Freelancing in 2025

Honest reflections you won’t find in an AD…

Ame_data analyst

Apr 22, 2025

A few months ago, I got a message from a reader on Substack.

“Hey Amy, I saw your LinkedIn. You freelance, right? I just got laid off. Is freelancing worth trying in 2025?”

I wanted to quickly say, “YES, you absolutely should...”

I knew what I wanted to say. But I also knew what she wanted to hear. And those were different things.

For years, freelancing has taken a seat in the corporate ecosystem. There are freelancers in every sector you can imagine.

Art, ghostwriting, e-commerce, software programming, web development, business/data analytics, business automation, setting up an e-commerce store, and even helping students with homework and quick assignments.

Freelancing has also become a battlefield, and you WILL need armor.

There are stories about people making >$10k a month, and many of them are true. But those are not the only truths; here are other things you won’t see in ads or social media posts:

1. Freelancing is tough business

Before you decide to get into freelancing, know this:

FREELANCING IS TOUGH, FREELANCING IS HARD, FREELANCING IS CHALLENGING.

If these words sound harsh or discouraging, it’s because they’re facts, and more importantly, they’re my experience.

Your technical skills and knowledge are not the problem here. You might be outstanding at what you do, but landing a gig as a contractor is not a walk in the park.

The first and probably the most challenging thing with freelancing is landing a gig. Not a good gig, just any gig.

You’ve signed up, set up your bio and profile, posted some portfolio projects, and even created a specialized account. Upwork gives you your first 10 connects, and you start submitting proposals.

You begin with jobs you think you’re good at, and when nobody hires you, you start applying for jobs that have absolutely nothing to do with why you joined freelancing in the first place.

2. Rejected proposals and radio silence

This will be your first reality check. You know how you have applied for so many jobs and were denied by all recruiters?

Freelancing online is worse. One of the most exhausting things about freelancing is that you don’t get “rejection”. It’s radio silence and gone “connects” or whatever you use to bid for gigs online, in this case, Upwork.

You submit proposals, 5, 10, sometimes more. I’ve submitted 13 proposals in one month.

Think of proposals as your cover letter. You are telling the client why they should hire you, what you’ve done that’s relevant to their projects, and how you will tackle their problems and your tasks. You attach similar projects you have done, link your best projects, and your certifications.

You’ve heard it before: “personalize all your resumés to fit the job description.”

You submit and wait and wait and wait. No reply, no views. No response.

Eventually, you click on the job again and see that another person was hired, so you ask yourself:

“What did I miss?”

“Am I not good enough?”

“Was the other freelancer better?”

Was your proposal even opened. If it wasn’t, maybe you’ll get your connects refunded, but if it was viewed, those connects are gone.

You refresh your feed, try again, and still get nothing back.

Then you see that 50+ proposals were submitted to that same job, and while the job asked for 10 connects, those who can afford it bid 50–100 connects to stay in the top “4” submitted proposals for visibility.

You realized you didn’t even stand a chance with 10 connects. So, what do you do? You start “buying” more connects because now, it’s a competition, and you have to apply to as many jobs as possible and bid higher than other freelancers. freelancing is a competition.

The problem with that is you’re not making enough money to start splurging on connects. YOU JUST WANT TO LAND A GIG.

After a while, it starts to affect your confidence. Not because you’re not good, but “you’re pouring energy into a space that doesn’t respond”.

That makes freelancing slightly different from job hunting: the volume of silence is higher, and the lack of feedback is louder. No one prepares you for that, but you must learn to keep showing up anyway.

3. Reviews

Upwork thrives on reviews, feedback, and star ratings. You want to satisfy your client so that if they leave a review, it must be between 4.5 and 5 stars.

Anything lower, your job success score (JSS) drops from 100%, and once it gets below 80%, your profile gets deprioritized and less visible.

Potential clients may not want to work with you because of these reviews.

The problem with this is, Upwork wanted the reviews and rating system to be transparent, and because of this, you can’t see and don’t know what your client rates you UNTIL you rate them.

So, you may rate a contractor 5 stars and receive 4.2, maybe because you didn’t communicate enough or for any other reason.

It’s supposed to be an honest reflection of how the contract went and, except you “explicitly” discuss ratings with your client, which, in my opinion, feels awkward and patronizing; you can’t know what you’re rated or if the client was dissatisfied with a part or all part of your work.

Unfortunately, one mediocre review can change your profile.

4. Payment

when you start, expect to be seriously underpaid. Some freelancers earn $70-$200 per hour from the start. They either join on referrals, work through an agency, or do very niche projects, and clients are willing to pay a premium price or are simply lucky.

They are all hardworking, and I acknowledge that, but any active freelancer, especially on Upwork, is hardworking.

For the rest of us, it’s different. Your first few jobs as a data analyst or freelancer will be low, $25 here, $70 there.

You’re doing this to build your profile and get reviews. Remember, you’re starting and trying to secure some jobs to boost your profile or to show that you’re open to jobs.

If you expect to charge your dream rate from day one, you will quit early.

5. Upwork is brutally competitive

People quickly say, “Upwork is a scam,” when they don’t get results. I’ve been there. I’ve thought the same.

But Upwork is a business. It prioritizes freelancers who bring the most value, engagement, and money.

That’s why high-earning freelancers are more visible. That’s why connects are expensive, and that’s why it sometimes feels like a casino. You’re playing your best cards and still not winning.

It’s easy to say, “If you approach it with a good strategy, good profile, targeted proposals, and niche expertise, you’ll get results.”

This may not always be the case, and success isn’t guaranteed. And, if you treat it like a lottery, you’ll be disappointed when you keep applying, and there’s no hire.

Should you freelance in 2025?

Like a good freelancer said, “Think Retail — Not isolated freelancer” — David S (Upwork)

If you’re willing to:

Get rejected often
Work below your value (at first)
Pitch yourself again and again
Deal with silence and ghosting
Manage your own time, money, and mental health
be uncomfortable, and keep at it for a long period,

Then, freelancing may be the one for you.

In 2025, freelancing should not be a backup plan, or you will be highly disappointed. It’s unpredictable and sometimes very demoralizing. You’ll question your worth and doubt your skills sometimes.

And some months, you’ll earn nothing.

But you may also gain something most jobs can’t give you: ownership, autonomy, and some freedom.

Freelancing will teach you a few things:

1. How to sell yourself: Since you’re constantly reviewing your profile and writing proposals, eventually, you have the right words and templates to sell yourself and create a winnable pitch deck. You learn to talk about your work with confidence.

2. How to solve real problems: Having a good portfolio has always been a proven way to showcase your skills, but nothing beats real client work. They show future clients that you have done the job before and can do it again.

3. You’ll figure out how to survive without a boss: You become your own boss, both a blessing and a curse. Over time, you learn to manage yourself like a boss and serve others like an employee. You also learn how to manage expectations.

And one day, maybe, you’ll look back and realize this chaotic thing called freelancing made you more capable, resilient, and self-aware.

So, to answer the question, YES. You should freelance in 2025. But only if you’re willing to show up like it’s a business. Because that’s what it is.

And NO, you shouldn’t freelance in 2025 if it’s your backup plan because freelancing is tough, and it will take time before you hit the kind of success you see others talk about.