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Yes. $500,000 just working on my laptop and clicking buttons from all over the world.



If you think that freelancing could be a real career move for you or members in your family, check out my profile, so you can see that I’m talking the talk and more importantly, walking the walk.

I finally reached a couple of crazy milestones that I set for myself when I originally joined as a freelancer.

Here’s a few of them below…

  1. Increased my rate to 500/hr (Complete)
  2. Made over half a million (Complete)
  3. Became Top Rated (Complete)
  4. Have over 100 clients (Complete)
  5. Become THE top earner on Upwork (Pending)

I’m not trying to rub this in your face. I’m actually just impressed with myself that the goals I’ve set for myself have mostly been completed. I can’t stress enough how important creating goals and then a system to achieve those goals is to the process of growth, but I’ll get into that later, or in a separate post.

In this post, I want to talk about exactly what lead me to make half a million through Upwork, and how I stay pretty stress-free while earning that.

Honestly, it certainly doesn’t feel like I even have a job sometimes. l pretty much wake up when I want (or until the new baby allows us to rest) and I start working after I’ve given myself some me time, usually consisting of a beach run/walk (mostly walk) with Puffin the dog. I also love to watch the Today Show for some reason, so I feel like I’m in the know.

Life was a lot more stressful before Upwork….

Earning and Learning has been a major commitment I chose to pursue a couple of years ago, after failing with my own businesses and being smashed and squooshed by an immense amount of debt and compounding interest.

I’m sure I’ve discussed this at length in my Quora discussions and on other blogs, but here’s a quick summary…

  • My father urged me to declare bankruptcy.

  • I owed my friends a ton of money.

  • I owed several banks a ton of money.

  • I had a crazy amount of personal and business credit card debt.

  • I had zero savings.

  • I blew my 401k on an app.

I basically didn’t have 2 coins to rub together and the job that I was currently working, to make ends meet, went out of business because of a squabble between the owners of the business.

Oh, and to top it all off, my landlord was going to knock my apartment down because he sold it to a private equity group that wanted to build new condos.

To make it even better, I fell for a girl from Belgium. Yes THAT Belgium. How in the world was this relationship going to work? After all, my ONLY source of income was Unemployment. How much can you do with 600/week? Not much at all.

I knew that I was tired of being a victim of circumstance and that I needed to control my own destiny. Basically, I needed to stop being a wuss.

I remember the day as clearly as any…

There was this beautiful Southern California day with the sun pouring in through my temporary apartment and I knew it was a special day.

I rearranged my room and shot this video below:

It was time to do work. I knew I had experience and I’ve worked with enough people in this field to make an impact. It was go time!

Even though it looks ridiculous, that video was one of the best things I’ve ever done.

So that’s just the start. I broke out the top things I do in the list below. I’ll continue to get deeper with each, and will probably make a separate little mini blog to support each one.

Here’s the list

1. Make a video

Like I mentioned earlier, this was by far my best move when breaking into the scene.

Having a video definitely gave me an edge by allowing the potential clients to get to know me before they even got on the phone. This was like eliminating first dates. By the time we did get on the phone, we were already looking to get to second base.

2. Build a hefty profile

Many people think they should keep their profiles short and sweet. Bull! You were fortunate enough to get someone to visit your page. Why are you in such a hurry to get them off the page and look at other freelancers?

You should make your profile as long as you need. The more content that’s on there, the more the potential client is going to learn about you. Of course, if it’s boring, they can bounce and check out others, but leave that up to them.

I can guarantee that if it’s super short, they’re going to check out other freelancers anyway.

The other goal is to come up in search. This means you want to fill your profile with as many keywords as possible without getting weird. Now when people post jobs using the same keyword as you mentioned, you’ll start to pop up more on potential clients’ feeds for their job posts. Exposure, baby!

3. Take a job you can bang out in under 1 hour.

This is absolutely essential when getting started. You NEED reviews, and that’s going to significantly help with your social proof and build your authority in the space. In order to quickly receive your first few reviews, you can’t sink your teeth in huge projects right away. You need to dial it back and take on things you can turn around quickly. Sure, it’s cool to make some money quickly, but your primary goal should be to establish relationships and positive reviews.

4. Impress

When doing jobs for people, especially early on, go above and beyond. Most people just complete the perfunctory task at hand instead of ensuring the client is thrilled beyond their expectations. This doesn’t take much effort! It can be as simple as organizing the deliverable nicely, being faster than you originally quoted, and maybe performing an extra task. It really doesn’t take much. And if a client sees you doing this, you will create a relationship for life.

Because no one does that. And once a client finds a freelancer they love, they will never let you go.

5. Get a review or die trying

Once you’ve established a real and good relationship with your client, let them know how important reviews are to your career. 99.99% they are going to hook you up. The only time they won’t is if they suck as humans, or if you butchered the task. If you’ve followed my 1-4, you know there’s little opportunity to completely butcher a job, so make sure you aren’t allowing yourself to be paired with bad clients, who may bamboozle your career.

6. Take an hourly rate that gets you excited

After I rocked out my first gig and received my good feedback, my client asked me if I wanted to consult on a regular basis because he trusted my work.

He asked me what my hourly rate was and I replied back “$45”, which I thought was pretty awesome at the time since it was approximately 3 times more than I was paying myself when I worked at my restaurant.

And instead of smelling like a falafel, I was able to just turn on my computer, from any part of the world, and start earning money.

7. Give yourself a raise

Life is a game. And you should gamify your income to make it exciting. I often hear from my peers that they may receive a raise this year. And usually, it’s a raise of like 10-20k annually. Now let’s do some quick math.

$20,000 extra per year.
40 Hours you work every week.
There are 52 weeks in a year, of which 50 you work after vacation time.

So that’s 2,000 hours a year you’re working.

Which means that your raise is approximately $10/hr. AND THAT”S BEFORE TAXES.

What a joke.

You work your butt off for like 2 or 3 years only to get an extra $10/hr.

Since Upwork, I started at $45/hr. Went to $60hr in a month or two. To $75. To $87. To $97. To $150. To $197. To $225. To $250. To $297. To $375. And now I’m at $500.

Basically, after I complete a bunch of jobs, learn more, and feel like I have more value, I give myself a raise. It makes it fun. And for the first time, I feel like I make what I deserve.

8. Stop caring about the fees

So many people complain about the fees. I’ve probably paid over $100k in fees to Upwork at this point. Even more when you consider the agency and businesses I run through Upwork. Do you think I let it get me down? Of course not! And you shouldn’t too.

You’re finding clients for free and using their platform which allows a much more streamlined and efficient billing tool that helps you make a tremendous amount of money.

Bake the fees into your hourly price and stop making it an issue. Don’t ever try and pull clients off the site and get paid through PayPal or some other direct method. This is a really stupid mistake and will most likely get you banned.

You want Upwork to see that you’re making money. They are in business too, so if they see you’re killing it they’ll throw you at more jobs because they trust you’ll make clients happy. This is how they get paid. Don’t mess with their money and they won’t mess with yours. Treat them like a partner, not a necessary evil that you need to put up with. Every person that I’ve ever met from Upwork wants relationships to grow and for everyone to be happy.

9. Stick with it

One of the single biggest complaints I have when hiring my own freelancers, and also from what I hear from my clients, is that people are flaky and shifty as hell. They don’t say what they’re going to do, and they don’t stick with a project. They just let it go and stop communicating. What a horrible mistake. Don’t let this be you, because you’ll get destroyed with a bad score and it will be a huge uphill battle to compete for jobs in the future.

If you take on a job. Give it your goal. And if it’s clearly not going to work, a little bit of honesty goes a long way. Especially when dealing with clients that you’ve established a good core relationship with. Again – check out 1-4, where we go through those areas on relationship management.

10. Repeat

Rome wasn’t built in a day. If you wish to work from home, Rome, or anywhere else that’s not your boss’s office, you need to repeat this system over and over. I spent a lot of time working for my clients and I give it my all when working with them. I treat every project like my own, and that’s why people are willing to pay a premium. It’s much more expensive to pay two or 3 mediocre people that set the project back than one person that can hit the ground running and knock it out quickly.

Once you start getting in the habit of surpassing your clients’ expectations, you’ll find the repetitions to be infectious.

Please leave a comment below and let me know if you started or are planning on getting started with Upwork.

I’d love to help you!

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