How to Become a Successful Freelancer (from Scratch)

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Have you ever felt so lost that you don’t know where to start? That’s where I was in early 2016. I’d gone through a terrible life crisis in 2015 and couldn’t work for months (yes, months!). In 2016, I was much better. So, I decided to do a freelancing challenge so that I’d grow with everyone else. This was interesting. Read on for more juicy details.

What was the freelancing challenge all about?

The challenge was simple. I was to do the following:

  • Become a newbie in Upwork and PeoplePerHour
  • Dust off and optimize my old Fiverr account that I hadn’t worked on for 2 years or so
  • Look for work on online job boards.

In all these sites, I was looking for freelance writing and copy-editing jobs.

Remember I was not a beginner. I’d already worked online for 5 years (since April 2011). However, I’d lost everything in 2015 and had to start from scratch.

I documented my progress on my favorite Facebook group — Awesome Transcribers in Kenya (ATK). Since there were many people in ATK who also wanted to start from scratch, I made it a challenge, where I would show what I was doing step by step so that we could all learn from each other.

I totally believed I would make it, since I had been a freelancer for years. However, I really wanted to see others succeed.

I loved the results.

A few days into the challenge, guys just couldn’t stop posting on the group the fact that they had landed a client in the different sites named above. Many are still earning from the different sites they joined. The challenge was a smashing success.

I first wrote this post on August 17th, 2016. As usual, I keep updating my posts so that you get relevant info. Here’s how to succeed in the various sites and the strategies I used. I also tell you what is yet to work and give you my final thoughts.

How to succeed as a Freelancer in Upwork

Upwork is a merger of the former oDesk and Elance.

I loved Elance and had made some decent amount there before this merger. I hated oDesk, since it was famous for all the wrong things—mainly low pay and difficult clients. A couple of friends kept talking about oDesk but I had never given it a good thought.

When they merged to become Upwork, things got better.

Upwork Market Research

I did quite some research on Upwork and came across great information from different sites. Locally I got some great content from Sheeroh Kiarie’s Work Online Kenya and David Mbugua Kiongo’s FreelancerInsights.

Internationally, Upwork had some outstanding reviews, especially from Danny of FreelanceToWin and John & Radhika of FullTimeNomad.

Lots of guys in the Awesome Transcribers in Kenya Facebook group also expressed just how much they loved Upwork and kept sharing tips.

Whoa! This site just had so much love.

After reading all this, I was convinced that it’s a great site to work with.

Upwork Case Study Results

By the grace of God, I got these results from Upwork:

  • 20+ jobs, some long-term
  • Lots of 5 star reviews
  • A job success score that ranges between 90 and 100%
  • Top Rated Plus status!

Do you want to succeed in Upwork? Join The Upwork Mastery Course. Here, I show you everything you need to know to earn consistently in this amazing site.

Upwork 2016 screenshots

Here are a few screenshots from my Upwork profile that I took in 2016 just after starting this challenge.

Successful Freelancer Upwork Profile
See some of my Upwork reviews above.

I took these screenshots in August 2016.

Right now, I have multiple exceptional long-term clients who supply me with constant work every month. We’re already past the $10,000 mark with those a few! Upwork only charges me a small commission for big clients. In fact, Upwork clients have given me thousands of dollars worth of work. Some screenshots below.

Upwork 2017 Screenshots

Walter Akolo Upwork 2017 Reviews
My Upwork reviews in Nov 2017
Walter Akolo top rated in Upwork
Yaaay! I entered top rated status in Nov, 2017!

Upwork 2021 screenshots

By God’s grace, here’s where was by 2021:

Walter Akolo Upwork 2021

Here’s another 2021 screenshot showing some running jobs.

2021 Upwork Jobs in Progress

Of course, I’m updating this many years later, and things have been really great in Upwork. I’m glad I took the challenge.

My Upwork Success Strategy

Below is the strategy that I used to get to where I am in Upwork.

  • Research: When starting, I always had a Google tab on. I constantly researched all aspects of this site, i.e. profile, bidding, proposals, security, etc. I used a lot of information from the sites I named above. This brought OPTIMIZATION! I simply love putting the right effort into things.
  • Merging profiles: I merged my former Elance profile with Upwork. This brought MOMENTUM since I already had some few great Elance stats.
  • Complete Upwork Profile: I completed my profile 100%. This brought CREDIBILITY. Don’t start working there with a half-baked profile. I still keep updating my Upwork profile to today’s standards.
  • Testing: I tested different projects, rates, clients, proposal strategies, etc. My online mantra is TEST AND OPTIMIZE. Testing always helps me to PLAN AHEAD.
  • Using all connects: When starting, I made sure I use up all available connects every month. THIS INCREASES PROBABILITIES. Right now, I already have many clients from different sources other than Upwork. However, I still look for clients on Upwork almost every month. I believe freelancers should add a few new clients each month.
  • Targeting: I send my proposals to mostly “Intermediate” and “Expert Level” projects. This gets me into the sea of PROVEN, WELL-PAYING CLIENTS. I still send to awesome entry-level jobs. One of my long-term clients who paid decently had posted her job as an “Entry Level” post but at fantastic rates!
  • Reinforced proposals: I strive to write great, heavenly proposals and attach samples, links and any other useful evidence. This ADDS VALUE. Always reinforce your proposals with proof.
  • Rates: I only go for jobs that pay well and can even bid at rates that are above the client’s displayed budget. This shows CONFIDENCE but still enables me to build my REPUTATION.
  • Diversification: I diversify with direct clients. This SPREADS THE EGGS. Thus when not working in Upwork I still work for other clients/sites. In fact, I advise people not to depend on Upwork or any other site, but to look for their own direct clients.

I go deeper into Upwork success in The Upwork Mastery Course. But for now, those are general tips that should get you going.

How to Succeed as a Freelancer in Fiverr

Fiverr is still one fun site to work in. It is difficult to get a bad rating on this site if you’re good at what you do.

On the other hand, the flow of work here can be unpredictable. The primary model of this site is that you set up your service description (called a gig) and wait for people to order it. You can have multiple gigs (recommended).

I had already worked with Fiverr a few years back. One goal of this challenge was to revamp my inactive Fiverr account and start earning from it, too.

Fiverr Market Research

I did little market research on this since I already knew how it worked. You can check out my Fiverr review here.

I had a few friends from the Facebook group who were making it big on this site, so I took the plunge into it again.

Fiverr Case Study Results

Here were my Fiverr results:

  • 15 jobs
  • 14 gave me 5 star reviews and 1 gave me a 3.5 star
  • 1 long-term client who I worked with for years

My Fiverr Success Strategy

  1. Set up an excellent Fiverr profile
  2. Create fantastic gigs
  3. Apply for jobs (submit offers to buyers)
  4. Deliver your very best
  5. Ask for feedback
  6. Be an excellent communicator
  7. Share your gig on social media and forums, especially where potential clients may be

For this case study, I only used number 1, 3 and 4 above since I had already done most of the others earlier.

Other Methods

Below are some other sources of online work that I tried out as part of this challenge.

Job boards

I tried out so many job boards. Some of the famous ones include the ProBlogger Job Board, FreelanceWritingGigs and Craigslist. Through these, I got one long-term client.


I did not get any client yet from PeoplePerHour. In fact, out of all the bids I sent, I only got one response that did not materialize. However, a few friends from the Facebook group have been earning very well here.

One friend tells me she earns well here from simple tasks, such as writing a slogan. I’ve had so many trainees doing well in PeoplePerHour, too. One earned thousands of dollars in a matter of weeks.

I did not pursue the site much after this. I focused on the other methods here that keep giving me consistent income.


This is an excellent strategy that you can use to land high-value clients who pay hundreds of dollars per article. I already have clients who come to me through my networks or blog, but when my workload reduces, I use this method to get high-paying ones. My best one so far paid me $200 for a 750 word article.

Here’s an excellent article that will take you step by step on how you can cold-pitch to earn thousands of dollars per month.

Read: How to Make Money Online in Kenya as a Freelance Writer

Final Thoughts on Becoming a Successful Freelancer

It’s been so much fun rebuilding a freelancing career. It has also been quite some work.

As mentioned above, I’ve had some level of success on these sites. I’m still not where I should be, but I’m happy and content at how far I’ve come since March 2016 when I went back to freelancing.

It all started with freelance writing but right now I’m a Lead Digital Marketing Executive. By God’s grace, I’m way further than where I started.

What gives me great pleasure is that through this challenge, there were many more success stories. My definition of a perfect challenge is one that makes many people succeed, not only the challenger.

To be honest, I didn’t really think I would fail as a freelancer. I had already done it for years and I believed that my strategies were rock solid.

In fact, I still have some of my old connections who give me constant freelance work. I also keep actively looking for clients, though mostly direct ones where no “middleman” site is involved.

Because this was a public challenge, many learned from me and I equally learned from them. Big-up to all members of the Awesome Transcribers in Kenya Facebook group who made this a success.

My biggest prayer was to get as many people as possible into freelancing, and it worked just fine. I aired it all out here so that you can also make it.

What’s holding you back? Other guys, just like you and I, are earning as freelancers. Start now. If you work at it, you can also become a successful freelancer in a few weeks. If you’re a freelance writer and want to fast track things, join my article writing course.

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