Freelancing sounds like the dream: no boss, flexible schedule, working in your pajamas if you feel like it. But beyond the Instagram-worthy laptop-on-a-beach aesthetic, there are struggles we rarely talk about—ones that make this career path a rollercoaster of highs and nerve-wracking lows.
Convincing Others That Freelancing is a Legit Career
“So when are you getting a real job?” If you freelance, you’ve probably heard some version of this question more times than you can count. For some reason, the idea of working outside of a traditional 9-to-5 still baffles certain people, especially family members who equate stability with a steady paycheck. The reality? Freelancers work hard—often harder—juggling multiple clients, chasing down payments, and continuously marketing themselves just to stay afloat.
The Constant Battle with Impostor Syndrome
There’s no manual for freelancing, no step-by-step guide that guarantees success. Most of us feel like we’re making it up as we go, Googling solutions on the fly and hoping no one notices that we’re figuring things out in real time. Impostor syndrome is real, and even seasoned freelancers sometimes wonder if they actually know what they’re doing. Spoiler alert: Most of the time, we do. We just don’t always feel like it.
The Anxiety of Chasing Payments
Nothing says “adventure” like doing the work, delivering the project, and then…waiting. And waiting. And maybe nudging the client. And then waiting some more. Even with contracts in place, the time between sending an invoice and actually seeing the money hit your account can be a nail-biting experience. Late payments aren’t just inconvenient—they can mean rent stress, bill juggling, and the occasional “oh no, I have $3 in my checking account” moment.
The Dreaded Feast-or-Famine Cycle
One week, you’re drowning in work, barely keeping up with deadlines. The next? Crickets. No new projects. No emails. The silence is deafening, and the uncertainty starts creeping in. “Will I ever work again? Did I just make the worst career choice of my life?” Quiet spells happen to almost every freelancer, and they can be mentally brutal. The key is learning to ride them out without spiraling into a panic. Easier said than done, though.
The Social Media Comparison Trap
Every freelancer has, at some point, looked at someone else’s success and thought, “Why am I not there yet?” Social media makes it worse—endless posts about big wins, lucrative clients, and six-figure incomes can make you feel like you’re lagging behind. What we don’t see are the struggles behind the scenes: the years of hustle, the setbacks, the moments of doubt. The comparison game is dangerous, and the only real way to win is to focus on your own path, no matter how messy or unpredictable it feels.
The Reality Check
Freelancing isn’t easy, and it’s definitely not for everyone. It takes resilience, adaptability, and a willingness to push through the uncertainty. But for those who stick with it, the freedom and flexibility can be worth the struggles. Just don’t be fooled by the highlight reels—every freelancer has their share of unseen battles. And if you’re in the thick of them, you’re not alone.