Welcome to this week's Tuesday Training, where we tackle the uncomfortable truths about freelancing that nobody wants to talk about at parties. (Not that I go to parties. #IntrovertLife.)
Today we need to have a heart-to-heart about something that's happening right now in our community. I'm watching brave souls work through 10 Days to Paid, and I'm seeing a pattern that makes my heart hurt a little:
The 15-Proposal Panic Attack™ 😰
You know the one. You've been diligently following 10 Days to Paid. You've sent out 10... 15... maybe 20 proposals, and your inbox is giving you the silent treatment. NOTHING. Not even a "thanks but no thanks." Just... 🦗🦗🦗
And that little voice in your head starts whispering:
"Maybe I'm not cut out for this" 😰
"Everyone else is getting jobs but me" 😭
"I must be doing something wrong" 🫠
"I knew this was too good to be true" 💔
"Time to update my Indeed profile" 🙃
STOP. RIGHT. THERE.
Before you rage-quit and go back to scrolling job boards, let me normalize something for you:
It might take 40-50 proposals to land your first job.
Cue collective gasp and/or laptop being thrown
I KNOW.
That sounds like a lot.
That *IS* a lot.
But here's what's happening behind the scenes:
As a beginner, you're fighting against:
❌ No reviews (yet)
❌ No job history (yet)
❌ No "Rising Talent" badge (yet)
❌ The algorithm not knowing you exist (yet)
❌ Clients filtering by experience level
❌ 50+ other people applying to the same job
Notice all those "yets"? Because this is TEMPORARY. Once you land that first job and get your first 5-star review? The whole game changes.
It's like dating apps—you might swipe through 100 profiles before finding someone who doesn't think "u up?" is charming conversation starter. But once you find your person? The swiping stops.
(Okay, maybe freelancing is better than dating apps. At least clients PAY you for your time.) 💰
Why Your First 20 Proposals Feel Like Shouting Into the Void 🌌
Remember when River (my guinea pig kiddo) went through this challenge? Even with me literally coaching him through every step, it took 18 DAYS for one client to respond to a proposal he'd sent on Day 1.
EIGHTEEN. DAYS.
That's not because his proposal sucked. It's because:
Clients are busy (and disorganized) 🏃♀️
They post jobs then forget about them 🤦
They're comparing 50+ proposals 📚
They're waiting for budget approval 💰
They're on vacation 🏖️
They're just... human 🤷♀️
Meanwhile, you're sitting there like:
"Did I say something wrong?" 😰
"Is my profile photo giving serial killer vibes?" 📸
"Should I have used a different emoji?" 🤔
"Maybe I should just apply for a NEW soul-sucking job..." 😭
Look, I could tell you to "just keep going" and "trust the process" (which is true), but that's about as helpful as telling someone with insomnia to "just sleep."
So instead, I created something ACTUALLY useful: An interactive proposal checklist that ensures every proposal you send out is optimized for beginner success.
Why Your Proposals Might Be Getting Ghosted 👻
Here's the thing: Sending out 5 proposals a day sounds easy. But when you're being intentional—taking time to choose quality jobs, crafting personalized proposals—it's can actually be time-consuming AF. (Another thing that gets easier over time. Eventually you won’t even have to send out proposals anymore.)
On the flip side, if you're doing the "spray and pray" method—clicking random jobs, copying/pasting generic AI slop, hitting send while barely looking—you're basically playing freelance roulette with terrible odds.
Most people fall somewhere in the middle.
They're trying, but they're missing key elements that make proposals actually WORK.
That's why I created this checklist—to help you maximize EVERY proposal you send.
Introducing: The Proposal Checklist That'll Save Your Sanity 📋
I've built an interactive checklist that covers the 8 CRITICAL elements every proposal needs when you’re following my 10 Days to Paid program.
This isn't just some PDF you'll download and ignore—it's a actual tool you can use for EVERY proposal.
Access the Interactive Checklist Here
(Yes, it has confetti when you complete it. Yes, I'm extra. No, I'm not sorry.)
Let me walk you through each element and why it matters:
1. Craft a Compelling Proposal Hook 🎣
This is the hill I will die on. Your opening 1-2 sentences are worth more than the rest of your proposal combined.
This is THE MOST IMPORTANT real estate in your entire proposal. Those first sentences determine whether clients keep reading or move on to the next freelancer.
The difference between invisible and irresistible:
❌ INVISIBLE (aka Boring):
"I'd be happy to provide a comprehensive review of your website and deliver actionable feedback through a structured survey format."
I fell asleep just typing that. 😴
✅ IRRESISTIBLE (aka Attention-Grabbing):
"Need this done quickly, clearly, and without a single follow-up? I've got you. 🎯"
See the difference? One sounds like every other proposal. The other sounds like a REAL PERSON who gets what the client actually wants.
Pro tip: Ask AI to generate 20-30 different hooks for each proposal. Then use your gut to pick the one that makes YOU go "Ooh, that's GOOD!"
(I know it sounds woo-woo, but your body knows. When you read the right hook, you'll feel a little spark of "YES!" Trust that feeling. Yes, I'm the same person who creates spreadsheets for fun. We contain multitudes.)
You're feeling for:
😂 Humor that lands
😰 Pain points that sting
🎯 Specificity that shows you GET IT
💫 Outcomes they're dreaming about
🧐 Curiosity that gets the click-through
🫨 Disruption that makes them stop scrolling
Want to dive deeper into hook writing? Check out my previous training on attention-hijacking headlines and hook writing.
2. Offer Strategic Pricing Discount 💸
As a beginner, your pricing is your SECRET WEAPON. But it has to be strategic, not desperate.
If your profile says $25/hour, offer $15/hour and TELL THEM about the discount:
"My standard rate is $25/hour, but I'm offering a special introductory rate of $15/hour as I build my Upwork presence. You get premium work at a beginner price—win-win!"
Pro tip from River's playbook: His profile headline was literally "0 Upwork Reviews. 100% Committed to WOW You." He LEANED INTO being new. In almost every proposal, he talked about being eager to earn his first 5-star review.
Own where you are. Make it work FOR you, not against you. Clients LOVE being someone's first success story—if you position it right.
3. Polish Your Writing with AI 🤖
Look, I'm all about keeping it conversational and real. But typos and grammar mistakes scream "amateur."
Run EVERY proposal through:
ChatGPT or Claude (ask it to "please clean this up while using as much of the same word choices and phrases as possible")
Grammarly
Keep your personality. Lose the mistakes.
4. Target Recent Job Posts ⏰
Jobs posted 2+ weeks ago? Skip 'em. The client has either:
Already hired someone
Lost interest
Forgotten they even posted it
Sweet spot: Jobs posted within the last 3 days Acceptable: Up to 1 week old Pushing it: 1-2 weeks
The exception here is when the client has a high “Hire” rate (70%+) or is hiring multiple freelancers for the job and still has openings.
Newer = Less competition + Higher response rates
5. Verify Client Quality 🔍
Not all clients are created equal. Before wasting connects, check:
✅ High Quality Client Signs:
4+ star rating (more than 20 reviews)
Payment verified
20+ past hires
Clear job descriptions with realistic expectations
Look at their job history to see if they’ve historically left 5 star AND written reviews with previous freelancers they worked with.
6. Confirm Job Availability 👀
Before you spend those precious connects, CHECK:
Has the client already hired someone?
If they have, are they hiring multiple people?
Is the job still marked as open?
Nothing worse than crafting the perfect proposal for a job that was filled 3 days ago. 😤
7. Focus on Beginner-Friendly Jobs 🎯
I know you want to dive into your dream niche, but for your first few gigs, prioritize:
BEGINNER GOLD:
Surveys & feedback collection
Website/app testing
Simple research tasks
Basic data entry
Quick admin tasks
"Review our [thing] and give feedback"
Save for later:
Complex creative projects
Long-term commitments
Anything requiring extensive portfolios
Jobs with 50+ applicants already
8. Choose Small Scope Projects ⏱️
Your first jobs should be measured in HOURS, not days or weeks.
Perfect starter jobs:
1-4 hours of work
Clear, specific deliverables
Due within a few days
Simple requirements
Too big for beginners:
"Looking for long-term partnership"
"Need someone 20 hours/week ongoing"
Complex multi-phase projects
For bigger projects? Use the 2-hour trial method I teach in 10 Days to Paid.
Using the Checklist (And When to Ask for Help) 🚨
Here's how I want you to use this:
First 20 proposals: Follow the 10 Days to Paid system exactly. Don't overthink it. Start using the checklist. Experiment with different hook styles.
Proposals 21+: If you haven't gotten ANY responses, it's time for a proposal review. Drop them in our community chat, and I'll personally help you figure out how we can tighten up your proposals.
Remember: Some clients take a WEEK OR MORE to respond. River got hired for a job he applied to TWO WEEKS earlier. Patience, grasshopper. 🦗
The Reality Check You Need 💊
I'm not going to sugarcoat this: Those first proposals feel like shouting into the void.
It's demoralizing.
It's frustrating.
It makes you question if you’re cut out for this.
But here's what I know:
MY first 30+ proposals? Mostly crickets AND a ghosting client.
Fast forward a couple years? I haven’t sent a proposal in AGES and TURN DOWN new client work every month.
The breakthrough always comes RIGHT after you want to quit.
Your Homework (Yes, There's Homework) 📚
Download the checklist and bookmark it
Review your last 5 proposals against these criteria
Send 5 NEW proposals using the checklist
Track which hooks get responses in your proposal tracker (data is your friend!)
Share your wins (and struggles) in our community
And if you haven't started 10 Days to Paid yet? What are you waiting for? It's:
✅ Completely FREE
✅ 12+ hours of step-by-step training
✅ Includes templates, AI prompts, and swipe files
✅ Documents an actual success story (follow along as a 22 year old Starbucks barista lands their first jobs following this program)
✅ Will transform you from "what do I even offer?" to "I GOT PAID!"
And now it includes this shiny new checklist to make sure every proposal counts.
This checklist won't make much sense without the full strategy. It's like having a map without knowing the destination.
No paywalls. No "upgrade for the REAL secrets." Just the complete system that actually works.
The Bottom Line 🎯
Landing your first freelance job is:
20% having the right skills
30% sending quality proposals
50% not giving up when it gets hard
This checklist handles the quality part. Your persistence handles the rest.
Every "no" gets you closer to "yes."
Every ignored proposal teaches you something.
Every ghosted message builds your resilience.
And when that first "Hi, I'd love to work with you!" message lands?
Chef's kiss
It makes every ignored proposal worth it. And your first "You're hired!" message is closer than you think. 💪
Now go forth and GET THOSE GIGS! 🎉
P.S. If you're reading this after sending exactly 7 proposals and wondering why you're not rich yet... bb, no. That's like going to the gym once and wondering why you don't have abs already. Give it time. 😅
P.P.S. Seriously though—if you hit 25+ proposals with ZERO responses, tag me in the community chat. We'll fix it together. I've got you. 🤝
P.P.P.S. Yes, the checklist really does have confetti. Because if you're going to track your freelance progress, you might as well CELEBRATE it too! 🎉
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