.

 

It was just after the Great Recession hit. In late 2008, the economy collapsed in a way most of us had never seen before. Layoffs were everywhere. Companies froze hiring. Entire industries, especially those that traditionally welcomed entry-level grads, were suddenly inaccessible. College seniors like me entered a job market that felt practically impossible. 

 

After applying to 50 or more jobs around the country – met with just as many polite “no thank yous” or worse, radio silence – it seemed like the right time to go back to school. In August 2009, I began my Master of Public Administration degree at the College of Charleston, and by June 2010, I landed my first internship at the master’s level. That internship turned into my first job. It was the first of roughly 10 roles I’ve held between then and now, and at this point in my career, I feel like I’ve seen it all.

 

I have experienced toxic workplaces (at least a couple) where management had team members, especially the youngest of us, walking on eggshells. In that first job, a senior manager presented my work to leadership – and gave me 0 credit. When I tried to speak up, I was told to keep quiet. I’ve seen managers uplift and coach and empower, and I’ve experienced hands-off managers who expected the youngest among us to just “figure it out.” I’ve been my own boss at least a few times as well as tried my hand at managing others. If you’ve ever worn every hat in a business, you know it builds a kind of resilience (and resourcefulness) that no formal education could teach.

 

What I’ve learned isn’t revolutionary from the outside – but it is real, and it has been transformational for me.

 

I truly believe that most workplaces want to be supportive. Many fall short. Leadership can be life-giving or soul-crushing. Colleagues can become family or just people who share the same space. And what we need from work evolves, especially when we’ve come of age in the midst of recession, rapid tech advancement, the rise of remote work, and a global pandemic.

 

I share this not to say, “Hey, look at me – what a story!” but because I know I’m not alone. Some version of this path: the starts and stops, the mismatches and the milestones, is familiar to a lot of us. That is, afterall, how this company got its start. It was Kamber’s own experience as a millennial, entering a workforce that didn’t quite match her expectations. When she interviewed thousands of others, especially millennials, she found the same patterns again and again.

 

At the risk of painting with a broad brush stroke, we elder millennials have been in the workforce for nearly 20 years and have:

  • Entered the workforce during economic collapse. 
  • Watched workplace norms shift from in-office 9-to-5s to hybrid and remote work. 
  • Adapted to technology faster than any generation before us, while also remembering a world before smartphones. 
  • Been both labeled “entitled” and tasked with fixing broken systems. 
  • Moved up, moved out, burned out, and (hopefully) built something better.

We’re not new to the workforce anymore. But we still bring a drive to do meaningful work, to be heard, and to make things better than we found them.

So if you’re a millennial reading this (particularly you elder millennials), know this: your story matters. And if you’ve been navigating leadership, career pivots, or workplace friction, you’re not alone. We’ve been shaped by a lot, and we’re not done shaping what comes next. 

Written by: Jade Fountain, Director of Operations

Did you like this week’s post? Then you might like these posts below.

Future-Proof Your Workforce: The Benefits Gen-Z and Millennials Crave (And Why They Might Surprise You)

Transforming Talent Retention: The Benefits and Wellness Report

How to Get Your Team to Show Up to Work On Time

 

What’s Next?

If your team is navigating generational friction, stalled performance, or culture misalignment—it’s time to take action.

At GPS, we help organizations unlock clarity, communication, and performance across every generation. And we don’t just talk about results—we deliver them in 90 days or less.

🎯 Let’s build a workplace that works for everyone.
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