Every so often I have breakfast alone, and I ask Twitter to ask me questions. I enjoy it a lot ā 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.
ā 1 ā
Q: How do you get things done? Be productive?
To be honest, Iām 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 – itās very important to know exactly what youāre going to be delivering. Donāt be vague and assume that youāll improvise and figure it out – thatās 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 youāll 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. Iāve seen friends earning more than me who are broker than me and more stressed than me for it. Youāll feel like you earned a reward. Keep your rewards small and affordable. Donāt 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. Thereās a small cost to having a filing system and a large cost to not having one. But you donāt feel the large cost until later. I now make sure to add āmeta-notesā. In the software world I believe this is called ācomment your codeā. Any serious side project is going to require this. Comment with your intent, the contextā¦ 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 Iād 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 donāt want to be responsible for you. Be. Specific.
Generally, āHey 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?ā 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 havenāt 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 youāre asking for help, youāre also helping them. Youāre giving them a reprieve that could give them some fresh POV on things. Youāre giving them a chance to feel like theyāre giving back. The rule of all human relations: itās not about you!
Q: If any, what podcasts do you listen to?
I donāt know why but podcasts have never really become habit forming for me. Sometimes I put Alan Watts or Elliott Hulse on YouTube if Iām doing the dishes or laundry. Iāve liked a few specific Tim Ferriss episodes.
Q: How to not get riled up by first world problemsā¦
You could try contextualizing your problems against the horrors other people are going through. Depending on your character/personality itās 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 š I think in hetero relationships thereās 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 ā 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.
ā 2 ā
Q: How much should i prioritize learning opportunities when finding my first job?
Very, very highly!! Especially when youāre young and you can make trade offs like endure a shitty commute, etc. Iād say the most important things are āwork with good people you respectā & ālearn as much as you canā. 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. Itās part of why I tweet and write so much. Talking to other people forces you to be clear about whatās most important. Iām very sketchy and improvisational & have lots of false starts
Q: How do you make the “right” career choices for yourself?
Big question. Iām no expert but: Know what youāre 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 itās good to think very long term, ie decades
The devil is really in the details for this one. I donāt know if itās possible to make ārightā decisions. Maybe better to frame as āavoid wrongā. Ie doing work for a shitty boss or a dying industry if you can. Do your research . But also donāt overthink it too long šš
Q: In person, do you talk like you write?
More or less. More Singlish with my friends. More ums and ahs, obviously. Hereās 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 wonāt have to do an unpaid internship (Iām extremely not a fan), youāll have to do some unpaid work for yourself, on the side, in preparation for entry.
Hereās a thread about my process. TLDR youāll have to demonstrate that youāre someone worth taking a bet on, and you do this by learning all you can and communicating that learning – I personally like to blog. āStudent blogsā 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 youād 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 āSingapore things to doā 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. Whateverās 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: Whatās the overall quality of life like in Singapore? In America, itās really great to be rich and great to be bankrupt but kinda grinding/rough in between.
Singapore isā¦ safe. Itās clean. Itās pretty cramped & crowded like any major city – but itās also a country, and there isnāt really anywhere onsite to escape the pressure. Itās fantastic if youāre rich. Itās not fun if youāre 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.
š¤ sounds complicated. Iād generally stay away from working for family and family-friends if possible, unless the upside/opportunity is really substantial. Youāll 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 ā it’s kind of seeped into our everyday reality. Software is eating the world, etc.
ā 3 ā
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 Iām a bit pathological about this. I have a rather compulsive need to surround myself with people I trust and admire. I think Iām 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 donāt know if thatās enough to motivate me? Lots of things would be nice, after all.
I think rather Iām motivated by a sort of fear. The world is changing pretty quickly. Iām not confident that my place in it is secure. I donāt 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. Iām still in the process of it, but having left my first job (was there 5.5 years!), Iāve 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 didnāt think Iād last a year.
Somehow, I ended up there 5.5 years! If Iām 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 Iāve 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 – Iām 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 wonāt, etc. To do this I have to unlearn my own repression.
Q: Do you consider yourself a āleader?ā How do you define or frame āleadership?ā
This is another thing Iāve been changing my mind about a lot. Iāve 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 ā 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 donāt know anything, though! Then I realised, damn, neither does anybody else.
Thereās a quote from Tina Feyās Bossypants thatās goes, āIn most cases being a good boss means hiring talented people and then getting out of their way. [ā¦] 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!ā I love that š
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 š
For me I canāt really change one part of my life without changing everything else. I woke up early consistently when I was in the military but thatās 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
- āgiftedā-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 itās 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.
ā tbc! ā