In July 2022 I closed down CoachLancer Hotline because of a constant overload of young freelancers asking for guidance and feedback. The only way I could scale up my support for freelancers was to create a webinar course consisting of 9 topics related to building freelance businesses.
So, I started running webinars with those who can invest their time and money in learning skills they do not yet possess. The skills that make all the difference when going online and trying to get business on freelance sites like Upwork.
And you know what? It’s been super fun! What makes it so great is all those questions that the participants pose. Unique perspectives, interesting theoretical challenges, and great stories of failures that lead to an increased understanding of how to do things right.
Here are the best questions I got over the period of about 2 months, the first 2 batches of the Freelance Like a Boss interactive webinar course. But first, let’s examine why the webinar course is one of the most efficient ways for those who want to learn how to freelance remotely from their homes.
The problem: Trying to learn how to freelance remotely without feedback
What makes freelancing hard is the lack of feedback. You might have seen those thousands of people on the Upwork Community forum, LinkedIn, Facebook, etc. posting their freelancing experiences that are usually described as “I’ve sent 100 proposals without any response from clients.”
Yeah, let’s face it. When you’re trying to build a business on a platform that does not provide any feedback, the process is slow. Either, you keep sending Upwork proposals until you randomly get a job, or you go somewhere to learn how to write those proposals, then send a few and nail your first jobs with minimal effort.
Sending lots of Upwork proposals when knowing you’re not good at writing Upwork proposals is insane.
It’s the lack of feedback that kills the process for many. Fortunately, it only takes a little bit of guidance and feedback to get things going compared to getting no guidance or feedback at all.
The nasty thing about many communities that rely on other freelancers’ goodwill is that those others who are supposed to help you might see you as a competitor! Why would they give good tips that might reduce their own income? What makes you think their advice is valid?
For instance, when you get tips on Upwork Community Forum from people whose profiles aren’t even publicly visible, would you trust that person’s feedback or would you rather trust the feedback from recognized experts whose profiles are visible and everything else is transparent too?
The world of online freelancing can be brutal, and everyone must play for themselves first. Only after success comes the luxury of putting time into helping others.
The guidance and feedback I gave on CoachLancer Hotline
Before running the webinars, I had CoachLancer Hotline on for about two years. It worked really well with a service-for-service kind of model. I helped people to get their freelancing going and in return, they rendered some services to me. And it was fun with most people!
I must highlight some great personalities that I came to know via the Hotline. Not only did I manage to help them but also I learned quite a lot from the descriptions of their challenges.
Rafael Barreto-Garcia was the second-last “Hotliner” and perhaps the best success of all times that I was lucky to witness in terms of speed of getting the first gigs and starting rates. After working on his profile for a calendar week at the end of July 2022, it was finalized in August on a Monday. On Wednesday of the same week, he got his first job worth $300!
Rafael is the only person whose first clients are willing to pay 3-digit figure hourly rates (the client-side fee is 5%)!
And that’s the normal part of it. As a lawyer with degrees from 3 countries, we had an understanding that a guy with his qualification should not need to start from the bottom. So, he set his hourly rate as $99 from the start! And then, within the next week and another couple of weeks later he already had 3 jobs with that rate running hot!
So, that’s how “hot” CoachLancer Hotline was. Cash-burning hot!
What’s the webinar course all about?
Over the number of years I’ve been helping freelancers to do better business online, it got clear that it is the guidance and feedback that people need most. The world is full of free tips, guides, videos, and so on, but what people struggle with is figuring out how to apply all that information to their own cases in the right way.
Even a small amount of guidance and feedback can make a huge difference in a new freelancer’s business-building efforts. As Hotline got limited by numbers, I figured it was time to scale up a little.
The other factor was that I gave a presentation for the Upwork community in the Philippines a couple of months earlier and because of the topic Charging 3-Digit Figures Per Hour And Increasing Your Value (without breaking a sweat), there were many times more people hoping to join us than what the webinar platform allowed. Only the first 300 registrants got in.
Giving a 90-minute Upwork LIVE presentation was one of the drivers for creating my own webinar course.
The questions I got (after having my coconut) were coming in such numbers that Avery, the host of the event, had to start filtering them quite heavily. Some of the questions were good, some… well, not so intelligent. From this experience, I realized that there are so many dreamers, wishful thinkers, and those who hope to become something they will never become, sadly.
This is, I believe, one of the crucial factors in becoming a true freelancer. Having an intelligent approach, realistic goals, and clear learning paths to improve your freelancing skills are the factors that make or break your first-year freelance business.
Unfortunately, it is very difficult to do all that, particularly when you don’t have a long career behind you when you decide to go solo. Then, the only practical way is to seek mentorship that speeds up the process and gives you a chance to get it running sooner rather than later.
What has it been like
It’s been a ride! I never imagined that I would get so many new freelancers joining an unestablished unknown webinar course just like that with minimal marketing effort! And all the participants are serious people; serious about learning how to freelance, and serious about how to build a one-person business quickly.
My freelancing tips also go by the name ”100% Natural Coconut-based Anti-peanut Smootheners”… and they come in pairs! Humongous pairs!
And no, coconuts do not end there. See? Because I cannot advise any freelancer, even a new one, to work for peanuts, going for coconuts is the only reasonable way to get started. I managed to demonstrate more or less the full lifecycle of coconut too!
Find the “black sheep” among these coconut-infested screenshots of the webinars!
As I am writing this, Freelance Like a Boss webinar course batches 1 and 2 finished a couple of days ago. There were 9 webinars in each batch with a joint Grande Finale by a prestige guest speaker. Tom Stotesbury, an English communication coach for freelancers and entrepreneurs, gave an excellent presentation on communication skills that freelancers need to build. And loads of practical tips and hacks with examples!
Tom Stotesbury’s absolutely beautiful and highly inspiring Coconut Special. 🙂
What it has been like is basically this:
- I bought an extra coconut every morning so that I have a “display coconut” for the webinar in the evening (10 pm my time).
- I made the course materials, examples, and presentation slides in the afternoon (for the first batch).
- At 9:30 I went through the presentation and made sure the polls that enable interactivity in each session are set up on my GoTo Webinar
- At about 9:50 pm I set up the session and allowed people to join in.
- Exactly at 10 pm sharp, the coconut show started!
- Afterward, within the next week, I wrote comments and feedback on the participant’s homework assignments such as optimized profile drafts, mock Upwork proposals, business plan drafts, and so on.
My punctuality seemed to produce issues for those with “flexible” concepts of time. I remember being asked to summarize the previous points for a person who came in late, hahah! It felt like a lazy pupil coming late to school walking to his desk and asking the teacher to summarize the previous 15 minutes because he wasn’t there… thus, making everyone else listen through everything twice!
Fat chance of that! 😀
Anyway, most participants joined in on time, most participants had great questions, and most participants did their homework assignments very diligently. Actually, I have extended the discussion with many of the best students to topics slightly outside the coursework, have featured them in my newsletter, and given all kinds of additional support – because they deserved it!
The best questions from webinar participants
Because of the unmanageable number of questions that I got already after the Upwork LIVE presentation, I was prepared to answer quite a load of them after each webinar presentation. But it was not really the number of questions that amazed me… it was the quality.
So many good questions!
Well thought-through, well-formulated, properly typed questions. I loved to answer them all! Below there are the 45 best questions that I answered during batches 1 and 2. And this is just a start!
Basics questions
These are the questions many who just signed up on a freelance site seemed to be asking:
- Is there any best time of the day to send proposals?
- Do we need a portfolio website and is it worth having one?
- Upwork has the Specialized Profile option, what to do with that?
- How can one create a virtual assistant’s portfolio without work experience?
- Should we add lists to profiles, or should the profile only be in paragraph format?
- Will an unoptimized profile affect the chances of getting a gig negatively?
- For new freelancers with little or no experience, what do you advise they answer when asked to describe their recent experience with similar projects?
- How should I write the first sentence in an Upwork proposal?
- How do you propose a new milestone for the project and how should it be defined?
- If I use a specialized profile to apply for a job and they click on my profile, will they see all the other profiles I have?
- Is this good to be included as the CTA in a proposal: “Let’s schedule a meeting to discuss how I can bring my expertise to the job”?
- How do you answer the question “describe your recent experience with similar projects “ as someone just starting on Upwork with no experience?
- How long is an Upwork proposal supposed to be?
- “Let me know when you are available to talk”. Is that a bad CTA (call to action)?
- Sometimes there is a very short job description and not much information in it. How to respond to such a short job description?
- What is the best way to submit a proposal for fixed jobs when you need to define the duration and milestones?
- I have faced many instances where clients asked me to make a demo app before they give me the actual job. Should we make those demo apps?
- Is it wise to go below the budgeted amount for the job to attract the client?
- Many times clients put preferred qualifications in job postings. How should I accommodate them if I don’t meet every single qualification?
- Must we attach a link to similar jobs to every Upwork proposal?
- Is it wrong to set a lower price than what the budget of the job is?
- Is it advisable to send proposals to a job that already has over 50 proposals from others?
- As a writer, does attaching a sample to my proposal help me get the job?
- How can a newbie in the gig economy with no prior experience write a proposal that wins?
- How do I know the client’s name so that I can address the person appropriately?
- Sometimes clients ask for a free demo without looking at my portfolio. How to deal with such clients?
- Are all the jobs posted by clients with unverified payment method scams?
- Is it better to use the Available Now badge or not?
Advanced questions
These questions came from those who had started already some time ago:
- For profiles of social media managers, do we need to focus on one social media niche or all of them?
- Should we increase the technical skill before charging money for it? Or can we go straight to it and learn the skill while doing the job?
- On Upwork, we can set earnings to be private so that others don’t see them. Would you recommend doing that?
- How do I convince my old clients about my new price?
- When raising rates, what can we do with our past track record that demonstrates low prices? (I have earned $5K at $15/h, should I refund that because it was a low-price job?)
- How much does the Job Success Score on Upwork impact the chance of getting into an interview after sending a proposal?
- What exactly does boosting a proposal with extra Connects do on Upwork?
- How do I prove to the client that I am the right fit for the job knowing that I am new on Upwork, I’ve not earned any money, I have no Job Success Score, and I can’t share files of things I have worked on earlier because of the confidential nature of my job?
- Besides Upwork, what other platforms do you recommend?
- How do we see what others are pricing for a particular job?
Funny questions
There were several questions that made me smile a little… and sometimes not just a little. Despite these questions being slightly funny, it is important to understand that new freelancers have all kinds of expectations and assumptions about freelance sites! Whether or not they are realistic, useful, or relevant at all, is what I tried to clarify during the Q&A sessions.
These were some of them:
- Is it true that you need to be awake at certain times of the night to apply for a job on Upwork?
- Which is better when submitting proposals, writing them on a laptop/desktop computer or using a mobile device?
- Can we ask clients to come to a video chat even if they didn’t ask to do so?
- If you made a mistake in the interview or feel you did not do well, how do you ask for another interview or prove to the client that you are competent in some other way?
- How long do clients usually wait for a reply from freelancers?
- How much money can you make by freelancing? Or what would be expected “normally”? Some small pocket money only unless one puts a lot of effort into it?
- How to convince clients that currently I don’t have any similar experience but I can learn things while I do this job?
Want to learn how to freelance remotely?
All those questions had valid points, even the funny ones. There are no stupid questions about freelancing when there are so many things you do not know yet.
It is difficult to learn anything without guidance and feedback. Why this issue is persistent in freelancing is only because of the mindset of new freelancers! There are plenty of resources available, both free and paid, but usually, it’s only the paid ones that provide the most useful help.
No surprise there. 😉
Nobody else has any interest in a new freelancer’s business unless there is a mutually beneficial business deal that creates the interest!
What freelancers have to understand is the expected income with and without guidance and feedback. Imagine this scenario: you try to learn everything alone and with all the free tips from others you can find. But you do not get personalized feedback or guidance for your learning process.
This process is the trial-and-error process. Lots of mistakes will be made. Many issues arise with the first clients because of not having any means to predict how things will go when you start your first projects.
The opposite is to start freelancing under the guidance of someone who has succeeded before. This approach reduces the number of mistakes with the first clients, provides a framework for learning what is essential, and creates a structure for getting to understand all things that running a freelance business involves.
A fictional example of freelancing income in two cases: learning everything alone or guided learning with feedback.
The numbers at the end of the first year would be entirely different! Imagine your maximum income doing what you do best being $2,000 a month as a freelancer. When starting alone, struggling alone, getting only theoretical tips that you don’t know exactly how to apply into practice, your first months are… well, you’ll probably work for peanuts regardless of how many hours you put in as effort.
When new freelancers realize they need a good process for finding clients consistently and manage to build the process, magic happens. In this example, you’d finally get past earning some hundreds per month to $1,000 per month! Typically, it takes about 6 months to get there. Until that, it’s just a long learning process because of the trial-and-error nature of learning everything by yourself.
Now, imagine getting a kickstart for your freelancing where there are upfront costs. Say, it costs you $50 and all of your time for the first month. And instead of trying to get work during the second month, you keep practicing. So, after two months, you got no income at all but paid that $50. Sounds like a bad idea… and it is if your time span is weeks to a couple of months!
But if you plan to freelance properly and seriously, you can look at your performance in a longer time span, e.g. one year. Now, if you reach the same milestone of creating a good process of finding clients in the third month instead of the sixth, your learning process pays off immediately!
Compared to the self-learning approach, the process with guidance and feedback would bring $1,000 in the third month minus the initial cost of $50 which makes it $950. This happens because you figured out your starting point and you got started right!
With the self-learning approach, you would not have any upfront costs but the learning time would be much longer. In 3 months you would only have only $600, not $950. Now, when this accumulates into a faster learning process and you examine this in a span of the whole first year, the numbers speak for yourself.
You could reach the peak income of $2,000 per month in 7 months with guidance compared to 10 months with the self-learning approach. That’s a difference of 3 months’ income before the peak is reached.
And this is not all. Actually, if you get a good mentor who knows how to navigate freelance sites, you might go beyond your expectations in terms of your peak income! It might not be $2,000 any more!
What should you do to learn how to freelance remotely
Even if the example calculation is purely fictional, it should tell you one thing. Imagine your business growth in terms of your income. How fast can you reach your peak? Are you looking at something close to a full year or can it be done in a matter of months? The difference is what defines your income during the first year.
Good support, guidance, and personalized feedback can define your learning speed. Make sure you don’t waste your time in a nearly endless trial-and-error-based learning process. There are many who can help you reach your income goals faster.
One of the ways is provided on this site. The CoachLancer community provides a great way to learn how to freelance in a matter of months so that you don’t need to spend all of your time struggling alone. You do need to make a small investment upfront, though.
Want to get access to the webinar materials? CoachLancer memberships are now available! All CoachLancer members get recordings of all the webinars I’ve presented and a considerable discount on all services. Guest talks are still 100% live and unique sessions with no recordings available. Welcome to learn how to Freelance Like a Boss!
