Upgrade Your Upwork part 2: How to write an Upwork proposal

Hola, lovely logophiles! Last week, you learned how to write an Upwork profile bio that hooks clients from the first sentence. The second installment of the Upgrade Your Upwork series is a crash course on how to write an Upwork proposal that wins the gig!

I’ve written — and also reviewed — my fair share of Upwork proposals. Most of the early ones flopped because I had no clue what I was doing. They were stuffy and overly formal, and I didn’t have a whole lot of luck until I discovered the golden rule.

The Golden Rule: “Keep it simple, stupid.”

Y’all know I love me some Judge Judy, and this quip of hers is one of my favorites.

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My main piece of advice for writing a good Upwork proposal is not to overcomplicate it. As long as you pay attention and keep it relevant, you have a decent shot at getting the job.

Upwork proposal writing tip #1: Don’t tell the client your whole freelance story.

You graduated from The University of Hard Knocks summa cum laude? Congrats! But that info is (or should be) available on your profile already.

Your article was published in The New York Times? Fantastic! But that fancy feature should be included in your portfolio.

You’ve made $50k on Upwork? Brilliant! But — you guessed it — that info is on your profile.

Which leads me to my next Upwork proposal writing tip.

Upwork proposal writing tip #2: Refer, refer, refer.

Think of your proposal like clickbait. It should be attractive and engaging enough to make your client click on your profile.

Instead of info-dumping a bunch of qualifications and experience right in your job application, refer the client to your Upwork profile to learn more about your experience.

But before you encourage that client to peruse your profile, make sure your Upwork bio is up to scratch! Check out the first post in my #UpgradeYourUpwork series: how to write an Upwork profile bio.

Upwork proposal writing tip #3: Keep it relevant.

It’s easy to say keep it short and sweet, but that’s not the best advice for freelance writing newbies on Upwork.

Instead, keep it relevant. Only mention experience and qualifications which will increase your chances of getting the job.

For example, if you’re applying for a contract in the IT niche, you might not want to mention the time you spent writing for that comic book blog.

Upwork proposal writing tip #4: Pay attention to the job ad.

As a content editor who manages her own team of writers, I’ve reviewed dozens of Upwork proposals and made important hiring decisions based on them.

So please listen to me when I say read the job ad at least three times before sending off that proposal!

Many job ads include special instructions. One ad I applied for asked to include the word “Banana” at the start to prove I read the whole thing. (I got that job partly because I followed directions.)

Upwork proposal writing tip #5: Address the client/company by name (if available).

Upwork doesn’t always show the name of the client on job ads, but some clients include their own name or the company’s name at the bottom of the ad.

If that information is included, use it to your advantage.

Let’s say you’re a client on Upwork looking for a top-rated writer to join your team. Which of the following greetings sounds most appealing to you?

  • To Whom It May Concern:
  • To the crew at Influence Innovations:
  • [no greeting at all]

If you’re like me, you’d choose greeting #2, because it’s personalized and proved that the freelancer paid attention.

(You’d be surprised how far that gets you in the freelance world.)

Another Upwork proposal writing tip? Keep it friendly and casual. After all, your client is a person, not a brand, logo, or company. (But we’ll talk more about communicating with Upwork clients in another post.)


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When writing your Upwork proposal, remember the golden rule: keep it simple. I wish someone had told me this when I started out on Upwork — I could’ve saved so much time and effort!

Now that you know how to write an Upwork proposal that gets the gig, stay tuned for the final leg of our Upwork freelancing journey: how to communicate with clients on Upwork!

Not ready for that step yet? Got more questions about how to write a winning Upwork proposal? You know what to do, my freelancin’ friend. Drop them comments like they’re hot.

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