Honest Learnings from the Companies I Worked For
Except the current one... because, confidentiality
As I approach my 15th or 16th year of professional work life, I wouldn't claim to be successful, but I can share some insights from my past experiences. This reflection can hopefully serve as valuable lessons for others.
I began my full-time UX career in 2007 at Oracle, just after graduating from university. My experience at Oracle remains the longest tenure I've had with a single company. Here are some honest lessons I've learned from the various companies I've worked for:
2007-2012 — Oracle
My first job title was simply "Designer." I worked on a hybrid of user interface and marketing design, supporting a global corporate citizenship team running an e-learning platform and international student competition promoting 21st-century skills.
What I’ve learned:
Being a remote team member offers great freedom in managing time and work, but requires extra effort for accountability.
Boredom can strike, and sometimes you need to take the initiative to make your work more meaningful.
The comfort zone can be dangerous; after almost five years, I knew I needed a change.
2012-2013 — Bukalapak
My next job was an exciting but “scary” (because it’s beyond a comfort zone in many ways) gig at a local e-commerce startup. If you know Bukalapak, it’s a C2C marketplace that was one of its first kinds in Indonesia back then in 2012. Gosh, I feel old already now. I was the first UX designer, and my title was “Lead UX Designer”. It didn’t have any proper product team. Just engineering team.
What I’ve learned:
Sometimes it’s worth taking a pay cut (slightly) to join a scrappy startup when you are young, or when you have more financial stability in the future. It is refreshing to look at the things you can own and decide for yourself, as compared to following people’s orders.
It’s okay to focus on one thing, experiment and iterate. I was only doing UI design and a tad of UX research. I was happy, and it worked for the team. Nobody really knew what they were doing and everybody was kind of just doing it.
Having a great engineering counterpart is such a pleasure and time-saver. I was paired with an excellent front-end engineer and all my designs were translated correctly 100% to the pixels that I was amazed until now. Find a good teammate and treasure them.
2013-2014 — Ice House
I vowed to myself strongly that I would never work for a client-facing setting, or an agency. But here I was, as stupid as I thought I would be, working for one. Luckily, it was not a creative agency with the crazy demand and work hour, it was more like a software/internet development agency that has a proper working flow like any in-house design team. Say, like having your own product/engineering/UX team but outsourced. So I got to really work on a few projects and not jumping around quite often. My role was a Senior Designer and this is the first time I got to manage one designer.
What I’ve learned:
Boy was it wonderful to have a proper team and process in place. I am glad I didn’t join a random agency or just a purely creative one. I would have hated one. This is a proper, Silicon Valley-standard product development practice in place. I got to focus so much on what I love doing the best: UI and UX design.
When you love your job and team, and gain the trust of your leads, you’ll have wonderful things. For me, it was being trusted to be flown over to San Francisco to do design thinking workshop with them out of the blue. That was the highlight for me.
Being trusted to manage a design team moving forward was also something I learned so much from. You now have the success of the UX process, output and outcome of the entire company on your hands (and your team’s).
2014-2015 — DBS Bank (Singapore)
This is the first time I moved overseas to work. I was in the verge of moving to the US vs Singapore, but I finally chose Singapore. I worked as one of the first few in-house designer in Singapore’s largest bank’s first ever product design team. I was designer number 4 (quite proud of it, actually).
What I’ve learned:
Working in a big corporate environment again after 3 years leaving one is nothing sort of refreshing. It was frustrating at times. If you have to choose it, you better learn and provide time to “acclimatise” yourself to this environment.
Moving to Singapore, although technically close to home, and thinking I’ve been here a couple of times, still wasn’t easy. I was alone, without my wife and kid, and I decided I didn’t want to do it again alone. I committed to bringing all of them together with me the next time.
In general, I learned so much from this experience, good and bad. I would say that you really have to know what you want to do and what kind of company you want to work for. Don’t be tempted by the money alone.
2015-2016 — Ice House
Yes, I boomerang-ed back to Ice House. This time I was offered the role of “Product Manager”. I was part of their new “Presales/Solutions” team that comes before we get client to prospect new businesses. My role was, to put simply, act as product and UX planner and visionary for the prospect, by presenting potential solutions and conducting design thinking or necessary workshops beforehand.
What I’ve learned:
The title worried me. I didn’t want to be known as a Product Manager on my CV or LinkedIn. This made me really apprehensive of the whole situation and want to switch immediately to any design-related opportunity, although I was still doing half-and-half product and design. I became sure enough I want to be a designer. Everyone is different, but it’s just me.
I was so frustrated half of this employment tenure because I felt like I wanted to do design more. It affected how I see things and how I perform.
I wanted to be in design leadership position because that’s how I came before. I was back to an individual contributor.
I was actively looking to exit from the first six months.
Learning point: do not boomerang for any terms and expect that you would find the same team or opportunity, you have to negotiate and find the right opportunity for you.
2016-2020 — Vrbo (Expedia)
I wasn’t planning to return to Singapore, but fate decided otherwise. A friend recommended for an interview, and soon after, even a slight pay cut, I decided to go back. The opportunity to move together, and work for the travel space was just too enticing.
What I’ve learned:
If you come with an open mind and heart, you’ll enjoy and be more thankful of your situations.
Open-heartedness and willingness to learn comes first, the money and title comes later.
Finally, I was in a relatively stable job that I enjoy so much with a high degree of work-life balance! I enjoyed my work, enjoyed my team, and got to travel tons. I visited places like Austin, London, Gurgaon, Tokyo, Nagano, New York City, and Sydney all for work. Loved it to bits.
But come 2020, just before Covid-19 pandemic, I got laid off. This brought me to realise that all good things indeed come to an end and we can’t be complacent.
It is important to have a team that advocates for you, especially your manager, and even more if the majority of the team’s gravity is in other part of the world (in this case, the US).
2020-2021 — Shopify
I took this offer as a surprise because literally I was interviewing for them a year before and got rejected. I guess I wasn’t really up to par for a manager position in 2019, but I got an IC position a year later. I was still working in Singapore, which was a saving act for us all because we didn’t have to move back to Indonesia after the layoff from Vrbo.
What I’ve learned:
I learned that your manager defines your happiness.
Every western tech company based in Asia struggles with winning projects and visibility from their headquarters, usually in the western hemisphere. No exception. This is a long game and be ready to be tired.
Reorg is a staple in big companies. Be ready for it. I also experienced it quite a bit at Vrbo.
Working and excelling in async environment is a skill of its own. This is the first company that puts emphasis on it, in my career lifetime. It’s also the first time people really scrutinise my work setup at home (you have to make sure your voice is good and your camera is good and that you’re always visible and… the list goes on).
Burnout is real, I have to be honest I experienced it for the first time in my life here. But from it, I learned a ton. I learned how to work fast, write more succinctly, collaborate more effectively and how presentation skill during remote time is even more crucial.
That is all, folks. Hope you enjoyed my reflection. As of Tripadvisor, my current employer, I can’t really tell right now until I leave the company in the future. Please take all reflections above as my personal take, and not an objective evaluation of each company. Things can be different for you if you work for them. Always cover all sides and ask for as many opinions as possible before you decide.
If there’s one big lesson I learn is this: no company is perfect, and even if it was your own, it’s also not perfect — what’s perfect is you accepting yourself for whatever situation. Don’t push yourself too hard.