Freelance-Life Balance (freelance 40+)

Dan Burykin
11 min readMar 26, 2021

First of all, you can talk about Upwork in different ways, as well as freelancing in general. This will be about my own path and experience. Above all, Upwork, or any other freelance platform, is an IT product. This means, in some sense, it is a computer game. It turns out that you can and should play it in order to move up the levels. Certainly, I’ll tell you about my mistakes. It is difficult for a marketer to tell about own failures, but as a psychologist, I can share them.

For example, I am 40 years old and I am not a big boss, but a freelancer!

Communicating with clients through Upwork is, in fact, playing the role of your character on the platform. Because it is not you personally, but your persona, your character…

I have been in digital for 15 years, have promoted large brands, and have worked in global communication networks. By the age of 30, I had already delivered business presentations in other continents, but at the same time, I realized that I didn’t want to become a manager, regardless of the fact the business system does not allow you to grow if you do not want to manage others.

One reason people become freelancers is because they choose freedom, flexible hours, and don’t want to sit in an office and work for someone else. But, another reason is their actual readiness to freelance. Such a transition may happen in a quite natural way for those with a quick analytical mind, sufficient emotional intelligence and self-discipline. Unfortunately, I do not consider myself to be one of them, so I had to go a long way. In any case, it is important to define what everyone understands by freelancing:

  • Are you OK with being monitored by a tracking system to get the highest hourly rate and work, not for yourself, in fact, but for a freelance platform? Some trackers even have the ability to capture your face in front of the screen. With this approach, you, de facto, do not even do piece work from the customer’s project, because you are constantly in contact with them. Without time spent, only a freelance platform earns from your project, and you make it from selling your time.
  • If you, like me, are a sociable person, then you may be interested in promoting not only your services, but also the services of other specialists, your group or your agency. However, such deals are much more difficult to close.

When I first signed up for the Upwork and PeoplePerHour freelance platforms, I came across a Google project that recruits Google Ads trainers to teach their consultants in call centers in Barcelona and Lisbon. To be honest, at that time, I hadn’t done PPC advertising for a while, and at first I decided that I wasn’t a good fit for this project. However, after some time, I came across this project again and I decided to apply for it. I went through interviews with Google in 3 days and flew to Barcelona in a week. It was my highest pro level project ever and I gained a potential employment offer. However, I managed to stay true to my choice of freelancing. I definitely don’t regret it now.

Truth and myths about freelancing

Either a feast or a fastit’s true. Freelancing is often referred to as “Either a feast or a fast”. I can say that for the first 2 years, this is indeed what happens. It’s just that over time, these fluctuations become smoother and you learn to balance.

Temporary solution — it is, but not always. For many, freelancing is a temporary solution. Basically, those who go freelance who are not ready for it end up returning to employment. But even though I am now more stable with income and employment than in the last 10 years, I still have thoughts like, “What will people say?”, or “Son, what is your salary?”

Complete social isolation — it’s true. For me, nothing has changed in quarantine, apparently. At some point, since I’m a sales lead of our freelancer group, the lack of in-person communication makes me a more motivated and loyal communicator with clients. They feel that, which in turn makes them more loyal. In addition, I also have a psychologist’s interest in intercultural communications.

You need to plan your financesit’s true. You need to create at least a P&L table at the end of the year, with data and a plan. To date, I fill in the table on a monthly basis.

Relaxing work — this is a myth. A lot of sweat and nerves are required. It is completely impossible to predict and manage clients reviews and ratings. Perhaps, if you build relationships with clients analytically, then these risks can probably be better predicted. Or you can just keep doing more jobs.

The freedom to be lazy — this is a myth. Yes, I can wake up any time in the morning, and I can easily take a day off. But, in general, when you wake up, you are already working, and when you finish working, then it’s time to go to bed.

One-time jobs — this is a myth. Most, or at least half of the projects on freelance platforms, are not one-time jobs. Clients are often looking for permanent contractors. Certainly, there are one-time orders, but in fact there is a huge flow of various projects, and you can choose the ones that suit your specific skills best.

You need to know English perfectlythat’s a myth. It is enough to understand the topics and basic phrases, catch the general meanings, and respond with intelligent humor.

Losing your qualifications — can be both true and a myth. First of all, it is a matter of flexibility. If you lose one qualification, you may gain another. For example, I am acquiring the qualifications of an international B2B sales manager. At the same time, I cannot say exactly how much, over the passage of time, I remain a qualified hired manager. I think that the truth is, first of all, that certain skills are always rapidly changing, and the one who wins is the one who remains in continuous business with organizations that need use of these skills.

For IT developers only — this is a myth. On Upwork and elsewhere, you can find work for any specialization and expertise. But as a rule, projects there, one way or another, are tied to work with certain IT products.

Sales funnel

1. Discover your prospecting client

Constantly monitor the flow of new jobs. On Upwork, for example, you can set up a filter and receive email notifications from your custom RSS feed. My new job notifications go to my Telegram group. Besides the formal job requirements that fit your expertise, pay attention to a number of other indirect signs: is their average customer rating high enough, what is their rating, and how many bad reviews did they leave for other freelancers, etc.

2. Attract a client with your proposal

The whole point is in creating and sending a proper cover letter. There is no specific algorithm or advice about what works and what doesn’t. It is necessary to send, send and send, and test hypotheses. So-called industrial espionage can also help. Register on a freelance platform as a client, post a typical project that you would like to receive yourself, and monitor cover letters of your competitors. This will help you to consider which proposals you want to respond to, and which letters, on the contrary, would cause less confidence and more irritation. There is no need to send templates; the text should be minimal and as customized as possible in accordance with a particular project.

3. Work at the negotiation stage

We try to get into the head of the customer, trying to understand their tonality and wishes. Then we become the one they are looking for, in a way that compels them to feel that we are the ones who will solve their problems and tasks. At this point, the approach is very similar to the empathy stage of the design thinking technology.

4. Sell of the beginning of cooperation

A technique that works well is to offer something for free to interest a client, if you can afford it. If not, then set a clear framework for what you will do for less money first.

5. Cooperate to increase the cost of services

If your service niche is very structural and branching correctly, i.e. where additional services can be naturally built in, this is an excellent opportunity within the framework of a specific project to sell related additional services.

As I said above, freelancing is a certain way to organize your work. At some point, it is a transition between two parties: an employee and an owner. In order to grow from freelancers to an agency, it’s important to be effective in each of these identities. In general, there is no pure service or pure product. There is always some hybrid of product and service. A freelancer provides a service applied to a particular product, for example, a developer in a particular framework. The agency stage is when you are both a product and a service, and also a client. This does not mean that you need to resell other freelancers like you on Upwork, but with a lower rate. They might deliver some simple parts of your services, or its initial sale through the funnel described above.

As a summary, here are 7 tips from my article for freelancers in one of the local media — they are still relevant. Some of the ideas are already provided above.

1. Work on several freelance platforms at once

There are many sites where local and international clients hire freelancers to work on their projects. The range of orders is wide: all kinds of software development and design, copywriting, search engine optimization, recruitment, finance, management consulting, coaching, and much more. Should you focus on a single freelance platform? My experience and basic logic says that it makes sense to promote yourself on several platforms at the same time. Your expert profile on each of them can be different. This is influenced by the first orders that can be obtained. It doesn’t matter if for the first order you have to perform a completely non-core job. The main thing is that this opens the door for new orders, and they will help you get closer to your main area of expertise.

2. Actively apply for projects

Here I wish everyone strength and patience. Yes, you need to respond quickly to all new requests from the freelance platform — it is desirable to apply for jobs on Upwork within 15–20 minutes from the moment the work is published. In your cover letter to a potential client, you need to sell yourself. I would never have thought that I would be engaged in sales, let alone internationally.

On a freelance platform, you are not engaged in active sales, but respond to a request to do this or that job. Therefore, if you, just like me, categorically considers themselves a “non-seller” — take the situation as consulting, the purpose of which is to involve, not sell. Keep in mind an important nuance: your messages should be as personalized as possible to the customer and their request. Look for the customer’s name in their reviews and include it in your greeting. Have a minimum of cliches in your proposal and be sure to add something about the client’s business, your experience, and also ask questions about the assignment.

3. Invite the client to call to discuss the project immediately

Immediate invitation to communication is an element of active selling on a freelance platform. And it is better to do it not by chat, but by voice or video. Imagine that you are a doctor and you need to listen calmly to the patient who is in pain.

Carefully study the client’s reputation and how much they, according to the statistics of their profile, are willing to pay. As a rule, the less the order cost is, the more stress it will cause. But, at first, you will have to put up with it.

4. My client’s client is not my client

More than half of orders on freelance platforms are placed by small agencies that outsource services for their clients. And they build relationships in different ways. First, they try to lower the cost of your work. Second, they want to get more expertise from you than you are willing to provide for the same money. However, they are not interested in your reputation growth on the platform… Though here, as elsewhere, there are, of course, exceptions, but they are rather frequent outside freelance platforms.

5. Offer a responsible payment model

There are two main payment models: fixed amount (by project or by milestone) and hourly rate. The format depends on the type of services and their conditions. Freelance market customers are often entrepreneurs who think on a piecework basis. And in some situations, it is beneficial for both parties to share the financial risks. But you can negotiate a good bonus for a result higher than the agreed one.

6. Freelance relationship: don’t be cheap or greedy

When starting a game on freelance platforms, you should not indicate your value higher than a beginner, even if you have plenty of expertise, because, at the start at least, your rating is very sensitive to lots of factors. Any mistake can easily cut prospects for further orders. As a freelancer, you create your own added value with your own hands. You are literally playing a character on the freelance platform who speaks at least three languages:

  • Customer attraction language
  • The language of service and product expertise
  • The language of relationships with the team, partners and stakeholders

A successful freelancing strategy is the role of a negotiator in which he is most stable, open to mutually beneficial exchange, passionate and sober at the same time.

By presenting yourself to a client, you are talking about yourself. It is important to be aware of how you want to be perceived and, if possible, play yourself. For example, my thing is sarcasm. Through it, I sell myself and fulfill the objectives.

7. Form a full range of services to make new sales to existing clients

Both one-time projects and regular clients in your portfolio indicate your successful and viable freelancing. Of course, you can offer new services to your loyal clients.

I’m Dan Burykin, the Free Call Tracking creator and a top-rated marketer. Together we are Top-Rated Team — an international group of independent Google Ads and MarTech pro. Each of us has been setting up and optimizing paid traffic for eCommerce, B2B and B2C lead generation in the United States, Canada, UK, Germany and Ukraine for over 10 years.