6 Concrete Steps to Start Your Freelancing Career

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On Tuesday, I gave some pretty strong opinions about traditional office jobs and showed my enormous bias in favour of freelance work.

And a lot of you may have thought: “great, rub it in our faces a little more, don’t worry about actually trying to help us or anything.”

And yeah, I’ve made my preferences clear, and I’ve even written an article on how to function as a freelancer when you’re already there, but I’ve never laid out how to get there.

Well today, I’m here to give you some actionable steps to get your very first freelance job. No motivational fluff. No enlightened swami BS. Just actual advice from someone who’s been there.

Let’s get into it!

1. Take a Gander

When I talk to people about being a freelancer, the first question they ask is always about how I find my clients. Personally, I use the freelancing website Upwork.


Not necessarily because it’s the best, but because Danny Margulies, the person who inspired me to become a freelancer, uses and promotes the site as a good place to do business. And so far, no complaints.

And just so you know, they make their money by taking a chunk of your earnings, but it’s more than worth it to get all those fish in a barrel! I would hate to be spending my days making cold calls instead of actually working.

But, let’s move back a few steps. Before I worked up the nerve to actually contact potential clients, I looked through job posts that piqued my interest on a few freelancing websites to figure out what clients were actually looking for.

That way, I could figure out where my skills met their needs and what I might have to try to improve. When you see people absolutely confounded by things you know how to do with ease, it helps boost your confidence.

It also just helped to know that people were interested in finding freelancers who could do the type of work I was interested in.

Pretty much every friend who has asked for tips has said: “I don’t want to be a writer, I’m passionate about X skill, but I don’t know if there’s a need for that.”

So first, get looking!

But, the rule of thumb is: if it is a skill people get paid for in an office, and there is a way to do it online, you can be a digital freelancer with that skill. End of story.

2. Sharpen Your Skills

Once you know what kinds of skills people are looking for in your field of interest. It’s time to make sure you know how to deliver.

If you’re a complete newbie, don’t worry about it. There are tons of places where you can learn free or cheaply, like Skillshare, Allison, Coursera, and Open 2 Study, just to name a few.

If you’re not about structured learning, you don’t have to go that route. You can just start googling the industry you want to break into and learn as much as you can about it that way.

A word of warning though, it’s really easy to get stuck in this phase. If you’re at all nervous about approaching potential clients, you may never reach a point where you think you know enough to charge for your knowledge.

But here’s the thing. You don’t have to reach a point of expertise on the subject, you just have to be knowledgeable enough to help a client out. And, most clients are on freelancing sites looking for help because:

1. They have no knowledge in that area and;

2. No time or desire to learn.

You, on the other hand, can just keep learning on the go. If you don’t immediately know it, go find out!

So, here’s how to know when you’re done this step. Find a friend who knows of the industry, but doesn’t really know key concepts. If you can teach them 3 or more things they didn’t already know, feel free to move on. Otherwise, read just a little more.

3. Polish Your Online Presence

Now that you have your fancy new knowledge and skills, start letting the world know that you have them. Get on LinkedIn and give it an update. Pick a freelancing site and craft a killer profile!

If you’re curious, here’s mine.  

Make sure your professional profiles are 100% complete. Not only does it look better to clients, most websites will bump you up in their search engine or give you other special goodies for putting in the work.

And take the time to search your name, cause you can bet that at least 90% of the people who find your profile are going to do it.

If you find anything unsavory (I mean we were all stupid teenagers at one point), delete it, ask your friends to delete it, report yourself to the app to get them to scrub it. Do what you can to get rid of it

Not everything will be 100% doable, but if you can make your online presence even marginally more professional, it’s worth the effort.

4. Find a Price You’re Comfortable With

Aside from how to find clients, how to determine your pricing is what I get asked most frequently. I recently heard some advice I loved while listening to a podcast on Gimlet Media…I wish I could remember which one, but I basically listen to podcasts all day while I’m working.

It went like this: stare at yourself in the mirror and start saying ascending numbers from minimum wage until you start laughing. The point where you start to laugh is what you should be charging for your time.

I actually love that, but if it doesn’t quite float your boat, here’s what I did. I took the salary I was already making, roughly calculated it into an hourly wage, and rounded it up slightly. It ended up being $20.

I felt comfortable charging it because someone else had already valued my time there.

Once I got going, I realized I was definitely undercharging for my time, so I raised it to $25. I realized I was still undercharging, so I made it $35. And, I’ll probably raise my rates again in early 2018.

At first, I feared raising my rates, but other than very quick blips of emptiness, I have never had an issue getting clients to pay me more per hour. Because, I know (and they know) that the quality product I offer is making them a hell of a lot more.

So, be confident in your pricing! It’s gonna feel weird for a bit, but you’ll realize you’re worth it.

5. Learn to Craft a Convincing Proposal

First, forget everything anyone’s ever told you about writing a cover letter. This is useless to you now. In my experience, clients want to see a few things:

1. Your personality. So, don’t be stuffy and formal. Instead, be friendly and helpful.

2. That you can do the job. So, give them a few ideas upfront about how you would solve their problem. Be specific!

3. Examples of your work. So, if you don’t have anything to give, create a brief version of something similar to what they’re looking for to prove you have the ability to do what they need.

One resource I ALWAYS recommend to friends is Freelance to Win. This site is by the same guy who I mentioned was my inspiration for getting into freelancing in the first place, and he has some extremely helpful advice.

For help with this step specifically, I recommend reading this article by Danny. I had to adapt his advice slightly for how I operate best, but it was an invaluable starting point for me. I referenced it many times during the first few (dozen) proposals I sent out.

6. Send a LOT of Proposals

When I finally got up the nerve to start sending proposals, it was incredibly discouraging. Freelance websites are heavily based on feedback, so if you’re looking for your first job, it’s gonna be tough!

Luckily (I guess), I was so miserable at my job that the misery of people ignoring my messages or promising me work only to disappear, was less painful than the idea of staying where I was. So, I pushed forward with every fiber of my being.

But, if you’re in that wishy washy middle ground where you’re not 100% sure that freelance is for you, it’s going to be an ego destroying nightmare. Be ready for that, and be patient.

I promise that your resolve will get results!

Here’s an example of my results: Upwork allows you to send out 30 proposals a month. I went from all of them just to get a few jobs for about 4-5 months, to almost never using them because clients consistently come to me for work.

As I’m writing this, I actually got another job invite!


That’s my advice! I’d love to hear what you think about it in the comments below!!

Are you pumped to get started? Did I miss something important? Let me know!

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