When Passion Becomes Work: Does Everything You Love Need to Make Money?

When Passion Becomes Work: Does Everything You Love Need to Make Money?

Ever wondered what it takes to enjoy what you love without turning it into a side hustle? This Encouragementology episode with professional life and recovery coach Kendell Boysen looks at the pressure to monetise passion and asks whether that pressure quietly steals the joy out of it. Through her own stories, Kendell shares how a simple craft hobby shifted the moment it became a booth business.

Instead of asking, "What do I feel like making?" she found herself wondering, "What will sell?" The same thing happened with Senior Connect, a support group she facilitates for older adults. When she tried to turn it into a paid programme, she realised, as her husband pointed out, that the real magic was in the personal connections she already had with the group.

Kendell brings in psychological research too, explaining intrinsic versus extrinsic motivation and how external rewards can dampen natural enjoyment. She also talks about different ways of relating to work—as a job, a career, or a calling—and reminds you that having a steady job and a rich life outside of it is perfectly valid.

You’ll hear references to Cal Newport’s idea that passion can grow over time as you build skills, plus a gentle challenge to stop asking your career to meet every emotional, financial and spiritual need. Instead, Kendell suggests sorting your life into what supports you, what energises you, and what fulfils you—and letting different activities sit in different boxes.

With a reflective journaling companion mentioned in the show notes and a closing challenge to question whether your hobbies really need to "become something more", this episode is ideal if you’re in recovery from overworking, perfectionism or simply feeling guilty for enjoying unpaid joy. Could it be that "sometimes joy is reason enough" for you too?