How to Start With Freelance Work as an Engineer

Gregor Ojstersek, founder of the Engineering Leadership Newsletter, walks through how freelancing moved him from software engineer to CTO. He breaks down three models: contractor roles, project work, and coaching. Start by doing free work for testimonials, build a portfolio, then scale through word-of-mouth or platforms like Upwork and Toptal.
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Freelance work has been my secret for the growth in my career from engineer all the way to CTO. My experience would be way smaller without it, and I wouldn't be able to do my full-time roles so well without it. If you don't know me yet, my name is Gregor Ojstersek. I am the founder of Engineering Leadership Newsletter, and in this video I'll be sharing how to start with freelance work as an engineer. All right, so, um, let's first start with why should you do freelance work. And yeah, I mentioned this a bit in the beginning, and I wouldn't be able to grow in my full-time career from engineer all the way to CTO without it. My experience and my overall perspective has grown immensely because of it, and I wouldn't be able to do this without, you know, doing coaching and mentoring, without doing, you know, projects, without doing also consulting with different, different companies as well. And I like to, I like to tell this example, which is like, if you're working on the same thing for 5 years, then you will have like limited perspective. But if you work on multiple things for 5 years, then you will have really, really broad perspective of various different topics, various different challenges, and you're going to be able to solve like new challenges a lot faster. Especially for people that are, that are in certain company and they're working on a very niche type specific projects. If they don't try and go through and expand their horizon, they will be just limited to that specific context. So yeah, I think, you know, it's extremely powerful if you get perspective of the various and different things, you see what works and what doesn't. And over time, you know, you're going to be increasing your experience so much more. And also, this is a good example about why, you know, why it's so important to do freelance work. Software engineering is not about, you know, just finishing tickets and tasks. It's about understanding the problem, getting to know the domain, thinking about a solution, then building the simplest solution to solve the problem. And you can't learn how to do this only if you are, you know, just working with tasks, with tickets, and you don't actually think about, you know, what is going— is this actually the best solution? Is this actually the best thing to do this? And so on. And this was my response on this LinkedIn post, which is problem solving is key. And that's why doing some sort of freelance work is what I suggest to every engineer. You can't just pick a ticket and hope that the client is automatically going to be happy. This is what you learn. You learn about good communication, you learn about organization in general, good planning. You learn about, you know, doing consulting because you're not just a builder. You're basically— you need— you are expected to deliver work that your client needs, right? And in 99%, they will actually ask you to do something, but it's going to be a wrong solution. You need to find what is actually, you know, the simplest solution, what is actually the best solution for the client, what they are looking for. And you only learn that if you are actually responsible for full projects from start to finish, and you're also doing communication, you know, that can be with clients, stakeholders, etc. So how do you start with freelance work? There are, there are 3 different types that— for freelance work, freelance work that you can do. And obviously the first one is contractor work. This one is if you're like, if you, if you want to do part-time or full-time work as a contractor, you, you normally join a team or there are already engineers there. Maybe there may be also like other, other types of cross-functional members there as well. And yeah, as I mentioned, you can do full-time or part-time. The second type is, you know, project work, though that's the type of the work that I did the most as, as a freelancer. And you can do, you know, work for non-technical clients, technical clients, you know, companies from various different industries and so on. You know, that can be websites, web applications, desktop applications, mobile applications, etc. I did basically a combination of all different types of work here. What I did and what worked really well for me is when I, you know, especially in the beginning of my journey as an engineer, I said a lot more yes than no. And what I did was Whenever I took a new project, I learned a lot from it. I learned a new framework. I learned what I need to do to build this project from start to finish. And that's how I increased my perspective immensely. I wouldn't be involved— I wouldn't actually be doing any kind of like a desktop applications if I wouldn't be, you know, building a desktop application for a client. And then the third one is coaching, mentoring, consulting, advising. This is also a really amazing way to do freelance work. You— I like to say that when you're teaching, when you are helping others, you are also learning. And especially, you know, consulting, advising, this is something that you get perspective on various of different challenges that companies are facing. And yeah, I've been— it has been extremely, extremely useful in my career, especially in my engineering leadership journey from team lead, engineering manager, head of engineering, VP of engineering, and then to CTO. I wouldn't be able to do such a great job in these full-time roles without me doing consulting, advising with, with other companies as well. So this is how to start, right? Always, always start with, you know, something. You need something. You need, you need to build credibility in some way first, right? So if you don't have like a lot of experience in finishing projects or, you know, in a lot of experience with full-time roles, try to do something for free first. And the reason is that people are going to come to you a lot more easily if you can already show that you have actually finished types of projects that, you know, your clients are looking for. So building credibility is, is extremely important. That can be in anything, also in coaching and mentoring, consulting, advising. If you can showcase that you have did this with, you know, a couple of people or a couple of companies, people and companies are going to be more prone to to work with you. So yeah, that is the second step, is, you know, getting the, that social proof, getting testimonials that you, you can do it. And if you have that, you know, companies and people are going to be a lot more prone to working with you. And that, that goes to the third part, which, which is show what you've built. That can be either a landing page, that can be a website that you share to your, to your potential client. That can also be, you know, just handing, sending them a list of websites that you have done, something that, you know, you can, you can inspire trust with, with your client about yourself. What about scaling your freelance work? So once you get, you know, the first clients, you know, you can use sites like Upwork, Fiverr, freelancer.com, Toptal, or other. I personally haven't used sites like, like this. For scaling my freelance work because I got a lot of clients came from mouth-to-mouth recommendation. So what I did was I did a great job with, you know, with one client, and then that client recommended me to 2 to 3 other clients. And that kind of like went a long way. And it even got me to a place where I got so many people reaching out to me that I couldn't— I needed to say no to a lot of these requests. So I didn't— that's why I didn't use these sites. But if you wish to scale further and you wish to have more clients, those are some other ways. I especially heard some good things about Upwork, but yeah, can't really say my personal experience with them. But for coaching and mentoring, I heard a lot of great things about these sites, and I would— that would be also my recommendation. Personally, again, I haven't used them, but I heard really, really good things about MentorCruise and similar sites like that, which is like the hardest thing about, you know, getting your coaching clients or getting your— the people who are going to, to ask you either for a consultation. You need visibility and you need people to find you, right? And if you're not doing actively like any kind of, you know, writing online, social media, any kind of posts on social media, it would be hard for people to find you. Of course, you can do, you know, if you, if you, if you do a certain— if you do have already a certain coaching clients, it's a lot helpful if you, you know, that mouth-to-mouth recommendation goes a long way. And if you do a good job with one, that person is going to recommend you with a lot of others. But, you know, having a site like that, that's, that's already, you know, people are looking for people that are experts in certain areas, and this will be great for, for your visibility. The third thing is, you know, if you're doing projects, it's a really great way to kind of like team up with a certain person. If you're an engineer, work together with more product manager, business and marketing sales-minded person, some person that can help you with, you know, getting more, getting more opportunities, getting more projects. And that has worked really, really well for me. I teamed up with a person who was really, really good at, you know, talking with, talking with clients, managing multiple projects. And we worked together for a long time and we did so, so many projects together. The fourth thing what you can do, you know, if you have so many projects, you can potentially create your own agency, a product or a specific niche service, whatever, whatever works and whatever you've seen is working for you, right? And obviously it's an interesting road to take. I didn't decide to go that route, and the reason was that, you know, I then grew to become team lead, engineering manager, etc., and I focused a lot more on engineering leadership roles. But that was really, that was on my mind to potentially start my own agency. But you know, once you do once you do projects for clients, you can see what kind of asks and what kind of problems these companies or people are facing, and you can build a certain product based on that as well. So potentially, like, if you see— if you're working with a lot of, like, travel agencies, you can potentially see what kind of challenges are these travel agencies, you know, working with, and then you can build a product just for, for example, for those travel agencies. And that can be extremely a good, good way to, to find like a good, good, good product. And also, you know, the fifth part is start building your social presence and writing online. This is crucial because that's how you can scale. It's going to be hard for you to get continuous inbound requests if, you know, if you don't build credibility, social proof, and, you know, show to everyone that how great you are. And that's where writing online, you know, writing a newsletter, you know, being active on LinkedIn, X, or something else can go a long way. You need to build some sort of like a personal brand that is going to showcase, showcase that you're an expert in what you're doing. And if you do that, you're gonna get, you know, people are going to come to you instead of you needing to reach out to others. I hope this was helpful to you. To learn more, you can subscribe to my newsletter. It's called Engineering Leadership. There are more than 150,000 people already reading it. I publish 2 new articles every week. And yeah, thanks for watching. See you in the next one.
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