Good morning,
There's an old story about a fellow who walks into a men's clothing store and tries on a suit that's about four sizes too small.
The salesman assures him they can make it work.
First, he pulls up one sleeve and tells the customer to bend his elbow to keep it in place.
Then he hikes up the trousers and tells him to squeeze his knees together so they won't fall down.
By the time they're finished, the poor fellow is standing there with one arm twisted, his knees pressed together, and his body contorted into a position no human being should have to maintain.
The salesman steps back, admires his handiwork, and announces:
"See? Perfect fit!"
I thought about that story during our Tuesday night training with Heidi.
Because I've watched an awful lot of intelligent, experienced people do essentially the same thing when they're looking for freelance or consulting work.
They find a job that looks interesting.
They read the requirements.
They start wondering whether they're qualified.
Then the contortions begin.
"Well, I haven't actually done that particular thing, but I've done something sort of similar."
"Maybe if I rewrite my profile..."
"Perhaps I could take a quick course..."
"Maybe if I lower my price..."
Before long, they're trying to squeeze themselves into a job that was never a particularly good fit in the first place.
And they're spending hours doing it.
Two jobs. Two very different answers.
On Tuesday night, Heidi and I demonstrated a new approach using a fictional professional named Laura Benton.
Laura has extensive experience managing customer service operations, training employees, and developing procedures that help organizations run more smoothly.
We gave our Job Suitability tool an actual Upwork-style assignment: an HVAC service company needed help creating five standard operating procedures and improving its employee onboarding.
The budget was $1,100.
At first glance, Laura might have hesitated.
After all, she wasn't an HVAC expert.
But here's what the analysis discovered.
The client didn't primarily need someone who understood air conditioners.
They needed someone who understood how to make complicated operations work reliably.
They needed clear procedures, consistent training, better communication, and fewer mistakes.
And Laura had years of experience solving exactly those problems.
The tool gave the opportunity a suitability score of 90 out of 100.
More important, it explained why she was such a strong candidate and how she could communicate that experience without pretending to have technical qualifications she didn't possess.
It also identified a legitimate concern: whether the $1,100 budget would adequately compensate her for the work involved.
That's the kind of judgment you want before making a commitment.
Then we tried a second opportunity.
This one involved preparing a volunteer welcome kit.
It sounded perfectly respectable. Laura could probably have figured out how to do it.
But the analysis revealed a different picture.
The project wasn't closely aligned with her strongest experience. She lacked some of the supporting portfolio evidence, and the work offered relatively little value toward the consulting practice she wanted to build.
The suitability score was 65 out of 100.
My advice?
Unless she had a compelling personal reason to pursue it, keep looking.
Not because Laura wasn't capable.
Because she had better things to do with her time.
Here's something I've observed during 19 years of helping people build independent income.
One of the biggest obstacles isn't a lack of ability.
It's the sheer amount of mental energy people spend second-guessing themselves.
Should I apply?
Am I qualified?
What should I emphasize?
How much should I charge?
Will the client think I'm too expensive?
And after spending an hour wrestling with those questions, you still haven't written the proposal!
Until recently, preparing five thoughtful proposals in a week could easily consume five to seven hours.
With the tools we're now teaching, much of that work can be compressed into an hour or two once you've learned the process.
But the real benefit isn't just speed.
It's learning to recognize where your experience gives you a genuine advantage.
The software doesn't make the decision for you. Its scores aren't guarantees that you'll win a job.
Instead, it helps you see the evidence, identify the risks, and understand what makes an opportunity worth pursuing.
And the more you use that reasoning, the better your own judgment becomes.
That's a skill worth developing, regardless of what technology you happen to use.
You make it easy for the client to connect the dots between your experience and their solution.
You don't need to fit every job
I sometimes think that experienced people have a peculiar disadvantage when they first enter the freelance marketplace.
They know how much they don't know.
After decades of working in organizations, they've seen projects go sideways. They've dealt with impossible deadlines, difficult personalities, confusing instructions, and budgets that looked perfectly reasonable until the work began.
So when they read a job description, they recognize potential complications that less experienced people might completely overlook.
That can lead to hesitation.
But it can also be a tremendous advantage.
The trick is to stop asking, "How can I convince this client I can do the job?"
And start asking:
"Which clients have problems that my experience makes me unusually well equipped to solve?"
That's an entirely different way of approaching the marketplace.
And it's a much more enjoyable one.
No twisted elbows. No squeezing your knees together.
And definitely no pretending that a suit four sizes too big is a perfect fit.
Come see how this works on Saturday
This Saturday, November 14, Heidi and I are hosting the first of two free, interactive workshops:
Your Winning Advantage: Find Better Upwork Jobs & Write Stronger Proposals
We'll take you through the process slowly, using realistic examples, and show you how to evaluate opportunities, identify your strongest qualifications, and turn that information into persuasive proposals.
On November 21, we'll build on that foundation by showing you how to refine and polish your proposals.
Both sessions begin at 10:00 a.m. Central Time, and there will be plenty of time for questions.
Can't join us live? Register anyway. Both workshops will be recorded, and you must be registered to receive the recordings.
I'd love to have you join Heidi and me.
And remember: Somewhere out there is a client who needs precisely the experience you already have.
Your job isn't to squeeze yourself into every opportunity.
It's to find the ones that fit.
Winton
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