#UpworkSuccess Is Real: 10 Things I Learned After Submitting More Than 500 Upwork Job Proposals

#UpworkSuccess Is Real: 10 Things I Learned After Submitting More Than 500 Upwork Job Proposals

The unprecedented number of people who lost their jobs in 2020 was astounding.

We all know the culprit. Covid. I had issues myself, my problems were personal though (i.e. health anxiety, stress, frustration, loneliness, etc).

But unlike Joe across the street, I didn't whine for months on end. Not that I enjoyed any part of the lockdown and my son not being able to visit Grandma, but the lockdown ended up presenting me with time to reset my mind - and most importantly exercise my creativity as pertains to generating some income online.

We all know that the transition from a regular day job to something totally new online can pose a daunting challenge to anyone...

But one bold, distinctive and open conversation with an old partner from across the continent about my situation quickly changed everything for me. He’s a creative head who wants to one day own the world. Literally. He runs a digital marketing agency with a dozen freelancers working under him. It was easy and straightforward for me since we had interacted professionally before.

With a team relying on me and literally tens of mouths to feed, I knew I had to put my best foot forward. I did. And so far it's been an amazing success story...

The following is an honest breakdown of some of the most practical lessons I’ve learned after submitting more than 500 job proposals on Upwork:

1. Brevity is Key

Your client is probably someone busy running their business. They do not have time for fluff. They don't have all the time in the world to read hundreds of words of your pitch.

When submitting your proposal, make it brief, personalized, and punchy. Show what you can do for them. Tell them little about yourself and more about their business. Tell them exactly how you will solve their problem without too much fluff.

2. Clients Love it When You Refer To Them By Their Name

What better way to show someone you care about them than to call them by their name when shaking their hands?

It also applies when submitting job proposals on Upwork!

But how do you know the name of a client you have really never met? To hack this, I employed a rather nice trick...

To get their name, simply scroll to the bottom of the project page. You will see reviews from past projects they have hired before. When giving a review most freelancers call the client by their name and that is your chance to grab it and use it!

I found this specifically really powerful as it shows that you really ‘care’ about that person. When you refer to them by their name they are more inclined to respond to you. And in such a competitive environment as Upwork, a response from a client could be the start of something big if you handle the communication well…

3. Ask Questions - This is Key

After writing tens of proposals and not getting a single response, I finally decided to try something different. Instead of jumping to the fluff of how I was experienced in this and that, I decided to go directly to the point and float a question to the client about their project which would consequently help me better understand their requirements.

The results were simply magical! Three out of five proposals I wrote got a response -- on average.

The trick here is to initiate a conversation. Once a conversation is going, you have a better chance of demonstrating your skills to your prospect.

4. Clients Do Not Always Care About How Much They Are Paying You - They Care About Value and Results

On my way to bidding for more than 500 jobs on Upwork, I discovered that many clients have not really decided or settled on how much to pay the right freelancers.

Unless someone has been subcontracted and given strict instructions, which is rare, most clients have an open budget.

Surprisingly, many clients will even push away freelancers who bid very low under the assumption that they will not offer them quality!

So what does this mean for you when placing your bid? Do not at all care about pricing. Float a genuine bid with a clear strategy on how you intend to add value.

And sit and wait for work!

5. A Little Effort Goes A Long Way

In such a competitive platform like Upwork, generic bids won't win you anything.

They will just waste your time and connects.

But if you go a step further and add a little effort and thought to your bid, your client will not have an option but to hire you - Immediately!

I’ve had so much success by just going a step further and creating a simple Google drive document and sharing it with my clients that I’ve made it a habit.

A practical example of how and when to go about this is when for example a tire manufacturing company is looking for someone to craft the taglines for their brand. In this case, I quickly create a Google document and spin out two of them and share it with them in my proposal and let them know that if they give me a chance to work with them, I will push the list to 10 and they can choose the tagline they love the most from that list.

I actually did this, and in this case, specifically, the client was driving and after seeing the effort I had put in all this without even winning the project, they pulled over and hired me immediately. Needless to say, I got the job, bagged a few hundred dollars for just writing a few taglines - and got the bigger job which was to rewrite their website content for $1200.

Not a bad pay-day for a little effort if you ask me.

[ Hint - I usually give the document the name of the client or the name of the business to make them feel more at home and send the message that I was thoughtful about them. Try it - you will crush it with this one tactic alone! ]

6. Bid Immediately When a Job Is Posted

One of the most practical things you will learn today is to place your bid early. I tried all the tricks in the book but I found this one to be really forthcoming. You want results. You want to win that job. Throw out your job proposal an hour or less after it's posted on your feed. Do not overthink it. Just do it.

You stand a higher chance of getting a response from your client when they see your bid and they are online than after a week when they posted and went on vacation or have found out other alternatives.

Simply bid early, strike the nail when it's still hot - or don't waste your time and connects!

7. Show Character and Attitude - This Will Open Doors For You

I noticed that the reason many freelancers do not nail projects on Upwork is because they are begging.

You are skilled and you can add value. Show that with your words when placing your bid. Do not use words that shout desperation. Your client is not a ‘sir’ or a ‘dear’.

Just keep it simple and professional. They want to know you have a life and you value your skills and you are not begging for survival.

8. Stories. Sell. Anything!

Listen, do not be afraid to get creative with your pitches on Upwork. I have tried it and seen results. Very positive results.

You see, clients want to hire, but they are also tired of the old and boring proposals.

Change that narrative.

Tell stories. But I know you are already asking how...well, tell stories about your past success with clients. Simple. They will totally love it. It's unsolicited social proof, but it works.

Be careful about this because clients will ask for proof. And from my experience, if you can provide it, you already have the job!

I ran into this trick by accident - but I am able to nail hundreds of highly competitive and well-paying jobs on Upwork without even a complete profile or any elaborate portfolio to show. I let my story be my portfolio. And it always works!

9. Criticize - But Be Smart About It

Most people are looking for ways to improve their businesses.

This means that most types of input are welcome - Especially if it helps them move forward. And as a freelancer, they look at you as an expert and trust your word.

You can always make use of this by telling them about what is missing in their business. This works if the client provides some information about their business or even better includes a link to their website in the project requirements.

For example, you can view the website and tell them something about it which you think you can/they improve.

10. Follow-up - But Do Not Nag!

Lastly, remember to always follow up whenever you get a chance with your clients.

The fact is that clients are busy. They will post a job and forget about it. Sometimes it pays to nudge them and remind them about your discussion with a message.

Remember that as a freelancer you are a participant in a race. Resilience is key. Following up is the only card you have. Don't be shy to throw it into play. But be careful, be professional, and do not nag your client.


Word has it that the average time for a client to hire on Upwork is 3 days. But I think that is just the time the client takes to sort out the fluff.

The tips shared above gives you a chance to stand out and get hired immediately. I've put these into use and seen a single-paragraph job proposal knock out 48 of my competitors, and I nailed the job.

Remember that there is a cut-throating competition on Upwork. There are millions of highly skilled freelancers out there (some honestly better than you) - so it's all about the tactic you use to get that job.
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