So… you wanna freelance, huh?

You’ve seen the TikToks of the dreamy latte next to the MacBook, the “work from anywhere” vibes, the designer who somehow manages to travel, eat croissants, and still hit deadlines. Adorable. Now let me tell you what really happens: you’re hunched over your desk at 1:47 a.m. in sweatpants you haven’t washed since the client’s first round of revisions, whispering, “just one more thing,” while wondering if your Venmo will ever see a payment again.

The reality hits harder than your third espresso shot.

When you first start freelancing, it’s all heart and hustle. “I just want to create,” you tell yourself. “I’ll never sell out.” But guess what, you need funds, and funds require clients, and clients require selling yourself. Congratulations, you’re now a marketer, a salesperson, and the sole member of your legal department. You’ve become the very thing you swore to destroy: a walking, talking small business.

And that’s when it happens: the shock.

Asking for money is the first heartbreak.

How do you value yourself when you’re still figuring out who you are as a designer? “Uh, I guess… fifty bucks?” you whisper, terrified that saying a real number might scare them away. Spoiler: it will. And that’s okay. Because the clients who run from fair pricing are the ones who’d text you at 11:43 p.m. asking, “Hey can you just move the logo up a pixel?”

Your job isn’t just to make things pretty. It’s to set boundaries, overcommunicate, and lead. You’re not being paid for your time, no, you’re being paid for your taste, your brain, and your ability to translate someone else’s mess into something coherent. That’s a superpower, not a commodity.

My first client, Mitch, taught me that lesson the hard way. He ran a real estate business and took a chance on me. I was eager, overconfident, and blissfully unaware that “scope creep” wasn’t a compliment. I said yes to everything and delivered nothing close to what either of us envisioned.

The lesson? Honesty > ego. You can fake confidence, but not competence.

If you thought freelancing was just you and your tablet, think again. You’re also:

The sales rep, trying to hook clients like fish while praying they don’t wriggle off the line.

The account manager, juggling timelines and folders like your life depends on it (because it does).

The legal team, rewriting contracts you copied from Google Docs at 3 a.m.

The therapist, listening to clients cry about how their nephew “could probably do it for free.”

And when you’re finally done, they’ll ask, “Can you make it pop?”

No, Karen. I cannot “make it pop.” I’m not Magnitude from Community.

I failed with Mitch. Then I failed with twenty other clients. Some ghosted, some didn’t pay, and some just made me question my life choices. But those failures carved the designer I am today.

Freelancing humbled me. It taught me to stop romanticizing the “creative struggle” and start learning from it. To see freelancing not as rebellion against the system, but as a bootcamp in communication, resilience, and self-worth.

Eventually, I learned to love the fight. I realized I was addicted to it. The chase, the revisions, the moment when you finally crack the idea that’s been haunting you. It’s sick, but it’s honest. I found purpose in the process.

Practice saying no in your daily life, because you’ll need it in business.

Clients will test your boundaries. “Can we hop on a quick call?” (There’s no such thing.) “Can you throw in just one more layout?” (No, Linda. No, I cannot.)

When you set boundaries, you don’t lose clients, you gain respect. Learn how long your work takes. Time yourself. Quantify your value. There’s nothing sexier than a designer who can confidently say, “That’ll be $1,200 and a two-week turnaround.”

If they flinch let them go.

Freelancing either builds you or breaks you, but both outcomes make you stronger. The ones who quit already lost before they began.

The unfortunate truth is you’ll burn out. You’ll question your worth and end up Googling “career change ideas” at 2 a.m. while half-watching The Office reruns. But then you’ll get an email from a client saying, “We loved it.” And suddenly, you’re whole again.

If you crave freedom, chaos, purpose, and the thrill of never knowing if you’ll get paid on time… absolutely freelance.
If you like stability, predictable paychecks, and 401(k) matching… run the other way and don’t look back.

But if you’re one of the weird ones, like me [the ones who’d rather fail their way to freedom than succeed in a cage] then welcome to the club. Grab a drink and a snack, open Illustrator, and get ready to chase the thing that both ruins and saves you:
the love of creating.

written, out loud