Getting Lucky on Upwork

Early success on any platform relies on two factors –


You can go online and learn about succeeding on any platform.

But generally speaking, the advice shared does not emphasize this outcome:

Getting your first gig, is all about getting lucky – there, I said it.

But people don’t understand luck.
Think they can’t change luck.

The simple fact is that one needs
To prepare better, execute better
To be more ‘available’
To get struck, by luck.

Here are my (ugh I know it’s a listicle   – I am sorry) tips to succeed on Upwork:


1  –  Start with 3 profiles
On Upwork, you have a general profile, + you can set up two additional.

Use them to your advantage, it will improve your discoverability and give you more flexibility when applying to jobs.

Just make sure these profiles are not duplicates of each other and add on to your offering, not cannibalize it.

2   – Get off-platform testimonials
On your profile and in your cover letters, include endorsements from other platforms, getting some LinkedIn endos are an excellent way to get started, ask your past coworkers/employers.

3   – Don’t have templates, Have Blocks
I do not recommend using a template for your cover letters, instead what I will say is to have ‘blocks’ of text ready to swap in and out to your proposal as you apply, blocks like:
– Project History
– Client Testimonials
– Skillset or Tool

4   – Make a loom intro video
Yes videos are being abused by everyone, everyone that is doing well   – you know who doesn’t have a loom video in their proposal? Probably you   – so get comfortable, record a 2 minute general video going over your skill set. Do a custom one for jobs you love.


1   – Learn to search for the right jobs
You can use boolean operators on Upwork advanced search (Mind blown? Maybe?)
Make use of ‘Saved Searches’ feature and prep 3 -4 feeds for work that matters to you.

2   – Balance connect spend, optimize for stats
Yes every platform wants money now, no more VC money to burn, boo hoo, guess who gets to pay? You do, yes you.

But don’t fret, connects are still cheap, and if people don’t wanna buy them, less competition for you, right?
The number 1 goal should be to get viewed when starting out, not get hired.
Learn to track stats   – aim to get 5 views on 20 proposals consistently.

3  – Learn to write hooks
The first 3 lines of your cover letter is all that matters when you are a newbie, no other stats exist to convince the poster, work on your hooks, make them better, and make them stand out. Get a nice headshot too, that is a bonus.

4   – Keep At It
Sounds cliche but it works, the best way to get better at everything above is to keep applying, and keep optimizing   – untill you land that big first client –

Then you can also claim you got ‘lucky’

If you do all this, will you get your first job? Not sure
But are you more likely to get it faster? Definitely

Keep Applying!

Getting value from what you see? A sub ensures that the content keeps flowing.
All efforts on SK NEXUS are passion led – the best way to keep the show running is by showing up. Thank you!