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Laura Pennington – Guide to Killing It On Upwork as a New Freelancer
Everything you need to know to win jobs on Upwork!
Let’s take a trip back to 2012.
I was driving ninety minutes each way to the middle school deep in the heart of Baltimore where I taught. The kids were hard. The supplies were non existent. The system was convoluted and inefficient. Needless to say, I was burned out.
With a master’s degree and smack in the middle of my pursuit of a PhD, I didn’t want to teach anymore. I was left with a question that seemed impossible to answer: What now?
(My old classroom, circa 2011. These were the only students out of 110 who behaved well enough to have a guest speaker in the classroom.)
Then, the Navy placed my boyfriend on leave without pay for three months before he ed his internship. Suddenly, we were a one income family and it all fell on me. What ed as a Google search for “How to become a freelance writer” grew into an amazing online business. I left my teaching job and accepted another position while I figured out what was next.
In the year that followed, I:
- Became a success story featured on the Elance.com homepage
- Worked with over 100 clients
- Got my first $50,000 contract
- Met and surpassed my monthly day job income
Elance actually sent me on a trip to do a photo shoot across Washington, D.C. This picture was on their homepage for three years and it was taken just three months after I got ed as a freelancer.
Not to sound cheesy, but freelancing really changed my life.
It got me out of a rut. It helped me heal emotionally from a series of dead end jobs. It allowed me to work with some incredible clients like TrueCar and Microsoft and learn some amazing things from them.
I even had my cold pitch to write on Business Insider accepted instantly – thanks to my freelance story.
What if YOU were making an extra $500/month on jobs you won on Upwork?
- Would you pay down your debt?
- Would you be able to cover the bills?
- Would you be able to save for a great vacation?
- Would you working towards leaving your full-time job, just like I did?
This is why I’m so passionate about helping other people find their freelance voice and turn it into a marketable skill that brings them recurring revenue from premium clients.
The easiest way to get your foot in the door as a freelancer and to convince people that it’s really possible is using online job board sites and in particular, Upwork. Since clients are already pre-sold on needing a freelancer, you’re more likely to book them quickly. Your clients often know what they want and give clear instructions. And many of these same clients can be converted into ongoing work.
One pattern I’ve noticed among wannabe freelancers though, is that they find the process of getting ed overwhelming. They might be bidding on jobs at Upwork, but they’re not winning. They don’t know what they need to fix, often asking questions like:
- Am I charging too much?
- Is my lack of feedback on Upwork hurting me?
- Am I bidding on the wrong jobs?
- Is my profile inviting business or not?
- Does my pitch suck?
I get it because I’ve been there.
That’s why I took everything I learned in 4+ years working on Elance/Upwork and put it into one course.
If you’re ready to make money, hustle, and get away from that soul-sucking job you hate, now is the time.
Are you ready to your freelance career but feel overwhelmed with all the tech setup?
You know Upwork has the clients you want to work with – but you don’t know how to get noticed.
If you’ve ever used a freelance job board or service before, you know it can be challenging to:
- Find the right jobs for you, while not getting lost in the array of bad opportunities
- Set up your profile for maximum visibility and success
- Get the ball rolling with a new client to increase your chances of getting paid and having repeat relationships
- Discover which clients are the ones to avoid
- Figure out how to deal with problems like unreasonable clients or disputes
But it is possible for you to make a killing on the site if you follow my strategies!
You just need a little guidance on how to set up your profile to stand out in the crowded freelance market, identify good and bad leads, and work with clients effectively so that they keep coming back for more.
And that’s where I come in.
If you’re thinking that there’s no way you can pull this off as a totally new freelancer or Upworker, you’re wrong. Let my story show you just how you can go from zero to hero pretty quickly.
This course is for you if…
- You’re totally new to Upwork
- You’re an established freelancer but never had much success on Upwork
- You’re bidding on Upwork but not getting any bites
- You’ve never landed a job on Upwork.
This course is NOT for you if:
- You’re not willing to do the work
- You’re not critical or self-reflective at all (If you tell me your profile, pitch, work, and process are all perfect yet you’re not booking business… there’s a problem.)
- You’re already making six figures on Upwork.
Your Instructor
I’m Laura Pennington, a 5-year veteran of the freelance market.
In this course, I take you by the hand and show you step-by-step how to create your profile to show up in client searches, write proposals that get noticed, and wow your clients so you can build referrals and testimonials.
These are the exact same steps I used to match my full-time income just three months after joining Elance. And now that they have merged with Odesk, the possibilities for you on Upwork are endless, once you get it set up correctly.
Course Curriculum
- Module 1: For Upwork Newbies: Basics of the Site (47:42)
- Module 2: Membership on Upwork (4:18)
- Module 2: Understanding Upwork’s Freelancer Violations & How to Avoid Them (4:34)
- Understanding the Fees You Pay to Upwork Per Project (5:19)
- Freelancer Violations- Taking Work Off the Platform (5:07)
- Module 3: Upwork Profile Details (7:21)
- Module 4: 3 Ways to Win Jobs on Upwork (4:03)
- The #1 Way to Land Your First Job on Upwork
- Module 5: Why Denying Invites is a Must-Do (2:04)
- Module 6: The Makeup of a Winning Proposal (57:26)
- Module 7: Managing Client Relationships (14:23)
- Module 8: How to Search to Find the Right Jobs (9:49) (9:55)
- Module 9: What is a Hidden Proposal and Why Should I Care? (6:21)
- Module 10: Laura’s Upwork Proposal Walk Through (6:42)
- Module 11: Doing Some Research to Determine Why Your Proposal Might Have Been Declined (2:54)
- Behind the Scenes: What Clients See When Creating Jobs (4:39)
- Behind the Scenes Analysis: Good vs. Bad Proposals (6:26)
- A Deep Dive Into Disputes on Upwork (8:36)
- Clients to Avoid (7:53)
- Your Final Checklist
- Income Calculator for Freelancers
- 5 Killer Upwork Proposal Templates That Highlight Your Strengths
- Bonus Upwork Proposal Templates for General & Tech VA Gigs
- Quoting with the Service Fee on Upwork (3:49)
- Crush the Discovery Call – A Guide & Sample Script
- What to Do After You Complete an Upwork Gig?
- Spotting a Scam Job on Upwork (1:39)
Proof Content

Sale Page: https://laurapennington.teachable.com/p/guide-to-killing-it-on-upwork-as-a-new-freelancer
Archive: https://archive.ph/wip/cFuir
Delivery Method
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