As most individuals become digital media users, many struggle to find balance in such use. This study adds to emergent research on how digital disconnection experiences reflect on well-being (Nguyen et al., 2021; Radtke et al., 2022; Vanden Abeele, 2021) by focusing on motivations and strategies to disconnect from digital media, as well as on outcomes for well-being. We set out to understand teenagers who have voluntarily chosen to disconnect in the post-lockdown period in 2021. Our qualitative study included 20 participants from Portugal between 15 and 18 years old. Among those who consciously chose to disconnect from digital media, motivations arose from realizing that digital media was not bringing enough benefits for the amount of time that they took from users. Specific forms of digital media stood out as particularly problematic for young people, especially social media, but also videogames and pornography. This realization seems to be strongly influenced by the media and is evident in the vocabulary and associations used by our respondents. Social pressure is felt both as causing anxiety when they are connected and when they are disconnected through fear of missing out. However, the group provides support when they engage in a progressive disconnection together. Radical disconnection is rare, especially during the pandemic, and can appear as a solution to a dramatic problem in young people’s lives, but it can also be reverted. More often, participants attempted to self-regulate their use of digital when they acknowledged the advantages of those services as well as their drawbacks. This is not a linear process but rather filled with attempts and reversals as unexpected feelings such as boredom arise. When young people grow different leisure and social habits, they experience positive outcomes of disconnecting from the digital.