digitalLIFT

For many of the learners we support, getting online is a powerful milestone. It creates access to jobs, education, healthcare, services, and connection. But digital inclusion is not just about helping people connect to the internet. It is also about helping them develop healthy, informed, and responsible relationships with technology once they are online. That is why conversations about social media use, misinformation, and digital well-being are becoming more important to digital literacy work.

We all love celebrating wins—happy clients, shiny metrics, and the occasional standing ovation. But the best lessons sometimes come from spectacular flops. After 18 years as a nonprofit, DigitalLIFT has had its share of “oops” moments, and here are five fabulous failures:

1. Not Listening to the Community: We rolled out programs we thought people needed, only to hear crickets. Turns out, our brilliant ideas weren’t actually what the community wanted. 

County leaders across the country are investing historic dollars into broadband infrastructure. We talk about first mile, middle mile, and last mile. We map fiber routes. We track deployment. We measure speeds. And all of that matters, but there’s a quiet truth underneath the infrastructure conversation – the last mile does not reach a person. If we are serious about digital equity, we have to go one step further. We call that step the “final inch.” We talk about miles, but digital equity is measured in inches.

When digital systems go live, the cost doesn’t disappear; it shifts. A housing application that once required paper forms now requires an email address, scanned documents, stable internet, password management, and basic troubleshooting skills. If an applicant doesn’t have those things, the burden doesn’t fall back on the agency that built the platform; it falls on frontline social service workers. Case managers become tech support, navigators become digital literacy instructors, and program staff spend precious appointment time resetting passwords and explaining upload buttons.

As hundreds of thousands of us prepare to walk down Martin Luther King Drive for one of the largest marches in the nation, we carry with us Dr. King’s vision of a Beloved Community. In San Antonio, DreamWeek reminds us that this dream is not just about where we walk, but how we care for one another in every space we inhabit, including digital ones. The theme for DreamWeek 2026 is “Revelations: Unlocking Our Full Potential.” As a Digital Navigator, I believe that unlocking our potential begins with feeling secure.

The internet is an incredible tool: information at your fingertips, communities forming across continents, and endless opportunities to learn and connect. But it’s also a place where truth and fiction can look exactly the same. Scams, misinformation, deepfakes, and AI-generated content are on the rise, and the stakes have never been higher. If we aren’t careful, we can easily share something false, mislead others, or fall victim ourselves. The reality is that nothing online should be trusted at face value.

The digital world just became less optional. As of September 30, 2025, the federal government has stopped issuing paper checks for benefits like Social Security. Payments are now deposited directly into bank accounts or onto prepaid debit cards—methods that require not only access to financial services but also the ability to navigate online systems. This is just the latest in a series of policy changes that assume universal internet access. From healthcare enrollment to unemployment benefits, tax filing to student loan repayment, more essential services are now available only online.

In an increasingly connected world, the ability to participate in civic life often depends on reliable internet access and digital skills. From voting to community organizing, digital inclusion—ensuring everyone has the technology, connectivity, and skills they need—is essential for building a more inclusive and engaged society.