Hey there, future freelancer! 👋
Welcome to the 10 Days to Paid Challenge – your step-by-step roadmap to landing your first paying client and that coveted 5-star review on Upwork.
Some links in this training may be affiliate links - consider it a way to tip for teaching you for free! I only use affiliate links for products I've used before and would genuinely recommend. (And no, Upwork isn’t one of them.)
Over the next 10 days, I'm going to walk you through EXACTLY how to set up your profile, find the right jobs, create proposals that get noticed, and turn those first clients into paying clients. No fluff, no theory, just practical action steps that get you PAID.
Before we dive in, let me make sure you're in the right place:
Haven't figured out what freelance services to offer yet? Start with my Find Your Freelance-Ready Skills training first.
Curious about my personal freelancing journey or why I'm so obsessed with Upwork as your starting point? Check out my challenge introduction video.
Ready to fully commit to the 10-day challenge? Amazing! Click here to opt in and get Days 2-10 dripped into your inbox. (Not quite ready? No pressure! This link will be waiting whenever you decide to jump in.)
Remember, this challenge is designed to be DONE, not just consumed. Each day builds on the previous one, and by Day 10, you'll have everything you need to start making actual money as a freelancer.
Let's get those first dollars flowing and that first 5-star review shining on your profile! 💰⭐
Oh, and once you complete today's tasks, I'd LOVE for you to share your Minimum Viable Profile in our group chat so we can celebrate your progress! I'll personally peek at it and let you know if there are any critical tweaks needed. (Remember, we're not going for perfection here, but that headline and hook really do matter!)
Let's Get Started! Day 1: Account Setup 🚀
Alright, enough big-picture talk. Let's get to the actual action step for Day 1:
Your Task: Set Up Your Upwork Account
Go to Upwork.com and click "Sign Up"
If you've had an account before: Try to resurrect it instead of creating a new one (Upwork only allows one account per person, EVER)
Follow their basic signup wizard
IMPORTANT: When it starts asking about your professional title, skills, education, etc. — just put in the absolute bare minimum for now
You can literally type "Test" or gibberish if needed
Don't waste time perfecting anything yet!
Once you have basic access to the platform, come back here
WHY AM I TELLING YOU TO HALF-ASS THIS? Because most people waste HOURS trying to perfect their profile before they understand what actually works.
We're going to build your Minimum Viable Profile next—just enough to start applying for jobs and getting results. Your profile, proposals, and portfolio will ALL be constantly upgrading as we progress through this challenge.
Remember: A mediocre profile that's actually live will make you more money than a "perfect" profile that never gets finished. ✨
Creating Your Minimum Viable Profile
Alright, let's talk about what actually matters when setting up your Upwork profile. (It's not what most beginners think!) 🔍
The Perfectionism Trap (And Why We're Avoiding It)
Listen up, fellow over-achievers and perfectionists (hello, that's me too!) – we have a tendency to keep ourselves stuck in "busy work" mode. Perfecting. Tweaking. Building samples. Creating portfolio pieces. Rewriting our profile for the MILLIONTH time.
Let's call it what it is: procrastination disguised as productivity. 💅
The hard truth? Many people won't even finish this challenge. So spending 17 hours crafting the "perfect" profile before you've even landed a job is like buying a wedding dress before you've gone on your first date.
The ONLY productivity we care about right now is getting you landing jobs. Everything else is a distraction.
Day 1 Task: Profile Research & Setup
This is a two-parter that will give you both platform familiarity AND intelligence on your future competition.
Part 1: Competitive Intelligence Gathering
Go to Upwork and click the search bar
Change from "Jobs" to "Talent"
Enter keywords related to the service you want to offer
Add these filters:
Job Success Score: 90%+
Earnings: $10K+
Hours billed: 100+
Think of this as an intel mission. 🕵️♀️ These people are your future competition. I want you to study:
Their profile photos (professional? casual? creative?)
Headlines (what's grabbing attention?)
Hooks (the first couple sentences visible in search results)
Hourly rates (what's the range in your niche?)
Total earnings (how much volume is possible?)
Your task: Find 5 profiles of people charging rates you'd LOVE to be charging who have billed a substantial amount through Upwork. Copy their:
Headlines
Hooks (first few visible sentences in the search results)
Remaining Profile
Rate
..into this spreadsheet for your research purposes.
Pro Tip: If you struggle to find 5 solid profiles, that's valuable feedback! It might mean:
Your search was too specialized (zoom out a level)
The niche has lower rates than you hoped (try a related category)
There's not much volume in that specific niche
You should have pages of results even after applying filters. If not, broaden your search.
Part 2: AI-Assisted Profile Creation
ChatGPT: https://chatgpt.com/
Claude (my personal favorite for writing): https://claude.ai/
Perplexity (AI search engine that also does pretty good copywriting, math, and formulas): https://www.perplexity.ai/
Emojipedia: https://emojipedia.org/
Once you have your 10 examples, head to ChatGPT or Claude with this exact prompt:
I am new to Upwork and I'm standing up my beginner profile. I am interested in offering services in the [YOUR NICHE] space. I don't yet have proven experience on the platform yet. (If you do have relevant experience in your chosen space, share that here. If you don't, just skip) I researched 5 top profiles in my space and here are their headlines, their opening hooks and their full profiles for review. Please review these and create a hypothesis as to why these people are landing jobs with these profiles - what common themes do you see?
[PASTE YOUR RESEARCH HERE]After the AI responds, follow up with:
Perfect. My goal is to disrupt someone's attention while scrolling and STAND OUT among profiles like these. So I don't want my headline and hook to mirror theirs but rather stand out in a unique and unexpected way that hijacks attention and earns the click-through in my profile. I want you to create 10 headline/hook combos to choose from using a variety of tactics like humor, curiosity, stats, etc. Remember the idea here is to be different from the examples I showed you while still competitive despite my lack of platform success yet.Review the outputs, select your favorite, and then tell the AI
Awesome. I love this one:
[PASTE YOUR CHOSEN HEADLINE/HOOK]
Now please go back to your original hypothesis on why those other profiles perform well and create the rest of my beginner profile that will help convert and land me new clients. Please use a casual but professional tone of voice (like how you'd speak to a co-worker at lunch) and use simple, everyday language.Keep in mind that Upwork doesn’t allow traditional formatting, like bolding, italics, bullet lists, etc. Format creatively using CAPS (sparingly), emojis or other characters to create a cohesive, easily-readable designed profile.If the output doesn't feel quite right, give the AI feedback on what's missing. (I’ll get into copywriting with AI a lot more heavy in future trainings, but I want us to keep our eye on the prize right now. Be OK with “good enough” for the moment.
Focus more on getting the tone/personality right than having every detail perfect. Just remove anything that feels false or inaccurate, and you'll have a solid starting point.
REMINDER: Your headline and hook are 80% of what lands you jobs. The rest is mostly for the algorithm to help you show up in searches. We'll optimize for keywords later, but for now, "good enough" is perfect.
The best part? You can easily swap headlines and hooks later to test which ones perform better. This isn't tattooed on your forehead forever. 😅
Getting to 100% Profile Completion
Once you have your core profile content, your next goal is reaching 100% profile completion. This isn't just for show – it's one of the requirements for earning the "Rising Talent" badge, which can fast-track your success.
Source: https://support.upwork.com/hc/en-us/articles/34924882793107-Build-a-100-complete-profile
Required Items (50%):
✅ Profile Photo (Professional Headshot)
Use a clean, well-lit photo cropped around your face
Pro Tip: I've created this Canva template where you can drop in your photo with a colored outline – this tiny addition helps you stand out!
No professional photo? Use AI! I've used:
Remini (Free trial, just remember to cancel)
Aragon AI ($35-75 for 40-100 headshots)
Headshot Pro ($29-59 for 40-200 headshots)
✅ Profile Overview
This is where you'll paste the content we created above with AI
✅ Hourly Rate
Set your rate between $15-25/hour (even if you have tons of experience and make way more in your day job)
This is just your profile rate—we'll be discounting it in proposals
Strategy: If your profile shows $25/hour, you can apply at $15/hour positioning it as "$10 off my standard rate"
We will walk this rate up FAST after you get those first few reviews
Don't overthink this! Your first goal is landing jobs, not maximizing hourly rate right now
✅ Employment History
Add at least 3 past jobs to max out your points (30%)
99% of clients don't actually look at this – it's for the algorithm
Just need company name, city, country, title, and dates
Yes, include non-relevant experience! (My healthcare jobs still help me get matched with healthcare clients)
✅ Skill Tags
Choose at least 3 (the more the better)
Focus on skills aligned with your desired work
Include specializations you want to explore
Optional Items (Get to 100%):
✅ Education History
Even just high school gets you 10%
College (even incomplete) gets you the full 20%
Again, clients rarely are looking at this
Choose from these to reach 100%:
Link a social account (10%)
Add certifications if you have them (5% each, max 10%)
Create a profile video (10%)
Add other experience items (5%)
WHAT TO SKIP (FOR NOW):
❌ Portfolio Section
Complete distraction at this stage
We'll add this after you have actual client work
❌ Creating Project Listings
Just the basics for now
Save your energy for applications
Why This Matters
The "Rising Talent" badge is freelancer gold for beginners. It signals to clients that Upwork sees potential in you, even without a strong work history yet on the platform. A 100% complete profile is one of the key requirements.
When you start consistently applying, landing contracts, and earning high ratings, you'll be positioned to earn this badge – which can dramatically increase your visibility and chances of landing better jobs.
Source: https://support.upwork.com/hc/en-us/articles/211063228-Rising-Talent
🎉 CONGRATULATIONS!
If you've completed these steps, you now have a profile that's ready to start applying for your first freelance jobs!
Tomorrow (Day 2), we'll cover some essential housekeeping before you start submitting proposals:
Legal, Banking, and Tax considerations for freelancers
Upwork 101: Avoiding common scams and protecting your profile
Understanding Upwork costs and fees
Membership options and how Connects work
This might not be the sexiest content, but it'll save you from expensive mistakes and frustration later!
Your Day 1 Checklist:
☐ Sign up for your Upwork account and complete the setup wizard
☐ Complete competitor research on 5 successful profiles
☐ Use AI to analyze findings and create your profile content
☐ Select your headline and hook
☐ Add a professional profile photo
☐ Fill in your employment history (3 jobs if possible)
☐ Add relevant skill tags (at least 3)
☐ Complete education section (2, if possible)
☐ Add 1-2 optional elements to reach 100% completion
☐ Drop your shiny new profile link in our community group chat so we can celebrate with you!
☐ Officially OPT IN to the 10 Days to Paid Challenge to get Day 2 in your inbox tomorrow. (Days 2-10 will NOT be posted here on Substack.)
REMINDER: A "good enough" profile that lets you start applying for jobs TODAY is infinitely better than a "perfect" profile that never sees the light of day. Let's get you making money! 💰
With caffeine and optimism,
P.S. If you're feeling overwhelmed or have questions, drop them in our community chat! Remember, everyone starts as a beginner—even the people currently making six figures on Upwork.
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