Working for someone vs. doing your own thing

I’ve wanted to write about this subject for quite some time and only today decided to finally sit down with no distractions. I put my phone aside and tuned into Spotify's "focus" playlist. At long last, I've finally collected my thoughts together. This is a topic that’s very close to my heart. It’s felt like a brain bug that's been needling me and forcing me to ponder over my current situation, so I figured the only way to force it out was to put it into words.

This is more of a brain dump or an internal monologue. I don't intend to prove any point or convince you to start your own thing. Neither do I want to reassure you that working for someone else is the best option for most people. My goal here is simply to get my thoughts out so I can think clearly again and rationalize this thing that's been nagging me.

Let's start by putting it all into a little context.

I've been working full-time as a developer since I got off the college circuit in late 2014. Well, okay, it's a bit over five years now. When I was at school I started to work on side-projects regardless of how busy I was. It became a thing that I would usually do. I don't know what motivated me to build stuff on the side. Still, I guess I did it to satisfy my intellectual curiosity and maybe because I just adored making things. I never asked myself why I loved it so much because it never occurred to me that the answer might be necessary. So I continued building a new project almost every year since I graduated.

I knew I had to land a job when I finished school. As most people do, I moved with the flow and followed my friends' path. I never stopped to ask myself what I enjoyed doing in life. I was an international student, so I didn't really have any choice other than finding an employer who could sponsor my visa. I didn't want to leave the country and go back to my birthplace. I felt I’d invested so much into my education; it would have been a waste of time and money if I had then bailed.

So I landed a new job right after school and moved to New York City. I started to climb the career ladder in the tech industry. Funny, but even when I started my first-ever full-time job in the USA six months in, I started working on a new side-project for fun—a simpler version of Goodreads called Booknshelf. Then, after a year, I changed my job and joined Buffer. Buffer is the company that introduced me to remote work.

Over time, I started to value my time a lot more as I grew up, so I decided that if I ever built another project, I wouldn’t do it for free. I have to charge for whatever I'm making so I can cover the project costs and justify my time. I wanted a side income. That all happened in 2018, when I built and launched my project. It's currently making close to 1K monthly.

Now, after two years starting a side business and four years of a full-time job, I’ve begun to think about my next steps and the different paths I could take from here. I’ve started ruminating about the next rungs in my career and life. What's the right direction for me? Do I have to choose it now, or can I do what I'm doing now and decide later? If so, why are these questions disturbing me now and not in the future? How do most people work out what’s the right path for them to take?

But let's step back for a moment. Does it have to be either or can you do both things together—have a full-time job and do your own thing? Why am I struggling to accept that both paths can exist together and that might very well be a viable path for me? I think because I'm afraid if I commit to two things at the same time, I won’t be successful at either of them. I've always considered myself a generalist with very diverse interests. However, this time something is pushing me to go deep into one thing.

I know what most people's heuristics is when they face this uncertainty: think about ten years from now and figure out where you want to be. And do the thing now that gives you more options to get there. I wish it was as simple as most people claim. Looking back to the twenty-year-old me and the person I've now become, I see almost no similarities, interests, or passion. I was a completely different person back then and the only thing that has stuck with me after all these years is my love of soccer. How do people predict the future? Clearly, I'm no good at it.

I admit it—I'm not a very self-aware person. Because of that, I’ve taken the portfolio approach so far and tried many things to find out what I like to do most. Now, after a couple of years, I have succeeded in developing a general sense of the things I like and do not like. I wonder whether, as we grow older, the rate of change in our interests slows down too? If this is true, maybe I should bet on my current interests in order to build my future?

For argument’s sake, let’s say I decide to quit my job at some point and work on my own thing full time. Would I experience it in the same way as I am now? I imagine working on your own thing full time and on the side are definitely not the same; it's scary, to be frank. If my side-project became my full-time work, might my passion for my project dwindle and become yet another job? How would it differ from my current job?

I know what you're thinking. You say, but y’know, Tigran, you will learn how to manage your working hours and can work from anywhere you want. If this is a luxury I'm aiming for, then I already have it with my current remote work. Also, I think your working hours would become even worse. When you own a business, you have to make sure it runs uninterruptedly. I guess it might also depend on the type of business you run. However, right now, I'm talking about an SaaS (software as a service) business that I own.

I think it's important to know what type of business fits most comfortably with the lifestyle you want to have. Some people dream of having passive income businesses. I like the idea that you can earn money while you sleep, but are those businesses fun? I know if I have a ton of free time, I'm likely going to work on something that I like. I might pick some new hobbies, but most likely, I will get back to programming.

How about financial wealth? Financial well-being and independence are clearly important to me, but I don't believe there’s only one way to get there. Yes, if you want to get extremely rich, then probably you should own huge equity and run a business, but what about others who don't fancy that life? I'm pretty sure there are people like me who are okay just living reasonably well (it's relative for each person). Most VCs claim (for obvious reasons) that the fastest way to get rich is by starting a startup. There is also another side of the argument that claims the opposite—that working in big tech companies might be a wiser choice financially.

I've been working remotely for four years now, and I know that working alone can make you lonely. Eventually, you need to socialize with people and co-workers. If I work on my own business alone, I won't have co-workers until I hire them. Getting to the point where I can hire a team might take years or even longer. And I know there are supportive online communities that I can participate in, but I don't think they provide the same value as in-person networks do. How hard is it to build a social network when you work by yourself full time?

One of the things that I care a lot about is my rate of learning. I'm pretty sure that building a business exposes you to a broader domain of problems that you otherwise wouldn’t have access to when working for someone else. It's an incredible opportunity to learn about a lot of things. How can we accelerate our growth while working in a company? If it's too slow compared to starting a startup, is that reason enough to quit working in a company?

Of course, there are many other metrics you can measure this argument against. However, I’ve tried to focus on the metrics that are somewhat important to me. I'm pretty sure that with the rise of the passion economy, we will change the way we work. Maybe in ten years, all my questions here will no longer be relevant because there will be one definite solution. In any case, I do want to believe that we can build an economy where we can make a living through our passion. It could be writing, building websites, or teaching online.

They say we should think a lot about what we want to work on. If that's true, maybe this was my humble attempt.