Success Story: Upwork Side Hustling Mom

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Today, we will feature a success story of an Upwork side hustling mom who was my former colleague in one of the construction projects I was also involved in.

Back in 2020, I had the opportunity to chat with her and learned about her side hustling job in Upwork. She also encouraged me to try it. However, due to time and family constraints I was not able to proceed.

Fast forward, when I started this blog, I thought of featuring success stories of people especially moms, who are making money through side hustling.

I thought of sharing her story so that anyone who wants to enter the world of freelancing in Upwork can get inspiration and may answer some of your questions.

I was able to chat with her and asked her question about Upwork side hustling. Hope that this will inspire you as it did to me.

But before we proceed with my interview with Roanne, let us have a brief background of what Upwork is.


Upwork is an online platform that connects freelancers with clients seeking various services, such as writing, graphic design, web development, marketing, and more.

Freelancers create profiles showcasing their skills and expertise, while clients post job listings outlining their project requirements.

Freelancers can then submit proposals for these jobs, and clients can review the proposals and select the freelancer they believe is the best fit for their project.

Upwork provides tools for communication, collaboration, time tracking, and payment processing to facilitate smooth project completion.

It’s a popular platform for both freelancers looking for work and businesses seeking to outsource tasks or projects.


Can you briefly introduce yourself and your background?

I’m Roan de Guzman and I graduated Business Management in Philippine School of Business Administration.

I have worked in different entities like banks, BPO and in 2007 I went to Dubai, UAE.

I started first my career in oil and gas and eventually, I worked with different construction companies my last project was in Abu Dhabi Airport project.

How did you first get started with Side Hustling on Upwork?

I started freelancing in Upwork year 2016. I just saw my friend’s post regarding freelancing. So, I asked her, and she joined me in this freelancing group of Online Filipino Freelancers, and I just read about it.

I am impressed with the people who do freelancing. It’s not about being an employee it’s about being a businessperson because we’re rendering our services to other people.

How long have you been freelancing on Upwork?

I started in 2016, so basically like 8 years or so.

What motivated you to choose Upwork as a platform for your side hustle?

I chose Upwork because the freelancers and the companies are secured.

So, this means that if ever you find a client, and they want you, as a freelancer, to render your services to them.

It’s just that, the client needs to send the contract and then once you approve the contract, you can have this contract settled in your Upwork account. And after the task or the project is done, it will be paid directly to your account whichever you choose.

It’s more of, it’s prepaid, the client already deposited money in their client account, and then once they choose a freelancer, the freelancer can get the money once the task is done.

That’s one of the safest platforms I know, though there will be a lot of platforms, they are all the same. I just found Upwork very convenient.

How do you optimize your Upwork profile to attract clients?

I optimize my Upwork profile to attract clients by updating my profile every time I learn something new.

I do self-learning, so in any case that I have new skills to offer to clients, I will just update my Upwork profile so clients can see it.

Can you share any tips for crafting effective proposals that stand out to clients?

Crafting effective proposals, for me, would be straight to the point and whatever the client needs, they will discuss it in the Ad that they posted, so they already know what they are looking for.

Just in case they have bullet points of skillset that they need from a freelancer, you just have to inform them or answer their questions on how would you help them to deal with their business.

Basically, it’s being straight to the point.

How important is building a positive reputation on Upwork, and how did you go about achieving it?

Building a reputation is very important.

What I do is, once I get clients, I already know that I can do the task.

I don’t apply to clients where they already specify the tasks. And I don’t fake my skills because faking them means that you cannot do it.

Being truthful and the clients’ trust is important since you are a freelancer.

This is like the leverage for other clients that you are looking forward to.

Have you faced any challenges in maintaining a good reputation, and how did you overcome them?

Yes, I’ve faced a lot of challenges. It’s different when you’re working virtually and in the office.

It’s really hard because you have to be accountable for all the mistakes you make. And I just tried to explain to my client some errors that I encounter, and you just have to accept your mistake and be accountable for it.

Overall, I just get clients’ trust back.

Did you focus on a specific niche or industry on Upwork? If so, how did you choose it?

Basically, when I learned that there is a freelancing job out there, business, rather. I already choose what I can do, so it’s not like I need to re-enrol myself on something I don’t have knowledge about.

So, I just focus on what I can do at the moment. So, I know how to work on MS Office and Google Suites, I know how to do writing, and it makes sense that it’s already my skillset.

And I just have to upgrade, you know, from time to time but still it’s closely related to what I’m doing.

How do you continually upgrade and showcase your skills to stay competitive?

Concerning this question, I self-learn, self-study, or enrol myself in new skills that are also related to my current skills, so it will not be hard for me.

How do you establish and maintain good relationships with your clients on Upwork?

I establish and maintain good relationships with your clients on Upwork by communicating with them properly. So just in case, I don’t understand what they wanted for the task, because you don’t usually talk to them.

It’s just that, it’s most of the time they will message you, and email you when they have instructions. However, some of the instructions are not clear to you, so it’s good that we are certain of their instructions so, I ask.

Most of the time I also answer and just plainly say “hi” to them, during weekends I say, “Happy weekend”. So, they would know that there’s a virtual friend concerned with them.

Can you share an example of a challenging client situation and how you resolved it successfully?

A challenging client situation was when I worked as a Virtual Assistant at that time and my client wanted me to be the team leader. So, during that time it’s not easy because I’m juggling between my household and work. So, it became stressful.

Since I am teaching other VAs who are not of the same understanding as me, yes, it’s a very hard situation.

I just resolved it by informing the client that I was having a hard time. During that time, I was not prepared to do it, since I had a baby and another kid.

Balancing a side hustle with other commitments can be challenging. How do you manage your time effectively?

Balancing my time is having time with my kids. The most important for me are my kids, doing things for them like cooking for them, preparing things for their school, and everything that they need during the day.

I usually work after lunch on something that’s the most urgent task that the clients need.

Do you have any strategies for handling multiple projects simultaneously?

The strategy I got is having a subcontractor and yeah, it’s effective. I trained a few people, and they are learning the process so that’s my strategy.

Hiring a subcontract is a win-win situation since I can do simultaneous projects with a subcontractor who is paid as well.

And I also ask the client if it’s okay to have a subcontractor. And if they said yes, then that’s the time that I am teaching the subcontractor of the task.

How has freelancing on Upwork impacted your financial situation?

It gives more flexibility when it comes to work and the pay that I am receiving from my clients are reasonable.

It’s just that, I don’t need to spend so much outside, going to the office, spending on transportation and food, so it’s a big help for me.

Though it’s not really big compared to other freelancers, who are full-time with their clients, it’s really helpful.

I saved a little, I have small savings and some insurance. It’s not that much, but it helps a lot rather than doing nothing. Yes, it helps.

Can you share any insights into setting competitive yet fair pricing for your services?

It really varied when I started freelancing.

I got my first job offer from a Malaysian client who is a subcontractor company in Malaysia doing, I think, MEP for Malaysian airport during that time. Blessing in disguise that I’m also working in our MEP department in Abu Dhabi airport project, so it’s really more of doing the same thing.

Fair pricing, I am not sure if it’s fair, but it’s okay as I started with 3 dollars an hour.

If I’m going to compare it with selling, if I do sell and I didn’t sell anything in an hour, maybe that’s my comparison. So, I think it’s fair.

As you grow and continue upscaling, you’ve got the chance to increase your price and you’ll know your worth.

How do you stay updated on industry trends and new skills relevant to your freelancing work?

As I’ve said, I upscale, I self-learn, and I read from other freelancers’ success.

I also asked co-freelancers for different types of strategies that they have for their clients, of course, though it might not work for everyone, at least it gives me information about what I’m doing.

Have you faced any significant learning curves, and how did you overcome them?

Well, since we do like a variety of tasks and clients have different sets of platforms that they use. So, sometimes when the platform is new to me. Of course, I need to learn, and it will take a little bit of time.

So, I just do research, it would usually be available on Google. Research is the most important part of freelancing.

What advice would you give to someone just starting their side hustle on Upwork?

If you plan to do just a side hustle in Upwork, then you should be thinking in a wide range.

It’s good to ask, but more importantly, it’s good to research first rather than asking so much. Most of the time, its common sense, so you’ll have to have a lot of time.

Some people like to do freelancing business as their only way of earning. So, they don’t go to the office anymore, because comparing it, then they still have to earn more doing business at home or maybe sometimes they’re traveling. So is easier and more convenient.

If it is just a side hustle, there are a lot of things.

You also need to know your skills, because you’re going to offer the clients virtually.

You just have to know what skills you have that can be offered virtually, because you cannot see them or interact with them personally.

Are there any mistakes you made early on that you would caution others about?

There would be, of course, mistakes, each and every time.

The first thing would be, that you must read, and be mindful of how you understand the instructions. And it’s because we are virtually working with clients, of course, we need to be thinking in a wide range in a sense that you should also put yourselves in clients’ shoes, so you would know how to do the task.

Communication is very important, that you communicate with clients rather than assuming that you’re doing the right thing, but you are not. So, you wouldn’t waste time.

Do you plan to continue freelancing on Upwork, or do you have other long-term goals in mind?

Yes, I plan to do this until such time that I can still do it. Then my goal is to work full-time, and I would love to deal with different clients as well.

How do you see the freelancing landscape evolving, and how do you plan to adapt?

We are in the internet technology, and I think, it will never stop because everything or most of the things or tasks can be done remotely.

It’s just there would be lots of changes by using different platforms and adapting to it is like learning some platforms that make your freelancing a successful one.


Upwork is a great side hustle opportunity and offers advantages just like what Roanne mentioned.

You can enjoy flexible work hours that accommodate various schedules, have access to a diverse range of job opportunities across different industries and regions, and the potential for skill development and professional growth through exposure to a variety of projects and clients.

However, you must be aware that side hustling on Upwork include intense competition for projects. Also, the platform’s fee structure can reduce overall earnings, and there is a potential for inconsistent income due to the unpredictable nature of project availability.

Overall, while Upwork offers numerous opportunities for side hustling, you should carefully consider these factors and your conditions before committing to freelancing on the platform.

Remember that Upwork side hustling is just one of the numerous opportunities you can make money online.


If you’re ready to take plunge and start your side hustling job or business in Upwork, or if you’re a business owner that is looking for a freelancer, you can check out the below link for more information.

Biography: Roanne is a full-time mom of 2 boys and a part-time freelancer on Upwork.

She started her Upwork freelance journey back in 2016 in Abu Dhabi while she was pregnant with their youngest son.

She is now enjoying her time with her boys while side-hustling everywhere she goes.

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