Could Gamifying Your Work Week Make You Better at What You Do?

The hosts of Squiggly Careers, Helen and Sarah, dive into the controversial idea of gamifying your work week—not as a productivity hack, but as a psychological experiment in motivation and self-awareness. Helen, who lives a deeply gamified life (tracking sleep, exercise streaks, and diet), sees gamification as a tool for autonomy and progress. Sarah, in contrast, starts from zero—she doesn’t track anything, doesn’t use streaks, and finds joy in activities without external rewards. Their debate reveals a core tension: gamification can fuel engagement by tapping into self-determination theory (autonomy, competence, connection), but it risks turning meaningful habits into performance theater—like the time Helen nearly rode a Peloton drunk to unlock a badge. The episode doesn’t push gamification as a universal fix. Instead, it reframes it as a personal design challenge: if you’re not motivated by points or badges, what would make you more capable? The answer isn’t a game—it’s intentionality. The real takeaway? Focus on consistency in what matters, not on collecting digital trophies. The episode ends not with a verdict, but with a provocation: Are you more Helen, the gamifier, or more Sarah, the skeptic who just wants to do the right thing without a scoreboard?