How She Booked Three Clients on Upwork After Being Rejected Multiple Times

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One thing you need to know about freelancing is this.

You’ll be rejected…a LOT.

You’ll spend your time creating proposals and cover letters…

…only to be seen-zoned by a prospect.

You’ll get tons of NOs.

You may not like it.

But it’s the reality.

Take a look at Gladys.

“I’ve always been rejected in Upwork before, so many times that I cannot count anymore.”

She’s a supply chain management professional but she wanted to earn extra income to pay off her debts and save up for house renovation.

So she tried freelancing.

“I’ve been trying to do freelancing since last year. I had my first job as a freelance writer but eventually stopped because of the demands of my regular job. When we had the lockdown, I went back to trying it again. So I decided to enroll in the VA Bootcamp to know more about how to become a VA.”

This is when things started to get better.

“When I started fixing my profile through  the help of Sir Jason’s advice on VA Bootcamp videos and uploading the assignments in my portfolio, I eventually got accepted.”


Now, you might think that it’s already a bed of roses for her.


“I spent 2 weeks submitting proposals, got interviewed by some but they didn’t turn into contracts. I felt like a failure, it never happened to me in the corporate world. I always get hired after the interview. I know I have the skills, but it’s so hard to find someone to believe in you when you haven’t build your freelancing profile yet. No clients, no earnings, and no feedbacks for them to see.”

So what happened next?

How she was able to land 3 clients on a platform that previously rejected her?

What  she did to get a freelance project that’s aligned to her corporate job?

Find out on this replay of another inspiring episode of JasSuccess.



Gladys Cabrera, a full time corporate worker by day, and freelancer at night. She started working as a freelancer last September 2019. She wanted a part time job which lead to freelancing. She is now enjoying both job as a Supply Chain Professional and a Freelancer.



  • I didn’t think about it (VA Bootcamp) as an expense, but rather as an investment.
  • If you really know your value, If you really know that you can do the job, let your client feel that they need to hire you. That you can help them with their businesses.
  • Never stop learning even if you have already found your niche. You can always learn more para ma-improve and try others baka kasi mamaya mas okay ka pala doon. Like now I am also studying ecommerce. Aside from supply chain, I’m trying to divert to another niche as well, just to add up to the skills that I have now.
  • And just don’t give up. Ilang beses akong nareject sa upwork so I thought hindi siya para sa akin. Pero mas matindi yung urge ko na maging debt free within this year and save up for my house so I tried freelancing and this is it.
  • Every time I got rejected, I’m thinking “okay, so it’s not the right time”. I’ve been trying since last year before I job hop to another company again, so I thought I can do freelancing by that time so I’m not lucky yet.
  • Then this lockdown, I think of it as a blessing in disguise on my part, I was able to focus on learning new skills.
  • She’s been working in the corporate world for 10 years.
  • She finished her Master’s Degree in supply chain in 2019.
  • She decided to take freelancing as her part-time job because she was unable to save  money for the salary provided was only enough to pay the bills.
  • She’s been applying to different job posts on Upwork since 2017 but got rejected multiple times.
  • She enrolled at VA Bootcamp to learn more about freelancing.
  • With the help of VA Bootcamp, she got certificates and improved her portfolio that managed to get her profile approved on Upwork.
  • Then she was interviewed by several clients but she was never hired.
  • Soon enough, her first client messaged her for a test project and she asked him to pay half of her rate for it instead of doing it for free.
  • She got hired by the same client for a full contract after the test project.
  • She was interviewed and hired for an inventory position from her second client within two weeks from her first full contract.
  • And eventually, she was promoted by her second client as supply chain manager after a month of work.
  • After getting her second client, she submitted proposals regarding excel works, which led her to have an interview for her third client.
  • She is now enjoying her career in her corporate job and as a freelancer for three different clients.


Bakit hindi mo nilibre yung test project mo?

Kasi I believe na you should not sell yourself short. It’s not that I’m desperate to the point that I would give it for free. For me kasi, I know I could do the job; I could give it to you for a lesser price just to prove my value that I can do what you need, then let’s do about the full rate after you liked what I did.

 How were you able to keep yourself in that mindset (that you could do the job)?

I always think of my highest value. What you’ll give your clients naman is your expertise, so they really have to pay for it.

Was there anything you ever did significantly that made you gain two clients consecutively?

I focused more on applying to jobs that I know I can do. So it’s more on supply chain talaga siya.


Gaano po ka imporante ang reviews for us freelancer?

Yung review yung magde-determine kung iha-hire ba kayo ng mga next na ina applyan niyo. Yung mga clients kasi nag tse check sila ng mga reviews kung maganda ba yung work mo, yung relationship mo with them, with the previous clients. So it’s actually the challenge kapag starting ka palang kasi wala kang reviews; wala kang previous clients; wala kang earnings. So challenge talaga yung pagkuha ng first client.

What is it that you did na para ma-maintain mo yung attitude mo with these three clients na nakuha mo sila agad-agad?

Communication is the key. I always communicate with my clients. I make sure na nagagawa ko kung ano yung mga gusto nila. And if ever na hindi ko naman sila matapos, I always inform them. With my three clients, nagka problema ako sa time management kasi having them all at the same time and all our hourly contract, syempre hati yung oras ko sa kanila. I’ve been honest with them so I told them I can only do 2 hours with them every day. Unfortunately, yung dalawang client ko, they both want me to work full time, which I cannot do because  meron din akong corporate job. So I politely declined them and told them that I can only commit this much and they understand naman.

Being a job hopper, what platform can you recommend aside from upwork?

Onlinejobs & Hubstaff, marami rin mga job posts. Although sa Hubstaff, kaunti lang nakita ko doon na in line sa profession ko.

Bakit ka ba adamant sa field of expertise mo here in freelancing?

Since I am more comfortable doing this job and I know mas makakapagbigay ako ng mas magandang output kapag alam ko kung ano yung ginagawa ko.


Would you recommend people to focus on just one particular niche just like you?

Not just one, maybe at least two or three niches. And yes, kung ano yung alam mong kaya mong gawin that you love what you do. Kasi sakin, I love supply chain kaya nag master’s rin ako ng supply chain. Aside from helping my clients with my expertise, kung ano yung industry ng client ko ngayon, yun yung inaaral ko. And doon din ako naga upgrade just like now, nag-aaral ako about amazon and other e-commerce that forms. So yun yung second niche ko, e-commerce.

When did you discover that you love what you’re doing right now?

Working student kasi ako before way back in college, so first job ko talaga is procurement. It started in supply chain, hanggang sa after graduation yun parin yung naging work ko. So hindi na talaga ako nawala sa supply chain kaya yun na rin minaster ko. And yes, I’m enjoying my field so kung mag freelance ako, I better choose what I love to do.

Did you ever notice if there was a common question that these three clients asked?

With regards to the interview, all they were asking was your related experience. “What have you previously done?” That’s the same as what they need. If you prove the clients na kaya kong gumawa ng ganito, nagawa ko na yan before, and I can definitely do it for you as well, they will hire you.

What was the most difficult question that the three asked you?

I think it’s “If I hire you, what can you do to make this business grow?”. Meron din kasi mga clients who’re looking for someone who has real concern with the business and that they can see if they want to grow with them.

What can you offer to the business’, How should a newbie freelance answer that in your opinion?

For freelancers, maybe you can offer your best service. So kung ano yung sa tingin niyo na kaya niyo i-contribute kahit small, it can make an impact.

Is there a way that you could make your client like you during the interview, or would you only be able to do that during your contract already?

You could already do that during the interview. What I did with my second client was I told him how I was able to compute for the inventory count, and I also offered him to make his inventory process a better one. So what I offered him aside from the inventory calculation, I could also monitor his inventory and audit the warehouse’s counts to ensure na hindi sila mawawalan ng stocks. And that hit him so I was able to land the job as well. Offer your other services aside from what was asked from you.


Are you going to job hop as well in freelancing, do you intend to close your contracts some time in the future?

For freelancing, I think it’s the other way around. The longer you stay with your client the better. Mas mahirap maghanap ng new clients especially if palagay na yung loob mo sa current client mo and naka build na kayo ng magandang relationship, so it’s better to stay with them.


What gave you the encouragement to do this?

When I check the website, aside from the money back guarantee, I ensure na hindi niyo pababayaan yung enrollees and students; and I have red vlogs as well as reviews and it’s very positive. I know naman na I have the knowledge but not in the freelancing world.

Were you not ever interested in the other skills that we (VA Bootcamp) taught you?

Interested ako mostly in bookkeeping and e-commerce, that’s why I got the accelerated package. Currently I’m managing amazon inventory, so naga upgrade parin ako ng mga skills, nanonood ako ng mga videos about amazon and shopify kasi isa rin yun niche na gusto kong i-pursue and i-accomplish.

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Jason Dulay

Jason Dulay

Jason is the founder and CEO of Work from Home Roadmap and VA Bootcamp. Aside from teaching Filipinos how to succeed working from home, he likes traveling, playing board games, and drinking coffee.

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