Ep 83: The Honest Truth About Freelancing: What You Gain and What You Give Up

Jennifer Fleury
Apr 30, 2026By Jennifer Fleury

https://youtu.be/G6kN94LvNvY

The Freelance Shift
Ep 83: The Honest Truth About Freelancing: What You Gain and What You Give Up http://thefreelance shift

After my sister found a new job and said she hopes to stay there until retirement because she never wants to interview or onboard again, I realized how fundamentally different my freelance life is—I'm always interviewing, constantly onboarding, and working with multiple companies simultaneously. The pros of freelancing are real: I get variety and exposure to different industries that makes me better at my work, I can work for multiple clients without anyone complaining, I have flexibility over my schedule and can take time off when I want, I can refuse projects that don't align with my goals, and I've built long-term client relationships that provide stability without sacrificing autonomy. But the cons are equally real: I'm constantly proving myself, I don't have paid vacation or sick time, nobody's contributing to my retirement, the flexibility can turn into working all the time if I'm not careful, I'm viewed as an outsider at organizations I work with, my income can be unpredictable, and I handle everything from accounting to marketing myself. For now, I'm happy with the freelance model and genuinely enjoy the variety and autonomy, but I'm realistic enough to know that what works for me now might not work forever—maybe in five years I'll crave stability and employer-sponsored benefits, and if that happens, that's okay too, because work doesn't have to be a permanent, unchangeable decision.