What Could Have Been: Lessons and Regrets from My First Job

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Last night, I was reading a story online that mentioned the woman that was the CEO of the first organization in which I worked after college. As I fell down a rabbit hole of reading associated articles, it mentioned her successor, the woman that had been the VP of Finance when I was there – in other words, my boss’s boss.

The more I read, the more I found myself thinking about that job and that organization.

I started in late 2002 and, around the same time that I began, about ten to fifteen others also came on board in various roles all over the building. All of us were similar: under the age of 25, relatively well-educated, eager, and enthusiastic. For an established nonprofit that had been doing the same things for years, to have such a group of young people – especially of all races and ethnicities – was more than a rarity. It was a coup.

Over the next decade, countless ink would be spilled about millennials working and living in cities and how organizations are always trying to court them and bending over backwards to make them happy. But here we were, one of the first waves, and it had happened organically. The combination of energy level and idealism in twenty-somethings is pretty remarkable. We’d all work a ten or twelve hour day and then go out until the early hours of the morning and get up and do it all over again.

We could feel it. There was a palpable sense of a sea change.

We felt like we were the future leaders of the place.

We were so naïve.


Within four years, all of us were gone.

We worked on different floors, for different people, within different departments, but it wasn’t long before we all realized that our futures were elsewhere.

There was not one specific instance that led us to this decision, but rather just the vibe we felt and the resistance we encountered. An organization’s culture permeates everyone and everything and this one was staid and unimaginative. It was old, bland, and predictable. Everyone knew it and everyone agreed that the culture needed to be overhauled. However, the best way to do that was not so unanimous.

Some of us wanted it to be more relaxed. We wanted to make it more like a startup with jeans and kicks. Those in the corner offices wanted it to be more professional. They wanted to make it more like a Fortune 500 corporation with business casual at least. They got their way (of course) and instead of incorporating new ideas and different approaches, they rejected them even more, falling upon the clichés of “best practices” and “acting as if.”

It is never wise to discourage youthful idealism,” Stephen Kinzer once said, but that’s exactly what happened.

I wasn’t raised in the Not-My-Child Generation. When I was kid, everyone didn’t get a participation trophy. I was cut from teams and left out of cliques. I knew I was new and young. I didn’t make demands. I had worked in manual labor and the service sector. I knew what was what.

We didn’t want to take over. We just wanted to have input. We genuinely wanted to help. Instead, we were blocked at every turn:

We appreciate your taking the initiative, but we’ve done this way for years and we see no reason to change.

That’s not a bad idea, but we would prefer that you allow senior leadership to come up with the vision and then you can execute it.

You’re too young.

You’re too inexperienced.

You don’t know anything.

Maybe one day you’ll learn.

Just keep working hard.

Stop asking questions.

We’re going to do it our way.

Naturally, this led to frustration and disillusionment.

Sure, there are things I wish I had done differently. I wasn’t as professional as I should have been. I know that. My ego (and my mouth) were out of control, particularly at the beginning. While I respected the hierarchy, I don’t think I fully appreciated it. I didn’t know how things really worked, particularly from an optics standpoint. After working in multiple places of varying size and success – from healthcare facilities that lose money on a yearly basis to corporations that generate hundreds of billions in revenue annually – over the past ten years, I’ve learned things that would not only have helped me back then, but have also changed my perception of what they were trying to accomplish.

Still, they could have met us halfway. They didn’t have to give us the Heisman and push us away to the point that we jumped ship. They could have given us projects or even indulged our ideas to the point of explaining why they wouldn’t work. Instead, they treated us like unwanted stepchildren that that they tolerated. They didn’t even pretend to care.

This wasn’t bothersome from a personal standpoint – business is business – but we truly felt we could have improved the place and, as a result, improved people’s lives and the city. This was one of the biggest nonprofits and fundraising enterprises around, so any improvement would have been a win for the entire community. We were committed and determined.

We were the future.

They didn’t see it that way.

True visionaries update and change their vision based on reality and circumstances. Plans can change. People can adapt. Driving towards your goals while ignoring everything else isn’t vision, it’s tunnel vision. There’s a big difference.

Of course, they got their way, ultimately resulting in a completely revamped organizational structural and eventual merger with seven other chapters, so it certainly worked out for them. It worked out for us too, but reading those articles, I couldn’t help but dwell on the ideas and dreams we had, the plans we made, and, ultimately, how almost none of them came to fruition.

Maybe that’s for the best. Maybe it’s not. But it would’ve been nice to have at least had a chance to try.


Christopher Pierznik is the author of eight books, all of which are available in paperback and Kindle. His work has appeared on XXL, Cuepoint, Business Insider, The Cauldron, Medium, and many more. Subscribe to his monthly reading review newsletter or follow him on Facebook or Twitter.

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