How to Succeed on Upwork and Get Freelance Clients.
Today, let’s learn the strategies that really work on Upwork.
Finding freelance jobs and clients in today’s market is harder than ever. And the question ”How to Succeed on Upwork” it’s now repeating more than ever.
We spoke with Jovan Pop-Petrov, Top Rated Plus freelancer and founder of UpworkBoost, about what actually works when platforms are crowded, and what freelancers must change to succeed.
Meet Jovan Pop Petrov,
A simple, grounded person who enjoys a calm life in Macedonia while working with clients worldwide.
With over 19 years of experience in IT and web development, Jovan spent 12 years working in companies before building his own path, launching his agency Flow2Web and later UpworkBoost.
Through years of real experience on Upwork, he built a strong, well-paid profile, and now helps other freelancers do the same.
Let’s dive into Jovan’s interview and solve the Freelance dilemma…
💬 What’s the biggest achievement you are proud of?
My biggest achievement is not money. It is that I can stay close to my family and help other people start their path. For me, that is real success.
💬 How did your past experience prepare you for freelancing on Upwork? How important is it to have some experience before starting?
You do not need experience to start on Upwork.
But you need patience. You need strong nerves. And you need to trust the process. Also, listen to advice from someone who is already there.
If you are, for example, a farmer and you want to work from home, it is still possible. First, learn a skill. Take a course. Watch YouTube. Practice every day. Spend hours in front of the computer.
After that, get a small certificate if you can. Create a LinkedIn profile. Create your Upwork account. Build your profile step by step. Then start applying.
It is simple, but it is not easy.
That is the recipe.
💬 Why did you have the urge to create UpworkBoost, and what was the moment you saw that it really helps freelancers?
At first, I did not plan to create UpworkBoost. I was just helping people for FREE, with coffee talks and online calls.
But I saw that most of them did not follow my advice. They wanted success, but they did not do the work.
A friend told me to create paid packages. I was not sure. I did not want people to think I just take money.
Then I understood something simple. When people pay, they become serious. They start working.
When I saw freelancers getting their first jobs after following the steps, I knew it worked.
That is how UpworkBoost started.
💬 What does ‘protecting reputation over profit’ mean, and why is it especially important today when everything is visible and digital?
On Upwork, your NAME is your BRAND. Everything is public. Reviews stay there for years.
Protecting reputation over profit means sometimes you lose money to protect your name. You refund. You fix mistakes. You work extra if needed.
Money can come again. A bad reputation is very hard to fix.
That is why I always choose my name over quick profit.
💬 Most freelancers apply but hear nothing back. What’s the real reason they’re being ignored, especially if they’re just starting out?
Let me give you a simple example:
Imagine I say I am a doctor, but I wear normal clothes, no badge, no office, nothing. A patient comes and asks, where is the doctor? I say, I am the doctor. He will not trust me.
It is the same on Upwork.
Many freelancers apply with empty or weak profiles. No strong photo, no portfolio, no proof. It looks like spam.
Before applying, spend 2 – 3 weeks building your profile. Fill it properly. Ask someone experienced to review it.
First, build trust. Then apply.
💬 If freelancers had to stop doing one thing immediately because it no longer works in crowded marketplaces like Upwork, what would it be and why?
They must stop applying with a weak profile.
Many freelancers do not understand the platform. Some open Upwork for the first time and start applying the same day.
First, fix your profile. Fill everything. Add portfolio, skills, photo, description. Make it complete.
Second, stop sending copy-paste or ChatGPT cover letters. Clients feel that. Be simple and honest.
Also, stop quitting in the first month. Upwork is a business. You need time and some investment.
Build first. Then apply.
Jovan as a Guest at the Freelancers Hangout Podcast
💬 What’s the biggest invisible mistake that instantly weakens client trust, even when the skills are strong?
The biggest invisible mistake is a lack of seriousness.
You apply for a job, but you are late to reply. You promise things you are not sure how to deliver. Clients feel that very fast.
They read your reviews. They search your name on Google. If they find nothing, no LinkedIn, no presence, it creates doubt.
Even if your skills are strong, small signs of unprofessional behavior break trust.
Trust is built in small details.
💬 From a client’s perspective, what early signals make a freelancer seem high-risk or high-maintenance before the project even begins?
First, clients check your profile. They read reviews. They look at the portfolio. They check if your profile is complete.
If the profile looks empty or rushed, it feels risky.
Then they Google your name. They check LinkedIn. If they find nothing, it creates doubt.
Also, if you write long, complicated messages or look desperate, it feels high maintenance.
Clients want calm, clear, and reliable freelancers.
Trust starts before the project even begins.
💬 When should a freelancer lower their prices to compete, and when can they feel comfortable raising them?
Lower your price when you are new, and nobody clicks your profile.
On Upwork there is a Reports section. You can see profile views and impressions. Very few freelancers check this, but it is very important.
If you are new, start with a lower price. For example 8$ per hour. When you get your first client and good feedback, slowly increase it. Maybe 12$, then more.
Raise your price when you have reviews, more profile views, and steady work.
Use data, not emotions.
💬 For freelancers landing their first job, what signals make clients click and invite them to an interview or collaboration?
The number one thing is reviews.
Clients first look at feedback. If you have even one good review, it makes a big difference.
After that, they check your portfolio. If you attach real work to your reviews, even better.
Then they look at the full profile.
But reviews are the strongest signal. They show proof.
💬 If you had to reduce a strong pitch to just three essential elements, what would they be?
If I must choose 3 things:
First, a complete profile. 100% filled. Nothing empty.
Second, real proof. At least a few strong reviews and real portfolio projects.
Third, visibility. Be active, turn on Available Now, and use Boost when applying.
Strong profile. Real proof. Be visible.
That’s it.
💬 Building long-term client relationships vs chasing one-off gigs: Is there a type of work or timing where one approach works better than the other?
It depends on many factors.
Long-term work is good for stability and a steady income. But sometimes working too long on the same project can become boring.
Short projects are good for variety and fast growth. You learn more and meet different clients.
For me, the best balance is projects that last 2 3 months. Not too short, not too long.
In the end, it depends on the client and your personal energy.
💬 Upwork has badges. Does the hard work to earn them really pay off? What behaviors or habits actually lead to these statuses?
Yes, badges matter.
When clients see a badge, they feel more trust. It helps.
But badges come from simple habits. Deliver on time. Communicate well. Do not disappear. Keep clients happy.
Also, badges are a motivation. Each badge brings more confidence, more visibility, and more opportunities.
They are not magic. They are earned.
💬 You’ve helped many freelancers succeed on Upwork. What is your most effective method or package that fast-tracked their success?
The Basic package is the most popular.
It focuses on fixing the profile, portfolio, and proposal strategy. Simple steps, done correctly.
Some people cannot pay, and I still try to help them with calls and Trello tasks. But honestly, only a small percentage really follow the steps.
When someone takes it seriously, results come. Many freelancers who followed the Basic structure now work for 15$ per hour or more.
The method is not magic. It is structure, discipline, and action.
Jovan as a Mentor at the Freelancers Hangout Podcast
💬 Outside of sending proposals, what underused strategy should freelancers develop to gain more control over their client flow?
Build your presence outside Upwork.
Create a LinkedIn. Post your work. Connect with people. Let clients find you, not only the other way around.
Inside Upwork, use the Boost option. At least 30 connects if you really believe in the job. Yes, it costs money, but that is how the platform works today.
Write a unique and real cover letter. Not copy paste.
There are many more small details, but these alone can change your results.
💬 How important is personal branding for freelancers, and what do you see as the future of freelancing?
Personal branding is very important.
Today, clients do not hire only skills. They hire people. They Google your name. They check LinkedIn. They want to see who you are.
If you look serious and consistent online, trust grows faster.
The future of freelancing will be more competitive. More people will work from home. AI will change many things.
But discipline, communication and responsibility will always win.
Freelancing is not a trend anymore. It is a real career path.
💬 Are you using any AI tools (and which ones) in your freelance work, or do you mostly use them just for research and not for execution?
Yes, I use AI tools every day. I use ChatGPT, Google Gemini and some paid tools.
In development, AI helps me save time, reduce mistakes and lower the client’s budget. It makes maintenance easier too.
But I do not depend 100% on AI. Maybe 50%. The rest comes from my experience.
AI is a tool. Not a replacement.
I use it for research and for execution, but always combined with my own thinking.
Sometimes I joke and say, I am the AI.
💬 For freelancers feeling discouraged or stuck, what concrete reset plan would you suggest?
I understand them. Many freelancers feel stuck in the beginning.
First, do not panic. Upwork needs patience.
Go back to basics. Fix your profile. Improve your portfolio. Read the simple guide on my website UpworkBoost. The recipe is there down right side in green color circle.
If someone needs more help, they can check the Basic package or contact me for advice.
But the most important thing: do not quit too fast.
Success on Upwork is not instant. It takes time, nerves, and consistency.
💜 Jovan, what’s one lesson, mindset, or mantra you keep coming back to?
Success is not about being the most talented person in the room.
It is about showing up every day, even when you feel tired, ignored or doubted.
Stay patient. Stay honest. Protect your name. The results will come, but only if you do not quit too early.
I truly want everyone to succeed on Upwork. You do not have to buy my packages.
But please, respect the advice. Do the work first. Then come back and say, Jovan, I did this.
When you take action, you motivate yourself. And you motivate me to help you even more.
If you’d like to learn more about Jovan’s web development work or how he can help you get more Clients, we encourage you to reach out directly to him.
