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đź’Ľ đź’¸ Day 14: Writing A Winning Proposal - Asambe! đź’Ľ đź’¸
Be Intentional and Purposeful Today
Phemelo Kebinelang
June 23, 2025
23 JUNE 2025
đź’°THE DIGITAL ECONOMYđź’°
"S’Phanda Sonke Online – Asambe"
Newsletter
"Empowering Youth and Communities to THRIVE in this DIGITAL ERA!”
Day 14: Writing A Winning Proposal - Asambe!
Happy Monday, Future Remote Superstar!
Today is Day 14, the last day of the second week of the challenge.
While most young people feel helpless and slow down for the week, we’re quietly building empires.
You’ve got your CV, polished profiles, and some solid interview practice under your belt.
Yesterday, you went through the practice of handling objections.
Today, we pull all of that together into one of the most crucial skills for any remote pro: writing a winning proposal.
On platforms like Upwork, you don’t just send a CV, you send a proposal.
Think of it as a mini sales pitch.
It answers the key question: "Why am I the perfect person to help right now?"
Mastering this skill separates freelancers who struggle from those who thrive.
Let’s get to work.
The Proposal Writing Playbook: Your 5-Step Guide to Winning Jobs
A winning proposal isn’t a generic, copy-pasted letter.
It’s a custom-crafted solution that shows you’ve read, understood, and are ready to solve the client’s specific problem.
Your task today: find two interesting projects on Upwork or LinkedIn and submit killer proposals for each.
Step 1: Unpack the Job Post
Before typing a single word, read the client's project description three times.
What’s their real pain point?
Are they stressed about time?
Worried about quality?
What specific words do they use?
Underline them.
Your proposal must directly address these points using their language.
Step 2: The First 2 to 3 Lines
Clients see a preview of your first two lines before clicking on your proposal.
Don’t waste this space with "Dear Sir/Madam, my name is..."
Start by addressing their need directly.
Instead of:
"I am writing to apply for the Social Media Manager position."
Try:
"I see you're looking for a Social Media Manager to increase engagement on your Instagram page. I have direct experience helping brands create compelling content and can start immediately."
Or start with something that shows you’ve done your homework:
"I noticed [specific company achievement/challenge/news], which reminded me of when I helped [similar situation] achieve [specific result]."
Step 3: Propose a Mini-Plan (The "How I'll Help" Body)
This is where you show your value.
Don’t just list skills; outline a brief plan of action.
It shows you’re a proactive problem-solver.
Example:
"Here’s how I would approach this project:
First, I’ll analyse your top 3 competitors to identify opportunities.
Next, I will develop a content calendar with 5 post ideas for your approval.
Finally, I’ll design and schedule the first week of posts."
Connect their needs to your experience with specific examples:
"Your need for [specific requirement] aligns perfectly with my experience [specific achievement with numbers]. For example, I recently [relevant story] which resulted in [quantifiable outcome]."
The PROOF Section (2-3 bullet points):
Use bullet points to highlight your most relevant achievements that address their top 3 requirements. Each bullet should follow this format:
"[Specific action] that resulted in [measurable outcome] for [context/company type]."
The VISION Close (2-3 sentences):
Paint a picture of future success:
"I'm excited about the opportunity to bring this same [specific skill/approach] to help [company name] achieve [specific goal mentioned in job posting]. I'd love to discuss how my experience with [relevant area] can contribute to [their specific objective]."
Step 4: The Confident Close (Ask a Question)
End your proposal by inviting a conversation.
Reiterate your enthusiasm and ask a smart, clarifying question.
This makes it easy for them to reply.
Instead of:
"I look forward to hearing from you."
Try:
"I'm confident I can deliver the results you're looking for and am excited by the opportunity. Before we begin, could you tell me a bit more about your target audience? This will help me tailor the content perfectly."
Step 5: The Polish and Submission Strategy
The Final Review Checklist:
Read your proposal aloud to catch awkward phrasing and ensure it flows naturally.
Check company name accuracy, verify all links work, and confirm you've addressed their top requirements.
Personalisation Verification:
Include the hiring manager's name (research it if not provided), reference something specific about the company, use their preferred terminology, and avoid generic phrases like "I'm a hard worker."
Strategic Timing:
Submit applications Tuesday-Thursday between 10 AM-2 PM in the company's timezone for maximum visibility.
Follow-up Planning:
Set a calendar reminder to follow up in 5-7 business days if you haven’t heard back.
Prepare a brief, valuable follow-up message that adds new information rather than just checking in.
The Mindset of a True Professional:
It might be tempting to find two jobs quickly and send the same generic proposal to both.
Trust me, that’s a waste of your time and energy.
It’s far better to spend an hour writing two highly customised, thoughtful proposals than to send 20 copy-pasted ones in the same time.
Why?
Because you’re not a robot spamming applications, you’re a professional consultant offering targeted solutions.
This mindset shift is everything.
When a client reads a proposal that clearly understands their unique problem and offers a clear plan, you instantly stand out from 99% of the competition.
Every hiring manager lies awake at night worrying about deadlines, targets, and challenges, and you’re about to position yourself as the solution to those sleepless nights.
The remote job market is competitive, but it’s not flooded with candidates who can write compelling, research-driven proposals that speak directly to business needs.
By mastering this skill today, you’re not just boosting your application success rate; you’re developing the strategic communication abilities that will make you invaluable throughout your remote career.
Your dream remote job is waiting for someone who can clearly and compellingly articulate their value.
Today, you become that someone!
The skill you’re building, the ability to listen, diagnose a problem, and propose a solution, is the absolute core of a successful remote career.
Make your Monday count.
đź”— Proposal Writing Learning Resources:
👉 Please click on all the links below to explore the resources.
Don’t skip, every insight counts!
đź“© Tip: Take 40 minutes today to go through these materials.
You're in this challenge to win, so let’s build the knowledge that powers digital income.
đź“‹ TODAY'S ATS MASTERY CHECKLIST:
âś… Research the 2 target companies thoroughly
âś… Write 2 customised proposals using the 5-stage formula
âś… Include specific company references and value connections
âś… Proofread and optimise for impact and clarity
âś… Submit both applications at strategic times
âś… Set follow-up reminders for next week
âś… Celebrate mastering the art of persuasive proposal writing!
A reminder to all participants.
We’ve created a WhatsApp group - 21-Day Challenge Remote Jobs for easy and timely access to the challenge's daily tasks, updates, resources and opportunities.
We encourage you to join the group.
Follow this link to join the group: https://chat.whatsapp.com/DINLpaRZ1PfEfYsvzhH1dH
Let's go together
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