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February 09, 2018

Freelancing can be intimidating. The landscape is broad and as a result, it can be difficult to find your niche within it.

On one end, there are full-time freelancing gurus like Ramit Sethi. They’ve hustled to a point where they can command rates that sound like a startup’s earnings report.

Conversely, there are people who have a full-time job and just freelance for fun. They might have an Etsypage. They’ll shoot the occasional weekend wedding. Or they’ll design and sell custom cards for the holiday season.

While it’s easy to find people on either end of the spectrum, that leaves a large gap in the middle. So what about people who want to make a modest, but consistent living from freelancing?


The other day, a friend on Facebook asked about how to get started freelancing on Upwork. He just set up an account and asked for some tips.



Here’s where I come in.

In August, I left my full-time role as a digital marketer to take on independent contracting work (I also went to Mexico). I don’t have an agency background or a massive database of contacts. I haven’t even been in the workforce very long. So despite my initial motivation, I had the creeping concern I was in over my head.

Using Upwork however, gave me a good foundation. It took me time to develop a system. But, by grinding out proposals and keeping a strict schedule, my workload picked up.


Here are a few things I learned along the way. I’ve thought about this A LOT and delayed writing this article for weeks because it just kept getting longer.

These tips involve some Upwork-specific content. But, very little of this is exclusive to Upwork. So, pick and choose what works for you. I’m sure at least one of these will help you step up your game and eventually land that dream project.

Tip 1: Don’t stand out from the competition — avoid it entirely. Upwork has a number of helpful features. One simple yet unique feature is the competition metric.

If you like the looks of a job, and you want to apply, check how many others have applied first. Under ‘Activity on this job’ Upwork provides an estimate of submitted proposals. Are there more than 5 to 10 proposals? Move along.


It’s not worth your time to compete, especially if you haven’t built a reputation yet on the site. Unless you’re 110% confident in your qualifications, it’s best to pick your battles. And you can pick wisely by sticking to the ones you can win.

Tip 2: Find a niche, even if it’s not your niche yet. My background as a digital marketer is pretty general. Sure, I have some specialties. My day-to-day involved PPC, social media advertising, email marketing, and website management. But compared to people who spend time on just a fraction of those activities, I’m a generalist. Some people need marketing generalists. But more often than not, you can further skirt competition if you have a specialized skill. In my case, I leveraged my familiarity with MailChimp.



I wouldn’t say I’m an ‘expert’ but I certainly know more than most people.

I’ve learned quite a bit by picking around and I’m confident in my ability to learn things as I go.

Note: DO NOT falsely tell clients you can do something and then charge them for it. However, as long as you are transparent about the amount of time you expect to take, it doesn’t matter if you’re an expert. There’s nothing wrong with taking on a challenge.

This means you’re not only getting paid to work as a freelancer, you’re also getting paid to learn and grow. While I chose MailChimp, you can do the same thing with WordPress, Squarespace, Adobe Creative Suite, or any other platform you can think of. The key is to be specific.

Tip 3: Sell yourself with ‘pizzazz’. You don’t need to take a ton of time on each individual proposal. Instead, invest in a few pieces of evergreen material. My go-to’s include:

  • a cover letter/proposal template;
  • three distinct images that show past projects;
  • a custom website on Squarespace.


Always take time to understand individual clients’ problems. But don’t reinvent the wheel every time you apply for a gig!

Test a few sales scripts. Stick with what works and ditch what doesn’t. If nothing else, you’ll establish a good foundation that allows you to apply to a high volume of jobs.

Each piece of evergreen material will exponentially improve your appearance to others. For other tips on re-thinking how to sell yourself, check this out.

Tip 4: Speaking of maintaining momentum… don’t give up. In other words, keep proposing, closing contracts, and completing jobs successfully. Although you have a limited number of ‘Connects’, they do not roll over; so if you’re not using every single one each month, you’re leaving money on the table.



This is easier said than done. Nevertheless, one good way to start out is to pursue quick and easy jobs. Do things below your pay-grade (in terms of money and experience). There’s no shame in it.

If people are suspicious, be authentic. Tell them that you’re looking to build a reputation above all else and that you’re excited for an opportunity to create value for them. Finding these high urgency/low skill jobs can be a great way to build a reputation quickly. By getting hours worked + positive reviews under your belt, you’ll be more prepared to land ‘big fish’ gigs later on.

Tip 5: Create value upfront. I’ve already mentioned the value in taking high urgency/low skill jobs. Beyond that, you can impress clients by offering a discount. For example, offer a 15%, 20%, or even 50% discount on their listed rate. Say something like this:

I see a lot of potential for work together in the future. I’d be happy to take care of this for 25% off your listed price as an opportunity to show you my quality of work. Would you be willing to take me on with the expectation that would we could collaborate more in the future?

Hell, you can even work for free if you think it’s worthwhile. You’ll have to do that outside of Upwork, but plenty of people have used free work to their advantage.

Tip 6: Don’t just sell clients on vague opportunities. Identify ways to create future value. Getting a client to like and trust you is valuable. But don’t use that to ‘make up’ unnecessary projects.

As you do work, you’ll inevitably notice other parts of the client’s business. Many of these parts could use improvement.

For that reason, I keep a running Google Doc which contains what I’ve done and things I would do if I had more time. This includes notes on how to improve a client’s systems and processes in the future. That way, you’ll maintain an efficient pace on the project at hand; but you’ll also have documentation to refer to later.

Once you complete a deliverable, let your client know what you noticed. See what they think and if they too see it as a problem, offer a solution. If you’ve demonstrated value and identified a real client need, they’ll be happy to give you more work!

Tip 7: Cover your ass. Of course, you want to establish your credibility with others. You have something to prove. But sometimes when you’re hunting around for odd jobs, you’ll come across some sketchy situations. These scenarios can range from slight exploitation to outright fraud. Keep an eye out for red flags including very low competition; vague descriptions; an unwillingness to answer easy questions; lacking work history; nonexistent digital footprint; etc.

Don’t forget that you need to trust your client as much as they need to trust you.

A Disclaimer, A Conclusion, and A Send-off

I should be clear. I am no freelancing guru. But by getting my feet wet these last few months, this is the best advice I can offer. These strategies have saved me time and made me money.

If you want to check out some other folks who I’ve learned from here are 3 quick recommendations:

1. Ramit Sethi, as I mentioned earlier, is the internet’s resident expert on freelancing. His website, videos, and courses are extremely valuable. This podcast, “How Creatives Should Negotiate” is a great place to start.
2. DestinyLalane, is full of crazy stories and great advice on freelancing and personal branding. She has some great material on her website here. Fun Fact: we also went to high school together.
3. Derek Magill is Director of Marketing at Praxis. He writes, speaks, and demonstrates a great way to get the attention of clients and employers. A lot of his content is relevant to this article, but the best place to start for beginners is his Ebook, How to Get Any Jobyou Want.

Freelancing will cause you headaches, but it can also bring a sense of fulfillment you’ve probably never experienced. If you have any questions, respond below or contact me personally.

Recommends are cool. But I’d be much more excited if this gets you results. So if you have a story about how any of these tips changed the way you do things, I’d love to hear it.

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