My Experience with Upwork in 2025

Lets face it. The job market is tough for the typical tech worker in 2025. I’ve been struggling myself to find enough work to pay the bills for about a year now. I figured a quick and easy place to pivot to find short term work to pay the bills would be Upwork or other similar gig working platform.

I’ve spent about a month on the platform, and here’s the good and bad in my experience. I’m sure others have had different experiences, but for me, this is what I got.

The Good

Profile Setup

Technically speaking, the profile setup was easy.

I think the two most complicated things I had was:

• defining my services,

• creating a portfolio.

I still don’t know if I’ve done it right, but I’ve at least started it. Being a generalist that I am, it was pretty difficult to know what I am good at now and what I can be good at, and where I want to focus my attention. Especially when I know I’m getting very close to not being able to pay the bills. I just want to apply for everything in hopes I’ll get something, but I have to be careful, since connects are a paid feature and I have to use them wisely.

For my portfolio, I linked to my website and created a portfolio category I’ve been steadily adding to as jobs come up.

There is a cool feature that I have yet to take advantage of, creating different profiles for different services I can provide. That gives me the ability to break down my offering and share the profile thats best fit for the job I’m applying for.

Job Searches

Upwork does a pretty decent job showing me the jobs I can potentially do based on my skillset. I don’t know if they do curate the list, but I found the list I was presented with had many down my alley I could apply for, although not perfect, was good enough that I wasn't scrolling through hundreds of unrelated jobs. Don’t know if thats a feature or just a basic necessity, but hey, it’s there.

The other benefit is I could filter by US only, which helps me work with jobs that are in my area without having to filter for positions that aren’t based in the US. Since the US based jobs usually have higher wages, I’m sure other countries are taking advantage of this feature if they are presented with the same feature.

Verified

The verification goes both ways. I need to be verified and they need to be verified…. Mostly. It is up to the applicant to confirm that payment is verified or if I’m willing to work with an unverified payer, with no rating, while also spending connects to bid on the job.

The Bad

In my experience the bad has definitely outweighed the good. I expected Upwork to be like Uber for knowledge workers. I thought I could just list my skills and they would funnel suitable jobs my way, making finding work a relatively sure thing.

That is definitely not the case.

Paid, Paid, Paid

I get this feeling that Upwork is not made for those who don’t want a career out of Upworking. They want professionals dedicated to the Upwork workspace.

• If I want the best success on Upwork, I probably want to pay for their membership. It’s $20/mo and gives me extra connects, better job insights and better customization among other things. As someone who doesn’t have money for maybes this is something I can’t afford to take advantage of.

• I get 10 connects per month. This is enough for me to apply to one lower tier job only per month. Jobs that generally have unverified payments and hasn’t spent money on Upwork. While its fine, it definitely feels like Upwork doesn’t set me up for success, and only provides top work to people willing to pay to win. Sure, connecting unverified job posters with unverified workers may be a way to sus out the bad, it will more likely lead people like me who may get stiffed with a bad taste in my mouth.

• If I want to “be at the top of the proposal list” I have to pay additional connects to get there. Does it work? Who knows? Just because I’m at the top of the list doesn’t mean I’ll be selected, but they sure let me know thats an option.

• If I want to boost my profile so it’s the first on the job posters lists, I can pay additional connects.

• If I want to set my availability badge, I can pay additional connects.

• If I want to boost my catalog, I can pay additional connects.

None of these are sure fire ways to get a job, it feels like LinkedIn Premium “I can get 2x better views”. Thats great, I’ll see if my landlord accepts views to pay my bills.

Even their advertisement at the top of the “find work” page, 3 out of 4 of the carousel cards are all about me paying them for better views, not the benefits being on Upwork may provide me.

If they changed the model to results based payment, like after I got the job because of a clicked boosted profile, I’d be much more likely to contribute. But its not.

No Filter

It seems many companies are going this way, removing all the filtering and sorting features, pushing me to scroll through all the jobs, just to find something that may fit my skillset. While yes, they do a good job filtering things that are based on my profile, it’s clearly driven by algos that are mediocre at best. I can’t even filter from newest posted so I’m left scrolling past jobs that are clearly dead as they’ve been there for 3 weeks. What if I wanted to filter based on long term, or fixed budget jobs? Nope. Its by relevance only. Hope ya like it.

Left Hanging… All the Time

I feel like this is becoming the norm. Ghost, Ghost, Ghost.

I have to use connects to send a request but if no one gets hired for the position, it is in the job posters best interest not to cancel, and let it languish until it expires, that way there is no negative report on the job posters profile, meanwhile, I lose all my connects spent on the application. So that’s what the job posters do, leave it to expire. Leaving me with the curious question of did they cancel the job? Should I boost the connect? Who was picked? What can I do to improve my chances of getting picked?

I’ve applied for 5 jobs on Upwork. Only one had a profile view.

There doesn’t seem to be a way to share that this position or job has been filled. It just sits in proposals. I have to click into the proposal, then view job post to see if someone was hired for that position, otherwise I have no closure on the job.

So far, out of the 5 jobs I applied for, only 2 have had hires reported on the job page. The rest are still there, active, just languishing until they expire. One curiously had no interviews, but moved straight to a hire, so who knows.

Final Thoughts

While I’m a bit desperate for a job now, Upwork definitely doesn’t feel like the place to turn unless I already have spent some time building it up and have some semblance of a work history on Upwork under my belt.

I feel the success is definitely based on your skills, and area of expertise. Since I’m sure I’m not the only desperate technology job seeker out there, or likely the most skilled, it’s probably going to be a slog for me.

I’ll keep trying. I have nothing to lose, but definitely feels like a gamble, where the house always wins. In this case, the house is Upwork. And I’m left holding the bag, hoping, wishing for a job poster to accept my heartfelt request to eat, the same way I’m applying for jobs everywhere else.