Every so often I have breakfast alone, and I ask Twitter to ask me questions. I enjoy it a lot – I find it to be a great way of getting out of my own head and getting a sense of what other people are thinking. Here are some of the questions people have been asking me. I’ve expanded a little on some of the answers.

— 1 —

Q: How do you get things done? Be productive?

To be honest, I’m not great at this myself. But at my best:

• Be as precise as you can about the individual components of the work you have promised to do
• Have a simple routine of checking in on yourself, I find it useful at the start, middle and of every day

Most importantly you want to be honest with yourself about why you might be avoiding some task. Does it feel pointless? Does it seem overwhelming? Does it involve asking somebody for help, which feels weird? Articulating this with kindness to yourself minimises procrastination.

Also – it’s very important to know exactly what you’re going to be delivering. Don’t be vague and assume that you’ll improvise and figure it out – that’s a recipe for spending too much time meandering around and that will make you late. I like this visualization from @joulee on what a good, systematic process looks like, visually.

What traits should I look for in a romantic partner?

Big question! It largely depends on what you want out of a relationship, what your values are and so on. But broadly, I recommend finding people who can laugh at themselves, who are kind to others, who are good at communicating openly, and are sensitive.

My advice to young people would be not to worry too much about the romantic part, and just spend lots of time meeting lots of people. There are a lot of people in the world, and they are more varied than you can imagine or fathom. Actively seek out the different-est people you can.

I think the first half of your life is about recognizing that your taste is still a work-in-progress. Trying to look for something that fits your existing taste is probably less optimal than trying to refine and expand your sense of what is good.

Just to reaffirm: your concept of the dating market (and the world) is definitely limited and simpler than reality. Even what you read online suffers from selection bias. Soulmates are BS, but there are some amazing, nourishing, funny humans out there keeping a low profile.

Q: How to do good, earnest work (Art, creative output, even general relationship building) when there is not a crisis or urgent need to produce something from a hardship? Where getting a steady paycheck, etc seems to dampen creative outbursts

Salaried life definitely boxes you up. I struggled with this for 5.5 years even though I had amazing colleagues, managers, bosses, amazing work environment. There is no magic answer. You just gotta struggle through it.

That said, there are some ways to struggle smarter.

• Always be producing a little output every day. Beware the delusion that you’ll suddenly be inspired to write a book in one sitting or have a whirlwind romance. Write a sentence, send a text. after you wake / before you sleep.
• Save your money / beware lifestyle creep. I’ve seen friends earning more than me who are broker than me and more stressed than me for it. You’ll feel like you earned a reward. Keep your rewards small and affordable. Don’t reward yourself with debt. Freedom is the ultimate reward
• Write meta-notes. A frustration I have is looking back on my body of work and seeing lots of half-written essays and repetitive notes. There’s a small cost to having a filing system and a large cost to not having one. But you don’t feel the large cost until later. I now make sure to add “meta-notes”. In the software world I believe this is called “comment your code”. Any serious side project is going to require this. Comment with your intent, the context… your future self will thank you. Read your old notes for what you wish it included.

Q: How do you network more effectively?

If I were to start from scratch, the first thing I’d do is do an inventory of all of the people already in my life – FB, Twitter, real life. Who do you wish you knew better, spent more time with? Make a list. Next, ask yourself how you could be useful or interesting to them.

Who would you like them to introduce you to? What do you want to learn from them? Be precise. The mistake people make is being vague and tedious. Good people like to help other people. But we don’t want to be responsible for you. Be. Specific.

Generally, “Hey x, I really liked what you did with y. Would love to talk with you about Z. Can I buy you a coffee to chat about it?” has a very high success rate. I would say yes to a random kid who sent me this if they seemed earnest and thoughtful

Maybe the best way to understand how to network well is to know what NOT to do. Do not ask dumb 101 questions that show you haven’t done any reading of your own. Nobody wants to babysit or tutor someone else for free. Do not send 1,000 word essays detailing your life story; rude

Maybe the secret is this: while you’re asking for help, you’re also helping them. You’re giving them a reprieve that could give them some fresh POV on things. You’re giving them a chance to feel like they’re giving back. The rule of all human relations: it’s not about you!

Q: If any, what podcasts do you listen to?

I don’t know why but podcasts have never really become habit forming for me. Sometimes I put Alan Watts or Elliott Hulse on YouTube if I’m doing the dishes or laundry. I’ve liked a few specific Tim Ferriss episodes.

Q: How to not get riled up by first world problems…

You could try contextualizing your problems against the horrors other people are going through. Depending on your character/personality it’s also possible to go overboard with this, so be wary? But practice being grateful for what you have + compassionate towards others, basically.

Q: Ways to handle (& mishandle) a relationship with a big age gap when you’re the older party. And when you’re the younger party.

Oh wow I am very unqualified to answer this 😂 I think in hetero relationships there’s also a gendered component to this. IMO the important thing is making sure both people are very clear about their respective expectations, goals/interests, and the power dynamic itself.

Q: Is marriage easier or harder than you imagined?

Harder in many ways, but also more warm and cosy. It’s an incredible commitment and a huge life change, so it’s kinda crazy that people get into it kinda… casually? I mean, everyone knows that marriage is a big deal – and yet, somehow, it does seem like a lot of the people who end up in unhappy marriages are surprised or confused because the reality of their situation is different from their expectations going on. Marriage is a lot of work. It can be more work than work. It involves enduring the consequences of your partner’s mistakes and failures, and subjecting your partner to the consequences of your own. And yet. My wife is my favorite human, my best friend, and I’m so glad and so honored that she continues to think of me as someone worth hanging out with.

— 2 —

Q: How much should i prioritize learning opportunities when finding my first job? 

Very, very highly!! Especially when you’re young and you can make trade offs like endure a shitty commute, etc. I‘d say the most important things are “work with good people you respect” & “learn as much as you can”. Also build relationships + take notes

Q: what ways of learning work best for you?

Re: my learning style, I learn best by doing, & by communicating with others, teaching others. It’s part of why I tweet and write so much. Talking to other people forces you to be clear about what’s most important. I’m very sketchy and improvisational & have lots of false starts

Q: How do you make the “right” career choices for yourself?

Big question. I’m no expert but: Know what you’re good at. Talk to people about their experiences so you can correct your expectations. Prioritise learning and growing, and try to work for good people. I think it’s good to think very long term, ie decades

The devil is really in the details for this one. I don’t know if it’s possible to make “right” decisions. Maybe better to frame as “avoid wrong”. Ie doing work for a shitty boss or a dying industry if you can. Do your research . But also don’t overthink it too long 😂😅

Q: In person, do you talk like you write?

More or less. More Singlish with my friends. More ums and ahs, obviously. Here’s a vid.

Q: How do you enter a new industry that you don’t have any experience in, particularly if you can’t afford an unpaid internship?

This is a tough one. While you won’t have to do an unpaid internship (I’m extremely not a fan), you’ll have to do some unpaid work for yourself, on the side, in preparation for entry. 

Here’s a thread about my process. TLDR you’ll have to demonstrate that you’re someone worth taking a bet on, and you do this by learning all you can and communicating that learning – I personally like to blog. “Student blogs” are powerful.

Q: Best strategy for learning new things?

Might vary for other people, but I basically immerse myself in it as much as I can, follow relevant people and make friends with them, etc. Think about how you’d learn a new language when dropped into a foreign country

Q: What would you say has had the most impact in influencing you? Book/movie/person/event/whatever

My wife. When we were about 19, her parents insisted that she either break up with me, or leave home and never speak to them again. She picked the latter. Our 6th wedding anniversary in Dec. She’s the smartest + funniest person I know.

Q: Most underrated/overrated parts about life in Singapore?

I googled “Singapore things to do” and the first result was Sentosa. Sentosa is an island resort at the south of Singapore (where Trump met Kim) and it is extremely overrated compared to the gorgeous beaches in the region (Thailand, Malaysia, Indonesia).

Where you can never go wrong in Singapore is the food. Just, so much good food everywhere. Ask locals for recommendations. Whatever’s on your mind. Great stuff everywhere across the entire spectrum, all sorts of cuisines. If you come here, find eating buddies and share dishes.

Q: What’s the overall quality of life like in Singapore? In America, it’s really great to be rich and great to be bankrupt but kinda grinding/rough in between.

Singapore is… safe. It’s clean. It’s pretty cramped & crowded like any major city – but it’s also a country, and there isn’t really anywhere onsite to escape the pressure. It’s fantastic if you’re rich. It’s not fun if you’re poor, but not as grotesque as it can be in so many parts of the world.

Q: Is it ok to do exposure work (writing a report) for an NGO run by my mother’s friend? They do have money seeing as they are holding this event in a 5 star hotel. But they got very defensive when I mentioned money and said, better you just attend the program, don’t have to work.

🤔 sounds complicated. I’d generally stay away from working for family and family-friends if possible, unless the upside/opportunity is really substantial. You’ll have to be extra sensitive and mindful of everything.

Q: Do you have any belief shifts that you once attributed to social media but now believe would have occurred regardless of medium?

I became more feminist after a few conversations with friends online (bless them, they were so patient and kind), and I’d like to think it would have happened eventually anyway just through exposure to other people’s stories. I don’t know if we can really think of social media as a unique, differentiated medium anymore – it’s kind of seeped into our everyday reality. Software is eating the world, etc.

— 3 —

Q: How do you generate/maintain social energy? Like eg your engaging with lots of people and occasionally finding friends – it’s appealing but exhausting to me!

The honest answer is that I’m a bit pathological about this. I have a rather compulsive need to surround myself with people I trust and admire. I think I’m overcompensating for feeling like a social outcast and misfit growing up.

So for me, socialising is part of a long game of building, brick by brick, a place I can call home. There are push and pull elements. It would be nice to be surrounded by cool people. But I don’t know if that’s enough to motivate me? Lots of things would be nice, after all.

I think rather I’m motivated by a sort of fear. The world is changing pretty quickly. I’m not confident that my place in it is secure. I don’t have a particular ingroup or tribe that I trust to take care of me. So I need to build my own trust network, person by person.

Q: What have you unlearned recently?

Oooh, good question. I’m still in the process of it, but having left my first job (was there 5.5 years!), I’ve been thinking lately about how that had shaped my perspective on work, on what I owe others, what I owe myself. Responsibility and accountability.

My ex-boss took a huge chance on me by hiring me – I had no prior work experience, no qualifications, and on retrospect, a bunch of unresolved personal issues that affected my ability to perform at work. I was 22, broke, newly married and extremely desperate and anxious. I didn’t think I’d last a year.

Somehow, I ended up there 5.5 years! If I’m honest with myself, the last year was not my best. I was starting to coast. I had hit diminishing returns on multiple fronts but I struggled to accept it or be honest about it with myself.

So what I think I’ve been unlearning is my mental model of myself as a free agent. I think even at work in an incredibly open and supportive environment, I was using an outdated model – the student in the classroom. On retrospect this was a disservice to myself and my teammates.

The next time I get a job, or get involved in any sort of endeavour, really – I’m going to be a lot more mindful of my own interests, of my goals, of my plans, of what I want to achieve, what I will tolerate and what I won’t, etc. To do this I have to unlearn my own repression.

Q: Do you consider yourself a “leader?” How do you define or frame “leadership?”

This is another thing I’ve been changing my mind about a lot. I’ve kind of cycled back and forth on this. There are different kinds of leadership in all sorts of contexts. First let me queue up an old thread about perfectionist ideals re: leadership qualifications.

As a child, I thought leadership was nonsense, a bullshit idea invented by people in power. “Student leaders”, etc – it’s just about who gets to wear the special hats, right? Then I thought, actually, I want to be Commander Shepard. (The protagonist of the Mass Effect series, who challenges and inspires her squadmates to be better). Then I thought, shit, I don’t know anything, though! Then I realised, damn, neither does anybody else.

There’s a quote from Tina Fey’s Bossypants that’s goes, “In most cases being a good boss means hiring talented people and then getting out of their way. […] Contrary to what I believed as a little girl, being the boss almost never involves marching around, waving your arms, and chanting, “I am the boss! I am the boss!” I love that 😂

Leadership in practice is really about taking responsibility for a context and an outcome, and of taking care of people. Often it means empowering others and getting out of their way. I like how Benjamin Zander puts it, as a conductor: “The conductor of an orchestra doesn’t make a sound. He depends, for his power, on his ability to make other people powerful.”

Q: How do you find it easiest to develop habits?

I am terrible at developing habits, next question 😂

For me I can’t really change one part of my life without changing everything else. I woke up early consistently when I was in the military but that’s a pretty extreme method of habit formation. I have a bunch of thoughts and ideas about how to change habits, but I’ve never been particularly great at changing my own, so you really shouldn’t listen to me on this until I’ve actually succeeded at them. I’ll write something when that happens.

Q: In what ways do you think you’re abnormal among the general population?

I am…

• Left handed
• tall + have big feet
• minority race in my country
• inarticulate in the minority language
• a writerly book nerd
• “gifted”-schooled + not Uni-educated
• no exes + married young
• high openness
• agnostic

Q: How do I move past guilt?

Big question. I still wrangle with this, but fundamentally I think it’s about taking a deep breath, zooming out to see the big picture & asking yourself what would be best for everybody moving forward. Usually, some work has to be done. The guilt should inform, not get in the way.

— tbc! —