Scratching your head why you have not landed your first freelancing job yet? Ask these 5 freelancing questions first and get the proper head start to an awesome work at home gig. 


You’re ready to take the plunge.

You’ve heard of stories, read about successful freelancers making a killing working from home.

You want to get in on the action.


Before you quit your job though (which I advise you don’t do yet), it’s crucial to set a road map for yourself, like a good old recipe guiding your first steps to becoming a freelancer.

Being a freelancer is not for everyone. You should be very honest with yourself and ask if it’s something you really want. The idea of working without a regular paycheck is enough to rattle most people. Let alone experience it on daily basis.

So what am I saying? Am I dissuading you against freelancing?

Absolutely not.

What I want is for you to have a clear vision first of what you want to get out of freelancing, instead of jumping on board ASAP and figuring out your way as you go. While that might work, personal experience taught me that having a road map is essential to freelancing success.

Question #1: What skills can I use in Freelancing?

Legendary copywriter Gary Halbert once wrote, “Money, especially big money, is a product of enthusiasm.”

You should do stuff that you love doing because that’s what’s going to make you money. So don’t go around learning how to code if your passion is in writing, just because you hear that’s where the money is. Don’t try to force yourself into doing stuff that don’t excite you at all.

Freelancing Questions

Do you think we’ll be scrolling on our Facebook feeds right now if Mark Zuckerberg forced himself to become an architect? I wouldn’t be able to type this if it wasn’t for Bill Gates coming up with Microsoft Windows.

What do you think would’ve happened if Bill tried his hand on body building instead? Maybe he thought Arnold Schwarzenegger was raking in big bucks back then and realized that’s where the money is.

Though it would fun to see a hulking Bill Gates smash real windows with his biceps, I’d take the one who gave us MS Windows any day. Because I don’t think advancements in technology would have been possible without him.

Now that you and I agree (I hope) that passion is an excellent compass in pointing to the right freelancing direction, it’s now time to identify which ones will prove the most viable.

Make a list of your talent and skills

Let’s go old school and pull out a piece of pen and paper. Get in a quiet place, sit down, and start to think about stuff that you’re really good at. Be honest! And don’t be shy. It’s important to be genuine with your answers.

Write down “I’m good at giving baths to my dog” if that’s your thing. Heck, I’ll write down “I’m a champ at washing dishes” if I was to do it. Because I really am! Hand over those dirty plates and glasses and I’ll turn them into squeaky clean pieces of art ready for display at the mall’s “Kitchen and Dining” area.

The point of this exercise is to come up with a laundry list of actual skills that you use on the daily. Nevermind coming up with some silly ones. We just need to get your brain juices flowing to get to some pretty good answers. Once you’re done, I promise you’ll have at least 1-3 things that you can honestly identify as freelance-able skills.

Here are some excellent questions to guide you in this exercise:

  • What activities excite you?
  • When you were younger, which skills did you use the most?
  • Which activities make you feel strong?
  • What types of compliments do you usually receive from others?

Question #2: Where and how can I get my first client as a Freelancer?

Let’s start with the most popular one: UpWork

Why do I recommend it? Because it’s the biggest online talent marketplace that allows you to bid on jobs. Also, you can use it for “research” to look at job posting descriptions and get a feel of what clients are looking for in your niche. Since UpWork is the largest of its kind, you can use it to check winning contractor profiles and use them as guides on how to structure your own. Cool, huh? See below for a couple of more website suggestions.

Other Popular Freelancing Sites for Beginners 2018

Freelancer – Another popular freelancing platform with a huge marketbase.

OnlineJobs.PH – A top local talent hub linking Filipino talent with clients worldwide.

Fiverr – Reached global recognition thanks to their $5-jobs that ranges from professional to odd ones. They also introduced the “Hourly” format that serves as a pre-paid number of hours package for completing a task.

People Per Hour – Uses the same “Hourly” format as Fiverr.

Guru – A smaller site compared to others on this list in terms of users but still a good one to check out for specific tasks.

Want to check out more freelancing sites? This article I’ve written for Grit.PH lists down the top 20 sites to look for remote jobs.

Lists of Popular Jobs offered in Freelancing websites

To give you an idea of the range and scope of these talent marketplaces, here’s a table of the most popular ones:

Virtual Assistant App Developer Web Designer & Developer Web Content Writer/Producer
Digital Marketer Software Engineer Marketing Specialist Customer Service Representative
Web Content Manager/Editor Systems Engineer Video Producer/Editor Online Tutor
Client Services Specialist Technical Writer Copywriter Sales Account Executive
Business Analyst Quality Analyst Virtual Assistant Graphic Artist/Designer

Related: How to become a Virtual Assistant

Question #3: What tools and resources can I use to help me with Freelancing?

I strongly recommend you check out these sites for tips and suggestions on how to become good at freelancing. Combined, these sites offer hundreds of broad and niche-specific guides that will help you improve your skills as a freelancer. Also, if you chose copywriting as your freelance skill, you can learn a lot from reading each article’s style and format. Trust me, you’ll find gems in here.

Top 5 Blogs about Freelancing



The Freelancer by Contently


Double Your Freelancing

Question #4: Do you see Freelancing as something you can do in the long term? Is it sustainable?

As you get more used to doing freelance work, either one of two things can happen:

  1. You love freelancing and can see yourself doing it full time
  2. You have a hard time completing jobs and tasks. It’s hard.

If you answer number 1, then good for you. Clearly you have a good shot at doing this full-time. It brings us back to our first exercise, which was to identify that thing you love to do. Me, for example, I love to write. I’ll write even if I don’t get paid. Why else would I be writing this 2,200+ word article if I didn’t like it? Sometimes you just have to write stuff down for yourself, but even better if your goal is to help others. Which is what I hope to do here.

Here’s a true story as proof that I love to write simply for the heck of it and  as a way to help others out. In 2003, I was playing a PC-based strategy game called Etherlords II. I loved the game so much that I wanted to share the experience with others and also help them with finishing the game.

So what did I do? I wrote a strategy guide for it and posted it on Gamefaqs.

The guide is still live, surprisingly. You can check it out here (scroll down to the bottom of the guide for my name).

The moral of the story? If you’re doing something you genuinely love, the passion will be your fuel to keep your engine running even on days when you don’t feel like doing it. Your love for the craft will lead you to mastering it, even if you don’t actively pursue it. Putting in hours and hours of writing for clients helped me improve my skills and develop systems that I use today as a full-time freelancer.

What if I picked answer number 2, you ask? Well, it only means either you have not nailed down that one thing you love doing or you simply have to apply for other gigs you enjoy more.

For example, my second writing gig as a newbie freelancer was to write 20 articles about prescription glasses (you’ll read more about this in a bit). I had to force myself to read, research, and come up with a bunch of write-ups about glasses. I didn’t know anything about it, never wore one.

Still, I was thankful for the job so I did my absolute best to complete it. Did I enjoy it? Not really. Later I realized that writing about stuff that interests you helps, cause it makes the job both easier and more bearable.

So, did I avoid doing any stuff or topic that I didn’t want to write about? No, I still took some jobs not within my forte.

Why? Because I wanted the experience and training it will give me. It also helped me accumulate 5-star ratings faster for my profile. As a newbie, I just wanted to land as much jobs as I can get my hands on, I wanted to really get the feel of being a freelancer.

And it has an added benefit, mind you. Writing about a wide variety of topics made me realize I didn’t mind writing about some topics I thought would be boring (gadget reviews). In fact, I learned to like writing about some of them.

Here’s your key take-away: If you feel like freelancing is not for you after doing a few gigs, don’t quit completely yet. Maybe the jobs you picked are not the best match for you. Try to experiment a bit and take on other jobs (or in my case, topics to write about) until you find something that feels right. If after this exercise you still don’t like completing your new jobs, then maybe freelancing is not really for you.

Related: How to Double your Freelancing Income


Question #5: What other things should I know before starting


Tip #1: Don’t expect to get your first freelance job right away.

With the gig economy surging, there’s a hell lot of more competition out there. Be patient on those first few days and weeks. Build up your portfolio, clean up resume, polish your site profile, and make sure to send out compelling cover letters. And send out a lot of applications.

I started freelancing 7 years ago. I made an oDesk account (now UpWork) and took on part-time jobs as a writer. I figured I should use my free time to earn some money on the side instead of wasting weekends playing games online. It wasn’t easy landing my first client, I think it probably took me a two weeks before getting hired for a quick transcription job.

I spent more than an hour typing it and realized transcription was a lot harder than it sounds (kudos to transcriptionists out there). I found out that 1 minute of audio is a lot of words. And you have to follow a format. I remember being given a template that I had to use. Overall it was OK though and got me a 5-star rating.

Tip #2 You have to go beyond your comfort zone

My second job that month was to write about prescription glasses. Did I know anything about it? Hell no. But I figured with some solid research and good writing I know I can do a decent job.

Here’s the actual job description if you’re interested:


This job had me writing stuff even on weekdays after doing a full-shift at work. Did I hate it? No, not really. Maybe sometimes if I was dead tired from work or felt like playing a couple of games before bed, sure—but I always reminded myself that I chose to do this and I had a deadline to hit.

See, when you’re just starting out freelancing, you’ll realize the importance of managing your time. You have to schedule tasks otherwise you’ll run into all sorts of problems that will stress you out. That constant, nagging feeling of anxiety you’ll get after blowing off precious hours doing dumb stuff will hunt you until the deadline. I should know, I was bad at managing my time.

Which brings me back to our advice: Learn to grow out of your comfort zone. As you do more freelance work, you’ll be forced to come up with systems that will ensure you’re doing your job right and not missing deadlines. Because if you do miss deadlines—oh boy, that’s a 1-star waiting for you after the job. Good thing I never had one, ever. *fist bump*

Here was my client’s feedback for the job:

*yup, my first name’s Mark 🙂

Tip #3 Be ready to show some samples and/or do paid tests

If you check out the last line of the screenshot of the actual job post, the client wanted to do a test article before anyone gets hired for the job. For newbies, this is actually an advantage. Why? Because the clients will depend on your sample heavily to see if you’re fit for the job. It levels the playing field against other veteran freelancers because the client will want samples, not glowing testimonials as their reference on who to pick.

When this happens, do your damn best for the test. Bring out the big guns. And if in case they don’t hire you, you can use the test job/article you made for your portfolio. Cool, huh?


In Conclusion

If you have read this far – congrats – you now have a basic groundwork for starting freelancing. You can go trial and error style, sure – or you can ask these 5 questions and experience true freelancing joy faster. Good luck!

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