The 10 rules for accelerating your product design career

And a personal story of how I got into product design

👋 Hey, it’s Filippos! Welcome to this issue of the Designary newsletter. If you are new here, I write about product design, including career advice, UX tips, frameworks, and thoughts on product in general. I also run a product design challenge monthly.

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My product design career started shortly after university and was riddled with a lot of conflicting opportunities.

I studied software engineering, and I absolutely loved it. The career path was fairly clear; I was a half-decent engineer, and everyone around me seemed to be getting good opportunities in the field.

But something felt slightly off.

I liked engineering when things worked but hated it when they didn’t. Building something from scratch was fascinating to me, and I could easily code all night. Debugging and maintenance, on the other hand, made me feel sick.

I couldn’t see myself following engineering as a career path.

I was way more interested in the “why” behind building apps and products. The problems being solved, the end user experience, and finding ways to delight users.

First steps into product design

During my university years, I did a lot of side projects: some paid, others completely voluntary.

Side projects were a great avenue for me to actively practice my skills, build connections and also get some real-world experience to counteract the purely theoretical nature of my studies.

One of these side projects led me to meet someone who genuinely wanted to invest in me. They knew little about me but offered me a junior product role at an up-and-coming startup with an international audience.

Rule #1: Side projects are one of the most effective ways to practice and get exposure early on.

The role wasn’t design-specific: I could code, had designed a few websites and apps, and had a lot of drive. It was more of an open invitation to “join us and do whatever you can to make things work”.

It’s important to note that I wasn’t offered a role because of my technical skills — at this point, I had little real-world experience, and my knowledge in product was in its infancy.

I was offered a role because I showed drive and passion to learn/explore.

Rule #2: Early on in your career, determination and drive will often outperform technical superiority.

I didn’t know exactly what to do, but I knew I needed to deliver value from day one.

Progressing to senior

Progressing is often a combination of different parameters:

• A personal aspiration that acts as the North star

• A healthy environment that fosters growth

• Ambitious people around you that fuel that growth

I was lucky to have all of them in that first startup role.

So in that year, I did everything I could to grow while delivering value to the business.

1. I learned everything I could possibly learn about UX.

2. I helped with any type of product work there was: web apps, mobile apps, websites. This made me highly adaptable, which proved to be one of the most crucial skills for my career progression.

3. I helped engineers with their challenges — even beyond design — which made me understand what they value and what makes their job easier.

4. I helped build investment decks, which taught me the value of storytelling and — very importantly — the “so what” behind data.

5. I helped with internal presentations, which taught me that your designs and features are only as good as the level at which they are presented.

I didn’t care about specializing (yet). I didn’t mind that there was no process or prioritization framework. What was important for me at that stage was to deliver value to the business to prove I deserve a long-term role.

Which brings me to one of my most important career rules.

Rule #3: People care if you deliver value. They rarely care how you do it.

So I went all in on that.

It meant I was in for quite a bit of pressure, but it also skyrocketed my progression to senior in less than a few years.

The breadth of problems I was tackling meant that I had to quickly upskill in:

• Every aspect of UX

• Business thinking

• Problem solving

• User research

• Storytelling

• Writing

Looking back, it all feels chaotic.

But it was also one of the quickest learning experiences I’ve ever had in my life. It taught me skills — soft and technical — that would take me years to build on if I started today.

That brings me to my fourth rule, and one of the most important ones:

Rule #4: You will have limited chances of exponential growth in your lifetime. When you do, you need to go all in.

Tackling scale

My second role in product design was quite different.

A year and a half later, I was hired as a senior product designer at a high-growth consumer tech startup.

Even though the company was still quite early-stage, the scale was drastically different: It was a consumer business with exponential growth and tens of thousands of daily customers.

Here is the problem: I was good at going from 0 to 1 but had never experienced going from 1 to 10.

This also meant that what mattered previously didn’t matter much anymore: I wasn’t doing pitch decks or taking on small side projects.

As a senior, I needed to focus on driving scale for the product and the business.

So I invested in three key areas:

1. I started working with data daily. Working with marketers and engineers to understand the why behind data, figuring out ways to move that data, and realizing that a 1% increase might mean five or six figure changes in annual company revenue.

2. I had to build a design system to drive that scale. Multiple products, multiple countries, and tons of ongoing experimentation meant that things could go rogue easily unless there was a centralized system to allow for consistency and speed.

3. I learned the importance of building authority and influencing strategic product decisions. My early work in that role helped me build trust with the founders and key product stakeholders, which meant that very soon, I was having an active say in what we were building and why we were building it.

The third point was one of the most influential ones to my career, which also brings me to a crucial rule:

Rule #5: To get a voice at the table you need to first build trust. Most people demand a voice without doing the hard work.

Tackling problems at scale helped me grow in a very different direction than before.

Going from a B2B startup to a B2C scaleup was daunting at first, but it accounted for the majority of my early learning and growth.

Rule #6: Every role you choose should help you evolve in a specific area. If you are doing the same thing again and again, your growth will halt.

Breaking into the international market

After several years of working in the Greek market, I felt stuck.

I had already worked with promising startups but was nowhere near my growth aspirations. I wasn’t learning anymore, and I had little to aspire to.

The local market had brilliant people, but it was only a handful.

So I made the decision to target the global market and work with international teams.

I wanted to work with:

• Product designers and design managers that were 10x better than me

• Engineers that were top of their league

• Seasoned product managers

• Ambitious founders

Rule #7: Surround yourself with people that are much better than you; that’s the only true way to grow.

So here is what I did:

Firstly, I devoted a good year to building a very strong design portfolio and being more outspoken with my work by sharing it on different platforms.

Getting featured on these platforms meant that I started getting a lot of exposure to great product and design teams worldwide.

Secondly, I felt like I was ready to lead teams internationally, therefore I also wanted my salary to reflect that.

So I effectively doubled my rates before going out to the market.

Jumping from local to global rates. These are sample yearly salaries from 2016.

Through my portfolio work, word of mouth, and a bit of luck, I was able to secure a long-term contract with an international company at my new rates.

🤯

At first, I felt like an imposter.

But looking back, I know that every time I thought, “Do I deserve that?” and pushed beyond my uncertainty, it became a step change in my career.

On the other hand, every time I undermined myself and asked for less than I deserved, I was unhappy and ultimately regretted it.

Rule #8: Ask and you shall receive. Then do everything you can to prove yourself.

Big tech, failure, acceptance, growth

After several years of remote work, I once again wanted a change.

Working remotely was great, but I wanted to be where all the action was. I wanted to meet the teams I was working with, connect with new founders in person, even talk about obscure design or engineering problems over coffee.

At the time, a recruiter from Big Tech approached me to relocate and join their team in London.

This felt like a great idea: It would facilitate my move abroad, be a great new opportunity for me to grow and learn from, and give me experience in much larger-scale problems.

The feedback I received after each round was extremely positive, and the process was progressing rapidly.

The ego part of my brain kept repeating, “It would be impossible to lose this”.

And then 5 interviews and several flights in, I got rejected.

Rejection from big tech hit hard but gave me three profound realizations:

1. Humbling moments in life don’t come often, but when they do, you need to fully embrace them and learn.

2. Even though I was good at what I was doing, my ways of doing it didn’t necessarily conform to the needs of big tech at that point in time.

I realized that the narrative I was presenting — helping things during early-stage — was somewhat irrelevant to teams of such scale. The feedback that cost me that role was that I “didn’t have experience in a big established team”.

Which leads me to another crucial rule:

Rule #9: You can’t be good at everything. But there should be one thing where people around you go “You are the best at X”.

Throughout this process, I also realized that London was the city I wanted to be in; everything about it just clicked.

So I made the decision to move, regardless of the company and role.

A few months after my move, a co-founder of an ambitious health tech startup in London approached me. We had worked together in the past, and they needed someone to help kickstart things in product and design.

Rule #10: The best career opportunities come from building long-term relationships

The mission was big, bold, and ambitious, all of the things I love doing.

So I joined them.

A year later, that same big tech company from before approached me again. By then, I knew the enterprise world wasn’t for me.

To this day, I only work for early-stage companies.

Hope you enjoyed the story. 👋

In summary

• Rule #1: Side projects are one of the most effective ways to practice and get exposure early on.

• Rule #2: Determination and drive will often outperform technical superiority early on.

• Rule #3: People care if you deliver value. They rarely care how you do it.

• Rule #4: You will have limited chances of exponential growth in your lifetime. When you do, you need to go all in.

• Rule #5: To get a voice at the table, you must first build trust.

• Rule #6: Every role you choose should help you evolve in a specific area.

• Rule #7: Surround yourself with people who are much better than you; that’s the only true way to grow.

• Rule #8: Ask, and you shall receive. Then do everything you can to prove yourself.

• Rule #9: You can’t be good at everything. But there should be one thing where people say “You are the best at X”.

• Rule #10: The best career opportunities come from building long-term relationships.