skip to Main Content

How to Become a Successful Freelancer (from Scratch)

Disclosure: Some of the links in this post are affiliate links. This means that, at zero cost to you, I will earn an affiliate commission if you click through the link and finalize a purchase.

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.

Share this Article

I'm a freelance writer, blogger, trainer, and internet marketer. My joy is to see you making money online. Feel free to browse around and leave a comment. I strive to reply to all queries. You can also follow me on Facebook and Twitter .

Newest Posts

Get Free Tips

Join over 20,000 subscribers on FreelancerKenya’s FREE mini-course for writers

Footer Newsletter

Your Names(Required)
This field is for validation purposes and should be left unchanged.

Notify of

Inline Feedbacks
View all comments

Hi, thanks for the insights. Can you get the upwork profile to be 100% complete without having worked before? How do you ensure credibility if it is not possible?

Brown Janetson

Great post Mr Walter.Thanks soo much for taking us to another step of life.You’ve been of great help and you’ve helped me out when i was a newbie.I am so greatful,may God bless you.

Reply to  Brown Janetson

This is very helpful content especially for newbies and those who want to be perfectionists of the job.

Blessings Walter


Kudos! great article, thanks for the information it still very helpful


Wao Wao wao, I follow your post and by the time I read it up to the end I become speechless, I really can’t explain what is holding me back but will look for your post every where I can coz they rekindle my fire,passion and will power to earn online, thanks and God’s blessings.


Great stuff, as usual, Walter!

I realized that one of the things I love most about you is you never pooh pooh any opportunity but always look at (and showcase) their best side. There’s a lot of talk in the market about how bad content mills are and how they are a complete waste of time – and here you are, showing proven ways to make them work for you without selling your soul in the process.

Proud to have known you, my friend – all the very best for everything you do in life 🙂

Dennis Mwangi
Dennis Mwangi

Hey… Sir Walter.

I unexpectedly landed the link to this challenge in the Remarkable s writing group; my personal dictionary on freelancing issues, since am just a newbie. Mark you, you are the person that added me to the group. After getting the group link through your highly beneficial free training. I am planning to join the premium program immediately once I settle financially.

Through my close scrutinizing eye I have discovered your content is cliche word free. Is this one of your secret? consider telling us one day in your frequent posts in the group or through the emails. Also surprise d but happy to know that someone can acquire Elite plus status, in two months

Allow me to tell you this, you are one in a million. I highly appreciate God given generosity to new writers. Giving is a gift and is not common among many, I believe you can bear me witness.

In case you have time respond. If you have overwhelming work I would glad to be part of your newbie writers team. In addition, you can even rate or point out mistake in this piece of quickly complied appreciation.


Hello Walter, I must say I always feel so indebted to you for the constant great insights on this noble course. I’m whom I am now, thanks to your generousity in sharing about online works. You’re just gonna continue thriving since a candle loses nothing by lighting another.


Hi Walter,

Again and again, I always find your articles timeless!
It’s a month now since I registered for your online course, all these points here are very applicable. So far I have found #1, #5 and #7 working for me am yet to implement all and I know I will win with these points


Hello Walter. I desire to begin writing. where do I start?

Andrew Baraza
Andrew Baraza

Hello Walter,

Just stumbled on to this site today! I have found it to be awesome.
Have never done freelancing before and now I passionately want to do it full time.
Still pressing up with my own research but would really need your help, please.

Kind Regards.


Jambo Walter,
Am newborn here, am passionate about writing, plse can you offer training coz currently hava no job ni hustling tu


There is this content writing site I stumbled upon called Does anybody here has experience with them? Seems to have some good earning potential for content writers too. Though I am still new there. Will update you guys how it goes.



I like your weekly newsletter via my email, am now a guru at with only 4 months

God bless


Wow! I’ve learnt a lot from your post. It’s a challenge to me. Look forward to earn phenomenal amounts from content writing. Be blessed

Ludiah Mong'are

Hi Walter,
Thanks for the informative post. Of all the three, I writer, PPH, and Up work I have online managed to work on I writer where I have two clients adding me on their favorite list. Other websites clients just send me to Skype and get lost.


Walter you are a real blessing.God bless you so much for the great information that you share with us.


Powerful information. thank you once more for the good work you are doing towards my source of bread, stay blessed every time


If you lighten up other people’s paths, God brightens yours. Well, this guy is a living example. Keep up the good spirit Walt. God bless.


Joined Freelancer yesterday… I would like to know how you got conned. I came to that part which requires my VISA ATM card number but skipped it very fast. How were you conned?

Shiro Maina
Shiro Maina

Great work Walter! I feel energized to revisit my Fiverr account. It has been close to 2 years since I cared to check it. has no business this year. Thanks.


Must be interesting. Will return…

Ajobe salim
Ajobe salim

Thanks for the insights Walter. I was well versed with academic writing. I learnt about article writing and blogging from you. Mostly have been in to learning than bidding for jobs. Have tried bidding on fiverr,freelancer,pph,and iwriter with out success. Of late have felt tha i have more than enough on article writing and blogging. So i have tried bidding continously on iwriter without getting any job. My aim is to first build my portfolio then bank on that to search for jobs later.

Ajobe salim
Ajobe salim
Reply to  Walter Akolo

Okay, thanks for your response. On iwriter i havent been bidding but looking for standard rate jobs. On other sites i bid like once no response i give up. Have tried to bank on iwriter and freelancer for jobs.

Ephraim K
Ephraim K

Thanks a lot Walter for that informative article. I have completed two jobs so far but my “Job Success Score” is yet to change. Can you help?


weird enough, I have an old upwork account and since I embarked on online jobs I still haven’t landed a job. my old pph account is quire the opposite. After just two days of bidding I got a job. its already on level 3. I love reading your posts. always something new to learn. thanks :).


Great Post.
The secret to freelance writing is to do lots & lots of research on the topic given.
Mistakes are made when someone tries to wing a topic.
Good for you Walter, You are a shining example.
I will also take the challenge and write a bestseller from scratch.
I look forward to the day I will write a post entitled; “How to write a bestseller”
Your article has given me great faith.


That is really great and insightful….I am still taking up the challenge and I hope by the end of this year…things will be great. Thanks again for the motivation bwana Walter


Awesome stats on Upwork, Walter! Keep it up.

Indeed Upwork is an awesome site. It might have some challenges here and there, but it’s moving in the right direction if you ask me. Thanks for the mention 🙂

Reply to  Sheeroh

You two guys are doing great, Thanks for the updates on freelancing, Mrs.Sheeroh and Mr. Akolo!


Thanks so much Walter your information is so powerful and very informing to people like me who are very green to online jobs.But do believe with your support and from Sheeroh i will make the right decision which area to concentrate on.Thanks and God bless you


Your always an inspiration Walter, your determination and spirit motives us…
Than you

Vincent Odhiambo
Vincent Odhiambo

You always give back to the community by inspiring others,telling them they can make it in the writing arena. God bless you.

David Mbugua

Excellent insights Walter. Testing and optimizing is the name of the game. Congrats on your success.

John Nyakangi
John Nyakangi

Hi Walter,
I am pleased to read this blog, for it has a lot of informed contents on making money online through writing. Keep up the good work. We’ll engage more since I also do a lot of proposal writing, data collection, and analysis. I would urge everyone to take this information on making money online seriously because it rewards handsomely. Cellphone:+254733974374

Ren Mumbo
Ren Mumbo

You are creative Walter, not all could imagine of such a challenge, you innovated it to keep the freelance wheel going. What do I say more? You are a blessing to many!


Bravo Walter for the great insight. I read this article 6 times to get everything right.

Aggrey Amimo

I joined upwork where I am now workin. I also reopened iwriter account. The only account I have a challenge in is feverr. I have not just cracked it. But anyway the challenge and the motivation was worth it.

Charles Sifuma
Charles Sifuma

Thank you very much for your timely advice regarding the freelancing industry. I started well on IWriter getting above 4 stars rating… But one client gave a 1 rating and from that point my rating dropped to 3.2….I had already made some good money (as a newbie). I lost hope in IWriter and sincerely i have never withdrawn the money… I was pissed off.

About UpWork
I have an account with a 100% profile…. I have completed several tests successfully. Unfortunately my proposals have always been rejected.

I have a Writers lab account and am doing great

-Those writers thriving in their accounts should inform others the secret
-Freelancing requires patience and dedication

-Kila mtu ako na account yake… U can do good in one account but not another and vice versa
-Help a friend to help a friend
-I will reconsider your advice and i have started working now

Nolan Ross
Nolan Ross

Great post Walter. Your blog really helped me out when I was a newbie. Am grateful…always.

Lactor Joseph

Hello Akolo
I have been writing for account owners for two years now but most are roudy and unfaithful when it comes to enumeration. I therefore decided to try out opening newbie accounts but despite hundreds of applications I got none working so far. Is here anyway you could help me improve my profile and get an iWriter account? I look forward to spreading the word of how helpful your course can be in writing career to my aspiring friends and acquaintances. Thank you.

Later JM.

Mercy Opande

Not bad Walter, for me Fiverr was the deal breaker.

37 jobs
31 clients gave me 5 star rating
6 clients did not rate
3 permanent clients
I am a level one writer almost entering level 2

I am still trying to see how to succeed on Upwork while people per hour is kind of hard to crack as even though I got clients, they want to work outside PPH but all in all I am happy that one site worked and am using my Fiverr portfolio to gain more clients.

Back To Top
Would love your thoughts, please comment.x