The Hardest Thing about being a New Dad

It is 6.33am on a rainy Friday morning in Singapore. I am in the back of a taxi heading home after a 15 hour flight. As I look through my messages, I realise I will need to book flights quickly for another work trip the following week.

When I did this same flight a year ago, I raced home and slept until I woke up again naturally. Today my routine will be a bit different. About 5 months ago, our lives changed significantly. We made the decision to trade our carefree existence of champagne brunches, photography tours and museum exhibitions (ok ok, I mean Nandos, Netflix and salacious Daily Mail headlines) for breast pumps, teething rings and a constant stream of neon-yellow-poo-explosions.

When you have a new baby, you spend a lot of time being awake at ungodly hours. You are waiting for kettles to boil, washing cycles to spin and sphincters to stop doing their best impression of a contraband Chinese firework. If like me you have the attention span of a Ritalin-starved 5-year-old, your mind starts to question and hypothesize. When you are awake at 4am trying to prevent an errant phallus from destroying your soft furnishings for the nth time, you begin to question why any logical person would have children at all.

The first three months are tough. You have no clue what you are doing and you are as paranoid as a dictator with a high-speed internet connection. You have less time to do things like eat, sleep, shower and other stuff you like. You have less money for holidays, treats and other experiences you love. If people had the option to try being a parent before really committing to it, I wonder how many people would upgrade the one month free trial and sign up to the 18+ year commitment. Alas you don’t even get a free iPhone as a welcome gift!

But despite the change in lifestyle, the worst thing about being a new parent is not the “having to do new parental things”. After 3 months, you learn what to do and how to do it. The “new parental things” become a pleasure as your child develops and responds to your affection. The worst thing about being a new parent is the “doing the new parental things a lot and then suddenly not being able to do them for a while” part. Allow me to explain...

I see many of my peers transform very quickly from “single with no responsibilities” to “parent with lots of responsibilities”. In a short space of time, they take on bigger jobs, start families and suddenly have their own parents and other dependents to start taking care of. A big number of significant things happen in a small number of consecutive years. As every year passes from the early 30s to retirement, their responsibilities mount up exponentially. Free time becomes a scarce resource and is very carefully allocated.

As people progress in their career, work competes with family for time and attention. At the heart of this is a need for regular face-to-face interaction between people who live in different countries. The value of a productive worker in our information economy is less about the widgets they create and more about the decisions they make, the consensus they drive and the relationships they build. Technology has yet to remove the need for in-person discussions.

So if you go to any major airport on a Monday morning, you will see countless numbers of adults dressed in business casual attire tapping away furiously on smartphones and sipping on overpriced cappuccinos. Commonly known as “road-warriors”, this tribe spend a large part of their waking hours from Monday to Friday in a location away from their family. Each of them will have a story of a missed first smile, a postponed birthday party or a bruised knee that they could not kiss better. They will have made a deal with themselves to trade an inch of career progression for an inch of family harmony.

Yet despite the large number of people who maintain this lifestyle for months or years at a time, I’ve never heard anyone around me complain about it. It just seems to be a trade-off that people have made peace with. Like somehow it is logical to spend up to 70% of your week away from the people you love the most.

I casually interviewed a few people about this from both genders to check I wasn’t going mad. Each of these people shared a coping mechanism or some elaborate system to deal with the fact that their work would require them to be away from home. Some have enlisted a third-party to help run their household and help raise their children. Some have decided to divide and conquer responsibilities between partners. Some people maintain a very strict schedule so they can read a bedtime story via Facetime every night.

But no-one grabbed me by the shoulders and said “OMG, you are so right, how do people do this for years at a time? I thought I was the only one who was struggling with this!”. Secretly I was hoping one person would do that. Mostly so it would validate the feelings I find myself developing lately. As a new parent who will now travel a lot for work, this is a trade-off I never realized people had to make until I kissed my son goodbye and started the outbound journey of that 15 hour flight.
For many new parents, the feeling at the core of the trade-off is guilt. The guilt of leaving a partner to deal with issues at home. The guilt of not being there for bath-time. The guilt of not dealing with the crying + poo explosion combo at 3am. The guilt of missing the first smile or the first giggle.

A mentor of mine advised me to worry less about the guilt and focus more on the good example you can set to children when you demonstrate a strong work ethic and a determination to pursue a career passion. Good advice I guess; but probably relevant later on when baby becomes an impressionable child. Other advice included “taking the family along on some trips where possible” and organising “special coming-home activities” after every week away from home. These seem like very pragmatic ideas but are the exception rather than the norm. You cannot do these for every trip. I wonder if these efforts really help absolve the feeling of guilt many people feel as they kiss their kids goodbye and wheel their suitcase out of the house week after week.

I am curious to see how future generations will deal with this situation. I wonder if technology will make this trade-off more or less of a challenge? Imagine a world where teleporting and virtual reality removed the need to get on a plane and interact with customers and colleagues in person? Conversely one could foresee a world where technology further decreases the ability of humans to connect on a personal level. This would increases the need for more episodes of deliberate, distraction-free and in-person interaction.

If you travel a lot for work and have a family, how do you deal with this trade-off? Is this something that different genders feel differently about? Is this feeling just a natural part of being a new parent? Will it subside over time or does it become even harder over time to manage the trade-off? Do you know of people who have made an extreme commitment in either direction i.e. “committed workaholic” vs “retired out of the rat race”?

I guess this feeling is yet another thing we learn about ourselves during the crazy experience of raising a newborn child. I guess the feelings change over time too. Everyday I have a hundred questions and I am sure my son has a hundred more. I don’t have any answers and am not necessarily looking for any but I think it is important for people to think through this trade-off carefully!


Helping Entrepreneurs to Thrive and Sellers to Sell

Since I was old enough to understand them, I have been fascinated by marketplaces. Buy and sell. Supply and demand. When people can buy and sell as they please, they create opportunity for one another. In particular, I have always enjoyed helping sellers and suppliers create opportunities for themselves and others around them. I love seeing entrepreneurs overcome the odds and thrive.

My career started as an English teacher in Northern Japan. As a “seller” of education to an often unwilling pool of “buyers” (teenagers!) I enjoyed thinking of ways to engage students and keep them motivated. During a brief stint as a marketeer at Accenture in the UK, I loved devising creative ways to help our senior executives sell their consulting services to large corporations.

Over the last 9 years at Google, I have had an incredible opportunity to learn how advertisers and publishers buy and sell advertising real estate at mind-boggling scale. The last 4 years in Singapore have been spent building a superstar team who advise executives around building digital businesses for the next billion people coming online. I have loved collaborating with my team to enable our partners to build revenue streams. These revenues are used to finance the creation and distribution of localised content and services for South-East Asian internet users.

During my recent paternity leave, I had some time to pause, reflect and think about what I should do next. I made the difficult decision to leave Google so I could go and learn about a new type of marketplace. In September I will start an adventure with Airbnb in the Asia Pacific region. Airbnb provides millions of people around the world with an opportunity to be rewarded for providing hospitality. I am very excited to help hosts (the sellers of hospitality) across Asia to become as successful as possible in providing unique and memorable experiences for travellers.

The last 9 years at Google helped me to identify and develop my passion for coaching entrepreneurs and building strong teams. I was extremely fortunate to work with and learn from some very talented colleagues and partners. I realised that I am at my happiest and most content when I have the opportunity to help people build and execute a plan to be the most successful version of themselves and to realise their entrepreneurial instincts.

I am excited for the next adventure and grateful to be alive in an era where:
- Technology allows me to earn a living and provide for my family by doing something I love
- Entrepreneurs are able to build and scale great companies with cultures that encourage collaboration and learning
- 2 guys at Stanford gave me a job and created a service where I can type “monkey salesman” into a search bar and be watching a video of it within seconds ;)

Thank You Google :)



It is 3.08am. Minutes earlier, my 2 week old son’s bowels executed a flawless impersonation of Mt Vesuvius and subjected my caregiving hand to a fate similar to Pompeii circa AD79. As I laugh/cry to myself, he deftly follows up with another impression of tectonic activity by imitating a wild Icelandic geyser. This particular straw-coloured bouquet with light undertones of urea will no doubt be the biggest hurdle I will face in getting my apartment security deposit back. With the wall and my hand nicely redecorated, I put him down in his moses basket and fall asleep on the floor next to him.

Since I first put pen to paper here (or pawed faeces/urine-covered hand to smartphone keyboard), this article has undergone an evolution. What started out as “some jotted down memories for me to laugh at later” has now become a Quora-esque response to the question that every new dad will have in the weeks before birth, namely:

“Sparing me the sugar-coated bu$%*&it freely available across the web, what would you recommend I really do to prepare for becoming a dad?”. 

In reality this document is actually a journal of the prodigal talents of my son’s digestive/urinary system peppered with a few other realisations I am sharing with the benefit of hindsight. I hope you can derive some value from it. At the very least you can hopefully laugh at my Hungry Caterpillar-esque transformation from composed husband to clueless dad. Without further ado...

THE HEURISTICS (Duration: T-6 to T+2)

minus 6 weeks
Spoil your partner with attention and affection. Take her to her favourite restaurants, whatever movies she wants to see and whatever new exhibitions she mentions. As you lie around sending puerile messages on Whatsapp or laughing at a meme of a chimpanzee dressed in a tutu, the lady in your life is growing an eyeball or toenails or some other vital component of a human. She deserves to be celebrated more than ever right now.

minus 4 weeks
Go shopping for the things that your baby will need. As you get home, resist the temptation to leave everything in your garage until game time. Get that breast pump/pushchair/carseat/sling out of the box and try it out. Invariably your first need for it will be when your child is screaming, your wife and you are tired/dehydrated/hungry and you are running late for something important. Also ask other dads or the internet about what you need to do and what you do not need to do. For reference I have shared an excerpt of youtube searches I did that week below:

how do i assemble a medella freestyle breast pump
september earth wind and fire
fitting a maxi cosi into a taxi 
lil jon snap yo fingers
how to put on a nappy
how to put on a nappy with one hand
nappy fitting world record
hero enrique iglesias karaoke version
how does the placenta work
did moses sleep in a moses basket? conspiracy theory

minus 2 weeks

Do some things that you might not be doing for a while and get rid of any excess adrenaline or excitement you have. Your home should be an oasis of serenity and calm. I found it useful to see some friends, fit in some extra boxing training and to read some books (Home Game: An Accidental Guide to Fatherhood by Michael Lewis is hilarious) Talk to everyone you know who is a dad (across multiple generations) and ask them for any final pieces of advice. Practice swaddling, putting on a diaper and buy some hilarious outfits for your child (shameless plug I know but this process is expensive so I chose to embrace free-market capitalism rather than set up a gofundme page)

minus 1 week

Insurance. Check. Will. Check. Get any admin stuff you need to do out of the way so you can forget about it for a few months. Your most crucial role is the preparation of the GO bag - this will be what you take to hospital when the contractions become 4mins apart lasting 1min each for 1 hour. Stick in some clothes/snacks/home comforts for mum, some clothes for baby and a phone charger for dad. We found coconut water to be invaluable as well as some meditation exercises downloaded onto the phone. From this point on you need to do your best impression of the Greek goddess Artemis and protect your partner from errant taxi-drivers, nosy strangers and unsolicited advice.

The Day aka Day Zero

It is all a blur. But it is the best day of your life. You never knew you could love people as much as you love your partner and your new child. You call family and friends to share the happy news. Endorphins and oxytocin are in abundance - it is truly like no other experience. 
Make sure your partner gets to rest as much as possible and bring good snacks for her. I got shouted at by a nurse for sneaking a pizza into the hospital and then argued with over-enthusiastic medical professionals who encroached the personal space of the new mummy. My wife told me she had never loved me more. #smileyface.

Day 1-2

Take millions of photos - your baby is changing in appearance every hour. Their age doubles from 24 hours to 48 hours. Get as much time with your child and partner as you can - these are the precious moments that are finite and relatively stress free as you are likely still in hospital. Go home to grab a car seat and on your way back to the hospital start to think in forensic detail about what you are going to do once the hospital lets you out into the world with the responsibility of raising another living being to be a responsible contributor to the progress of society and mankind. No pressure. 
Also you will discover meconium. Meconium is this secret that existing parents don’t tell new parents about. Think of it like the worst kind of hazing for an entirely mediocre fraternity/sorority. But with more tar and a worse smell. You will wince in horror but maybe smile in pride that your offspring is able to manufacture such a potent substance. As we were leaving the hospital, we put our fresh-faced son in the car seat and called our friend to come and collect us. As we thanked the nurses, I heard what I can only describe as the “mating call of a tortured duck”. As I glanced down at the car seat, my smiling heir stared at me as he showed us the prowess of his metabolism. Back to the room it was for a nappy change and a phone call to our friend asking him to set off from home 15 minutes later than we agreed.

Day 3-4

You will probably encounter one of the most helpless nights of your life. Your baby will cry while developing his core competencies of defecating 10 times a day and draining your wife of the sweet milky nectar that nature gifts the better gender. It will be around this time that you will realise you have no idea what you are doing. If you are fortunate to have your mother-in-law or mother helping you, you will appreciate everything they ever did for you as a child. You will spend large parts of your day quelling a raging storm of yellow liquid poop like a young Kurt Russell fighting fire in the 1991 movie Backdraft.
Around this time, your body will start adjusting to not sleeping anymore than 3 hours at any one stretch. I wish I had a notebook with me to capture some of the weird things that came into my mind. In one particular sleep deprived hallucination, I formulated a crude comparison between infant nutrition and startup financing options. It is riddled with inaccuracies but this exemplifies the somewhat limited capacity at which my brain was working at this time:

Breastmilk = bootstrapping. You know what it is in it and you control it. It costs nothing to acquire but there is of course some opportunity cost to generate it (and yes it is tiring for mother and difficult/impossible for some people to do)
Breast-expressed milk = VC/Equity financing. Comes with some overhead and loss of control but allows you to do the thing you want faster than you otherwise could i.e. provide breastmilk to your child
Formula = whatever is currently deemed as bad for startups (it used to be convertible debt). It is costly, you lose control and you don’t know what you are getting unless you really study the details and which new parent has time for that? (but it is sometimes the only viable option at that time)

Day 5-7

Wait for it. Wait for it. Wait for it. BOOM. You just realised that you are spending more on nappies (diapers) than you do on nutrition for your baby. Yes that is correct - you allocate more capital to helping your baby s$%t than you do to preventing your baby from starving. As you become more skilled at changing diapers, your confidence will grow but be wary that it just takes one bad episode to knock you down. As my confidence grew, I started showing off to myself by wearing fancier and fancier clothes while I changed my son. I got cocky. Like Enron cocky. Then one day my luck changed and I hit a bad spell and ruined a lovely shirt. Dejected and defeated I went out to buy some cheap t-shirts to reflect my reclassification from intermediate to beginner status. These shirts have quickly became an organic collage of my son’s biological evolution. Kind of like a weird Damien Hirst exhibition but with fewer animals sliced in half and embalmed in formaldehyde. I hope to regain my confidence soon.
You will spend these days in a cycle of helping your baby get nutrition, defecate and sleep. I became jealous of the fact that my son had a lifestyle perhaps only matched by a small handful of African dictators. Typical day will start at 7am with a feed and a change. As baby sleeps, you have a couple of hours to try and eat breakfast, shower and stick a washing cycle on while also washing the dishes and doing other stuff to keep your household from overthrowing itself. By 10 you need to be ready for the milk/poo/change/lie down process again. Rinse and repeat through to about 7pm. Hopefully you will have found some time to do some of the important other stuff like getting him a birth certificate, applying for a passport and dressing him up in funny costumes to send to your family/friends. When your wife finally orders you to have a shower, you steal a few minutes to realise that you have never been so busy in your life but that you have never had so much fun in your life. 
A couple of feeds through the night will present you with some stolen moments of free time to do something awesome. In recent days I have used this time to research the financial reports of various nappy manufacturers (Unicharm who manufacture the Mamypoko brand have doubled their stock price over last 5 years ) and also to study some chinese flashcards (the character for mermaid is literally beautiful+person+fish or 美人鱼). Also in the sleep deprivation phase, I have found myself obsessing over ridiculous things like “how much margin could I make if I bought 10 million nappies from Alibaba and resold them?” and “what kind of regulatory challenges would I face if launched an Uber for breastmilk?”. I did a few press-ups too in a vain attempt to make up for a lack of exercise since the birth.

Day 8-11

With any luck, you will not have had to leave the house until now with your child. The first time you do this will be about as well executed as recent global quantitative easing measures. Everything will take twice as long as you think and not really work out anyway. We took our son for his first check-up with the paediatrician. While we were waiting for the appointment, I spent some time observing the dynamics in the waiting room. From my albeit limited observations, I noticed the unfair standards that society hold mum and dad to in providing parental care. A father is deemed a hero for doing simple things like attending a doctor appointment. A mother is tacitly judged when she has to breastfeed in public or is struggling to calm down a crying child. Anyway it seemed a good time to 1. remind my wife that she is doing an amazing job considering a week ago a human came out of her and 2. make fun of some weird looking kids sat near us.
On the plus side, this is around the time that you will feel ready to start getting family members involved in the joy you are experiencing. My wife and I live on the other side of the world from our families. We were hesitant to get our son onto Snapchat (like other children his age seem to be) but we have found video conferencing like Hangouts/Facetime to be a really great way of involving family and friends in this happy time. I am pretty sure babies born in 2025 will be able to use a messaging app to book their own taxi home from hospital and get a loan within minutes of being born to pay for that taxi. Anyway after a few calls, I can confidently say that there is no greater gift that you can give to new grandparents, uncles and aunts than taking the time to let them virtually interact with your child despite the many miles that separate you.

Day 12-14

Things are starting to settle down now. You start to interpret different cries as signals for different things. “I am hungry” is slightly higher pitched than “burp me”. “Do you want to see how I digested my lunch?” is more staccato relative to “Can you put me in my crib now please?”. You find little hacks to improve your effectiveness at doing things you have just learnt for the first time. 

“Put the new nappy under the old nappy unless you want to get into an infinite loop of costume changes”
“Set your alarm for 15 minutes before night feeds so you have time to slowly wake up”
“Have the nappy bag freshly restocked when you come home from being out rather than doing it hastily before you next go out” 

If you are already a father then no doubt you are chuckling at my naivety in thinking that things have settled down. And I guess that is probably one of the biggest learnings so far for me. Everything cannot and will not be perfect. You just have to do the best you can and ensure that it is good enough to make sure your partner and child are safe and happy. You basically have to make sure you don’t completely fail as a husband and a father. Becoming a father is a massive personal change but literally billions of people have done this before you. So before you start to panic, just find someone who has done it before and listen to what they have to say. Then figure out your own way to do the things they suggest.

A final piece of advice I heard was one I wanted to end with. It was something along the lines of not taking for granted the extremely wonderful gift that your partner has given in bearing a child for you both. Babies are fairly resilient so it is not a bad idea to focus your attention as a dad on your partner. 

Perhaps tonight at 3am as I dodge poop and burp my boy, I will ponder whether “if humans ever acquired the reproduction profiles of seahorses, would the male of the human species ever be as adept as the female at the gestation process?”. I think probably not but it would be interesting to try. Anyway time to go, the 6.23am train to Turdsville seems to be arriving with a full carriage...

Bonne chance!

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