It was our last day in New York City before a sixteen hour flight. We could have gone to an airport hotel, paid to give our daughter an hour’s sleep and stared at our phones. But we were in the greatest city in the world, staying across the road from Central Park. We wanted to enjoy it down to the last minute, what could go wrong?

We dropped our luggage at reception and headed for the Central Park Zoo. Our daughter waved and blew kisses at every animal we could find while we attempted to use up her infinite energy in preparation for the impossible nap.

We needed our daughter to nap in her stroller, something many babies do all the time, but our island baby had never done any such thing. We left the zoo and began to walk circles around the southern end of Central Park as our daughter protested. What inhuman torture, to take her to this exciting place and expect her to take a nap.

An hour of our daughter screaming from her stroller prison followed. You know it’s strange when New Yorkers take a second look, but the odd glances from passers-by could not deter us. We had no choice but to keep walking.

Our daughter finally passed out in the stroller we picked for her before she was born, at a store in this very city. We shared a celebratory look and kept walking. Praying the vibrant sounds of the city would not disturb her.

That’s when we made our first big mistake.

We looked around the park, at all the other parents relaxing on the grass alongside their sleeping babies in strollers. How nice it looked to rest our weary legs. To lie down on the grass and enjoy the shade of the trees waving in the breeze of this crisp spring day. “Let’s pull over under this tree.”

The screams reverberated across the park as our daughter’s hard-earned sleep was disturbed by the unscheduled stop. Some birds flew from their perch squawking in horror. We sheepishly returned to the path but the damage was done. The next hour of our lives would break our spirits as we attempted to get her back to sleep while the park stared and our brains melted.

Thirty minutes before we needed to leave for our flight she passed out again. There wasn’t enough time for a decent nap and heading back to the hotel along a busy street would almost certainly wake her up.

My wife suggested we split up. She could continue through the park to get to the subway so our daughter could sleep.

“Go get the bags, take an Uber to the subway station. We’ll meet you there.”
“This is a bad idea, we shouldn’t split up.”
“We have no choice, she has to have a nap or this flight is going to be a nightmare.”
“I’m not paying for an Uber to drive down the road.”
“Just get the Uber you can’t carry the stuff by yourself.”
“We shouldn’t split up, you don’t have data.”
“We have no choice, she needs to sleep.”
“Fine… We need to make sure we know where we are meeting because I can’t contact you, let’s meet at this entrance.”

I pulled up Maps on my phone and we agreed on an entrance. At this point I’m exhausted, my wife is exhausted, I don’t think either of us are thinking straight but I’m too tired to argue and don’t have any better ideas anyway. I noticed my wife was not really paying attention.

“Look at this carefully, we have to meet at this spot.”

While waiting for our bags to be brought out of the storage area at the hotel I’m convinced taking an Uber is ridiculous. The road we are on is a one way. The Uber would have to go around one of the busiest blocks in New York City to get me to the station. I don’t have time to be in a traffic jam. I’m then still going to have to push the bags around to find my wife who doesn’t have any way of being contacted.

The bags arrive and I stack them. The two large suitcases I decide I’ll roll, one for each hand. I lay the carry-ons on their sides on top of them. The crib goes on my back, the car seat goes on my back. What’s the point of going to the gym if I can’t pull this off?

As I navigate the bags through the entrance way the doorman offers to get me a taxi. I politely decline and begin to push.

For the third time that afternoon, the people of New York City stare at me. This crazy man is pushing a mountain of suitcases across the south end of Central Park while taxi drivers shout their offers of assistance. I get through the first block and my confidence grows. I’m doing this. It’s not taking too long. Nobody is trying to rob me. I must look too crazy!

Thankful this is not happening in the Cayman heat, I continue on as my tired feet and back complain at this newly introduced torture. I finally get to the end of the street and find an entrance to the subway.

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I squeeze onto a tiny elevator and make my way down. The pay gates to the train we need to take are right there. I position myself in front of them and wait. They’ll find me here, they can’t miss me with all these bags.

The minutes tick by and I start to panic. This is where you would naturally stop and wait, but my girls are nowhere to be seen. Why wouldn’t they come to the gates? I send a message in the hopes my wife finds some wifi wherever she is at but it’s time to leave for our flight and the clock keeps ticking.

As I mumble to myself about how bad this idea was I push the bags along the passageway away from the gates, hoping I’ll run into them. Surely they would have thought to look for me by this point? When I get to the end of the passage I only see staircases back to the street. They wouldn’t wait by a staircase. How would I get the bags down? This can’t be the place we agreed to meet.

I walk back to the gates. I haven’t received any payment notification from our bank so I doubt they’ve gone through, but I’m exhausted and becoming delirious with stress, so I go through the pay gates. Maybe they’re waiting by the train?

There’s a hill to get up to the train. I bend over further and put my back into it. All six bags come with me up the little hill and to the train platform. It’s rush hour. There are people everywhere. I see a lady with a baby, but they’re not mine.

I walk through the throng of people with all my bags to the end of the platform and back. My girls are not here. I go back down the hill, out the pay gate and back to the end of the station where I had found the staircases. Still no sign of them. As I push the bags back to the pay gates again, a shopkeeper who has been watching me push these bags up and down asks me if I’m OK.

“I can’t find my wife!” I exclaim. He laughs knowingly.

Sweating, completely freaked out, and certain we are missing our flight at this point, I pull myself together, determined that at the very least I need to find my girls even if it takes all night.

I head back to the tiny elevator, praying for a miracle. As I struggle to get all the bags inside again, a kind stranger attempts to help. I’m acutely aware of how insane I must look at this point, and again worry someone may take advantage of that and rob me so I refuse to let go of any of the bags as the person awkwardly tries to assist anyway.

Back on the street I now push my bags along the front of the mall above the subway hoping to find a different entrance. And can you believe it, there she is. My wife! Standing there in front of the mall. Phone in one hand trying to connect to wi-fi, our daughter being nursed in the other arm.

“Oh my word, where have you guys been? I’ve been so worried! I thought I had lost you guys, I didn’t know how I was going to find you!” I shout, tears welling up.

My wife looks at me bemused.

“I knew you were lost.”

In case you missed the name of my column I’m a dad, not a mom. So providing particularly juicy insight for Mother’s Day would likely fall under the category of mansplaining. So instead, I asked the two best mothers I know, my wife and my own mom, to share their insights and wisdom on this special day where we celebrate the most important women in our lives.

I started with the obvious, what do you love about being a mom?

My mom loves the maternal aspect, “nurturing and caring for your child from babyhood to adulthood,” while my wife called it, “unlocking a different type of love for another person.”

“I’m also discovering the world through her eyes as she learns,” my wife shared. “Yesterday we went on a leaf hunt and I ended up holding a bunch of beautiful leaves for her that I never would have noticed otherwise. I [also] love when she hasn’t seen me for a literal minute and I walk [back] into the room and she comes running with her arms wide open.”

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But being a mom is hard too, right? What’s the worst part about being a mom?

My wife pointed to what I think is also the worst part about being an expat, “the hardest part is not having any family nearby for support.” Interestingly, for my mom, distance was also the greatest burden. “When I went back to work, and had to leave my baby at a crèche. When my parents left the country… my mentor and friend wasn’t a phone call or visit away. Being a new mom […] I needed my mother. Now having my son living overseas […] and missing a lot not physically being [there for] the milestones in their lives.”

I asked if they had been given any advice before becoming a mom.

“I don’t remember life before our daughter,” my wife laughed, “but after she came, people kept telling me to sleep when the baby sleeps. She only ever slept on me during the day, so that was impossible. My brother gave me some more helpful advice, he told me every baby is different and you just need to figure it out.”

That rang true for my mom too, “A romantic fairytale picture is given about motherhood. It’s not reality. There are some extraordinary, special moments. But there are hard moments too.

No one has a manual for parenthood. One can read all the books and attend the maternity lectures but life happens and we’ve had to go with the flow and make the most of every day.

Many family members said babies sleep through from six weeks - this is totally not my experience which was so difficult to process.” Sorry mom! That was totally not our experience either!

“The challenging sleepless nights, the tantrums of toddlers, it’s for a short season. However when living through it, it seems like forever.”

I was curious if there were elements from their moms that they loved and may have shaped the way they are trying to be moms themselves.

“Whether in times of plenty or hard times - the family came first. She loved unconditionally, protected and nurtured no matter what.” Sounds like my grandmother could give Vin Diesel a run for his money in the Fast and the Furious. “My mom was the best cook and put her heart into all her meals. Super delicious. [My favourite memories are] the happy times around the meal table.

For my wife, it was her mum’s love of being a mum. “My impression of my mum, is that she loved being a mum. She was kind, patient, fun and created space for me. I want our daughter to know she is a blessing and I love being her mum.”

There’s always been a part of me that wants to leave a positive legacy in the world. My wife and I have spoken often since becoming parents about our daughter being our true legacy. That we may be forgotten in a few generations but what we’ve poured into her will be passed on.

My wife’s answer came from that same line of thinking. “The Bible has a verse in Corinthians1 that talks about love being the most important thing that remains after death. I want her to remember me making her feel loved, and cared for and special. I don’t need her to remember what I did for my career, or my views on the world.”

My mom was on the same track, “unconditional love. [That I was] always available to listen, to pray, to guide no matter what the circumstances and the physical distance.”

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I asked what wisdom they'd give their former selves on the day they left the hospital with their babies.

My mom with many years of wisdom under her belt had a lot to tell herself:

“Stay calm, enjoy every moment of every day, make the special memories as the early babyhood days pass in the blink of an eye. Trust God daily and never give up on yourself. Love yourself and keep your cup full so you can give out of abundance not from an empty cup. Be present 💝. Don’t sweat the small stuff. Remember, ‘this too shall pass’ [and] there are four seasons in life autumn, winter, summer and spring. Sow love, joy, hope, and peace into your family”

My wife kept it practical: “Don’t let your baby have a boob preference!”

Nothing triggers the frugal accountant in me like seeing a payment notification for a streaming service we didn’t log into that month. Having a kid has naturally meant our time to stare at the glass rectangle on the wall has gone down significantly, and with it our need to subscribe to all these services.

We used to get home, throw dinner in the oven and watch something together, maybe two somethings. Now we get home and the bedtime routine kicks in. We walk in the door and immediately start getting dinner ready. We try to eat together, which usually turns into a series of performances to get those last few bites down. We might start with reading a book, then move onto interesting distracting objects, and by the end we are blowing bubbles while the dog tries to bite them.

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Sometimes it’s a delight, sometimes it’s a circus, but by the time it’s all said and done we might have an hour of downtime before our own bedtime routine needs to kick in. No binge watching happening here.

We don’t pay for a TV package or cable in our home, but we do subscribe to multiple streaming services. Netflix, Disney+, HBO, Apple TV, Paramount Plus, Amazon Prime, YouTube Premium. It’s a lot. A never ending stream of content being funneled our way. We are wasting money on subscriptions we don’t always use. So we decided to try an experiment. It was time to let one of them go.

We had just paid for a yearly subscription for Disney+, so it was too late to let that one go and I may need to watch The Devil Wears Prada 2. in a few months.
Apple TV comes bundled with our other Apple services and I need the cloud storage for the five business ideas I’m simultaneously working on.
We only have Paramount Plus to watch Survivor and cancel it as soon as the season ends - can’t miss Season 50!
Our Prime subscription is more about free fast shipping than Beast Games so it doesn’t matter much that we rarely watch it.
We signed up for HBO Go / HBO Now / HBO Max / Max / HBO Max again??? when they were desperate for subscribers and locked in a great rate where we barely pay anything for it.

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So that leaves Netflix and YouTube Premium on the chopping block. If you are not paying for YouTube Premium and suffering through all those ads today you are a patron saint of patience. Once you stop watching ads, it’s very hard to tolerate them ever again. My MKBHD, and our Mr Beast and Ryan Trahan viewing must remain sacred. YouTube stays.

So Netflix got chopped. We weren’t watching anything in particular on Netflix, the movies and series we had watched more recently felt formulaic and forgettable. It didn’t feel like a big sacrifice.

I wasn’t sure it would last that long. But after five months we’ve barely noticed it’s been gone. We missed Stranger Things and even that couldn’t get us to sign back up. There is still way too much content to watch on the services we currently subscribe to.

That doesn’t mean we will never subscribe to Netflix again, I still want to see what happened to the girl that keeps getting nose bleeds but doesn’t carry around any wet wipes. But it has made me think that using a subscription-rotation makes more sense than subscribing to them all at once. $15 to $20 a month may sound small but when you’re paying that for five subscriptions you don’t use over a year it can add up to a plane ticket!

Take it from your columnist accountant, use five minutes today and cancel a subscription to a service you never use. You could use that money for much better things, like supporting this column instead.

A few months ago my wife and I paid $366 to sign our nine-month-old up for school in 2029. This is just to be put on a list, position unknown. A list that guarantees nothing but consideration to register at the school. The payment is non-refundable, and not put towards any future fees. There will naturally be an actual registration fee and deposit due if her position on the list entitles her to attend the school when we get closer to the time.

After procrastinating for months, including considering moving to multiple other countries instead of paying this ridiculous fee, my wife and I gave in and paid it. In return we got this:

Please find our payment receipt for your child’s 2029 registration fee attached to this email. As a gentle reminder this is not confirmation of placement but does secure her spot on the list.

Cheers!

Across these beloved Cayman Islands, mothers and fathers dig into their pockets and make this involuntary school donation because there is no other choice. School space is limited for our ever-growing population. You wouldn’t want your child left out.

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Caymanians who believe in the public education system can send their kids to government school for free. Technically everyone else can also send their kids to a government school but for a fee. $900-$15001 per annum plus external exam fees. That seems fair for the second most expensive place in the world2.

But due to very limited space, 46.7% of Primary School Children and 40.9% of high school children attend private schools.3 The high demand for education and low supply means the government must enforce a hierarchy of who gets placed first.

The admission hierarchy at government schools is: Caymanians and status holders first, then refugees and asylum seekers, then dependents of Caymanians, then dependents of government workers, then permanent residents, then everyone else if space allows.4 Space very rarely allows.

By not building enough public schools to meet the exploding population demand because, as then Finance Minister Rolston Anglin put it to a Finance Committee, the forecasting is “very unscientific,” the government has inadvertently created a market for eager capitalists to exploit. And exploit it they have.

Private schools currently charge anywhere from a whopping $18,000 to $36,0005 per annum with specialized support schools pushing that even higher. That’s a lot of money to give our little darlings an education, an education that they are only kind of, sort of entitled to.

The Cayman Islands Constitution doesn’t actually guarantee free education. Section 20 of the Bill of Rights says the government will “seek reasonably to achieve the progressive realisation, within available resources, of providing every child with primary and secondary education which shall [...] be free.”6 A sentence with so many hedges in it, it’s almost an apology in advance. We’ll try, if we can, maybe when there is money available, to move towards making school for all kids free.

In a country like Cayman, a wealthy developed tax haven, not a developing country, almost half the school-age population has no access to free education. Their parents, whose work permits and immigration fees fund a meaningful share of government revenue, do not even have the option of sending their children to public school.

I’m all for allowing the private sector to step in when the government can’t. Provide a premium service for those willing to pay for it. But with demand through the roof and supply short, basic economics means you’ll soon be selling your liver just so Johnny can learn to read.

There are of course consequences far beyond making expats pay through their noses to educate their offspring. The undersupply of government education, leading most expats to send their kids to private schools, could be inadvertently contributing to the us versus them dynamic that plagues us today.

People like to stick to what they know. I see it in Cayman all the time. People from the same country end up almost exclusively hanging out with other people from their country. It’s a disservice to yourself and the people of Cayman. But it’s human nature. Integration needs to be actively built into society or we will naturally stick to our tribes.

When kids share a classroom, their parents eventually end up spending a lot of time together. Time spent doing life with people is what leads you to discover that the person who looks different and comes from a different background is also exhausted, also proud of their kid, also trying to make the best life for their family, also winging it. You discover that we are more alike than different.

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I grew up in South Africa in a time when the country was actively trying to undo a system that had sorted people by race into separate classrooms, separate neighbourhoods, separate lives. Separating people sows distrust and animosity based on lies and hearsay instead of truth. It creates immeasurable damage. Damage that will take multiple generations to recover from.

By being in the classroom with kids who came from historically disadvantaged backgrounds, and then the lecture hall, and then the workplace, I learnt what the generations before me never could. These people that are different from me are just as smart if not smarter, they work just as hard if not harder and they have had to make incredible sacrifices to get themselves to the positions they are in today. They are just like me, maybe better.

Having a braai (BBQ) in each other’s homes, shouting for the same sports team, celebrating your commonalities and laughing at your differences. These are things that South Africa does well and has been the source of much of the healing that has taken place so far.

These are things that make a cohesive society. I want my daughter to have friends from every walk of life and every nationality on this island. To make real connections that will give her friends to visit in countries all over the world while also feeling comfortable to call this place home. Where the government has dropped the ball, parents will have to step up. We must actively reach across the divides to build the society we want our kids to inherit. All while coughing up $366 to get them on a list they just have to be on.

I knew lack of sleep would be one of the most difficult challenges to overcome as a new parent. But knowing what is coming is not enough to prepare you for its reality. The UN has recognized sleep deprivation as a form of torture. My involuntary, highly scientific investigation over the last fourteen months came to the same conclusion.

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Before I go on any rants about how difficult it is to function on little sleep at work, how trying not to snap while Steve is telling you he requires a unique description on his invoice which should have been issued four months ago but he waited until now and it’s an emergency if it doesn’t get sent today… I must acknowledge my incredible wife.

She has carried the team through these long nights, sometimes having to get up as many as seven times in the night to feed our little girl, only completely accidentally kicking me awake every other time. It’s been hard not being able to help her more, I wrote about our struggles with sleep last year:

While I understand why parents get to the point where they resort to cry it out sleep training, we didn’t have the heart to do it. This method involves putting your baby in their bed and only returning in the morning, letting them figure out the sleep thing on their own. But hearing your little one cry for you and ignoring it is excruciating. So we continued to sacrifice our sleep in the hopes that eventually she would stop taking after her father and our sleep prayers would be answered.

Yes, I am apparently the culprit. I am told I was a terrible sleeper as a baby. Things got so bad at one point that my wife began telling single women to check with any men they date if they slept well as a baby before spending any more time with them. It had been a particularly rough night.

Many people advised us that we would have to revert to the cry it out method. That it was the quickest way. At one point we did try a more hands on version where I would go over when she cried, reassure her and set her back in a sleeping position in her crib. I would go back, over and over, with increasingly long breaks in between.

It was brutal. Babies are strong negotiators. Even if you tell them it’s sleep time they tend not to agree. It’s hard to reason with very loud and impressively consistent screaming. We quickly gave up. The limited attempt was not in vain though, her wake ups reduced to once or twice a night.

After a bad round of teething, our little one’s sleep got worse and stayed worse. This time we came up with our own method of sharing the load while trying to help her learn to sleep. I would get up if it was before 3AM, reassure her without giving her food, and cuddle her back to sleep. After 3, she still got Mama.

At first when she realized I was trying to get her to go back to sleep instead of taking her to her mother, she was having none of it. She exhibited high potential for a career as a ninja by squirming, kicking and wriggling in an attempt to escape my clutches.

I tried singing, dancing, clapping, praying, anything to calm her down. After an hour, my arms maxed out from the craziest workout, she exhausted herself. Finally accepting my cuddles until she fell back asleep.

We kept going. After a few rough nights it started to work. My methodology got better. I would start by putting on my noise cancelling headphones allowing me to stay calm. After letting her complain for a bit I would sing her remixes of songs she liked, especially the ones Mama made up for her. The sessions got shorter, the wakeups reduced, and we didn’t feel guilty because I was there for her whether she liked it or not.

Then one night it finally happened. I got up to answer her cries, and as soon as she saw it was me and not her mother she let out a huff and put herself back to sleep. I was too thrilled to be insulted.

“Don’t go off the green path. When your basket is full, you are done. Ready? Go!”

You’d think such simple instructions designed for children would be understandable to a large group of likely educated adults, but the chaos was immediate and ferocious. People streamed into the once-abandoned mini golf course in search of hundreds of little plastic eggs with surprises inside.

With my curious toddler taking wobbly steps between my legs, we moved forward with the mob. Small children were being lifted up and carried through the bushes. Older ones were already sprinting in every direction, many carrying their own much larger baskets than the hotel provided.

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My wife and I eyed the bushes for remnants left after hordes of filthy hobbitses had ravaged them in seconds. We spotted a well-hidden one and encouraged our toddler to explore it. With both of us holding out cameras to capture the moment and my toddler reaching excitedly for the egg, a seven-year-old arm swooped in front of my lens to snap up the hidden treasure.

My wife's teacher skills immediately got the seven-year-old course-corrected and our daughter was able to find her first egg. As we continued on the path, children frantically hunted around us, baskets overflowing with bounty. A dad walked past, looking like he'd gone through a bush backwards, yelling to his oblivious kid that the eggs were all finished. He was holding out his shirt, bulging with eggs that couldn't fit into his child's extra-large basket. My P(doom) increased.

A kind staff member who noticed our daughter planted some eggs in her line of sight as we walked. She lifted one up in excitement as a little boy walked past and grabbed it straight out of her hands.

"Excuse me, can you give that back please?" I said to the little boy whose parents were standing immediately behind him doing nothing.
"She gave it to me!"

Sweating as the Caribbean sun beat down on us, we found the end of the path. Our daughter's basket barely a third full, our faith in humanity dampened. At least there was chocolate in our near future. How did Easter go from our Lord and Saviour sacrificing himself on a cross to co-parenting strangers' children in a mad dash for chocolate eggs laid by a bunny?

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In the Cayman Islands, Easter traditions include a spiced, dense, dark fruit loaf served with cheese and butter while camping on the beach — just as… Jesus did? People who like camping, not us, spend their long weekend avoiding showers and swatting at mosquitoes. But hey, if it means you can escape a three-hour fire-and-brimstone sermon with all the people who only show up to church twice a year, I understand.

Our attempts to attend church with a baby, especially when the service lands right in the middle of nap time, have proven tricky. We attend a church that meets in a stinky school gym but we either end up in a ball pit in the cafeteria or making a swift exit as the school halls echo with screaming. This year we didn't make it to celebrate Easter with our church community, but we did eat a lot of chocolate.

My wife and I have a tradition of hiding Easter eggs for each other and laughing as the other — normally me — takes ages to find them. This year our daughter and dog both showed me up with their incredible skills. I still haven’t found one of mine two days later.

While the traditions around it make no sense, taking a moment to think about God's grace in my life and His incredible sacrifice to fix humanity's mistakes is a worthy pause. As I danced around our living room with my daughter to one of her favourite worship songs on Sunday, I was overwhelmed with how good God has been to us in spite of what little I have done to deserve it. Though I have to have earned some Good Place points for parenting significantly better than almost everyone else on that mini golf course.

I walked out the office door and my wife didn’t waste a second breaking the news.

“The washing machine is broken.”
”What do you mean broken?”
”It doesn’t spin; it just starts counting down.”
”Ominous.”

An unfortunate but simply fixed adulting problem, right? But when you live in the second most expensive place in the world, which also happens to be an island, there’s no such thing as an inexpensive simple fix.

I set out to diagnose the problem. I’m a grown man. I have a degree. I can fix things. I was feeling empowered by recent successes with my trusty AI friend Claude, so I asked him for help. Claude walked me through which buttons to push to get a diagnostic error from the machine. The error apparently meant one of the circuit boards on the washing machine had given up under the weight of baby clothes and dirty gym towels. I quickly lost confidence in my abilities and decided to call in some ‘expert’ help to get the part replaced.

The ‘expert’ arrived on time, a shockingly positive silver lining in this saga, and after just ten minutes confirmed exactly the same thing Claude had already figure out. He then broke the bad news that Claude couldn’t. The part was not on island, it’s very expensive, and it would take weeks to get it here. Most of our neighbors with the same machine have already just replaced the entire thing. That’ll be $75. This guy should work for a consulting firm.

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My wife and I wasted a few hours in the island’s only giant hardware store considering our options while our daughter screamed to be let loose to crawl on the floor and whack the bathtubs indiscriminately. Do we bite the bullet and get something new? The dryer is on the brink of collapse too, with enough lint built up inside to label it a fire hazard. But none of the machines they have there can fit in our small apartment’s laundry closet. They didn’t have the part just as the ‘expert’ lamented. My wife and I go back and forth but given nothing is going to fit, and we want the fastest solution to a working washer we decide on ordering the part ourselves and flying it in. One week max.

I spend time online finding the right part and praying it’s the actual issue. Some kind friends allow us to wash our dirty underwear at their houses and we drag it home in bin bags to dry in our barely operational fire hazard. But when Monday rolls around I get an e-mail from the US parts supplier saying they have cancelled our order because they don’t ship to freight forwarders. We’re back to square one and the laundry is piling up.

During my Tuesday lunch break, we take a trip to the only other place on island that sells washing machines. We walk around the empty store as the salesman eyes us up without offering to help. We find a decent looking set of machines that will fit in our utility closet so we now need to engage with the salesman who has decided we’re not worth the trouble and has returned to his desk.

I don’t like talking to strangers so I urge my wife to ask him some questions. We walk up to his desk, preparing to spend way too much money on a washing machine and dryer. He doesn’t stand.

“Hi, what’s the difference between these two washer-dryer towers?”
“Not much.”
“O-K, so why is one more expensive?”
“It’s got some steam drying feature.”
“We probably don’t need that. Does it come with delivery? We live in town.”
“Delivery will be about $100…”
We literally live down the road.
“… and another $150 for installation. You’ll also need to buy some pipes for the washer and a plug for the dryer.”
“It doesn’t come with a plug?”
I finally join the conversation helpfully repeating my wife’s question, ”It doesn’t come with a plug!?”
“No.”
“And how much is that?”
“Probably another $60 for the plug and maybe $50 for the pipes.”

I’d had enough. I tell my wife we are just going to have to find another supplier for the part and for some reason we thank him before leaving. Now to be fair to the man we later found out it is normal for a dryer in North America to not come with a plug, but I can only tolerate so much madness before I refuse to spend money at a store ever again.

We went around the corner to their parts department where I had to look around and yell hello to find somebody to help us. The person quoted us almost three times the cost of the part we had already tried to order and told us it would take six weeks to get here.

When we got home we googled the price of the new machine we liked at Home Depot in the US. Less than half the price! Add in shipping from Miami to Cayman plus taxes, and we’d still be well below the sticker price at the local store. We gave in and I hit order.

No matter how long I live here I can’t get used to the terrible customer service stores in these beloved isles provide, making the sticker shock so much worse. Fancy hotels, who train their staff to smile through White-Lotus-level madness aside - residents frequently have to deal with surly, social media-scrolling staff. You’re made to feel as if you should apologize for trying to spend money in their store.

“I’m so sorry to interrupt your TikTok session Ma’am, but I really like the synopsis of this book. Would you be so kind as to let me pay you to leave the store with it?”
Grunt, teeth kiss.

I’ll be honest friends, these kinds of events have me feeling down about living in paradise. This saga started a month ago and our washing machine and dryer have only just cleared customs. We’re hoping it will be delivered tomorrow where I will now have to figure out how to install it because I refuse to pay $150-$300 for somebody to screw some things in for 30 mins. But God is good at reminding me when I’m starting to get ungrateful for my blessings.

Last week, my wife and I were enjoying an afternoon on Seven Mile beach. Recovering from our laundry woes and another round of washing at friend’s houses. Trying not to think about how much unexpected money we’d just blown. The weather was warm but not too hot, the water was beautiful, and our daughter was loving playing in the sand. Some tourists noticed my wife’s Canadian hat and struck up a friendly conversation. They were surprised to hear we lived in this beautiful place.

”Enjoy the rest of your vacation,” my wife said as they left.
”Enjoy your life,” they replied.

OK God, I hear you. Thanks for the perspective.

I’ve been a fan of the iPhone since watching Steve Jobs unveil the first one in his now famous keynote.

Today, we’re introducing three revolutionary products of this class. The first one is a widescreen iPod with touch controls. The second is a revolutionary mobile phone. And the third is a breakthrough Internet communications device.

So, three things; a widescreen iPod with touch controls, a revolutionary mobile phone and a breakthrough Internet communications device. An iPod, a phone and an Internet communicator… an iPod, a phone and an Internet communicator… are you getting it? These are not three separate devices. This is one device, and we are calling it iPhone.

Today, Apple is going to reinvent the phone.

Steve Jobs - January 2007

In 2008, the App Store was launched. Paving the way for the way we now interact and use our phones every day. Some of them making us better, connected, more productive people. Some slowly absorbing our souls with mindless scrolls. Having an App on the App Store is a tech nerd bucket list item, and today I ticked that off.

A few weeks ago I mentioned, after being amazed by the capability of Anthropic’s AI model Claude Code, that I was going to attempt to create an App. Many hours of prompting and troubleshooting later the idea I had has turned into a beautiful iOS App available to download today. Introducing…

Why CPD?

I listen to a lot of business related podcasts, and people who have successfully built businesses often solve a problem for themselves. If you have a problem you think is worth solving, maybe other people will need that problem solved too. For me the problem top of mind is getting my daughter to sleep through the night. While that remains a pipe dream I do have other problems worth solving. As I signed off my Continuous Professional Development for the year, I thought there must be a better way to track this.

I’m a Chartered Accountant of South Africa. One of the best accounting designations in the world, and one that requires a long, difficult journey to acquire. The professional body that governs this designation is called The South African Institute of Chartered Accountants, or SAICA. I made a video back when I miraculously passed my second board exam talking about the magnitude of that journey.
To be fair to my daughter I looked just as exhausted back then. Must just be my face.

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Most professional bodies just require you to prove that every year you’ve done a certain amount of verifiable (provable) training so that you stay up to date with changes and updates to the profession. A few years ago SAICA moved away from tracking hours every year for professional development and moved to a competency based approach.

This approach is very forward thinking and brilliant. Don’t just do a bunch of hours to tick a box. Think about where you may have gaps in your knowledge, where you want to go in life, and target the things you spend time learning around that. So much better than falling asleep during a random technical update course for a week to get forty hours of ‘learning’ under your belt.

The problem? When there are no strict guidelines, it can actually make it difficult to ensure you are not only meeting your yearly requirements, but enjoying the benefits of this modern way of encouraging professional development. SAICA has pages upon pages of guidelines to help with this, but that was not cutting it for me.

This is the problem I wanted to solve. And this is why I built CPDTracks.

I won’t go into the nitty gritty of the App here, but I encourage my fellow SAICA members to check out the App on the App Store. It’s free to play around with, and there’s a yearly subscription if you want to really start using it properly. Send me a message with what you think.

The AI App Building Experience

As I said in my article a few weeks ago, I’ve been using AI to build applications for work for a few years now. These applications have gotten increasingly sophisticated as I’ve gotten better at using the tools and as the tools have gotten increasingly intelligent. But building this application was on an entirely different level. I’ll break this down the same way CPDTracks breaks down your learning year.
I’m so clever. I should have been in marketing.

Plan

I started with the concept. Spending a significant amount of time ingesting the guidance provided by SAICA and then workshopping the way I wanted this to be presented by CPDTracks. Essentially building up what would turn into a monster starting prompt, broken into different files for the AI to work with.

Even though this was a big effort to start, I actually wish I’d spent more time in this planning phase. Changing things later is much harder than getting it right the first time. Kind of like everything in life. As I started building I came up with more ideas, added more features, and iterated over and over. All fine but it introduced a lot of bugs that would need to be fixed later on.

Activities

Monster prompt inputted, Claude Code set to work while I watched in amazement as a pretty decent first version came to life. It wasn’t perfect, it didn’t understand everything I meant, it took its own liberties on things based on what it believed an App of this nature would look like and we had words about that. But friends, this thing created a working app in one go with a decent prompt. That’s wild.

This is where the real work began for me though. Playing with what was there, keeping what I liked, throwing out what I didn’t. Coming up with crazy ideas and trying them just to see how it would look. It truly feels like anything you can think of could be possible with a bit of effort.

For example I thought it would be cool to have a safari animation at the top of the main screen. The jeep drives along an African landscape, goes fast, slows down when it sees a big five animal, other African trees and animals pass by randomly - some rarer than others.

A random idea, and the first decent prompt came up with a great start that told me this was achievable. I then spent hours refining it and making the animals and trees look better. Even throwing in some fun surprises if you watch it long enough. These little things make an App special, and were really fun to include.

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Reflect

Once the App was finally working I then got Claude to audit the work. Knowing full well how awful auditing is I subjected this poor AI to the ultimate pain. Sorry Claude. Go looking for bugs, explain why they are bugs and what we should do to fix them. I even prompted Claude to write the prompt itself. One that I would eventually use multiple times as I went through round after round of bug squishing. Slimy yet satisfying.

As I fixed problems, I came up with more ideas, more features, better workflows. The artist in me who is never done improving was switched on and loving the new challenge. Reflection returned to actioning activities and around and around we went. Finally my wife had had enough of me being on the laptop while she was trying to sleep, so it was time to wrap up development.

Prepping for the App Store

There are things about building an app I hadn’t even considered. Of course I asked Claude what I needed to do, and I was guided every step of the way. Is Claude my new best friend? Even as far as filling in all the different settings and forms when setting up your account on the App Store.

I needed a website, a support page, a privacy policy. Claude ran with it all. I’ve built a few websites in my time, coding them one line as a time like a slave. I have never made a website this easily that looks this good. (Check out cpdtracks.com). Claude went as far as finding a way for me to host it for free, and took control of my browser to set everything up.

Earlier this week I hit submit and my App went to Apple for review. When they came back with a few small issues, Claude walked me through fixing them and resubmitting. What a guy.

The Future Is Going To Be Wild

This experience has reiterated my excitement for what could be possible in the future. This is the worst these tools will ever be! That is insane.

Without having any experience building a native Apple Application I was able to make one that - if I do say so myself - looks beautiful and works really well to solve a problem I’ve been frustrated by for years now.

In a future where anybody with an idea can spend some time on it and make it happen with a relatively inexpensive tool like this, what incredible possibilities could be unlocked? What great new inventions could be created? What great medical mysteries could be solved? It’s an exciting, albeit nerve-racking time to be alive.

Survivor has been on screens since the year 2000. Derived from a Swedish show, it was a launching pad for a reality TV boom that was inescapable in that decade. While viewership numbers have declined since then, there is still a dedicated fan base faithfully watching as its fiftieth season recently kicked off. I am unapologetically one of those fans.

Voluntarily Starving on Television

I’ve watched Survivor from the beginning. The show would air on a free government-run channel in South Africa. The season we were watching was normally at least a full year or more behind when it aired in the US. Government channels have tight budgets. But social media hadn’t been invented yet to ruin the season winner so it didn’t matter that much.

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Every week I would watch as an eclectic group of Americans starved, played mind games with each other and competed in strength and endurance challenges that would test them to their limits. Ending each episode with the group democratically voting out (read stabbing in the back) their tribe mates.

Inflation over the last twenty-five years has significantly diminished the value of the million dollar prize pool. $1 million in 2000 is roughly worth $1.8 million today. But that hasn’t stopped the brilliant cast pipeline pouring in. It’s still a nice pile of cash — but the real prize, it turns out, isn't the cheque. Look no further than the current season which includes twenty-four players who have returned just to play against the best of the best - some who have already won.

While I may not be a die-hard fan in the sense that I stalk previous cast members online or know their children’s names, I have faithfully watched season after season and always look forward to the next one. We even dropped into the Survivor pop up in Miami when we were there a few weeks ago.

Jeff the G.O.A.T

Jeff Probst or ‘Uncle Jeff,’ the multi-Emmy Award-winning talented host, is the show’s constant guiding force. He’s been there from the beginning. Other local spin-offs of the show are never as good to me, which I think is largely because they’re missing a Jeff. There’s an art to presenting and narrating a competition like this that is not easily replicated. I vividly recall one of the South African hosts getting frustrated that the tribe he was talking to was not giving him the answers he wanted. The tribe just stared at him blankly.

What Makes It Magic

The show itself is so fascinating because it mixes so much of the human experience. Competitiveness, compassion, cunning, heart. Pushing yourself to the limit for no apparent reason other than to prove you can. It’s a game that can be played as a villain or a hero but it’s one of the few reality shows that has a built-in consequence for those who get to the finish line by playing the villain. In the end, the people you vote out decide if you’re worthy of the title of Sole Survivor.

My favorite part of watching the show over the last few years has become watching it with friends. It’s a brilliant excuse to get together every week, catch up, watch something entertaining, shout for our favorite underdogs (albeit much more quietly now that the baby is sleeping in the other room) and then pontificate on what we would have done if we were on that beach. We would probably be getting more sleep even with the bugs.

There’s this interesting relationship you build with a show you’ve watched over 20 years. This entertainment ritual that has been part of your life through so many of your own seasons. As a kid in your parent’s home, as a single person, as a couple, as parents, and if the show keeps going maybe even our daughter will sit down to shout for her tribe one day.

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Still On The Edge Of My Seat

Sure it’s just a television show, but in the age of throw away trash generated without effort or thought - today it may not even be generated by humans - there’s something so special about a show with this kind of lasting power.

Needless to say I’m on the edge of my seat for who takes the Season 50 crown.
"Survivors ready? Go!"

The magic of Valentine’s Day. An excuse to pause and, quite literally, smell the roses. For all the consumerism around any widely celebrated occasion, Valentine’s Day is a beautiful excuse to love on your favorite person in the world and do something special with them.

Yes, every day should be special with the one you love and blah blah blah. But life is busy and complicated. Having a day set aside to stop and celebrate love, that’s worthwhile.

I’ve always enjoyed celebrating Valentine’s Day with my wife. We used to have one person plan it and then switch roles the next year, which is a fun way to take turns in surprising each other. The last two years though have been a lot more low key with a little one. This year we ordered some sushi and feasted under the shadow of my wife’s large flower bouquet after the little one went down.

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Having a daughter is giving me reason to consider this day more carefully. As her father, I am setting the example of what she will expect from the man in her life. Not only how I treat her mother and celebrate her - which I always want to do exceptionally well - but also how I celebrate her on these days. It will put a standard in her heart and mind of what is acceptable or not. I want that standard to be exceptionally high.

Not in the sense that she should feel entitled to exorbitant gifts or exotic shows of affection, but that she is worth taking the time to celebrate and love on. That Valentine’s Days for her are special memories with her parents before she falls in love.

My mom often used to get me a card and chocolate growing up, which I did not appreciate enough - thanks mom! My wife’s mom did the same. Maybe that’s why we both like celebrating this day. My hope is that we can pass on a tradition of celebrating love rather than cynicism.

I hope your Valentine’s Day was fun. If not, take solace in the fact that heart shaped chocolates will be on sale this week.

From novice to pro

When ChatGPT first started becoming mainstream in early 2023 I began playing with it as a coding tool. My coding experience centered around building websites and digital magazines at school, you can tell I was cool, all self-taught and very limited.

After just a few months, I was building applications and automations for a bunch of different tasks. I was automating things that would once have taken hours of manual work, done in minutes or even seconds. I had found my work happy place. I was making inefficient things efficient, and removing tedious work from the agenda.

When I started using these AI models, building an application took a few months with my limited coding experience. Last year, with the latest models available to us at work and a few years of prompting and bug-fixing under my belt, I updated one of the applications I had built in less than a month of part-time work. This month, I’ve completed another major upgrade using the latest AI tools in less than a day. A week of robust testing and iterative updates all guided by my AI professor followed.

The future is here and it’s only going to get better. We now live in a time where if you have an idea to build something you can do it. It may require some patience and problem-solving, but if you have the vision for what you need these tools are powerful.

In that vein I’ve started doing something I’ve always dreamt of doing. Building my own iPhone App. For my first App, I’m trying to solve a basic problem for myself that may help a few others too. It’s a practice run to see what’s possible with just an idea and an AI tool. I’ll share more about what the App is for in the future but today I want to focus on what my experience with the latest tools means for our future.

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Now anything is possible

Being able to explain an idea you have, how you want it to work, look and feel in your native language and then have AI bring that idea to life in just a few minutes is mind-blowing. It takes years of technical learning out of the way and allows you to identify a problem, carefully plan a solution and execute it, with an expert at your beck and call. The hype is not just real. It’s understated. It’s cinema, as the kids say.

It doesn’t have to just be an automation or an App, it can be something in the real world too. I’ve followed instructions on how to grout a shower for example. Taken pictures of broken things and gotten instructions on how to fix them. In our family we use it for cooking instructions, taking pictures of ingredients and asking for custom recipes. We are constantly asking for advice on things to feed our daughter that are both good for her and won’t end up on the floor. The floor is still covered in food, but she’s healthy and eating well.

Need a comprehensive and complicated concept explained to you like a child? Done.
Have an idea that you want to mock up before building it? Done.
Ready to build it? Let’s go!
Need someone to tell you not to buy that outfit? Sorry, only someone who truly loves you will do that.

I literally have an AI agent working through my latest App spec in the background while I type this, I’ve told it some ideas I have for how my new App should work and it’s running off and making them happen. I describe what I want, it builds it. I iterate based on what I see and it builds that.

This is a great equalizer. Most of these AI applications currently have decent free versions available for you to use right now from your phone. If you are not playing with these tools, you are missing the boarding call.

But what about the downsides of these powerful tools?

The problems with AI

A lot of people today are focusing on where these tools fall short. The mistakes they make, the abuses people are already using them for —Grok, ahem— the fabricated facts they share. But take a step back. If you told most people ten years ago that tools like this would even exist they would think you were living in a fantasy world with light sabers and slug kings.

I’ve mentioned before that my P(doom)1 is on the higher end of the scale. Humanity has proven that we will choose greed, repeat wars, ignore warnings, and hurt each other in the name of progress. So these tools could very well mean the end of us. These fears are not unfounded, most AI leaders are petrified of what could go wrong even if they’re barreling ahead anyway.

For now, I’m choosing to focus on what I can achieve with these tools while keeping my ear to the ground on where it could all go wrong. We tend to lean towards a negative outlook as people, it’s one of the things that has kept us alive for this long despite animals being superior to us in many ways. But humanity has also come an incredibly long way from playing with sticks in the mud.

We’ve cured diseases, built giant things and microscopic things. We’ve improved quality of life and life expectancy across the board, even managing to slow a global pandemic to the point of ignoring it. Nothing like being back in an airport with everyone coughing and sneezing while standing right on top of you. Almost everybody in the world has incredible access to information never dreamt of in the palm of their hands. Humanity is making progress despite the horrors we see in the news.

Focus on what you control

We can live in a world of fear and worry. Will these incredible tools take my job, will it lead to a recession, wars, the end of humanity?
You can also live in a world of utopia. Will technology solve poverty, sickness and climate change?

While it may be interesting to ponder these big questions, the reality is most of it is out of our control. The billionaires are going to do as they wish, and build what they will and we’re going to be left with the consequences. But we’re a hardy bunch. We’ll do what humans always do. Adapt, recalibrate to a new normal, and bound forward to achieve incredible things. Now if only AI could teach our daughter not to throw her food on the floor for the dog.

I am writing to share with you that I am alive and well. My beautiful wife has given birth to a little miracle and we are so thankful for their healthy presence, made known through awe-inspiring volume.

In the last year I have seen your messages. Your invitations out for an evening drink, to join you at a gig jamming to sweet sounds, to battle it out on the sweaty pickleball courts of this grand island, to film something in a fit of inspiration and put it out on the internet for all the world to see. For these invitations I am extremely grateful.

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We thought we could do it all. Keep up the DINK1 lifestyle. Just strap the nugget to our backs and head out into the world. Be as strong as our social media influencer inspirations. But we have found ourselves living in what some have termed, ‘the real world.’ This is a most upsetting discovery, for which I did try to submit a complaint but nobody in customer service would take my call.

In this real world we have found that time is not infinite. That waking up six times a night does not fill you with the energy of a thousand suns. That every minute we have must be spent on keeping the nugget alive, keeping ourselves alive, and breathing in every beautiful moment of this incredible journey.

While we may have pulled back from some of our exotic pastimes such as saving money, we are finding our feet in this new life filled with priceless moments. We are reintegrating cautiously but optimistically into society. But be warned we are different.

A powerhouse of love and forgiveness. A nappy changing crew envied by the greatest F1 pitstop teams. An inseparable unit. We can vibe to Old MacDonald, hit record to capture an incredible moment in milliseconds, and these arms can carry and juggle the squirmiest precious cargo.

Looking forward to catching up on what you’ve done with all that free time of yours.

All my love.

This is Charlie,

my five year old, mixed breed pup. He stands 54 centimeters tall and around 1 meter from snout-to-tail. I couldn’t get him to stand still enough to measure accurately. He curls up very nicely to snuggle in your lap. Or stretches out to take up the entire back seat of a Kia Picanto. This dog’s got size versatility. While he fits in the leg space of the front seat of the car, he doesn’t like it, and he’ll be sure to look extremely miserable if asked to sit there while the recycling takes up his usual back seat position.

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Let’s talk build quality

A lot of dogs come with build quality issues from years of inbreeding to maintain a certain unique look. Our boy is built from all the best qualities of many breeds, and while his legs may be skinnier than a catwalk model, he is fast, agile and provides a firm handshake when a treat is involved.

His coat is always silky smooth, even when he hasn’t been bathed in a month. Which is good because he really hates being bathed. Like, really hates it. This model is built with incredible obedience, trust and loyalty. So when you’re doing something torturous like brushing his teeth, clipping his nails or bathing him, he’ll lovingly but miserably cooperate. Only attempting to sneak away when you’re looking in the other direction.

That brings us to performance

Loyalty and obedience play into his ability to be trained, and therefore what a joy he is to be around. There’s no insane barking, or destruction - except for the early months where a few shoes met their demise. He has even learnt that while it is incredibly exciting that your family member has come home after 5 whole minutes taking out the trash, and a parade is most definitely in order, sitting impatiently on your bed and waiting for the family member to put down what they are carrying and let you know they are ready for the parade is the right thing to do.

This feature has begun to malfunction in the last year due to sibling trauma, discussed later in this review. However it can still be activated with a stern ‘BED!’ command, repeated until you feel like you’re speaking another language. Some back talk can be expected.

The training mode on this model requires some patience but he learns fast and is more than willing even without treats. It’s got to be said, the excitement and joy to simply spend quality time without any thrills is an incredible feature.

In more recent years, the old dog new tricks trope has proven untrue with this model. He has learnt to spin, crawl and vacuum up left overs. All recent features provided through over the air command updates.

Herding is built into the model as standard. If family members are in separate areas of the house, they will be herded to one area for maximum quality time together.

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The hard truth

Not everything is perfect. The model has serious selective hearing, the bug is most obvious when new people have arrived in the home or when another dog is walking by and their butt must be sniffed immediately.

Poops are also enormous and difficult to coax from the model even though it is clear the time has come. Often one has to jog up and down a strip in order to ensure the poop comes out in an appropriate place. If this is not done, the waste management system may misfire on a cement walkway, usually in front of a busy gawking crowd.

Sibling Trauma

In the last year a sibling was introduced with whom the model now shares a room to recharge. The sibling’s late night loud demands for food has clearly disturbed the charging process. Their introduction has resulted in obedience features glitching and treat consumption for pain and suffering going up significantly.

However the protective features seem to have been turned up to a whole new level with family protection becoming a top priority. Unless I’m the only one in the house, at which point I am left to fend for myself while a much needed emergency recharge is completed.

Still - despite the odd malfunction - this model is too good to ever upgrade.

Should I get this model?

I have no issue recommending this model to anyone at all, but sadly for you - Charlie is one of a kind. He’s not for sale. While he may have some quirks and glitches, this model brings daily joy, laughter, and loyalty no designer could ever replicate. In fact it’s a bit unfair I’ve even shared this review with you given you can’t do anything but admire my good boy. Sorry.

“Everyone thinks they have the best dog. And none of them are wrong.” W.R. Purche

Dec 31st, 2024 - 10, 9, 8, we sat on beach chairs commandeered in front of the Ritz Carlton as the clock ticked ever closer to midnight. 7, 6, 5, A drunken idiot was lighting a firework in front of his face as I watched, nervous he would send it firing at my pregnant wife. 4, 3, 2, I held my breath, anticipating the year ahead that would change my life forever. 1, HAPPY NEW YEAR! The sky exploded all along Seven Mile Beach. 2025 had begun.

The baby’s coming

After driving our new family car out to a dusty track through the mangroves, my wife power walked ahead as the dog and I half jogged to keep up. She was determined to walk this baby into the world and walk we did. Every day, multiple times a day, with evening sessions in the gym bouncing on a gym ball. Months of preparation had led to the moment we drove to the hospital, DINKS1 for the last time.

My wife, cracking jokes whilst pushing out a baby, delivered our beautiful daughter who wasted no time telling the doctors to give her back to her mother immediately. 2025 is our daughter’s year.

It was messy, beautiful, exhausting, and exhilarating. It’s been fun to document some of it here. The highs were spectacularly high, the lows were unsettlingly deep. This is it, the adulting big leagues.

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Six 2026 Resolutions

As we bumble over the line into the new year, one can only pray 2026 will be filled with calm, precedented events. These are my hopes for the year ahead:

1. Family 1st - Prioritizing my family’s well-being continues to be my number one goal this year. I want to be my wife’s biggest champion, helping her thrive not just as a mom but in her own right. I want to be present for my daughter and celebrate her milestones. I want to travel slowly and purposefully rather than rushed and painful. I want us to laugh a lot, only crying when it’s meaningful. Most of all I want God leading us through it all.

   

2. Stress Less - Something we learnt the hard way over 2025 was that doing the same activities we used to do as a couple with a baby may be important, but they’re hard. Going to a restaurant for example takes preparation. From packing a bag, to ensuring nap times are hit, to successfully navigating a poop-splosion while walking out the door without everybody ending up in tears. At the restaurant you’re juggling adult conversations with entertaining and feeding a baby, while using your third arm to shovel food into your own mouth. Sometimes it all goes to pot and you have to cancel. Sometimes friends are late and you have to leave early. Sometimes you don’t know your arse from your elbow and your wife is doing it all while you pace in a circle malfunctioning.

   
   In 2026 I want to roll with the punches. Try to embrace the Cayman ‘Soon Come’ attitude rather than worrying about things that have never been under my control. Embrace the present, leave the past, let God handle the future. It’s biblical, it’s practical, it’s really hard to do.
   

3. Stay Healthy - Continuing to fight the dad bod trope is important beyond looking and feeling like a snack. If anything is going to kill me, I don’t want it to be me not taking care of my body. While I’ve been pretty good at keeping up on fitness in 2025, my fear of sitting in a cold harsh hospital and waiting mindlessly on medical staff to poke and prod at me has kept me from doing check ups I know I should be doing. See you in the waiting room.

   

4. Creativity - I’ve always been somebody who needs a creative side project. Especially since I started studying accounting. Not so secretly hoping that one day, one of those side projects will take off and become THE project. I’ve really enjoyed writing in the second half of 2025. I’ve loved creating “Dad the Accountant.” If I could incorporate some of my other loves in 2026 like making short films, music, or coming up with some wacky business scheme while including my family in the fun, that would be cinema.
   

5. Friends and Networking - While I’m not a socialite by any stretch of the imagination I do enjoy spending time with people. The thing is, I hate small talk. It’s so mind numbingly mundane.
   
   The weather has been hot lately…
   Yes we live on a tropical island.
   Those mosquitos though!
   
   And yet this is essential to meeting and making friends. Living in a transient place where your closest friends are always abandoning you leaving makes this an essential skill. Never mind that moving along in your career is all about connections and putting yourself out there.

   
   Plus, when you have a child, you're supposed to make friends with other parents, parents with whom your only thing in common is that you both figured out how to procreate.

   
   This year I want to put more effort in by going to the odd networking event, being friendly to other procreators and asking people about their deepest darkest fears before they start talking about some major sports event I have no desire to learn about.

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6. Wield the Robot’s Power - For all the hype around AI, people still haven’t really found ways to utilize it to its fullest potential. Most people seem to just be making funny pictures or sharing their strange pimples with a chat bot to see if they’re dying. I’ve found some fantastic use for AI in my workplace but I feel like there is a lot more I can learn and do here. Gadgets, tech, productivity, this stuff is my jam. But can I get it to make me some jam?

As we bring in the new year from our bed, knowing the nugget will be waking us up at 6AM regardless of what time we go to sleep, I wish you and your loved ones a Happy New Year.

What are your hopes for 2026? To get a cat will not be an accepted answer.2

The lights are up on the roundabouts as the traffic grinds to a halt around them. The stores are playing the classics while the Christmas chocolates fly off the shelves. The hotel lobbies are filled with giant Christmas trees — one hotel even has a giant bow wrapped around the outside. The pastors are blowing the dust off their favorite Christmas sermons as they prepare for their highest church attendance of the year. The most wonderful time of the year is upon us in Grand Cayman.

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This year, to save us from tears, we decided to stay home for Christmas. Our little one — while up for an adventure — is still figuring out this sleeping thing which regresses tenfold when we travel. I’ve also got to work through the holidays. Study accounting they said… It’ll be rewarding they said…
Sadly that means we miss out on spending this happy time of the year with family. Playing board games with our nephews and opening presents together while snow falls softly outside is magical and will be sorely missed.

Before traveling to Canada for the first time, I’d never even seen real snow. The closest I’d gotten was some sleet in Dublin on a short visit. I’ve grown up with hot Christmas days, family braais*, eating cold meats and swimming in the pool at my grandparent’s place. Living in Cayman is more of the same. However, for my wife who grew up with snow and cosy fireplaces, a hot Christmas is still an odd experience.

*barbeques, South African style

To try and make the most of Christmas at home, and because it’s our little one’s first Christmas, we got a real tree and blanketed the floor beneath it with presents. The air-conditioner is on max, Christmas sweaters adorned, hot chocolates in hand, and a faux fireplace crackles through the TV. Turkey and all the spoils are ordered for Christmas Day. My wife has even been practicing my sister in law’s amazing stew so we can feel a little closer, even from across the world..

While many escape to Cayman to celebrate Christmas away from the cold, Cayman residents who don’t have large families on island will often head off-island to spend it at home. Those of us staying put celebrate together with our blended families. Families made up of friends, colleagues, and friends of friends.

It’s a special time of year to appreciate the blessings we have. May this Christmas be magical, no matter how or with whom you get to celebrate. For me, the beautiful traditions are a reminder of an incredibly gracious God, who provided the ultimate sacrifice for an undeserving world.

Merry Christmas

The end-of-year sales bonanza used to be a one-day Black Friday event. Now it’s a smorgasbord of sale emails from every company you’ve ever interacted with, running from November to Christmas. For this frugal dad, it’s basically the playoffs.

Throughout the year, my wife and I have gotten better at anticipating big things we need/want to buy and holding off for a big sales event. Why pay full price when you can delay that gratification and add the budget euphoria of getting it at a discounted price? Living on an island where everything is at least a week or two away anyway means impulse buying doesn’t hit quite as well as walking into a Lululemon and walking out a much poorer but better dressed man.

Sadly, many of the sales advertised during this period are just scams. A marketing ploy to get you to spend money on things you don’t need, simply because there’s a false sense of urgency that you won’t see a price this good again. Luckily we’re smarter than the average bear.

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If you can find that magical crossover where the thing you were going to buy anyway at full price, suddenly goes on sale - it’s straight fire. That’s what the kids are saying these days. I learnt it watching Survivor.

Knowing the cost of the things you’re going to buy beforehand is therefore the key to not getting conned. Amazon very excitedly sent me a notification to say an item I had looked at before was 50% off. But the ‘50% off’ special price was the same price I had seen months ago when I first looked at it!

Despite the scammy sales floating about, this year we got some great deals I’m really proud of. I’m even more proud that I did not buy one thing on sale for myself on a whim. The baby was a different story.

This year’s sales haul savings report:

• Car seat for when the baby graduates from her current seat (and one which will last until she doesn’t need one anymore) - 20% off!

• Educational toys we were going to buy at full price throughout the next year - 25% off!

• Flight to see the grandparents - 33% off, making some smart use of a points sale and family card benefits! (Thanks Sharon!)

• Baby creams and soaps - 40% off!

• Broken outdoor camera replacement - 50% off!

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Saving money like this makes me unreasonably giddy! A 20% return on a no risk investment is unheard of. To save money on something you would have needed to buy at full price regardless starts to feel like you’re the Wolf of Wall Street - minus the drugs and unhappiness.

This doesn’t just have to be a Black Friday thing. Stores often have sales during other holidays in the year, allowing you to get great deals all year round. So the next time you need to make a big purchase, or maybe even basic supplies, put it on the wish list and start planning for the next big deal. Even the richest people love a good deal on diapers. Though maybe they’re paying someone else to change them.

Over the last few weeks we’ve finalized our summer 2026 plans and started booking our flights. Summer in the Northern hemisphere is an expensive time to travel, so naturally my inner accountant was activated. A board meeting of budgeting neurons was called, the staff passionately stirred up to find creative ways to make this cheaper. Concluded with a bang of the calculator, the inspired neurons were sent off to fire away while I’m trying to sleep.

Airline miles, airline credits, bank points and deal-notifying Apps were rounded up and booking began. While we will normally jump at a good deal, we try to fly with one specific airline. They have some of the most convenient flights in and out of Cayman, and we have status so it saves us money with perks like free bags and seats.

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Unfortunately

this airline has a bizarre flaw in their booking system that does not allow you to book your flight with an infant in your lap. Instead you need to book a flight for two and then contact customer ‘service’ to add the child to your booking.

This ridiculous rigmarole which does not appear to be a thing on other airlines, means speaking to a poor sod who is following the most annoying script of long winded flattery. I prefer to use a text chat because I can’t stand holding a phone to my ear for long periods of time, listening to heavy headset breathing, or the worst royalty free music an intern could find.

Over the week I ended up chatting with multiple customer ‘service’ team members to add our daughter to multiple flights. I also had to use credits, another unnecessarily complicated task, likely in the hope you give up in frustration and never use them. I’m sure they have a high success rate.

After booking our last flight with points I began a chat one last time to have our daughter added to the flight.

The Last Conversation

starts with an over zealous greeting from Parikshit - not a made up name - filled with promise on how happy they will be to help. When they notice I am a status holder, thanks and appreciation are heaped upon me for my existence.

Being the efficient, non-chatty type, I try to get straight to it with what I need. Infant added to my flight that I should have been able to book myself, and all the information they need to make that happen. I jump in the shower while Parikshit gets to work.

When I get out of the shower, Parikshit has realized my flight was booked with points and asked if they can transfer me to the only person who can handle such a bespoke request. Instead of doing the transfer, Parikshit waits a few minutes for a response and decides to close the chat.

I start up the chat again, and just my luck get reconnected to Parikshit! I confirm that transferring me to somebody who can get my daughter added will indeed be helpful considering that’s the reason I’ve started this chat in the first place. They shower me with praise on my status and ensure me they are very happy to help before reviewing my previous messages and finally transferring me to Ravi.

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Ravi is also extremely excited to serve me, and is also very appreciative of my loyalty as a status holder.

They ask me to confirm the information I have provided only minutes ago to Parikshit, in messages they can apparently read. I repeat myself. He is thankful for the information.

As an aside I discovered over my many times going through this exercise with different team members that they can actually see what you’re typing in the chat BEFORE hitting send. How creepy is that!?

While Ravi gets to work on this complex task of getting my baby ticketed, he wants to know how my day is going so far. Considering I’ve spent three hours arguing about flight credits with previous customer ‘service’ team members I kindly refrain from answering that question.

Updates follow in five minute increments.

I’m assured that he is still working on it for me.
He’s contacting an ‘internal team’ — I thought he was the expert?!
I am thanked for my patience…
Again I am thanked for my patience… @#$%&!

Finally he confirms, “I have added the infant on your reservation, and you do not need to pay any fare for the infant.” Praise be!

“Your satisfaction means everything to us.” That seems highly unlikely Ravi but thanks for the heartfelt canned messages.

My P(doom)1 is probably on the high side—especially when I see companies replacing people with machines. But after experiences like this I say go ahead, let the robots have their turn. Lord save us all.

’Twas the night after Halloween, quiet, not quite,
Not a creature was sleeping, just the dog out of spite.
The milk had been given, and even some food,
But the baby, for sleep, was not in the mood.

A scarier story, you’ve probably heard,
But a sleep bandit loose should make anyone scared.
Sleep is so precious, for growing and might,
But babies want mama all through the night.

“Give her sleep training, she’s old enough now,”
Said friends to us as they furrowed their brow.
“It’ll be hard, but the results will speak loud…”
So we dove in, determinedly unbowed.

She tossed and she turned and she shouted for mama,
But the dummy just kept being provided by dada.
The clock struck one, then two, and then three,
Dad prayed from the bedroom, “Lord, please help her Zzz!”

Finally it came; after hours of screaming,
A ray of hope, in spite of the teething.
The baba slept soundly for eight hours straight.
Maybe, just maybe, this sleepless chapter’s closing its gate.

Under a canopy, a little play-yard had been set up full of puppies. People were holding them around us, while volunteers shared stories and encouraged people to take the cuties home. We played with the rambunctious litter for a bit before my wife picked up Charlie. He sleepily cuddled into her arms and relaxed. We looked at each other. Charlie was joining our little family.

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Charlie was found in a bush in Bodden Town, his mother ran away from the people who found his litter, and they were scooped up and brought into the Cayman Islands Humane Society. A scrawny, malnourished little thing covered in mange. He was originally given a preppy British name by the Humane Society — but we loved the name Charlie.

Charlie came with us everywhere. He snuck into stores in my wife’s handbag, slept on my lap in restaurants as I ate a hamburger over his head. He came to friends’ houses, pools, long drives to Kaibo, even waited outside for me when I went for a job interview. Charlie became an essential part of our daily adventures.

It is amazing how much love and laughter [dogs] bring into our lives and even how much closer we become with each other because of them. John Grogan, Marley & Me

Since we had a baby Charlie has embraced his big brother role, especially since she started dropping food on the ground for him. Nobody can look as exhausted with the world as Charlie, even after a long day of napping to catch up on his much disturbed beauty sleep. In spite of how loud our daughter can be, he’ll check in on her to make sure she’s OK, coming to get us if he feels we’re not responding to her complaints fast enough.

My wife and I have a running bit where I insist it’s time for Charlie to get a job and stop being a free loader. I point to a dog working in the airport, or as a guide. She tells me he’s just a baby to which I retort he is absolutely not a baby and needs to get a job! Charlie is the only member in our household who has a birthright to work in these beloved isles! The truth is, Charlie has many jobs.

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He’s our welcoming committee when we get home, our therapist when we’re sad, our entertainment when he’s feeling silly, and the best coffee buddy on an early morning wake up with our daughter.

On his fifth birthday, the year he lost his only-child status, I wanted to write something to honor our boy. He has been and continues to be a huge blessing to our family. I can’t wait for him to read this. Love ya buddy.

In our mystical magical world, used items of any perceived value are listed on websites filled with oddballs buying and selling. The old local market but people communicate through cutting edge technology like cave dwellers trading fire rocks.

In Cayman we call this website eCayTrade. Similar to Craigslist, Gum Tree or Marketplace on Facebook. A cornucopia of people selling anything from a tennis racquet to their house. A cesspool that one must dip their toes into every so often to sell one’s own junk.

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As our baby outgrows her gadgets and gizmos we have begun to hawk her used goods online for a quarter of their shelf value. Thankfully my wife has taken the lead on dealing with those crazies. The only time I venture into the depths of the online marketplace is when I have furniture or a gadget to sell. After recently upgrading my phone, it was time for me to venture back into this black hole of lunacy again.

The Excruciating Selling Process

Immediately after posting any item on one of these websites you can expect to receive at least four messages asking if the item listed ten minutes ago is still available. Upon replying, “Yes, it’s available,” you are only 43%1 likely to ever hear back from the person ever again. I sometimes imagine these people have fallen into the ocean never to be seen or heard from again.

If you do get a reply the next questions will usually be about the thing you’re selling, which you have more than likely already answered in the advertisement they didn’t read.

If satisfied with your painstakingly copy and pasted response the negotiations begin. If you are dealing with a grifter, they may try some sly tactics like talking up the weaker points of what you are trying to sell.

“The phone’s maximum battery capacity only goes to 89%.”
”Yes that’s what it shows in the screenshot.”
”I may need to replace the battery soon, that is expensive.”
”You are buying a two year old phone, it’s unlikely but if you’d like to, replacing the battery is an option.”
”I’m not sure I can buy it.”
”OK…” (Then why the #$%@ are you messaging me?)

After the mind games they may then make you an offer. One buyer offered me 50% of the asking price, while another offered me their ‘new’ older model iPhone and an old iPad.

Meeting Up with Strangers

If you do finally find somebody willing to offer you a reasonable amount for your item, plus compensation for the pain and suffering of dealing with people, it’s time to meet up. My wife, when recently selling items for $10, has been asked to deliver them to the person’s door. She has kindly agreed - considering it’s a new mom who is buying this baby stuff and is probably going through a lot. I am not that kind. Given the cost of time and fuel we lost more money selling that $10 item than donating it.

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A few phones ago, when we were all still taking COVID seriously, I agreed to drop off a phone to someone in lockdown. They left a plastic bag of money on their doorstep and I dropped the phone in a box before running back to the car. I waited for them to confirm they were happy before driving away feeling like I’d just done a drug deal.

These days, unless I am selling some large piece of furniture I always ask to meet in a public place in case the person is a psycho. If they have been particularly weird in our conversations I’ll make sure it’s in front of a store or restaurant I almost never visit.

Upon meetup, awkward pleasantries out of the way, the item is examined by the buyer while the South African in me is concerned the person may be a flight risk. Yes, it does indeed appear to be an iPhone. No alarming differences from the pictures and it turns on. Great. Cash is exchanged and I try to walk in the opposite direction. Nothing more awkward than saying goodbye to a stranger and then walking alongside them for five minutes to your vehicle.

Still Worth It?

Every time I do this I say never again, but trade ins just don’t give you enough compared to selling the phone to normals. Hopefully one day I'll be rich enough to just give my old valuables away. Until then, every few months you’ll see me online selling something of meaningful value. Please don’t ask me if it’s available.