It had to be there—listening to the buzzing discord of a 56k modem firing up in my teenage bedroom, what it took to send exactly one Juno email—that the true potential of the internet first dawned on me.

Before Facebook and Web 2.0, before the dotcom bubble and subsequent crash, before The Cluetrain Manifesto where hyperlinks subvert hierarchy, it was just me: a lonely, anxious teenager trying desperately to reach out and connect with others like me.

The hefty Packard Bell desktop computer, gifted by my estranged father, held special significance for its ability to transcend space and time, providing me access to the world beyond the homogenous culture I grew up in. There was magic in those first breathless A/S/Ls—and a bit of hidden danger. Maybe that’s why it was so appealing.

How digital was being positioned as a utopia to the world

Years before my own personal digital revolution, “The Conscience of a Hacker” had already influenced a generation of soon-to-be Silicon Valley billionaires with its forecast of a forthcoming digital utopia: a place “without skin color, without nationality, without religious bias.”

You can draw a straight line between The Mentor’s curiosity-driven exploration of a world without borders and Mark Zuckerberg’s accidentally prophetic mantra of “move fast and break things.”

Breaking down the world’s walls was supposed to be an incredibly democratizing force; technology used in the service of expanding our borders was meant to to keep the world free.

But there’s been both good and bad.

In subsequent years, flashes of that potential have been evident, but so have the unintended consequences of mass connectivity. While Twitter powered the Arab Spring, it also gave a platform to authoritarianism. Cell phone videos shined light into dark places in American society, where power, fear, and racial bias collide. But for every Black Lives Matter movement, we’ve seen hate groups with no traditional infrastructure using the internet to prop up our worst ideas. We no longer talk about freedom because of technology, we ask for freedom from technology.

My digi-piphany

A few tortured years and a few thousand miles into my 20s, a “digi-piphany” came to me in an MBA marketing class.

I’d recently given up on a theological seminary degree to learn how business works, believing the push/pull of economics had the potential to tangibly improve people’s lives. I wanted to do good in some way and was especially interested in the persuasive power of communications.

We were spending days discussing mass media communications while I was having one-on-one conversations with employees at my favorite Fortune 500 companies. I found the dissonance fascinating. By then inspiration was coming to me in 140 characters, rather than mindspace between waiting for dial-up to land.

I was especially transfixed by the changing power dynamics between groups of people and traditional institutions of power. It was the early days of social media, when interconnected relationships seemed to have infinite potential. While studying product, price, place, and promotion—the old-world pillars of marketing—I was participating in a defined shift in human exchange. I steered my career toward helping companies navigate the new waters.

In retrospect, the intersection of capitalism, network effects, and technology was always going to have problems. But back then, as I joined the chorus of consultants saying every company needed to have a Facebook page and Twitter account, the road ahead seemed clear. It could only be a good thing that companies could hear directly from their customers about what they wanted. The changing power dynamics could work in both parties’ favors, creating a mutual value exchange: the customer being heard, the company being informed.

But attention economy leaned in favor of the business. So I moved back toward issues that mattered. And saw the digital flaws were a reflection of society.

A tragedy of the commons

As it turned out, the business model of the Attention Economy alone doesn’t encourage a healthy public discourse. Platforms raced to optimize what we wanted to engage with over what we needed to hear. The consultant chorus moved a slew of reach-and-repeat marketers to the platforms, lining the pockets of tech entrepreneurs and Wall Street investors alike. And social media became less a way to be heard and more a way to complain. A tragedy of the commons as applied to the largest “commons” in human history.

Seeking the elusive intersection of digital transformation and social impact eventually led me to political advocacy and progressive activism: connecting thousands of volunteers for important issues, shaking hands with President Obama and having him express gratitude for applying creative energy on Something That Matters.

It was a surreal experience, but working on issues like racial and LGBT equity was eye opening in other ways. As I worked directly with marginalized communities, listening to their experiences in public places, online or offline, I realized that breaking down walls didn’t mean creating safety; free speech for all will almost always mean hate speech directed at some. Connecting the world meant nothing if your world was already full of oppression.

As a digital strategist today, and someone trying to wrap his head around his own privilege, I often wrestle with the environment I may have unintentionally helped to create. Technologist Anil Dash has talked about “Tech’s Moral Reckoning,” claiming that most entrepreneurs are so worried about what happens if their product fails, they don’t think about what will happen if it succeeds.

Those of us who make our living within the digital world need to reckon with the same implications. How do we as strategists not just compete for attention? How do we contribute to the marketplace ideas instead of making the tragedy of the commons worse?

Maybe it’s Obama-embedded pragmatic optimism, but I’m still hopeful about the future. I still believe in the transformative power of “digital”: the implications for the application of rapidly evolving technology, interconnected data, and networks of relationships have more disruptive potential than most business leaders are willing to accept. But I no longer believe that transformative power is by its very nature good.

Some tech leaders are beginning to wrestle with the unintended consequences of their platforms—even as some question Silicon Valley’s ability to fix itself.

Others are thinking ahead to tomorrow, setting new standards for equality and non-discrimination in machine learning systems. Technological advances are still happening, but we’re waking up to how involved we have to be in making sure they have the right kinds of effects on society. We’re waking up to the idea that disruption is coming, but we’ll get the kind of disruption we’re willing to fight for.