An engineer’s path to career monogamy

Jan Omacka
Productboard engineering
10 min readJul 1, 2020
This is how it felt every time I decided to move on in my career

Have you ever read one of those articles about how often software developers should change jobs? They often suggest that both staying too long in one place and job-hopping are deadly career mistakes — and they might be right.

Having read a bunch of these articles, I often wondered whether it was the right time for me to make a change. I wanted to get plenty of experiences early on, but I didn’t know much about the industry and the diversity of companies.

So, when I found myself answering, “yes, the time for change has come,” another, much more difficult question arose: Where do I go next?

This is not an easy question to answer. Not only because the range of opportunities is so wide, but because every developer is a little different. Perhaps the best way is to learn from other people’s experiences and then try to find a path that works for you.

That’s why I’m writing this story of how I got to where I am today, with the hope that it might help someone who’s deciding what to do next.

So, let’s start at the beginning…

Fear of the unknown

When I was at university, I had no idea whether I’d be able to make a decent living after I was done studying.

I had a great friend there whom I studied alongside. We were making a little money creating small websites and Android apps. I’ll be honest with you, they weren’t much fun to work on, and the money was non-existent. Soon enough, impostor syndrome kicked in and made me believe I’d have a hard time finding a real job.

Jumping into cold water!

It was easier to just close my eyes and bury my head in the sand like an ostrich. All this career talk seemed far off in the future, even though I was already finishing my bachelor’s degree.

Several times I played around with the idea of leaving university, simply because I hated studying. But we never had the guts to do it. Don’t get me wrong, I’m not advising anyone to leave university. It’s a great place for many people. But it just wasn’t for us.

Just before summer began, my friend and I went for a beer. He told me how he got this awesome job at a cool-looking agency, working on projects for Silicon Valley startups. He was passionately describing all the toys they had in the office, including hoverboards, Nerf guns, even a jacuzzi on the roof!

All I could think was: damn, he had the courage! It’s like entering a bar for the first time and plucking up the courage to ask someone out. You know they are there for the same reason you are, that no one will get hurt if you just ask, and that it isn’t the end of the world if you hear the dreaded “NO”. But the fear of hearing it was paralysing me.

He offered to recommend me for an interview, so I decided to pick up the remnants of courage I had left and go for it. I knew I had to risk hearing “NO” for the first time, so I gave it my best shot.

I waited two weeks to get an answer, certain that this was a bad sign. And then finally, much to my surprise, I got a “YES!”. Obviously, I accepted the offer in ecstasy, without even looking at the amount of money they offered. Only later I learned that I was what they called a ‘wild card,’ and that they probably didn’t expect me to survive long.

Is it cool enough to give up work-life balance?

It was an amazing first experience. Just as my friend had described, the offices were seriously cool. The designers I worked with were crazy talented, with the look of our apps being the main selling point. We often tried a new stack full of cutting-edge technology, with relatively little responsibility for maintaining it in the future.

On top of that, we got to work with US-based clients while sitting in Prague. I even got the opportunity to work directly with our clients, without a layer of project management. How agile and cool is that?

But it wasn’t all rosy. Most of the syncs happened between 6–7 pm, which was a challenge considering that I’m more of a lark than an owl. The lack of project management meant that clients would wake me up in the middle of the night because the carousel wasn’t working properly, or some other rather silly reason.

Unlike my more experienced colleagues, I was too polite to turn off my phone for the night. Back then, it seemed an acceptable price to pay, even though my work-life balance was almost nonexistent, which was deeply frustrating my fiance. To be honest, I didn’t have any idea how a project should be estimated or managed.

It was a great but wild ride on which I didn’t want to stay too long. Many projects with beautiful faces came by so quickly that I don’t even remember their names. I felt I needed to try a different approach that would be more sustainable for me in the long-term.

Let’s get serious with a 9–5

I began to think about moving on. It wasn’t clear to me exactly what was wrong or what I should change, but I needed to bring some balance to my life. So, I decided to steer clear of startups for a while. This led me to another agency that was far less cool but offered bigger projects and more team structure, including project managers.

The moment I stepped into my new office, I missed all the cool toys and free food. But then I noticed something strange: I slept more, my life got calmer, and my communication skills improved while working with a project manager. I even had time to write tests! I get why people want to avoid the old 9–5 existence, but it definitely helped me achieve a better — or more predictable — work-life balance.

After a while, they offered me a project working for a large UK non-profit organisation, and I was so excited to start. But soon enough, I found out that they were just as confused about what they wanted as the clients at the previous company. This time, the project lasted a little longer, so I had a chance to remember their names. But it was long enough to know that my heart wasn’t really in it.

The last piece of a pie

Now that I had learned that most clients are the same no matter where I worked, I got an offer to build an app for a bank. Excited to keep trying new things, I jumped at the opportunity.

The idea was that my current company would “body-shop” me to a huge US consulting firm that was working with one of the banks in my country. I was dazzled by the name of the firm and keen to try to build a banking app — although I was afraid I could really screw it up.

Later on, I learned that I had nothing to worry about. The bank had so many testers and security checks that it wouldn’t allow any programming error to result in customers losing their money. It was actually refreshing to work for the first time with proper testing and in a well-organized Scrum team where people were excited about the methodology.

Working for the bank wasn’t at all as bad or corporate as I expected. They wanted their software engineers to feel as good as if they were working for a start-up, so the IT departments were no longer located in the basement. In fact, they gave us the top floor with a beautiful view of the city and a lot of natural sunlight. But the light prevented us from seeing the code on our dark screens, so we ended up closing almost all the curtains and creating a basement on the top floor.

Banks can be pretty kafkaesque. At one point, I needed assistance setting up a server for deploy, and I learned that there was exactly one person who could help. Unfortunately, he also had a passion for playing hide and seek. He stubbornly refused to install anything even remotely resembling Slack and almost never sat at his desk. Only the automatic response on his email offered a glimpse that he might actually exist. It took me a week to finally get a meeting with him.

Almost immediately after leaving the project, I received an offer for the same position, but this time directly for the bank. The salary offer was twice what I had been on before, when two companies were cutting their piece of the pie.

I refused the offer. I liked the people, but I just wasn’t excited about the product. It’s difficult to be passionate about a new loan process that will result in people paying more interest.

Time to leave agency work

This brought me back to agency work on startup projects. But by now, my view of this kind of work had changed. I was once again switching projects every few weeks. This is great if you just want to try new stuff, but it became difficult for me to become emotionally invested in projects that came and went so quickly — and not just because they didn’t end up being the next big thing.

Honestly, some of the ideas I worked on were pretty odd. I started to feel a little burned out, like the next gap in the market I would be filling would be a social network for ferrets, because nobody had thought of it yet.

A battle with the ego

Then a rumour came along that my company would be sold to one of the largest IT companies in the country, so I decided to move on. I got recommended by an ex-colleague at the consulting company I worked for. I successfully navigated the five rounds of their interview process, which boosted my ego for a while.

Then the bank, still unable to find a replacement, got in touch once again, offering a mad salary that would help me pay off my mortgage faster.

Around the same time, a former colleague from my first job contacted me to offer an interview with her current employer, productboard. It was still a small company and, if I’m being honest, I didn’t know much about their product. But I very much trusted my colleague, and that convinced me to get in touch with them. After a few intro calls and a lunch, I successfully passed their interview process.

Now I had three options on the table — something I couldn’t have dreamed of just four years earlier! So I asked myself: what do I actually want from the next chapter?

I wanted to work in an organisation where I could focus on quality and be proud of what I‘m building. I wanted to work with people from whom I could learn as much as possible. And I wanted to not only grow as a developer but also to advance my career.

The first two options started to feel like a dilemma between beauty and money, which led to the last option: productboard.

No more one-night stands

So here I am at the productboard. What’s life like now? Well, I love the fact that I’m working on just one product. I care about our product’s success and the direction in which it evolves. In fact, I enjoy spending my free time thinking about how I could improve it. And in the process, I’m learning new and better ways of working.

I realized how important it is to truly know the whole product and the discipline it’s designed for. This allows me to participate deeper in moving it in the right direction. I’m excited to leave my footprint, and I know I’ll be able to keep looking at it for a long time.

I finally have enough time to focus on quality and testing things properly. No client is breathing down my neck. It’s no longer about making it to the finish line on time. It’s about doing it right and not increasing our technical debt.

What’s more, I get to work with people with the same level of enthusiasm. I feel a healthy envy when I see how fast they are growing in different areas. This motivates me to keep up with them, to read the books I see on their desks, and to learn the technology they started using.

This is already the product I have worked the longest on. I see it growing, evolving, and improving. I’m no longer changing projects every few months. No more working on multiple apps at the same time while reviewing two others. My effort is focused on this one thing, and I want to make it as amazing as possible.

It’s like a long-term relationship. You can keep dating and being with someone new every few weeks, but then you are not really having new experiences. It’s always the same experience, just with somebody else. On the other hand, if you get married, those new experiences keep coming if you invest enough in the relationship.

I’m not saying there are rainbows everywhere, nor is it the perfect set up for everyone. But I’m a millennial, so I love the feeling that my job has purpose and I make an impact, whatever that means. And sure, the free food and beanbags are also pretty cool.

Interested in joining the Czech Republic’s hottest startup? We’re always on the lookout for talented engineers. Check out our careers page for the latest vacancies.

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