Freelancing in 2025: Learning, AI, and the Price of Doing It Right

TWP Office Hours Recap

November’s Office Hours started with a simple question – how do you even start freelancing when you’re still learning?

By the end, we’d talked about AI, the death of cheap clients, and why Fiverr can make you broke faster than it can make you famous.

That’s what I love about these sessions. They always start with a “how do I get started” and end up revealing the real problem – how do I stay consistent once I do.

The Learning Phase Isn’t a Waiting Room

Person asked what most people think but rarely say out loud:

“How should I approach freelancing when I’m still in the learning phase?”

You don’t “wait” till you’re ready. You use freelancing to get ready – but with intention.
It’s not about jumping into random gigs to “get experience.” It’s about building context through controlled chaos.

Freelancing isn’t a shortcut. It’s a discipline.
And if you treat it like a side hustle before treating it like a skill, you’ll stay stuck in the same cycle – building half portfolios, half habits, and no consistency.

I said it in the Upwork Masterclass before, and it still holds true: freelancing is harder than a regular job, not because of the work – but because of the structure. You’re your own HR, your own manager, your own marketing team.

If you’re still learning, focus less on “how do I get clients” and more on “how do I prove to myself that I can deliver?” That shift in mindset changes everything.

AI Isn’t Coming for Your Job – It’s Coming for Your Laziness

Another question came up that I hear every week now:

“How do I keep up with AI when it’s replacing junior-level work?”

Here’s the deal. AI didn’t kill junior jobs. It killed shallow work.

If your skill can be replaced by a script, it will be. But if you understand why that script exists and how to use it better than the next person, you’ve already leveled up.

AI is the new intern – tireless, cheap, and slightly stupid. The smart freelancers are the ones who know how to train it.

Don’t run from it. Learn it. Use it. Let it make you faster so you can focus on what actually pays – thinking.

Cheap Clients Are a Scam Dressed as “Opportunity”

The harsh truth: clients who want to pay you pennies don’t just waste your time – they ruin your trajectory.

You can’t build a premium career on discount habits.

Once you normalize undercharging, it seeps into everything – your confidence, your outreach, even your tone when you pitch someone new. Suddenly, $10 feels like your ceiling because you trained yourself to think it’s “good enough.”

Freelancing isn’t about making a few dollars online. It’s about building leverage.
And leverage comes from working with people who respect what you do – not just what you cost.

As I said in the session: Upwork isn’t free-to-play anymore. You might need to spend $200–300 just to land your first job. Painful, yes. But that barrier filters out the unserious ones.

Cheap clients are easy to find. Good clients are earned.

Fiverr vs Upwork – Pick the Game You Want to Play

Fiverr is great if you sell products. Upwork is better if you sell process.

On Fiverr, people buy you like a menu item. “I’ll take the logo design with extra revisions, please”.
On Upwork, they hire you like a partner – if you can prove you’re one.

The problem is, most people don’t decide what they want to be before they pick the platform.
If your work is transactional, go to Fiverr.
If your work involves strategy, conversation, or ongoing delivery – go to Upwork.

The difference isn’t the website. It’s the mindset. Fiverr rewards volume. Upwork rewards discipline.

Both can work – just don’t mix them. You can’t play both games at once.

Should You Bring Clients to Upwork?

Someone asked if they should bring a direct client onto Upwork so the client could hire them through the platform.

The answer is: it depends.
If it’s a long-term client you trust – yes, it helps you build reputation, reviews, and JSS.
If it’s a one-off or someone who’s already hesitant about fees, don’t force it.

Think of Upwork as your public record. Protect it like your résumé.

Your Portfolio Isn’t a Gallery – It’s a Sales Pitch

“Just making a portfolio isn’t enough anymore.”

That line came up in the session and hit home for a lot of people.

Your portfolio is not an art wall – it’s a proof of process.
Clients don’t care about what you made. They care about how you think.

If you can explain your work clearly – why it mattered, what the problem was, what changed – you’ve already separated yourself from 90% of the noise.

And yes, record a video. No one trusts faceless profiles anymore. A 90-second video builds more connection than five paragraphs ever could.

I’ve written about this before in Casing Up Your Portfolio – Don’t Show, Do Tell: show the story behind your work, not just the screenshots.

What It All Comes Down To

Freelancing isn’t just skillwork anymore. It’s brand work. It’s mindset work. It’s self-awareness work.

You can’t copy-paste your way to success here – you build it, tweak it, break it, and rebuild it again.

AI will keep getting better. Clients will keep getting pickier. Platforms will keep getting pricier.
But none of that matters if you keep getting smarter.

You don’t need to win every gig.
You just need to win the right ones.

If you missed the session, join our next Office Hours on The Wandering Pro Discord. Bring your questions, your doubts, your drafts – that’s what we’re here for.

And if you want to go deeper into the Upwork side of freelancing, start with the Upwork Masterclass on SK NEXUS. It’s free, honest, and built for people who actually want to do this the right way.

Because freelancing isn’t luck.
It’s clarity, consistency, and a little bit of chaos – managed well.

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