• Kaya Lemaire

How I Used Upwork as a Jumping Off Point For My Freelancing Career

Freelancing And the 4-Hour Work Week

I began my freelancing career on Upwork because I wasn't really sure how else to go about it. It is a great tool for freelancers just starting out, who are unsure of how to do cold outreach, market themselves, and don't have much of a portfolio already.


That was me in 2020. I had no experience and no idea where to start. There were a few articles and videos that really helped me when I was manifesting that 4-hour work week, "digital nomad" lifestyle that Instagram sells you.


I want to preface by saying that, at the beginning when I wasn't making huge amounts of money, I was working only a few hours a day and enjoying my life. This was great for the end-of-summer, feeling free kinda mood I was in.


Carrie, the OG freelancer

But when it comes down to making a living and really being successful as a freelancer, you're going to be working more than 4 hours a week.


Beginners tend to buy into the dream that is sold to us online: laptop on the beach, all that jazz... (for the record, working on the beach is a nightmare, it's way too bright for a laptop and impossible not to get sand in your butt cheeks while trying to meet deadlines).


Frankly, that dream is only viable for those who have scaled their businesses and have a team of people doing the actual work for them while they answer some emails in their swimming trunks.


For those of you just starting out, it will look more like: trying to figure out how to get clients, managing your finances/taxes as a freelancer, finding out what your self-discipline is like, learning what it's like to have 100% responsibility for the success of a project, and building your self-confidence as a professional.


If you fit the bill, then read on to find out how to get started on Upwork, and eventually get the heck off of it and start pulling in real business.



How to Start Freelancing on Upwork

First off, you need to do some research into getting your profile approved. It isn't a free for all and they do some screening to make sure that you know how to market yourself on their platform, or have something to offer. (Something like only 2% of profiles get approved, but don't quote me on that number.)


Here are a few screenshots of my profile, which has been edited over the last year, but should give you an idea of how much detail to put in.


My recently updated profile overview

It's important to overload your profile with information initially. Use anything you can to fill out your work history, portfolio, and education experience. The moz.com Guide to SEO that you see below wasn't a course or a certification, it's literally a free guide on their website. However, adding some relevant resources as training/experience really helps you appear more serious and professional.


As you can see, I was a teacher before, and I used that in my past work experience by framing it as relevant to my new career path. You can reframe almost anything to look relevant (which I go into more detail further down the page).






I read/watched a lot of resources to get the scope because the first time I tried to apply I got rejected. I'm not going to rewrite the hundreds of blogs that are already out there about getting your profile approved, but if you'd like an overview this is a good resource. If you're looking for more specific examples of successful profiles, you can also check out this blog.


The profile that got approved took me about 3-4 hours to finish. And that included gathering/creating samples, digging through old files, doing research, and writing/re-writing my profile until I was happy with it.


Having now been on the hiring and seeking side of things, I have a few insights about landing your first gig.


Choosing Clients and Applying On Upwork

Although this seems like a no-brainer, it's overlooked... When applying, put in some effort.


A lot of first-timers feel overwhelmed and don't really know how to choose clients, have imposter syndrome, or just blast out a bunch of applications in the hopes that one sticks. This is not how I chose to do it, and I don't recommend you do that either.


You might be thinking.. pssshht I would rather just spend less time and just push out tons of applications, then I would get more jobs and that's really what I'm going for here. Why would I waste all my time on one proposal?


Why: because you are not going to find high quality clients this way, make your way to rising talent status, and be able to triple your rates in just a few months if you take low hanging fruit and choose quantity over quality.


I won't lie, this advice is tied up in my philosophy about work. But it brought me success very quickly and I truly believe if you follow the same ethos in the beginning of your career, you will find success, too.


I think starting to freelance requires a mindset shift. In effect, you are becoming an entrepreneur and treating yourself as a business that needs to land clients to stay afloat. Getting into this mindset requires that you evaluate your priorities and preferences when it comes to work.


So, with that in mind, here are my top tips for landing your first good clients on Upwork.


1. Be clear about your interests and skills

It's important to be flexible when you start out, but don't let that push you willy-nilly towards jobs that you're not actually interested in and won't help you build your portfolio.


I took a lot of blogging jobs initially, because that's what I thought I wanted to do. Only later did I realized that the pay is *crap*, it's incredibly time consuming, and you rarely get to write about things you're actually interested in.


When I became a copywriter, I was lacking useful samples in my portfolio because I had only done content writing (aka blogging) up until that point. The moral of the story: be a bit selective, even in the beginning - you are probably more skilled than you think and you can go for that job you want! Just apply (with intention) and see what happens.


2. You have skills! You're not an imposter

The imposter syndrome is real when starting out as a freelancer. There are definitely some hard skills that you could be lacking (coding, photoshop, witchcraft), but many of these can be learned on the job. And if you're only going to take one thing from this whole article, let it be that sentence right there.


Remind yourself of the skills you already have and the things you can nurture. For me, it was writing.


I wrote a travel blog for friends and family while I was abroad in Asia for the first time. It was a lot of fun! And what I didn't realize, until I had so many people telling me, is that I got maaaad skills hunny! I joke, I joke. Actually, I didn't even believe them until I started getting clients.


I got clients because I could show them some of my writing samples and they liked it. Mostly I was upfront about my experience, but I made up for it with enthusiasm and a fire under my ass to learn quickly, on my feet, and smash deadlines like it was no one's business.


3. Almost anything can be reframed as "experience"

The age old saying of "fake it 'til you make it" should be your guiding light in times of despair and a blank portfolio. My very first portfolio literally had essays from my university days. But on Upwork, you can get way more creative than that. Here are a few ideas:

  • Critique someone else' work. You can show off your knowledge and display your own skills by pointing out the errors in someone else's.

  • Make suggestions on your client's product/website/design/other relevant thing. Depending on what your line of work is, you could showcase your knowledge by giving professional, respectful advice about the thing they've got that you want 'em to pay YOU to do.

  • Use your fun projects as professional samples. My travel blog was one of my portfolio pieces and it helped me land content writing gigs again and again.

  • Make up a fake client/project and complete it. Sounds sketchy, but why not?

  • Use samples from your university career, if anything is applicable. Even though my degree was in Anthropology, there were a lot of papers that I could use to showcase my in-depth research and analytical skills.

  • Analyze the skills needed for the work you want to do and see how your life experience fits into that. You can usually spin your experience to fit into the role you want. This is also a great exercise to fight that imposter syndrome! Know your worth.


4. Spend 20 minutes writing your proposal (and make it amazing)

When you apply for a job, the client can actually see who has put more effort into their proposals. They tell us who is "highly interested" and who has "spent more time than average on the application". I immediately replied to the one who spent the most time on their application and clicked hire within a day.



When I was applying for jobs myself on Upwork, I chose ones that seemed really interesting to me! So that applying was actually exciting and I enjoyed putting in the time to write a convincing proposal. I spent time researching the client and looking through their reviews to try and find their name (not always successful, but worth a shot). Using their name in the greeting goes a long way to make it more personal.


Here is the proposal for the first real content writing gig I landed that I loved:



Now, seeing that I am a writer, I wanted to showcase my skills while I was telling her why I was a great fit. Show, don't just tell. That being said, if you're a designer or developer, you might not want to write such a long proposal.


Generally the rule of thumb is to show your samples as early as possible so that the client doesn't have to feel like they are sifting through the proposal in an attempt to see your work.


Remain professional, courteous but not cold, and check for spelling mistakes or any details that need to be added. Often clients will put a note like, "write Snowman in your application to show you read the whole post", or something similar.


Don't be lazy about this step. I think it's really important to land those jobs that you really want and that will propel your career forward in exciting ways.


5. Choose the right jobs

I already mentioned above that you should try to choose jobs that can help build your portfolio. But I'd also like to share a couple of tips for weeding out the good from bad job posts on Upwork.


👉 Don't take the super low hanging fruit (jobs) because you feel desperate. Just don't do it.


I read on someone's blog (which I can't find anymore unfortunately) that you should set the bar high right from the beginning as a freelancer - aka have some self respect. Don't go for jobs that pay below average for someone of your experience and skillset. Here's an example of that type of client:

In case you're not versed in the rates for freelance writing, 1 cent per word is genuinely insulting. Especially since they are demanding SEO best practices and can't even bother to spell out the word "you".


👉 Don't waste time on very general posts with lots of applications already submitted.


Some jobs are so general that even your granny could do it. Don't spend much time on these, especially if they already have 20-50 applicants gunning for the position.

Getting these types of jobs can be good for building a rating on your profile (the coveted 5-stars), but long term they won't help you build an awesome portfolio that will get you off of Upwork. Because that's what we're really gunning for here, my friend.


👉 As a general rule, avoid clients who are super vague but somehow seem like they want the world from you. Like this guy:

Although the $850 looks attractive, the post is super vague, confusing, and unclear. You are not told specific tasks you'll be doing and he is not clear about the requirements, either. This kind of client might be a pain in the ass to work with. I've heard of clients demanding things then saying it wasn't what they wanted because they weren't clear about the instructions from the beginning. And even worse than that.


Remember that you are also vetting the clients here - it's not a one-way-decision street. And the earlier you adopt this mindset that YOU are in control of your own work relationships, the sooner you can land awesome clients who respect you and pay well.


👉 And finally, the most important: Get off of Upwork As Soon As Possible.


Although some freelancers develop their career within Upwork and get paid millions over the years, the majority do not.


Typically I would gauge the relationship with the client and if things went beyond a one-off project, I would ask them if they were comfortable moving out of Upwork. Usually I would get on a call with them or start emailing to discuss the transfer. Because technically you have to pay Upwork a fee for doing this (although I never had to).


Most clients are happy to move out of Upwork and continue the working relationship via email and Zoom. You can negotiate a new payment strategy, start sending them invoices, and get rid of that damn 20% cut that Upwork takes.


Feel the freedom. Taste the rainbow.


Sample Invoice - template in Google Docs

A few hot tips if you're feeling nervous about this:
  1. Ask for half of the payment upfront and half upon completion. Mention that this is standard practice, although I have never had a problem asking this from clients.

  2. Get comfortable with briefs. You can bring your own to the meetings and it will help you and the client organize the tasks, if they haven't already.

  3. If you're getting more experience, negotiate higher pay and tell them why. If their budget is tight, negotiate a *restructuring* of the project where you end up doing less, but it's packaged to look like equally valuable deliverables.

  4. Check out Copyhackers' 10x Freelancer resources - it really helps with your confidence. Although, this one is mainly for the marketers and copywriters out there.

  5. Do your research. Seriously, you will never stop being a student in this life. If you go into every situation ready to learn, you're gonna go far in your career, and quickly.


In Summary: Getting Clients Outside of Upwork is the Real Goal

Yes, even though this whole article is about being successful on Upwork, you should keep your eyes on the prize: that truly free freelancing career, where you have a great portfolio, have new clients reaching out to you through referrals, and feel confident in your specialization.


At the beginning it's normal to have more general goals with freelancing, but as you become more experienced and find out what you like to do, you'll likely find a niche.


"Niching down" is talked about a lot in the freelancing blogosphere, but I don't really recommend over-thinking it in the beginning. Especially if you are still in the discovery phase of your foray into freelancing (which you likely are, if you're reading this).


The plus side of specializing:

  • Charge higher rates

  • Target clients more intentionally

  • Gain expertise, giving you more negotiation power

  • Build authority in a field and eventually advise/consult others on this topic

All that being said, your freelancing journey will be unique based on your own goals, preferences and personality. My experience isn't something to take as a "hard guideline" for success.


At this point I've advised a few friends on how to get started with Upwork and in freelancing, so I wanted to make this information more widely available. For whoever needs it. 💌


As always, leave comments with questions and I'll do my best to help!

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