1. Review Upwork applications
🎥 Video lesson — video not yet migrated (source Skool video id:
d2af24d3f46249db83dae94dd1adf5ed).
At this point, you’ve completed your first full week of sending Upwork applications.
That’s a meaningful milestone.
You should've recorded around 60 Loom videos. By now, you don’t just know your pitch — you’re comfortable selling on camera. You know how to explain problems, walk through solutions, and speak clearly without overthinking every sentence.
Now it’s time to step back and evaluate what’s actually working.
Why We Do Retrospectives
Doing the work is necessary, but it’s not enough.
If you just repeat the same actions without reviewing results, progress slows down quickly. At the same time, the opposite mistake is just as common — people evaluate too early.
They try something for a day or two, don’t see results, and immediately change strategy. Then they repeat that cycle again and again.
The problem is that most things in real life have built-in lag. The applications you send today won’t always turn into closed deals today. If you judge performance too quickly, you’re usually working with incomplete data.
That’s why I suggest that you do these retrospectives weekly.
A week gives you enough volume and enough time for patterns to start showing up.
How to Run Your Upwork Retrospective
Set aside 30–60 minutes for this. Open a Google Doc or any notes app and write things down as you go.
Step 1: Identify What Worked
Start by looking at all replies you received over the past week. These are your successful applications.
Ask yourself:
- What do these applications have in common?
- Did I do something different in these videos compared to others?
- Were they in a specific niche?
- Did I apply on a certain day or at a certain time?
Don’t jump to conclusions yet — just note patterns.
Step 2: Look for Trends
Now zoom out and look at the types of jobs you applied to overall.
Are there certain industries, company sizes, or problem types that seem more responsive?
Are there job descriptions that consistently feel easier to reply to or explain on video?
You’re not trying to pick a niche yet — just noticing signals.
Step 3: Measure Your Conversion Rates
Now get a bit more quantitative.
- Count how many proposals you sent last week.
- Count how many replies you received.
This gives you your application → reply rate.
Then look at:
- how many replies turned into real conversations or clients.
That’s your reply → client rate.
Save these numbers. You’ll compare them week over week to track progress.
Step 4: Review Your Last Five Videos
Open the last five Loom videos you recorded and watch them fully.
Be honest with yourself:
- What did you do well?
- Where did you ramble or lose clarity?
- Did you get to the point fast enough?
- Did you clearly explain the problem and solution?
- Was there anything confusing or unnecessary?
This step matters more than most people realize.
Small improvements here compound fast.
Step 5: Decide on Small, Concrete Changes
Based on what you observed, write down a few specific tweaks you’ll make going forward.
These should be immediately actionable, for example:
- “I should stop saying X”
- “I should mention Y earlier”
- “I should show Z on screen”
- “I should shorten the intro”
- “I should be more specific about the outcome”
Avoid vague goals like “be better” or “sound more confident.” Keep it concrete.
Step 6: Make It Public
Once you’re done, create a post in Skool with:
- your main learnings from the retrospective
- the last five Loom clips you reviewed (use the play icon to attach them)
Making this public does two things:
- it locks in your insights
- it allows us to track your progress over time and give better feedback
Final Reminder
This isn’t about being perfect.
It’s about tightening the loop between action and feedback.
You’ve already done the hardest part — showing up consistently. Now you refine, one small improvement at a time.
Do this weekly, and your results will become more consistent.