4-Step Checklist to Getting Started on Freelancing Full Time


Dr. Atul Gawande, a surgeon, public health speaker, and New York Times bestselling author of the book, “The Checklist Manifesto”, argues that checklists dramatically increase effectiveness and reduces errors when conducting complex tasks or activities.

Case in point: In 1935, Boeing unveiled its latest aircraft bomber, the B-17. It was the most advanced and complex flying machine at the time. To test it, the Air Force sent one of their best and most experienced pilot, with decades of flight under his belt.

But as you may have guessed it, just seconds after takeoff, onlookers saw the massive aircraft stall midair, crash, and burn into flames.

Everyone watching couldn’t believe their eyes. How can Boeing’s most advanced plane crash and burn like that? It was only until after investigation that the real cause of the accident was revealed.

The reason? A missed routine step.

In the face of a highly-complex navigation system, the experienced pilot wasn’t able to cope and started to panic and forget even the most basic of steps that were supposed to have been ingrained into his brain.

When I first started freelancing on the side almost a decade ago, I knew jack-squat. All I knew is that oDesk (now UpWork) is where people go to look for online jobs. I created my profile, then went to apply for each job I can get my grubby hands on.

Days passed. Then weeks. I felt incompetent. As if oDesk told me I wasn’t good enough. “Hey kid, this place ain’t for you! Better go play somewhere else!”


It was frustrating. I started to doubt my skills. Clueless as to what’s happening, I was a pilot about to crash and burn.

Looking back, I realized I should’ve done things differently. Instead of being bitter about it, I thought I should share my experience with others so they won’t have to go through the same rough roads I drove through when I was started my freelance career.

Determine what you’re good at

It’s all about skills, baby. If there’s one thing right that I did back then, it was in figuring out what skills I can offer as a freelancer. In my case, it was copywriting. Here’s the thing though, I’ve never written “professionally” prior to setting up my UpWork account. Did lack of experience made me worry? No, not really.

To compensate, I made a bunch of writing samples, 500-word articles on topics I loved reading about. After completing about 5-8 write-ups, I placed it in my portfolio and sent them along with my applications.

By figuring out which skillset I’m comfortable using, I was able to build my portfolio with relative ease. I was also confident that I can start without much guesswork upon landing my first gig.

Do you like making digital graphic designs? Fond of chatting with people? Like acting as a middleman between two parties? Know how to code? Ask yourself, what activities excite me? What compliments do I usually get from others? By asking yourself these questions, you’ll be able to pinpoint your strengths and decide.

Where can I apply for freelance jobs?

Since you’re just starting out, I highly recommend OnlineJobs.PH. Not only will you have less competition, they won’t charge you a fee for working on jobs. Since it’s a Filipino-only talent marketplace, clients are already expecting to work with someone from the Philippines. This takes off a bit of pressure from your shoulders since clients already know what to expect.

Other top choices are UpWork and Freelancer, definitely take a look at those sites as well. Both make a good resource for checking out other freelancers’ profiles that you can use to craft your own.

For local jobs, check out Craigslist.PH. You can chance upon some great long-term gigs there.

Related article: 8 Ways on How You Can Land a Freelance Writing Job Even Without Experience

I’m stuck. Where can I get help with freelancing?

Google is your friend. There are plenty of websites online that offer tutorials on how to complete specific tasks. Some give advice on mindset and attitude about freelancing in general.

For a more local approach, you can also join Facebook groups for specific niches. I’ve been a member of a few copywriting groups and freelance mastermind groups where members share and trade ideas to help each other out.

Here are a few of my personal favorites:

Ask yourself, what’s my gameplan?

January of 2018, I left my full-time job where I worked for the last 6 years and went freelancing full time. It was scary. As a family man, there’s simply nothing more frightening than the idea of not having a guaranteed paycheck every 15th. I grit my teeth and prayed for the best. I trusted my skills (freelanced on-and-off on the side) and knew that it will only be a matter of time until I figure how I can make this whole thing work out.

Note though that I’ve been planning this for almost half a year, and discussed it with my wife to make sure we’re on the same page. Luckily, she trusts my decisions and skills enough to give me her blessing. I told her, “If I can’t make this work in 6 months, I promise I’ll look for a regular job again”.

Two months since quitting my full-time job, I was only able to land a couple of one-off gigs from UpWork. I opened an account in Freelancer and even paid to get a certification there, so my profile will be more marketable. Still, no luck. I was starting to doubt my decision of quitting my previous job.

Still, I was determined. I loved to write and I knew there are clients out there willing to pay for my services. I have proven it in the past. The only thing different now is that I can do it full time. And that made it more exciting, to be honest. I sent proposals regularly and checked other places for job posts. I was earning a bit with some of the gigs, so that took off some pressure from a financial standpoint.

It was only until I chanced upon a local copywriting job in the third month (via Craigslist.PH) that I started to have some semblance of job normalcy as a freelancer.

Related article: 20 Power Tips and Ways on How to Become a Better Writer

With a steady gig, I was able to relax a bit and continued looking for other semi-regular gigs. To cut the story short, I now have two regular copywriting jobs that pay me monthly, with three more on the side from UpWork. The UpWork clients are actually long-term, and quite profitable to be honest. I just can’t log in more hours since the 2 main jobs take up much of my time.

Here’s your takeaway: Don’t rush into freelancing full time without a concrete exit plan. I gave myself 6 months as a deadline. If after 6 months I only had one-off gigs, I will look for another job.

Freelancing is not for everyone. Before you take the leap, have a solid plan, invest in your skills, and be relentless in looking for jobs. Always be learning, especially when you still don’t have a steady gig. It will pay off tremendously later. Ask yourself these 4 questions first before you go at it full-time. Goodluck!

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