My favourite moments of self-doubt in 2020

Ha
6 min readNov 4, 2020

We are living in a strange time. I didn’t find any “5 tips for product designers in 2020 #agile” listicle that resonated with how I felt in this new normal — where most of my social interactions with friends and families were done through a tiny screen.

Spending the majority of 2020 alone in my bedroom office, I had a lot of time to reflect and second-guess many of my decisions at work, brooding over things that I could had done better. My self-doubt became my worst enemies, but also my best mentor. Here is a collection of my favourite moments of doubt and what I’ve learnt from them:

You do what you’ve always been doing, but this time, it doesn’t work like before.

As a 20-something, I joined the Carousell team full of energy. I came with preconceived ideas of how things were supposed to work. I couldn’t wait to contribute and make changes. My team was a bunch of open-minded and super friendly folks. I was met with a resounding “Yes” for all of my suggestions. No one really said “Hey Ha, maybe you should slow down and consider this.”

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I took a stab at it. Some things improved. Some things became worst, and I couldn’t understand why. I didn’t want to give up, so I continued to push. I followed up religiously on every small task to make sure things are done the way I wanted it to be. But when I stopped, everything revert back to normal. I felt as if my effort was unappreciated and I became exhausted.

What I learned about making changes:

  1. Change is a mutual process. You need to be willing to change by the same amount you expect from others. It is about finding the sweet spot, not about one party conforming to a new norm. For example: I wished to have more casual and shorter feedback loops between PM <> PD <> ENG to minimise miscommunication. Then, I too needed to learn how to document better and housekeep better, so people could find what they needed without having to always “jump on a quick call”.
  2. Everyone wants to grow and contribute meaningfully. Your feedback is always appreciated. But once your feedback is given, the ball is on their court. They get to decide what to do about it. People glow when they are given respect, time and space to make their own game plan.

You internalise your title, your last drawn salary and the amount of time you get to talk in a big-ass important meeting.

Before coming to Carousell, I was in ReferralCandy as the youngest person in the team. As a small and lean team, our CEO & Head of Design were in most of the sprint and planning meetings. It felt as if there was always someone in the room who could do and say the same thing that I could but better. So I thought of seniority as a ladder and it was a straightforward way to climb up.

When I came to Carousell, I met super talented designers who can do much cooler stuff than I can, but holding the same or more junior titles than I do. What I have is just a very different set of experiences, that fortunately fills in the gap the team needs at this very moment in time. Sometimes, I feel undeserving.

When some of our colleagues left, it could go either way — their new team could either be a better or worse fit. They would either get much more or much less appreciation from their new employers. But that has nothing to do with who they are and their values. It only has to do with “fit”.

This made me change how I behave in meeting and functioned in a team. I realised that:

  1. You always have something valuable to say in every meetings (no matter how fancy the meeting or whether it has the word “strategy” in it), because no one has the same experiences as you have. It also means that you should listen more closely to people who don’t speak up often. Because you don’t have the experience they have, and you haven’t heard from them often enough.
  2. Diversity is a strength. There is no need to compare or try to do the same thing someone else is already doing.

You think you are the only one with a terrible experience, because you lack “people skills”.

If you miss the reference: Urban dictionary

In my 6 years of working, I have experienced micro-aggression at work a couple of times. In the past, I had always managed to convince myself that I was the problem. No one really aspires to be a mean person. Sometimes, people are just unaware. So, I thought: if I could handle the situation with more tact, maybe there would be less friction. It is also easier to control how you react than to confront someone about something that’s so hard to pinpoint. However, the consequence is that you would experience distress and cognitive dissonance. You intuitively know something is not right, but you rationalise and make excuses for not addressing it.

When I finally shared my experiences with my manager and former and current colleagues, I learned that:

  1. When you are having a terrible time because of a person, other people are probably experiencing it too. Maybe you can handle the situation yourself without help and that’s okay. But if you do speak up, you can help the other folks in the same situation who may wish to speak up after you.
  2. It is not about justice or “getting even”. It is a learning process. It is only fair if you give your feedback before dismissing someone’s intention and ability to change.

You think you have no appetite for good food.

There was no longer a hard stop at 7pm when I left the office to have dinner with my partner and friends. Dinner was pushed back to later and later. I thought of just quickly having something simple because I wouldn’t enjoy it anyway. I would save a nice dinner for a time when it is right.

But there is never gonna be a right time for anything. You need to make time for it.

Here’s a pretty analogy I heard from one of my recent 1–1s:

  1. Life is a stool. When there are fewer legs, it is less balanced. Besides work, you need food, company, a nice walk in the park, or a gathering (that you dragged yourself to, but later on felt grateful that you did show up). The more legs you have, the more stable you will be.

What’s your favourite moments of self-doubt?

I’d love to hear about them!

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